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Group Title: Bulletin - University of Florida Agricultural Experiment Station ; 545
Title: Hesperidin, the principal glucoside of oranges
CITATION THUMBNAILS PAGE IMAGE ZOOMABLE
Full Citation
STANDARD VIEW MARC VIEW
Permanent Link: http://ufdc.ufl.edu/UF00026678/00001
 Material Information
Title: Hesperidin, the principal glucoside of oranges occurrence, properties and possible utilization
Series Title: Bulletin University of Florida. Agricultural Experiment Station
Physical Description: 43 p. : ill. ; 23 cm.
Language: English
Creator: Hendrickson, Rudolph
Kesterson, J. W
Publisher: University of Florida Agricultural Experiment Station
Place of Publication: Gainesville Fla
Publication Date: 1954
 Subjects
Subject: Hespiridin   ( lcsh )
Oranges -- Composition   ( lcsh )
Genre: government publication (state, provincial, terriorial, dependent)   ( marcgt )
bibliography   ( marcgt )
non-fiction   ( marcgt )
 Notes
Bibliography: Bibliography: p. 32-34.
Statement of Responsibility: R. Hendrickson and J.W. Kesterson.
General Note: Cover title.
General Note: "A contribution from the Citrus Experiment Station"--T.p.
 Record Information
Bibliographic ID: UF00026678
Volume ID: VID00001
Source Institution: University of Florida
Rights Management: All rights reserved by the source institution and holding location.
Resource Identifier: aleph - 000926391
oclc - 18276552
notis - AEN7062

Table of Contents
    Title Page
        Page 1
    Personnel
        Page 2
    Branch stations
        Page 3
    Table of Contents
        Page 4
    Main
        Page 5
        Page 6
        Page 7
        Page 8
        Page 9
        Page 10
        Page 11
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        Page 15
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Full Text


August 1954


UNIVERSITY OF FLORIDA
AGRICULTURAL EXPERIMENT STATIONS
WILLARD M. FIFIELD, Director
GAINESVILLE, FLORIDA
(A contribution from the Citrus Experiment Station)



Hesperidin, the Principal Glucoside
of Oranges

Occurrence, Properties and Possible Utilization
R. HENDRICKSON and J. W. KESTERSON


Fig. 1.-Hesperidin crystals magnified 120 X.


TECHNICAL BULLETIN


Single copies free to Florida residents on request to
AGRICULTURAL EXPERIMENT STATION
GAINESVILLE, FLORIDA


Bulletin 545








BOARD OF CONTROL
Hollis Rinehart, Chairman, Miami
J. Lee Ballard, St. Petersburg
Fred H. Kent, Jacksonville
Wm. H. Dial, Orlando
Mrs. Alfred I. duPont, Jacksonville
George W. English, Jr., Ft. Lauderdale
W. Glenn Miller, Monticello
W. F. Powers, Secretary, Tallahassee
EXECUTIVE STAFF
John S. Allen, Acting President
J. Wayne Reitz, Ph.D., Provost for Agr.3
Willard M. Fifield, M.S., Director
J. R. Beckenbach, Ph.D., Asso. Director
R. W. Bledsoe, Ph.D., Assistant Director
Rogers L. Bartley, B.S., Admin. Mgr.3
Geo. R. Freeman, B.S., Farm Superintendent
W. H. Jones, Jr., M.Agr., Asst. Sput.

MAIN STATION, GAINESVILLE
AGRICULTURAL ECONOMICS
H. G. Hamilton, Ph.D., Agr. Economist '
R. E. L. Greene, Ph.D., Agr. Economist :'
M. A. Brooker. Ph.D., Agr. Economist
Zach Savage, M.S.A., Economist
A. H. Spurlock, M.S.A., Agr. Economist
D. E. Alleger, M.S., Associate
D. L. Brooke, Ph.D., Associate
M. R. Godwin, Ph.D., Associate
W. K. McPherson, M.S., Agr. Economist 3
Eric Thor, M.S., Asso. Arr. Ecoromi-t:'
Cecil N. Smith, M.A., Asso. Agr. Economist
Levi A. Powell, Sr., M.S.A., Assistant
E. D. Smith, Ph.D., Asst. Agr. Economist
N. K. Roberts, M.A., Asst. Agr. Economist
Orlando, Florida (Cooperative USDA)
G. Norman Rose, B.S., Asso. Agri. Economist
J. C. Townsend, Jr., B.S.A., Agr. Statistician2
J. B. Owens, B.S.A.. Agr. Statistician 2
F. T. Galloway, M.S., Agr. Statistician
C. L. Crenshaw, M.S., Asst. Agr. Economist
B. W. Kelly, M.S., Asst. Agr. Economist
AGRICULTURAL ENGINEERING
Frazier Rogers, M.S.A., Agr. Engineer '
J. M. Myers, M.S.A., Asso. Agr. Engineer
J. S. Norton, M.S., Asst. Agr. Engineer
AGRONOMY
Fred H. Hull, Ph.D., Agronomist 1 2
G. B. Killinger, Ph.D., Agronomist
H. C. Harris, Ph.D., Agronomist
W. A. Carver, Ph.D., Agronomist
Fred A. Clark, M.S., Associate 2
E. S. Horner, Ph.D., Assistant
A. T. Wallace, Ph.D., Assistant
D. E. McCloud, Ph.D., Assistant 3
G. C. Nutter, Ph.D., Asst. Agronomist
I. M. Wofford, Ph.D., Asst. Agronomist
E. O. Burt, Ph.D., Asst. Agronomist
J. R. Edwardson, Ph.D., Asst. Agronomist
ANIMAL HUSBANDRY AND NUTRITION
T. J. Cunha, Ph.D., Animal Husbandman
G. K. Davis, Ph.D., Animal Nutritionist 0
R. L. Shirley, Ph.D.. Biochemist
A. M. Pearson, Ph.D., Asso. An. Husb.3
John P. Feaster, Ph.D., Asst. An. Nutri.
H. D. Wallace, Ph.D., Asso. An. Husb.3
M. Koger, Ph.D., An. Husbandman 3
J. F. Hentges, Jr., Ph.D., Asst. An. Husb. :
L. R. Arrington, Ph.D., Asst. An. Husb.
A. C. Warnick, Ph.D., Asst. Physiologist
DAIRY SCIENCE
E. L. Fouts, Ph.D., Dairy Technologist a
R. B. Becker, Ph.D., Dairy Husbanuman a
S. P. Marshall, Ph.D., Asso. Dairy Husb.'
W. A. Krienke, M.S., Asso. Dairy Tech.3
P. T. Dix Arnold, M.S.A., Asso. Dairy Husb. a
Leon Mull, Ph.D., Asso. Dairy Tech.3
H. H. Wilkowske, Ph.D., Asst. Dairy Tech.3
James M. Wing, Ph.D., Asst. Dairy IHusb.


EDITORIAL
J. Francis Cooper, M.S.A., Editor 13
Clyde Beale, A.B.J., Editor 3
\VWllim G. Mitchell, A.B.J., Assistant Editor
H. L. Moreland, Jr., B.S.A., Asst. Editor
ENTOMOLOGY
A. N. Ti-ot, Ph.D., Entomologist'
I. C. Ituitert, Ph.D., Associate
H. E. BIrntley, M.S.A., Assistant
F. A. Robinson, M.S., Asst. Apiculturist
R. E. Waites. Ph.D., Asst. Entomologist
S. H. Kerr. Ph.D., Asst. Entomologist
J. R. Christie, Ph.D., Nematologist

IIOME ECONOMICS
Ouida D. Abbott, Ph.D., Home Econ.'
R. B. French, Ph.D., Biochemist
HORTICULTURE
G. H. Blaclmon, M.S.A., Horticulturist 4'
R. A. Dennison, Ph.D., Hort. & Interim Head
F. S. Jamison, Ph.D., Horticulturist'
Albert P. Lorz, Ph.D., Horticulturist
R. K. Showalter, M.S., Asso. Hort.
R. H. Sharpe, M.S., Asso. Horticulturist
V. F. Nettles, Ph.D., Asso. Horticulturist
F. S. Lagasse, Ph.D., Horticulturist2
R. D. Dickey, M.S.A., Asso. Hurt.
L. H. Halsey, M.S.A., Asst. Hort.
C. B. Hall, Ph.D., Asst. Horticulturist
Austin Griffiths, Jr., B.S., Asst. Hort.
S. E. McFadden, Jr., Ph.D., Asst. Hort.
C. H. VanMiddelem, Ph.D., Asst. Biochemist
B. D. Thompson, M.S.A., Interim Asst. Hort.
M. W. Hoover, M.S.A., Asst. Hort.
LIBRARY
Ida Keeling Cresap, Librarian
PLANT PATHOLOGY
W. B. Tisdale, Ph.D., Plant Pathologist '
Phares Decker, Ph.D., Plant Pathologist
Erdman West, M.S., Botanist & Mycologist'
Robert W. Earhart, Ph.D., Plant Path.2
Howard N. Miller, Ph.D., Asso. Plant Path.
Lillian E. Arnold, M.S., Asso. Botanist
C. W. Anderson, Ph.D., Asst. Plant Path.

POULTRY HUSBANDRY
N. R. Mehrhof, M.Agr., Poultry Husb.1''
J. C. Driggers, Ph.D., Asso. Poultry Hush."
SOILS
F. B. Smith, Ph.D., Microbiologist1
Gaylord M. Volk, Ph.D., Soils Chemist
J. R. Neller, Ph.D., Soils Chemist
Nathan Gammon, Jr., Ph.D., Soils Chemist
Ralph G. Leighty, B.S., Asst. Soil Surveyor
G. D. Thornton, Ph.D., Microbiologist
0. F. Eno, Ph.D., Asst. Soils Microbiologist
H. W. Winsor, B.S.A., Assistant Chemist
R. E. Caldwell, M.S.A., Asst. Chemists'
V. W. Carlisle, M.S., Asst. Soil Surveyor
J. H. Walker, M.S.A., Asst. Soil Surveyor
William K. Robertson, Ph.D., Asst. Chemist
0. E. Cruz, B.S.A., Asst. Soil Surveyor
W. G. Blue, Ph.D., Asst. Biochemist
J. G. A. Fiskel, Ph.D., Asst. Biochemist
L. C. Hammond, Ph.D., Asst. Soil Physicist
H. L. Breland, Ph.D., Asst. Soils Chem.
W. L. Pritchett, Ph.D., Soil Technologist
VETERINARY SCIENCE
D. A. Sanders, D.V.M., Veterinarian 'a
M. W. Emmel, D.V.M., Veterinarian 8
C. F. Simpson, D.V.M., Asso. Veterinarian
L. E. Swanson, D.V.M., Parasitologist
W. R. Dennis, D.V.M., Asst. Parasitologist
E. W. Swarthout, D.V.M., Asso. Poultry
Pathologist (Dade City)
M. Ristic, D.V.M., Associate Pathologist
J. G. Wadsworth, D.V.M., Asst. Poul. Path.









BRANCH STATIONS

NORTH FLORIDA STATION, QUINCY
W. C. Rhoades, M.S., Entomologist in Charge
R. R. Kincaid, Ph.D., Plant Pathologist
L. G. Thompson, Jr., Ph.D., Soils Chemist
W. H. Chapman, M.S., Agronomist
Frank S. Baker, Jr., B.S., Asst. An. Husb.
Frank E. Guthrie, Ph.D., Asst. Entomologist
Mobile Unit, Monticello
R. W. Wallace, B.S., Associate Agronomist
Mobile Unit, Marianna
R. W. Lipscomb, M.S., Associate Agronomist
Mobile Unit, Pensacola
R. L. Smith, M.S., Associate Agronomist
Motile Unit, Chipley
J. B. White, B.S.A., Associate Agronomist


CITRUS STATION, LAKE ALFRED

A. F. Camp, Ph.D., Vice-Director in Charge
W. L. Thompson, B.S., Enlomnlogist
R. F. Suit, Ph.D., Plant Pathologist
E. P. Ducharme, Ph.D., Asso. Plant Path.
J. W. Sites, Ph.D., Horticulturist
H. O. Sterling, B.S., Asst. Horticulturist
H. J. Reitz, Ph.D., Horticulturist
Francine Fisher, M.S., Asst. Plant Path.
I. W. Wander, Ph.D., Soils Chemist
J. W. Kesterson, M.S., Asso. Chemist
R. Hendrickson, B.S., Asst. Chemist
Ivan Stewart, Ph.D., Asst. Biochemist
R. W. Olsen, B.S., Biochemist
F. W .Wenzel, Jr., Ph.D., Chemist
Alvin H. Rouse, M.S., Asso. Chemist
H. W. Ford, Ph.D., Asst. Horticulturist
L. C. Knorr, Ph.D., Asso. Histologist
R. M. Pratt, Ph.D., Asso. Ent.-Pathologist
W. A. Simanton, Ph.D., Entomologist
E. J. Deszyck, Ph.D., Asso. Horticulturist
C. D'. Leonard, Ph.D., Asso. Horticulturist
W. T. Long, M.S., Asst. Horticulturist
M. H. Muma, Ph.D., Asso. Entomologist
F. J. Reynolds, Ph.D., Asso. Hort.
R. B. Johnson, Ph.D., Asst. Entomologist
W. F. Newhall, Ph.D., Asst. Biochemist
W. F. Grierson-Jackson, Ph.D., Asst. Chem.
Roger Patrick, Ph.D., Bacteriologist
M. F. Oberbacher, Ph.D., Asst. Plant Physiol.
R. C. J. Koo, Ph.D., Asst. Biochemist
J. R. Kuykendall, Ph.D., Asst. Horticulturist
W. C. Price, Ph.D., Virologist
J. J. McBride, Jr., Ph.D., Assistant Chemist
D. S. Prosser, Jr., B.S., Asst. Engineer


EVERGLADES STATION, BELLE GLADE
W. T. Forsee, Jr., Ph.D., Chemist in Charge
R. V. Allison, Ph.D., Fiber Technologist
Thomas Bregger, Ph.D., Physiologist
J. W. Randolph, M.S., Agricultural Engr.
R. W. Kidder, M.S., Asso. Animal Husb.
C. C. Seale, Associate Agronomist
N. C. Hayslip, B.S.A. Asso. Entomologist
E. A. Wolf, M.S., Asst. Horticulturist
W. H. Thames, M.S., Asst. Entomologist
W. G. Genung, M.S., Asst. Entomologist
Robert J. Allen, Ph.D., Asst. Agronomist
V. E. Green, Ph.D., Asst. Agronomist
V. L. Guzman, Ph.D., Asst. Hort.
J. C. Stephens, B.S., Drainage Engineer
A. E. Kretschmer, Jr., Ph.D., Asst. Soils
Chem.
Charles T. Ozaki, Ph.D., Asst. Chemist
Thomas L. Meade, Ph.D., Asst. An. Nutri.
1. S. Harrison. M.S., Asst. Agri. Engr.
F. T. Boyd, Ph.D., Asso. Agronomist
M. G. Hamilton. Ph.D., Asst. Horticulturist
J. N. Simons, Ph.D., Asst. Virologist


D. W. Beardsley, M.S., Asst. Animal Husb.
R. S. Cox, Ph.D., Asso. Plant Pathologist
Donald M. Coe, Ph.D., Asst. Plant Pathologist

SUB-TROPICAL STATION, HOMESTEAD
Geo. D. Ruehle, Ph.D., Vice-Dir. in Charge
D. O. Wolfenbarger, Ph.D., Entomologist
Francis B. Lincoln, Ph.D., Horticulturist
Robert A. Conover, Ph.D., Plant Path.
John L. Malcolm, Ph.D., Asso. Soils Chemist
R. W. Harkness, Ph.D., Asst. Chemist
R. Bruce Ledin, Ph.D., Asst. Hort.
J. C. Noonan, M.S., Asst. Hort.
M. H. Gallatin, B.S., Soil Conservationist
T. W. Young, Ph.D., Asso. Horticulturist

WEST CENTRAL FLORIDA STATION,
BROOKSVILLE
Marian W. Hazen, M.S., Animal Husband-
man in Charge

RANGE CATTLE STATION, ONA
W. G. Kirk, Ph.D., Vice-Director in Charge
E. M. Hodges. Ph.D., Agronomist
D. W. Jones, M.S., Asst. Soil Technologist

CENTRAL FLORIDA STATION, SANFORD
R. W. Ruprecht, Ph.D., Vice-Dir. in Charge
J. W. Wilson. ScD.. Entomologist
P. J. Westgate, Ph.D., Asso. Hort.
Ben F. Whitner, Jr., B.S.A., Asst. Hort.
J. F. Darby, Ph.D., Asst. Plant Path.

WEST FLORIDA STATION, JAY
C. E. Hutton, Ph.D., Vice-Director in Charge
H. W. Lundy, B.S.A., Associate Agronomist
R. L. Jeffers, Ph.D., Asso. Agronomist

SUWANNEE VALLEY STATION,
LIVE OAK
G. E. Ritchey, M.S., Agronomist in Charge
GULF COAST STATION, BRADENTON
E. L. Spencer, Ph.D, Soils Chemist in Charge
E. G. Kelsheimer, Ph.D.. Entomologist
David G. A. Kelbert, Asso. Horticulturist
Robert O. Magie. Ph.D., Plant Pathologist
J. M. Walter, Ph.D., Plant Pathologist
S. S. Woltz, Ph D., Asst. Horticulturist
Donald S. Burgis, M.S.A., Asst. Hort.
C. M. Geraldson, Ph.D.. Asst. Horticulturist
G. Sowell, Jr., Ph.D., Asst. Plant Pathologist


FIELD LABORATORIES

Watermelon, Grape, Pasture-Leesburg
J. M. Crall, Ph.D., Asso. Plant Path. in Chg.
C. C. Helms, Jr., B.S., Asst. Agronomist
L. H. Stover, Assistant in Horticulture
Strawberry-Plant City
A. N. Brooks, Ph.D., Plant Pathologist
Vegetables-Hastings
A. H. Eddins, Ph.D., Plant Path. in Charge
E. N. McCubbin, Ph.D., Horticulturist
T. M. Dobrovsky, Ph.D., Asst. Entomologist
D. L. Myhre, Ph.D., Asst. Soils Chemist
Pecans-Monticello
A. M. Phillips, B.S., Asso. Entomologist
John R. Large, M.S., Asso. Plant Path.
Frost Forecasting-Lakeland
Warren O. Johnson, B.S., Meteorologist in
Charge 2
1 Head of Department
2 In cooperation with U. S.
3 Cooperative, other divisions, U. of F.
4 On leave


















CONTENTS


PAGE


INTRODUCTION ... -----... ..... ..... .... .. ....


REVIEW OF LITERATURE ................ -....-..-.. ....


PHYSICAL AND CHEMICAL CHARACTERISTICS ............


EXPERIMENTAL PROCEDURE ..........- ..........-


Varieties Investigated ...... .. .... ..... ...

Method of Sampling ............... ...........


M ethod of Analysis ............-.............

EXPERIMENTAL RESULTS AND DISCUSSION ..............


Study of Oranges .............. .. ........... ..


Hesperidin Content of Whole Oranges ...........


Hesperidin Content of Juice ...... .....

Distribution of Hesperidin .......... .......


Study of Other Citrus Varieties .......... ...

Glucoside Content of the Other Varieties .........


Glucoside Content of the Juice ..... .....


Distribution of Glucoside ......... ......


Component Parts of the Citrus Varieties Studied

POSSIBLE UTILIZATION OF HESPERIDIN ............. .


SUM M ARY ........ ...... .......-- ........... ..


LITERATURE CITED -.... .... ...... .. .......

A PPENDIX ...... .. ....... .. .......... .


.-. .....----. --.... 5


---- ---------- 6


------ -- ---- 8


.................. 12


...................... 12



.....- ............... 13


......-.....-.. ...... 13




................... 13


..........-..-...... 20
. ...--..--.-.- .....-.. 13







..................... 20
..................... 20


.- ---- -- 22


..................... 22


...-..... ..... 22


..... -.... 22


.. 30

...-- 30


.. .. ...-- 31


................- 32

S......... 35








Hesperidin, the Principal Glucoside
of Oranges

Occurrence, Properties and Possible Utilization
R. HENDRICKSON 1 and J. W. KESTERSON 2

INTRODUCTION

In addition to the more familiar components of citrus there
is a class of compounds called flavanone glucosides. Recognition
of their biological importance has increased considerably in re-
cent years. These glucosides occur only in small quantities, but
are found widely distributed in nature. Among those found in
citrus are hesperidin, naringin, aurantamarin, ponciridin, tan-
geretin, and eriodictin which are found respectively in sweet
orange, grapefruit, sour orange, trifoliate orange, tangerine, and
lemon. In sweet orange and lemon, both hesperidin and erio-
dictin are found, with hesperidin predominating. Hesperidin
has been found also in the leaves, twigs and bark of citrus trees,
as well as in such plant families as the Umbelliferae, Rutaceae,
Labiatae, Lobeliaceae, and Compositae (15).3 It is now estab-
lished that the glucosides are synthesized from carbohydrates,
the reaction being favored by low temperature, light and access
to oxygen (35). Although very little is known about the func-
tion of these compounds, it has been postulated by Hall (12)
that hesperidin, and perhaps other glucosides, serve as a medium
for the translocation of glucose synthesized in the chlorophyllous
tissue. He further believed the hesperidin to be combined with
glucose, forming a soluble, easily hydrolyzable compound that
can be temporarily withdrawn from metabolism until brought
to that portion of the plant where it is to be stored or utilized.
Much attention was aroused in 1936 (34, 39) by an extract
isolated from lemon that was found to improve the capillary
fragility of ailing blood vessels. Though named "citrin", it came
to be widely recognized as vitamin P, and has since been shown
to be primarily a mixture of hesperidin and eriodictin, a methy-
lated isomer. Administered orally, it has been used for vascular
purpura, angioneurotic edema, radiation hemorrhage, nephritis,
and psoriasis (29). Besides the above uses, the authors have

1Assistant Chemist, Citrus Experiment Station, Lake Alfred, Florida.
2Associate Chemist, Citrus Experiment Station, Lake Alfred, Florida.
Figures in parentheses (Italic) refer to Literature Cited.





Florida Agricultural Experiment Stations


demonstrated hesperidin to be an excellent intermediate for the
production of light-fast azo dyes in a wide range of colors. These
and other developments have led to the conviction that hesperidin
is a new citrus by-product of considerable potential value.
Methods of recovery have been available for a number of years.
Much additional information, however, is needed concerning the
quantity of hesperidin in oranges, and how the recovery of this
chemical can be tied in with the present practices of handling
and processing citrus.
The principal purpose of this investigation, therefore, was
to determine the distribution and variation of hesperidin in
oranges from the one-half inch size to full maturity. A similar
study of the glucoside content of lemons, limes, tangelos, and
tangerines was conducted and is also included.

REVIEW OF LITERATURE
Lebreton (25) in 1828 first noticed a crystalline substance
when he filtered a macerated tincture of oranges. This crystal-
line substance was found in members of the family Hesperides,
thus it was given the name hesperidin. He proved this com-
pound to be a natural constituent of oranges. It was not until
1876, however, that Hilger (20) and Hoffman (21) recognized
this material as a glucoside. Hesperidin was found in lemons
by Pheffer (32) as early as 1874, in citrons by Penzig, 1887,
and has been found in numerous other plants since then. Tri-
foliate orange, according to Webber and Batchelor (43), con-
tains a glucoside called ponciridin which was first discovered by
Penzig in 1887 (43). Sour oranges, on the other hand, contain
three glucosides, the predominant one being aurantamarin, ac-
cording to Tanret (40). Previous mention has been made of
hesperidin being present in citrons, while pummelo and grape-
fruit are distinguished by being the only fruit to contain narin-
gin (22). From tangerine peel, a pentamethyl flavanol was
isolated by Nelson (30) and was reported as the first instance
of a fully methylated flavanol occurring in nature. This product
was named tangeretin, and was found to crystallize from ethyl
acetate as white needles melting at 1540 C. It could not be
isolated from the tangelo, which is a cross between grapefruit
and tangerine. Tangeretin is isomeric with pentamethyl querci-
trin. Further reference to the glucosides of citrus can be found
in Braverman (7) and Webber and Batchelor (43).






Hesperidin, the Principal Glucoside of Oranges


In studying the glucoside content of oranges and other varie-
ties of citrus, it is necessary to realize that hesperidin is the
predominant but not the only glucoside of sweet oranges. The
attention given to "citrin" extracts established the predominant
glucoside of lemons to be hesperidin, with smaller quantities of
eriodictin present as in sweet orange (39). Bruckner and
Szent-Gyorgyi (8) thought that eriodictin was formed from hes-
peridin by demethylation during ripening. They reported that
unripe oranges contain large amounts of hesperidin but little
eriodictin. Later, eriodictin was found in high concentration
in the ripe fruit. The hesperidin content of Washington navel
orange peel was reported by Harvey and Rygg (13) as respec-
tively higher in the albedo and blossom end than in the flavedo
and stem end of the fruit. They further found a seasonal de-
crease in the hesperidin content of the dried peel, which analyzed
3.6 percent in November and 2.0 percent in April. In storage,
however, there was almost a 50 percent increase in hesperidin
after 46 days, with the largest increase occurring at the higher
storage temperature. According to Scarborough (35), Iwasaki
found 5.7 percent hesperidin in the dried peel of Mandarin
oranges, 1.1 percent in dried endocarp and only traces in the
juice. Davis (10) whose method of analysis was used by the
authors, found 0.12 percent hesperidin in California Valencia
orange juice, 1.6 percent in the albedo, 1.5 percent in the section
membrane, 1.0 percent in the flavedo, and 4.5 percent in the
core. The similar figures for California lemon, also on a fresh-
weight basis, were 0.05 percent in the juice, 3.0 percent in the
albedo, 1.9 percent in the section membrane, and 2.5 percent in
the flavedo.
In the past eight years many patents have been granted for
the recovery, purification and preparation of derivatives of hes-
peridin. Higby (19) was granted a patent on recovery that
involved an alkaline extraction of orange peel using both lime
and caustic followed by an acid crystallization. The hesperidin
was repurified by precipitation of the impurities from an alka-
line solution which was subsequently treated with isopropyl alco-
hol. This method was also the basis for a general patent on the
recovery of any flavanone glucoside (18). Another patent was
granted Higby (17) on a modification of his hesperidin recovery
method wherein the acidified extracting liquor was heated with
diatomaceous earth to hasten crystallization. The hesperidin
was subsequently dissolved and recrystallized. The specifica-
tion further described a method of repurifying hesperidin using






Florida Agricultural Experiment Stations


pyridine. An improved recovery process that uses only lime
and avoids one filtration by utilizing the chopped orange peel
as its own filter bed was granted to Baier (5). A patent was
granted to Lautenschlager and Lindner (24) in 1944 on a process
for purifying flavanone glucosides with special attention to
"citrin". The method depends on two solvents-methyl benzoate
to dissolve and remove ballast material, followed by ethyl acetate
to dissolve and concentrate the active "citrin." Because of the
low water solubility of hesperidin, an attempt was made by some
to make a water-soluble, acid-stable, physiologically-active de-
rivative. Relative to this, Wilson (44) was granted a patent
for his method of preparing alkylated hesperidin chalcone deriva-
tives, as was Ohta (31) for his process of making carbalkoxylate
derivatives of hesperidin.


PHYSICAL AND CHEMICAL CHARACTERISTICS

The physical properties of hesperidin resemble those of narin-
gin (22) by virtue of their similarity in chemical structure.
Unlike narigin, however, it is tasteless and is very insoluble in
hot water or common solvents. It is only sparingly soluble in
alcohol or glacial acetic acid. Hesperidin is considerably more
soluble in pyridine and dimethyl formamide, as shown in Table 1.
Hesperidin chalcone, which exists in basic conditions, is very
soluble in alkalis and precipitates as a yellow amorphous mass

TABLE I.-SOLUBILITY OF HESPERIDIN IN VARIOUS SOLVENTS.


Solvent


Water .....................................
Water ..............-..---. ..-
Water .....................--...........
Water .............................
Ammonium hydroxide 0.8 EI
Benzene ......................-....
A cetone ...............................
Carbon tetrachloride ........
Carbon disulfide ..................
Ethylene dichloride ..........
Ethyl acetate ........-- ......--- ..--
Ethyl alcohol ....................
Methyl alcohol -..............-
Isopropyl alcohol ........--.....
Isophorone ....................
Dimethyl formamide ........
Ethyl hexylamine .............
Trimethyl cyclohexanol .....


Temp. oC. Gms./100 M1.


7 0.0017
21 0.0019
65 0.0045
79 0.0076
29 0.19
80 0.006
56 0.03
76 0.007
46 0.04
83 0.008
77 0.015
78 0.14
25 0.28
82 0.06
30 3.7
22 25.0
30 2.4
30 2.1


-----------------


------------
............
------------- --- ...
---------------------
-1 -----------
..............
---------------
-------------- -------

......................


- . .






Hesperidin, the Principal Glucoside of Oranges


when neutralized at a low temperature. Much like narigin, hes-
peridin crystallizes as needles in a rosette pattern from dilute
acetic acid (Fig. 1).
















I-
'~ *1 ,' ,


Fig. 2.-Demonstration of the location of hesperidin in an orange by
addition of ferric chloride to the cut surface.

Hesperidin shows a color reaction with ferric chloride, pro-
ducing in great dilution a wine red color. Higher concentrations
of the glucoside produce an almost black color, which can be
used pictorially to show its physical location in oranges, as illus-
trated in Fig. 2. The yellow color that develops when sodium
hydroxide is added to a hesperidin solution is the basis of the
Davis method of analysis (10) used in this study. This method
was almost four times less sensitive to hesperidin than to narin-






Florida Agricultural Experiment Stations


gin. Unlike naringin, hesperidin solutions did not increase in
viscosity in the presence of alkali and di- or tri-valent cations
(22), even at higher concentrations.
The structure of hesperidin has been thoroughly investigated
over the past 50 years and has been proven by its complete syn-
thesis. It has the formula C8sHS301, mol. wt. 610.6. It is also
called hesperitin-l-rhamnosido-d-glucoside (29), and can be
hydrolyzed with dilute mineral acids to one mole each of hes-
peritin, glucose, and rhamnose (3). Hesperitin was synthesized
by Shinoda and Kawagoye (36) in 1928, yet its structure had
been established earlier by Tutin (41), who had made a com-
parative study of hesperitin, eriodictyol, and homoeriodictyol.
It has been found to crystallize in plates, melting at 2270 C., and
to give phloroglucinol and hesperitic acid (M.P. = 2280 C.) upon
decomposition. King and Robertson (23) determined the posi-
tion of the sugar molecule on hesperidin, but it was not until
1943 that Zemplen and Bognar (45) succeeded in synthesizing
it. This they accomplished by combining and later saponifying
hesperitin with acetobrom-rutinose in the presence of chinolin
and silver oxide. A synthetic hesperidin was produced which
had a melting point of 256-80 C. as compared to 261-2' C. for
pure hesperidin. Its specific rotation was also similar to that
of natural hesperidin, ( ) 1s = -75.00 in pyridine. Further-
D -
more, the octo-acetyl hesperidin derivative was formed and was
found to agree with the expected melting point of 175-60 C. In
1946 Pritchett and Merchant (33) showed that hesperidin could
be purified with formamide. They produced hesperidin with a
melting point of 261-30 C., which is in agreement with the high-
est previously recorded melting point.
In 1942 Wawra and Webb (42) announced that hesperidin
existed in equilibrium with its chalcone, which is the naturally
occurring compound, and that the equilibrium could be shifted
by changing the pH of the medium. The chalcone form was
favored in an alkaline medium. When crystallized, it formed
bright yellow crystals melting at from 2430 C. to 2570 C., depend-
ing on time of alkali contact, pH of precipitation, and exposure to
oxidation (16). This is in contrast to the colorless hesperidin
crystal melting at 261-2 C. The chalcone was shown to have a
characteristic colorimetric ultraviolet adsorption and was be-
lieved to be combined with a protein forming an enzyme that
acted as a hydrogen transporter in mammalian tissue. The
structural formula for hesperidin and its chalcone follows:







Hesperidin, the Principal Glucoside of Oranges


O OH
Cr H QH
0 H-C-O H.C 1 OCH
H C-0H HO-bH
C-H 0 H-C-OH 0 c" )
C-H3 .Hz OH \

(Rhamnose) (Glucose) (Hesperitin)
Sugar-O OH
HE5PERIDIN
C-CH=CH
011o 0
HESPERIDIN OH
CHALCONE
OCH3

The various attempts to make physiologically active deriva-
tives of hesperidin stem from the earlier mentioned discovery
of "citrin" or vitamin P. There still exists, however, some
controversy as to whether it can properly be classified as a
vitamin, since many of the more recent tests have employed
doses of a size that suggests a pharmacological action rather
than that of a vitamin (35). The chemical nature and physio-
logical activity of "citrin" and analagous compounds have been
extensively reviewed by Scarborough (35) and Sokoloff (37, 38).
The American Society of Biological Chemists and the American
Institute of Nutrition recently recommended that the term "vita-
min P" should no longer be employed (9). Much of the un-
certainty has arisen from the difficulty of assaying extracts
against "citrin", which is a mixture of flavanones crystallizing
as a complex. Its isolation depends on precipitation by lead
salts in neutral solution and by alkali in anhydrous alcoholic
solution. Extracts are assayed biologically by the curative ac-
tion on capillary fragility of guinea pigs receiving a special diet.
There are, however, numerous chemical methods for determining
"citrin" activity of extracts, such as: quantity of red color pro-
duced by treating "citrin" solutions with potassium hydroxide
(26), quantity of violet color formed by treating alcoholic ex-
tracts with hydrochloric acid and magnesium shavings (1),
quantity of brownish-red color from silver lactate purified ex-
tracts to which sodium cyanide and carbonate are added (2),
and other methods. The uniformity of results by the various






Florida Agricultural Experiment Stations


methods has not been conclusive, but biological assay seems to
be the most reliable.

EXPERIMENTAL PROCEDURE

Varieties Investigated.-The following varieties of oranges
were tested for their hesperidin content: Hamlin, Parson
Brown, Pineapple, and Valencia. Also included in this glucoside
study were the following other varieties: Meyer lemon, Tahiti
(Persian) lime, Dancy tangerine, Orlando tangelo, and Temple
orange. Because Temple is considered to be a hybrid, it was
not grouped with the other orange varieties.
This study of the glucoside content of oranges and the other
varieties of citrus mentioned was mainly concerned with hes-
peridin, the predominant glucoside of oranges and lemons. Be-
cause adequate information is not available concerning the other
glucosides, it has been found necessary by previous investigators
as well as by the authors to analyze these varieties as though
their glucosides were entirely hesperidin.
Method of Sampling.-Each sample totaled 16 fruits and was
made up of one fruit picked at random from 16 positions on
the tree. These positions were top inside, top outside, bottom
inside and bottom outside on the north, south, east and west
exposures. The trees used for this study were located on the
premises of the Florida Citrus Experiment Station at Lake Al-
fred, received uniform fertilizer and spray practices, and were
all on rough lemon rootstock.
Method of Analysis.-The samples were analyzed on a whole-
fruit basis or separated into the component parts: juice, rag
and pulp, flavedo, and albedo, depending on whether the fruits
were mature enough to give a moderate juice yield. After the
average diameter and weight of the whole fruit was determined,
it was coarsely ground in a Universal food chopper. The ground
sample was thoroughly mixed and a 100-gram representative
sample weighed directly into a Waring blendor. The peel was
further comminuted in the blender with 100-150 ml. of 95 per-
cent alcohol which facilitated the grinding and extraction. One
minute of grinding was usually more than sufficient to comminute
it to a fine uniform mass which was then washed into a beaker
with 95 percent ethyl alcohol to give a total volume of 500 ml.,
including the previous 100-150 ml. The finely chopped peel was
allowed to soak in alcohol for at least 16 hours with occasional
stirring. If necessary the sample could be conveniently held at





Hesperidin, the Principal Glucoside of Oranges


this point until time permitted the extraction to be completed.
The alcoholic extract was separated from the chopped peel by
squeezing the mixture in a cheescloth bag using a hand press.
The pressed peel was further extracted by adding 500 ml. of
water and 1 gram of dry C.P. calcium oxide. This was well
mixed and allowed to stand two hours; then drained and squeezed
out in similar fashion to the alcohol extraction. A third extrac-
tion was carried out by adding 500 ml. of water to the pressed
peel and heating to 950 C. immediately. After cooling and stand-
ing for two hours, it was drained and pressed. The three por-
tions of extracting liquor were combined, made to exactly 1,500
ml. and an aliquot was diluted for analytical purposes.
When other than whole fruit was analyzed, the procedure was
to separate it into albedo, flavedo, juice, seeds, rag and pulp.
The colored flavedo was first separated by means of a potato
peeler, after which it was halved and juiced with a hand juice
press that folded and squeezed a half fruit. The seeds were
manually separated and the rag and pulp pulled apart from the
albedo. Each of the separated portions was weighed, com-
minuted and then analyzed by the procedure used for whole fruit.
The juice was strained and analyzed directly.
The extracts were analyzed for hesperidin by the Davis method
(10) with the following modifications. One-half ml. of extract
was added to 24 ml. of 90 percent diethylene glycol and the in-
crease in color caused by adding 0.5 ml. of approximately 4 N
sodium hydroxide was read after 30 minutes. Comparison was
made against a standard curve that was prepared using a Fisher
electrophotometer with a 425 mu filter. All readings were made
at approximately 250 C.

EXPERIMENTAL RESULTS AND DISCUSSION
STUDY OF ORANGES
Hesperidin Content of Whole Oranges.-In this study of the
glucoside content of Hamlin, Parson Brown, Pineapple, and Va-
lencia oranges, the physical dimensions, wet and dry weight
of the fruit, and the total hesperidin content were recorded
(Tables 2 through 5). As with grapefruit (22), oranges were
found to increase in total quantity of glucoside per fruit until
the fruit reached an equatorial diameter of 1.8 to 2.0 inches.
Beyond this size there was practically no increase in hesperidin
content per fruit. Due to the increase in size and weight of
fruit, however, the percent hesperidin decreased, as shown in






Florida Agricultural Experiment Stations


Fig. 3. The change in percent hesperidin on a dry and wet basis
in Pineapple oranges, which was similar to that for other va-
rieties, approximated a normal growth curve. The noticeably
higher concentration of hesperidin in small fruit seemed to indi-
cate that glucosides may have considerable physiological im-
portance in the plant. Inasmuch as 35 percent of the dry weight

100
80- PINEAPPLE ORANGE
60


o Whole Fruit
* Dry Weight


0.4


I I I I I I I I I I I


A M J J A S O ND J F M A
1951-52 SEASON
Fig. 3.-Hesperidin content of Pineapple orange on a dry and
whole-fruit basis.


I I I I I | I I I t i I


"'''







Hesperidin, the Principal Glucoside of Oranges


of a one-half inch fruit is hesperidin, it does not seem possible
that it could be only a metabolic end product. Wawra and Webb
(42), who found that the hesperidin chalcone combined with a
protein and could serve as a hydrogen transporter in mammalian
tissue, believed that it could also have an important part in
tissue respiration of plants.
A graph of the total hesperidin content for the different va-
rieties of oranges shows Pineapple to have the highest content
(Fig. 4).
1.6r


1951-52 SEASON
Fig. 4.-Hesperidin content of four varieties of oranges throughout the
season on a per-fruit basis.










TABLE 2.-MONTHLY VARIATION IN WHOLE FRUIT, JUICE AND GLUCOSIDE CONTENT OF
HAMLIN ORANGE.*


Whole Fruit


Wet Dry
Diameter Weight Weight
Inches Gms. Gms.

0.49 1.2 0.35

1.5 26 5

1.8 51 9

2.2 93 15

2.5 132 19

2.6 158 20

2.8 188 25

2.8 196 27

2.9 202 29

3.0 236 37

3.0 219 34

2.9 206 33


Glucoside
Content
Gms.

0.1

0.7

0.9

1.0

0.8

0.8

0.8

0.8

0.8

1.1

0.9

0.9


oBrix









8.4

8.0

8.8

9.5

10.0

10.6

11.3

11.7


Juice


Glucoside
Acid Content
% % by Vol.








1.8 0.025

1.3 0.034

0.9 0.030

0.9 0.027

0.8 0.029

0.7 0.033

0.7 0.032

0.8 0.044


Distribution of Gluocoside--%

Juice Albedo Flavedo Rag
and Pulp








1.7 39.7 19.6 39.0
---- ----


1.7 39.7 19.6 39.0


Date

4-18-52

6-1-51

7-1-51

8-1-51

9-1-51

10-1-51

11-1-51

12-1-51

1-1-52

2-1-52

3-1-52

4-1-52


*Average values for 16 fruit.


2.9 37.1 21.9

3.1 38.5 19.4

3.0 41.1 20.2

2.9 43.8 17.5

3.0 45.9 17.9

3.0 48.3 15.7

3.7 45.0 15.0






TABLE 3.-MONTHLY VARIATION IN WHOLE FRUIT, JUICE AND GLUCOSIDE CONTENT OF
PARSON BROWN ORANGE.*


Whole Fruit


Juice


II FJ--- ---___ ____


Wet Dry
Diameter Weight Weight
Date Inches Gms. Gms.


4-18-52 0.50

6-1-51 1.5

7-1-51 1.9

8-1-51 2.4

9-1-51 2.6

10-1-51 2.8

11-1-51 2.9

12-1-51 3.0

1-1-52 3.0

2-1-52 3.1

3-1-52 3.1

4-1-52 3.2


1.3

26

58

101

142

186

214

215

252

252

243

260


Glucoside
Content
Gms.


"Brix


0.36

7

12

18

21

26

31

35

40

42

41

42


Glucoside
Acid Content
%/ % bv Vol.


0.025

0.027

0.027

0.025

0.028

0.031

0.031

0.058


Distribution of Gluocoside-%


Juice Albedo Flavedo Rag
and Pulp


17.5

17.9

16.4

20.9

13.2

15.6

12.2

12.7


* Average values for 16 fruit.


. . '


. .


8.3

7.9

8.8

10.4

10.0

11.0

11.2

11.0










TABLE 4.-MONTHLY VARIATION IN WHOLE FRUIT, JUICE AND GLUCOSIDE CONTENT OF
PINEAPPLE ORANGE.*


Whole Fruit


ii

1

1I


Wet
Diameter Weight
Date Inches Gms.

4-18-52 0.54 1.5

6-1-51 1.4 22

7-1-51 2.1 66

B-1-51 2.4 104

9-1-51 2.6 144

0-1-51 2.8 186

1-1-51 3.1 245

2-1-51 3.2 263

1-1-52 3.2 270

2-1-52 3.3 288

3-1-52 3.2 275

4-1-52 3.1 255

Average values for 16 fruit.


Juice


Brix


Glucoside
Acid Content
% % by Vol.


Dry Glucoside
Weight Content
Gms. Gms.

0.40 0.1

6 0.8

13 1.3

18 1.3

23 0.8

26 0.9

37 1.1

43 1.1

46 1.1

50 1.3

49 1.1

46 1.1


Distribution of Gluocoside-%


Juice Albedo Flavedo Rag
and Pulp


1.5

2.4

2.4

2.1

3.2

3.2

S 3.2

3.1


35.4

39.8

38.8

35.7

42.4

41.8

38.0

47.3


" "


0.025

0.027

0.024

0.020

0.028

0.031

0.029

0.032






TABLE 5.-MONTHLY VARIATION IN WHOLE FRUIT, JUICE AND GLUCOSIDE CONTENT OF
VALENCIA ORANGE.*


__Wh
Wet
Diameter Weighi
Date Inches Gms.

4-28-52 0.50 1.2

6-1-51 1.4 23

7-1-51 1.9 51

8-1-51 2.1 77

9-1-51 2.5 124

10-1-51 2.7 145

11-1-51 2.9 189

12-1-51 3.1 231

1-1-52 2.9 218

2-1-52 3.1 254

3-1-52 3.0 240

4-1-52 3.1 250

5-1-52 3.0 223

Average values for 16 fruit.


ole Fruit


t


ide
nt


SJuice


o


Dry Glucos
Weight Conte
Gms. Gms

0.39 0.1

6 0.7

11 1.0

14 1.0

20 0.8

21 0.7

27 0.8

35 0.9

33 1.0

39 1.0

37 1.0

40 1.0

37 1.0


Brix Acid
%








7.8 3.2

7.5 2.8

7.9 2.1

8.7 1.6

9.7 1.4

9.5 1.1

10.4 1.1

10.7 1.0

11.2 0.9


Distribution of Gluocoside-%
Glucoside i
Content Juice Albedo Flavedo Rag
% by Vol. ___and Pulp 'r


-q
.-- - - -





0.022 1.4 33.0 23.2 42.4

0.025 2.4 37.9 20.0 39.7

0.019 1.9 30.2 18.2 49.7

0.015 1.8 33.6 22.3 42.3 I

0.018 2.0 38.1 18.4 41.5

0.019 2.6 29.8 19.1 48.5

0.019 | 2.3 32.1 18.1 47.5
II
0.024 2.9 30.1 18.6 48.4

0.053 6.3 27.0 22.5 44.2





Florida Agricultural Experiment Stations


Hesperidin Content of Juice.-Anticipating that the hesperidin
content of orange juice would in some way correlate with the
maturity of the fruit, the degree Brix, percent acid, and percent
hesperidin by volume in juice were determined. These data are
presented in Tables 2 through 5. Degree Brix was determined
by refractometer at 28 C. and percent anhydrous citric acid by
titration with standard alkali in accordance with methods of
the citrus industry.
Since previous work by Maurer et al. (28) showed a significant
relationship between the naringin content of grapefruit and its
maturity, a similar relationship for oranges was expected. In-
stead, the percent by volume of hesperidin in juice remained
relatively constant for all varieties throughout the season with
the exception of the last month of analysis, when a slight in-
crease was noted. The percent hesperidin in the juice of the
oranges investigated was found to vary between 0.018 to 0.034
over most of the season. These findings and values were similar
to those for naringin in Florida grapefruit (22).
Distribution of Hesperidin.-It is shown in Tables 2 through
5 that about 75 to 80 percent of the herperidin was concentrated
in the albedo, rag and pulp of oranges. This was in agreement
with Braverman (7), who showed the principal location of the
glucosides to be in the carpellary membrane, at the boundary
between the juice segments and the albedo. Since this was true,
any attempt to obtain a higher juice yield by increased pressure
or deeper burring by juice extractors would increase the hes-
peridin content of the juice (14). Hence, the juice samples were
extracted with a hand juice extractor which required only a
moderate amount of pressure to remove the juice. These samples
were found to contain from 1.5 to 6.0 percent of the total hes-
peridin present. The hesperidin content of juice remained fairly
constant throughout the entire season except for the last sam-
ples, which were taken in April and May. These last samples
were taken from either overly mature or soft Parson Browns
and Valencias and gave a considerably higher concentration of
hesperidin in the juice.
The overall seasonal changes for the distribution of hesperidin
in Pineapple oranges are shown in Fig. 5, and were found to be
similar for the other orange varieties. This illustrated graphic-
ally that picking date was not a variable which influenced the
distribution of the glucoside. The distribution of hesperidin in
the component parts of oranges as the fruits approach and pass






Hesperidin, the Principal Glucoside of Oranges


maturity would, in most cases, be as follows: juice 1.5 to 6.0
percent, albedo 30 to 50 percent, flavedo 12 to 23 percent, rag and
pulp 32 to 50 percent.

100

80- PINEAPPLE ORANGE

-60-



IL



0


I-

0
z

z IO oAlbedo
a Rag 8 Pulp
cj 8- Flavedo
S- oa Juice
(n 6-
w
IL



z
0
I-4




I-
v,)





S 0 N D J F M A
1951-52 SEASON
Fig. 5.-Distribution of hesperidin in the component parts of Pineapple
orange throughout one season.






Florida Agricultural Experiment Stations


STUDY OF OTHER CITRUS VARIETIES
Glucoside Content of the Other Varieties.-As in the hesperidin
study of oranges, the physical dimensions, wet and dry weight
of the fruit, and the total glucoside content of Meyer lemon,
Tahiti lime, Dancy tangerine, Orlando tangelo, and Temple
orange were recorded in Tables 6 through 10. As previously
mentioned, the glucoside content of these fruits was analyzed
as though it were entirely hesperidin. Much like the varieties
of orange, these other citrus varieties tended to have maximum
glucoside per fruit while still very immature, with the excep-
tion of Dancy tangerine, in which the content continued to in-
crease throughout the season. The change in percent glucoside
on dry and wet bases decreased for all varieties and showed
normal growth curves, as was found for oranges. The physio-
logical importance of the glucoside was further emphasized by
the equally high glucoside content found in small fruit of these
varieties.
Analysis of the total glucoside content calculated as hesperidin
for the different varieties studied revealed tangelo to have the
highest content, as shown in Fig. 6. The monthly change in
glucoside content of Temple orange on a per-fruit basis, as shown
in Fig. 6, showed much resemblance to the per-fruit analysis of
the other varieties of oranges shown in Fig. 4.
Glucoside Content of Juice.-The degree Brix and percent acid
in the juice of these other varieties of citrus were found to have
no consistent relationship to glucoside content as was found for
oranges. The percent glucoside in the juice of these varieties
appeared to range higher than the percent found in the varieties
of oranges.
Distribution of Glucoside.-Tables 6 through 10 give the gluco-
side distribution for Meyer lemon, Tahiti lime, Dancy tangerine,
Orlando tangelo, and Temple orange. These data show the major
portion of the glucoside to be located in the albedo, rag, and
pulp. However, there are two exceptions, Tahiti lime and Dancy
tangerine, for which no values are given in the tables. In these
the albedo is not easily recognized and in this study it was
physically impossible to make a separation of this component
in these two varieties. The albedo, rag and pulp of the Meyer
lemon, Orlando tangelo, and Temple orange samples contained
from 70 to 80 percent of the total glucoside of the fruit.
The flavedo of the lemon, tangelo, and Temple orange con-
tained from 15 to 24 percent of the total glucoside present, which












TABLE 6.-MONTHLY VARIATION IN WHOLE FRUIT, JUICE AND GLUCOSIDE CONTENT O
MEYER LEMON.*


Whole Fruit


Wet Dry
Weight Weight
Gms. Gms.


0.69

29

66

102

147

203

235


0.20

5

9

12

18

24

27


Gluceside
Content
Gms.

.06

0.3

0.4

0.3

0.3

0.3

0.4


"Brix


Juice i_


Acid
%


Glucoside
Content
% by Vol.


0.042

0.032

0.022

0.020

0.022


Distribution of


Juice


2.1

3.8

3.3

4.6

4.5


Albedo


28.9

27.2

29.6

28.3


)F


Gluocoside-%

Flavedo Rag
and Pulp






18.4 48.9

20.0 49.5

25.6 40.2 Q

22.6 44.2


c ~


Date

4-28-52

6-1-51

7-1-51

8-1-51

9-1-51

10-1-51

11-1-51


Diameter
Inches

0.36

1.5

1.9

2.2

2.5

2.8

3.0


* Average values for 16 fruit.














TABLE 7.-MONTHLY VARIATION IN WHOLE FRUIT, JUICE AND GLUCOSIDE CONTENT OF
TAHITI LIME.*


8.5 5.6 0.042

8.0 5.6 0.025

7.4 5.7 0.012

7.3 5.6 0.016


2.7 ...

3.0 ... 39.9 57.1

2.3 .. 39.1 58.6

2.4 .... 37.9 59.7


*Average values for 16 fruit.
** Includes both albedo and flavedo.


3-11-52

5-1-51

6-1-51

7-1-51

8-1-51

9-1-51

10-1-51


0.3

0.3








TABLE 8.-MONTHLY VARIATION IN WHOLE FRUIT, JUICE AND GLUCOSIDE CONTENT OF
DANCY TANGERINE.*


Whole Fruit
Date Wet Dry
Diamete Weight Weight
Inches Gms. Gms.

5-27-52 0.50 1.0 0.37

7-1-51 1.3 14 4

8-1-51 1.5 31 6

9-1-51 1.9 56 10

10-1-51 2.1 73 11

11-1-51 2.5 108 15

12-1-51 2.7 135 21

1-1-52 2.8 148 22

2-1-52 2.9 145 26

3-1-52 2.8 132 27

Average values for 16 fruit.
** Includes both albedo and rag and pulp.


Juice
Glucoside Glucoside
Content Brix Acid Content
Gms. r% %b by Vol.

0.1

0.4

0.5

0.3 8.2 5.5 0.025

0.4 7.9 3.6 0.025

0.7 8.7 1.8 0.051

0.7 9.6 1.2 0.058

0.7 10.0 0.9 0.067

0.8 11.8 0.7 0.068

0.7 13.4 0.8 0.090
II


Distribution of Gluocoside-%
Rag
Juice Albedo Flavedo and Pulp







1.5 32.3 66.2

1.9 34.6 63.5

3.4 33.0 63.6

4.4 .... 23.6 72.0

3.9 ... 17.8 78.3

4.0 ... 17.4 78.6

4.1 .. 13.0 82.9










TABLE 9.-MONTHLY VARIATION IN WHOLE FRUIT, JUICE AND GLUCOSIDE CONTENT OF
ORLANDO TANGELO.*


Wh
Wet
Diameter Weight
Date Inches Gms.

5-13-52 0.51 1.4

6-1-51 1.1 14

7-1-51 1.7 41

8-1-51 2.0 71

9-1-51 2.3 110

10-1-51 2.9 183

11-1-51 3.0 212

12-1-51 3.2 257

1-1-52 3.3 280

2-1-52 3.5 308

3-1-52 3.2 252

4-1-52 3.0 223

Average values for 16 fruit.


ole Fruit


Dry
Weight
Gms.

0.49

4

9

14

19

28

32

42

47

56

47

44


Glucmsi
Conte
Gms,

0.2

0.6

1.1

1.3

1.0

1.2

1.2

1.2

1.3

1.5

1.1

1.1


ide
nt


SBrix


Juice


9.0 2.7

8.4 1.7

9.8 1.2

10.9 1.0

11.9 0.8

13.0 0.8

13.7 0.8

14.9 0.8


Glucoside
Content
% by Vol.


0.049

0.048

0.046

0.050

0.056

0.056

0.052

0.064


Distribution of Gluocoside-%


Juice


Albedo Flavedo R
and


33.8

40.2

31.0

36.4

48.4

38.8

39.2

38.6


" "


" "


"


.ag
Pulp









.2.0

6.7

0.3

34.9
!8.0

K6.3
S8.01


"








TABLE 10.-MONTHLY VARIATION IN WHOLE FRUIT, JUICE AND GLUCOSIDE CONTENT OF
TEMPLE ORANGE.*


Whol
Wet
Diameter Weight
Date Inches Gms.

5-13-52 0.55 1.6

6-1-51 1.2 14

7-1-51 1.8 40

8-1-51 2.1 75

9-1-51 2.8 102

10-1-51 2.6 134

11-1-51 2.8 168

12-1-51 2.9 189

1-1-52 3.0 225

2-1-52 3.1 222

3-1-52 2.9 211

4-1-52 3.0 212

Average values for 16 fruit.


.e Fruit


Dry
Weight
Gms.

0.53

4

8

12

17

21

26

31

37

42

41

43


Glucoside
Content
Gms.

0.1

0.5

1.0

1.0

0.7

0.7

0.8

0.9

1.0

1.0

0.9

1.0


Juice


] Distr


e- Fruit


Glucoside
Brix Acid Content
% % by Vol.








8.5 3.8 0.043

8.4 3.2 0.038

9.6 2.2 0.038

10.9 1.9 0.036

11.8 1.4 0.035

13.5 1.3 0.035

14.4 1.4 0.036

15.3 1.3 0.049


Juice









2.6

3.8

3.9

3.5

3.7

3.8

4.2

4.8


ibution of Gluocoside-%

Albedo Flavedo Rag
and Pulp








36.1 17.5 43.8

33.5 23.4 39.3

36.6 21.8 37.7
rC









43.2 19.2 34.1
46.6 17.5 32.2

42.8 20.4 33.0

46.9 15.2 33.7

47.6 14.2 33.4


71-





Florida Agricultural Experiment Stations


a.


0U6-
wI0

U 0.8
0

_j
S0.6


C0.4





0.2



0.0
.M A M J J A S O N D J F M A
1951-52 SEASON
Fig. 6.-Glucoside content of five other varieties of citrus throughout one
season on a per-fruit basis.
parallels the orange varieties studied. The flavedo of the lime,
on the other hand, contained approximately twice this percent-
age of glucoside. The glucoside content of the flavedo remained
fairly constant for each variety throughout the entire season,
with the exception of tangerine.
The data for Orlando tangelo were used to show the overall
changes in the glucoside distribution (Fig. 7). The percent of






Hesperidin, the Principal Glucoside of Oranges


the total glucoside content found in the juice of this variety
gradually increased during the season as it did in the orange
varieties and the other citrus varieties studied.

10Q
ORLANDO TANGELO
80-

60



Lr40

U-
LL
O


Z 20-
z
0
a_
2
0
0
8-




w 6

M 4

0 o Albedo
z / Rag 8 Pulp
0 / Flavedo
m 2 a) Juice
C 2

I-
T)
Q


S 0 N D J F M A
1951-52 SEASON

Fig. 7.-Distribution of glucoside in the component parts of Orlando tangelo
throughout one season.






Florida Agricultural Experiment Stations


COMPONENT PARTS OF THE CITRUS VARIETIES STUDIED
In this investigation it was found necessary to determine the
proportion of each component part making up the whole fruit
and the dry solids content of each component. These data, ob-
tained for several varieties, are included in Tables 11 through
19 and are found in the appendix.

POSSIBLE UTILIZATION OF HESPERIDIN
In 1936 Rusznyak and Szent-Gyorgyi (34) postulated the
existence of a new vitamin, which they called "citrin" or vita-
min P ("P" for permeability), that appeared to exert a vitamin-
like action in correcting increased capillary permeability. Their
early work showed that pure synthetic ascorbic acid was in-
effective in certain pathological conditions characterized by an
increased permeability or fragility of the capillary wall, such
as in cases of purpura sickness, while this condition could readily
be cured by the administration of lemon juice or paprika ex-
tracts. The active substance was found to be a mixture of the
flavanone glucosides, hesperidin and eriodictin. It has been shown
(39) that this vitamin-like substance is present in citrus fruits,
such as lemon, orange and grapefruit. Further research has
indicated, however, that some of the therapeutic activity of
hesperidin was due to the presence of an impurity. Earlier in-
vestigations failed to confirm (11, 46) these findings, but later
studies (4, 6) demonstrated that hesperidin and its derivatives
do affect capillary fragility and permeability. The discrepancies
in results obtained by various investigators must be resolved
by further research, but whatever the explanation of the vitamin-
like activity may be, the fact remains that under certain condi-
tions "citrin" derived from natural sources has a valuable thera-
peutic effect. It seems quite possible, therefore, that the chemi-
cal similarity between hesperidin and the components of "citrin"
will be used to more advantage in the future.
The authors have been successful in producing dyes by using
hesperidin as an intermediate. These particular dyes are acid
azo dyes formed by coupling various diazo solutions into hes-
peridin. This flavanone glucoside appears to be an excellent
dye intermediate having considerable possibilities, and the diazos
of 2-amino-8-naphthol-6-sulfonic acid, 5-nitro-2-aminoanisole, 1-
naphthylamine-4-sulfonic acid, etc., have been coupled with hes-
peridin to form yellow-red dyes that are quite bright and pleas-
ing in color. The application of these water-soluble dyes is






Hesperidin, the Principal Glucoside of Oranges


limited to wool, silk, and leather. However, there has been some
recent interest in these dyes for a newer type wood stain that
has exceptional light-fast properties.
Martin and Beiler (27) found that phosphorylated hesperidin
was an effective antifertility agent. The mechanism is de-
pendent upon effective inhibition of the activity of hyaluronidase,
which promotes sperm penetration. Phosporylated hesperidin
is a powerful inhibitor of hyaluronidase and is nontoxic.
Wilson (44) has prepared alkylated chalcone derivatives of
hesperidin that are acid stable, water soluble, and physiologically
active.
SUMMARY
An investigation was made of the glucoside content of four
varieties of oranges and five other varieties of citrus. The
oranges contained hesperidin as the predominant glucoside and
the other varieties contained related glucosides and also hes-
peridin in some cases.
The total quantity of glucoside in all the citrus varieties studied
was found to remain constant once the fruit had grown beyond
a certain equatorial diameter. This diameter was found to be
approximately 1.8 inches for oranges, 2.5 inches for Dancy
tangerines, and varied somewhat for the other varieties. In
each case the glucoside content on a percentage basis became
lower as the fruit grew larger.
The very high glucoside content of 19 to 37 percent on a dry-
weight basis found in the half-inch diameter fruit of all varieties
studied indicates that its physiological function may be im-
portant, although this has not been investigated.
The quantity of glucoside in the juice could not be correlated
with fruit maturity. It was found to vary between 0.018 and
0.034 percent by volume in orange juices, while juices of the
other varieties were found to have a higher range.
Between 70 and 80 percent of the total glucoside was concen-
trated in the albedo, rag and pulp of all varieties studied except
Dancy tangerine and Tahiti lime. The percentage distribution
of glucoside in the components of the fruit did not change ma-
terially as the fruit matured.
Whole fruits of each variety of citrus studied were separated
into their component parts. The moisture content of each com-
ponent and the percentage of each making up the whole fruit
at various stages of maturity were recorded.
Possible uses for hesperidin as a fine organic chemical include






32 Florida Agricultural Experiment Stations

the preparation of acid azo dyes and wood stains, and various
therapeutic agents.

LITERATURE CITED
1. ARCANGELI, E. F., and F. S. TRUCCo. Colorimetric determination of
the vitamin P. Ann. chim. applicata 34: 20-3. 1944.
2. ARMENTANO, P. L., E. B. HATZ, and I. RUSZNYAK. Determination of
citrin in the urine. Orvosi Hetilap. 82: 1016-19. 1938.
3. ASAHINA, Y., and M. INUBOSE. Flavanone glucoside. IV. Naringin
and hesperidin. Jour. Pharm. So. Japan 49: 128-34. 1929.
4. BACHRACH, A. R., M. E. COATES, and T. R. MIDDLETON. A biological
test for vitamin P activity. Biochem. Jour. 36: 407-412. 1942.
5. BAIER, W. E. Process for the recovery of hesperidin. U. S. Patent
No. 2,442,110. May 25, 1948.
6. BOURNE, GEOFFREY H. Vitamin P deficiency in guinea pigs. Nature
152: 659-660. 1943.
7. BRAVERMAN, J. B. S. Citrus products. 424 pp. 1949. Interscience
Publishers, Inc.
8. BRUCKNER, V., and A. SZENT-GYORGYI. Chemical nature of citrin.
Nature 138: 1057. 1936.
9. Chem. and Eng. News. Term "vitamin P" recommended to be discon-
tinued. 2827. Aug. 14, 1950.
10. DAVIS, W. B. Determination of flavanones in citrus fruits. Anal.
Chem. 19: 476-8. 1947.
11. DETRICK, L. E., M. A. DUNN, W. L. MCNAMARA and M. E. HUBBARD.
Vitamin C studies. 1. The effect of vitamin P (citrin) on vitamin
C deficient guinea pigs. Jour. Lab. and Clin. Med. 25: 684-687.
1940.
12. HALL, J. A. Glucosides of the Navel orange. Jour. Am. Chem. Soc.
47: 1191-1195. 1925.
13. HARVEY, E. M., and G. L. RYGG. Physiological changes in the rind of
California oranges during growth and storage. Jour. Agr. Research
52: 723-46. 1936.
14. HENDRICKSON, R., and J. W. KESTERSON. Orange concentrate evapo-
rator scale identified as hesperidin. Citrus 14: No. 10. 26-7. 1952.
15. HIGBY, R. H. The chemical nature of hesperidin and its experimental
medical use as a source of vitamin P. Jour. Am. Pharm. Assoc.
30: 629-35. 1941.
16. HIGBY, R. H. The chemical nature of vitamin P. Jour. Am. Pharm.
Assoc. 32: 74-77. 1943.
17. HIGBY, R. H. Method of manufacturing hesperidin. U. S. Patent No.
2,400,693. May 21, 1946.
18. HIGBY, R. H. Methods for recovery of flavanone glucosides. U. S.
Patent No. 2,421,061. May 27, 1947.







Hesperidin, the Principal Glucoside of Oranges


19. HIGBY, R. H. Process for the manufacture of hesperidin. U. S. Patent
No. 2,348,215. May 9, 1944.
20. HILGER, A. Ueber hesperidin. Ber. 9: 26-31. 1876.
21. HOFFMAN, E. Ueber hesperidin. Ber. 9: 685-90. 1876.
22. KESTERSON, J. W., and R. HENDRICKSON. Naringin, a bitter principle
of grapefruit. Fla. Agr. Exp. Sta. Tech. Bul. 511: 1-35. 1953.
23. KING, F. E., and A. ROBERTSON. Natural glucosides. III. Position of
the biose in hesperidin. Jour. Chem. Soc. 1704-9. 1931.
24. LAUTENSCHLAGER, C. L., and F. LINDNER. Process of obtaining purified
flavanone glucosides. U. S. Patent No. 2,359,126. Sept. 26, 1944.
25. LEBRETON, P. Sur la matiere crystalline des orangettes. Jour. Pharm.
14: 377. 1828.
26. LORENZ, A. J., and L. J. ARNOLD. Preparation and estimation of crude
citrin solutions from lemons. Food Research 6: 151-56. 1941.
27. MARTIN, J., and J. M. BEILER. Effect of phosphorylated hesperidin, a
hyaluronidase inhibitor, on fertility in the rat. Science 115: No.
2989. 402. 1952.
28. MAURER, R. H., E. M. BURDICK, and C. W. WAIBEL. Distribution of
naringin in Texas grapefruit. Lower Rio Grande Valley Citrus and
Vegetable Inst. Fourth Annual Proceedings, Weslaco, Texas. 1950.
29. Merck Index of Chemicals and Drugs. 6th Ed.. Merck & Co., Inc.
1952.
30. NELSON, E. K. The occurrence of a pentamethyl favanol in tangerine
peel. Jour. Am. Chem. Soc. 56: 1392-3. 1934.
31. OHTA, M. Derivatives of hesperidin and process for preparing the
same. U. S. Patent No. 2,350,804. June 6, 1944.
32. PHEFFER, W. Hesperidin, a constituent of some citrus. Bot. Zeitung
32: 529-40. 1874.
33. PRITCHETT, D. E., and H. E. MERCHANT. The purification of hesperidin
with formamide. Jour. Am. Chem. Soc. 68: 2108. 1946.
34. RUSZNYAK, I., and A. SZENT-GYORGYI. Vitamin P. Flavanols as vita-
mins. Nature 138: 27. 1936.
35. SCARBOROUGH, H., and A. L. BACHARACH. Vitamins and hormones.
Vol. VII 1-55 pp. 1949. Academic Press, Inc.
36. SHINODA, J., and M. KAWAGOYE. Polyhydroxychalcones, polyhydroxy-
hydrochalcones and polyhydroxyflavones. III. Synthesis of hesperi-
tin. Jour. Pharm. Soc. Japan 48: 938-41. 1928.
37. SOKOLOFF, B. T., and J. B. REDD. Study on vitamin P. Part II. The
chemical nature and physiological activity of vitamin P factors.
Fla. So. Col. Monograph 1: 3-58. 1949.
38. SOKOLOFF, B. T., and J. B. REDD. Study on vitamin P. Part III. Vita-
min P therapy. Fla. So. Col. Monograph 1: 3-54. 1949.
39. SZENT-GYORGYI, A. Methoden zur herstallung van citrin. Z. Physiol.
Chem. 255: 126-131. 1938.






34 Florida Agricultural Experiment Stations

40. TANRET, C. J. Sur quelques principles immediate de l'ecorce d'orange
amere. Acad. Sci. Paris Compt. Rend. 102: 518-20. 1886.
41. TUTIN, F. Constitution of eriodictyol, of homoeriodictyol and of hes-
peritin. Jour. Chem. Soc. 97: 2054-62. 1910.
42. WAWRA, C. W., and J. L. WEBB. The isolation of a new oxidation-
reduction enzyme from lemon peel. Science 96: 302-03. 1942.
43. WEBBER, H. J., and L. D. BATCHELOR. The citrus industry. History,
botany and breeding. Vol. I. 1028 pp. 1948. Univ. of Calif. Press.
44. WILSON, C. W. Alkylated chalcone derivative and methods of prepar-
ing the same. U. S. Patent No. 2,425,291. August 5, 1947.
45. ZEMPLEN, G., and R. BOGNAR. Synthesis of hesperidin. Ber. 76:
773-75. 1943.
46. ZILVA, S. S. Vitamin P. Biochem. Jour. 31: 915-919. 1937.







APPENDIX
TABLE 11.-DISTRIBUTION AND DRY SOLIDS CONTENT OF THE COMPONENT PARTS OF
HAMLIN ORANGE.


Date


Juice


4-18-52

6-1-51

7-1-51

8-1-51

9-1-51 4

10-1-51 4

11-1-51 5

12-1-51 4

1-1-52 4

2-1-52 4

3-1-52 4

4-1-52 4


Component Parts of Fruit-%
Albo Rag and
Albedo Flavedo I Pulp


0.5 ]

5.8 1

1.2 ]

7.5 1

4.3 1

4.2 1

1.7 1

0.1 1


15.9

L7.5

L3.8

14.5

L8.3

18.9

L9.5

L9.7


Seeds


Juice








8.6

8.2

8.9

9.6

10.1

10.7

11.4

11.8


Dry Solids--%
Rag and
Albedo Flavedo Pulp Seeds








21.6 23.5 14.3 30.0

16.9 21.3 14.4 30.0

18.5 24.4 14.4 32.0

19.4 24.9 14.2 35.0

18.0 23.5 15.0 40.0

20.5 25.3 15.6 43.0

20.1 24.0 14.8 42.0

20.7 26.0 14.9 50.0


Whole
Fruit

29.3

20.8

18.4

16.2

15.0

13.0

13.2

14.0

14.4

15.6

15.5

16.0





1 / I/











TABLE 12.-DISTRIBUTION AND DRY SOLIDS CONTENT OF THE COMPONENT PARTS OF
PARSON BROWN ORANGE.


Component Parts of Fruit-%
Rag and
Albedo Flavedo Pulp


Seeds


28.7

23.6

24.9

27.5

24.7

27.0

29.1

33.0


Dry Solids-%
Rag and
Juice Albedo Flavedo Pulp


2.9


8.5

8.0

8.9

10.5

10.1

11.1

11.3

11.0
1"


Juice


Date


4-18-52

6-1-51

7-1-51

8-1-51

9-1-51

10-1-51

11-1-51

12-1-51

1-1-52

2-1-52

3-1-52

4-1-52


Seeds


38.8

44.0

49.2

46.2

44.4

42.4

39.1

34.5


Whole
Fruit

28.4

26.8 .

19.8

17.5

15.2

14.1 C

14.5

16.1

15.7

16.6

16.9

16.2


30.0

35.0

36.0

35.0

38.0

45.0

43.0

50.0


"


; a








TABLE 13.-DISTRIBUTION AND DRY SOLIDS CONTENT OF THE COMPONENT PARTS OF
PINEAPPLE ORANGE.


Component Parts of Fruit--%


Rag and
Albedo Flavedo I Pulp


Date


4-18-52

6-1-51

7-1-51

8-1-51

9-1-51

10-1-51

11-1-51

12-1-51

1-1-52

2-1-52

3-1-52

4-1-52


Juice


Dry Solids-%_
Rag and Whole
Juice Albedo Flavedo Pulp Seeds Fruit

27.2

S 26.4


E


11.6 29.9

10.9 23.0

8.7 27.1

9.3 28.2

9.1 23.9

9.6 22.9

9.4 24.8

9.0 26.4


Seeds








5.6

5.2

3.3

3.2

2.9

3.0

2.4

2.7










TABLE 14.-DISTRIBUTION AND DRY SOLIDS CONTENT OF THE COMPONENT PARTS OF
VALENCIA ORANGE.


13.1 28.5

10.8 25.2

10.0 27.5

9.5 27.3

9.3 27.1

9.6 24.9

9.0 26.0

9.3 26.7

10.3 23.1


8.2 25.0

7.8 23.2

8.2 23.3

8.9 25.6

9.9 25.2

9.6 25.9


4-28-52

6-1-51

7-1-51

8-1-51

9-1-51

10-1-51

11-1-51

12-1-51

1-1-52

2-1-52

3-1-52

4-1-52

5-7-52


.... 32.8

.... 26.8

.... ... 20.8

17.9

16.1 .... 15.9

16.9 .... 14.5

16.4 .... 14.4

16.4 15.0

16.4 .. 15.5

16.8 .... 15.3

16.9 .... 15.4

17.0 ... 15.9

18.4 16.5


Date


24.6

22.8

25.1

24.7

26.0

26.5

27.0

25.0

27.4


18.0

16.4

12.6

13.6

13.5

12.5

12.4

13.0

10.8

















Date
Juice

4-28-52

6-1-51

7-1-51 28.5

8-1-51 36.6

9-1-51 31.9

10-1-51 39.0

11-1-51 42.8


TABLE 15.-DISTRIBUTION AND DRY SOLIDS CONTENT OF THE COMPONENT PARTS OF
MEYER LEMON.

Component Parts of Fruit--% II Dry Solids-%
i I Rag and Rag and
SAlbedo Flavedo Pulp Seeds Juice Albedo Flavedo Pulp




S...-.... .... 8 .1

13.0 12.9 35.0 2.5 7.9 17.3 19.0 13.9

14.8 9.6 41.3 2.4 8.1 15.5 19.1 12.4

12.4 10.7 35.8 2.1 7.9 14.8 17.2 12.1

13.1 10.4 32.3 1.4 9.7 12.8 16.4 11.2


Whole
Seeds Fruit

29.8

S 17.6

14.1

30.0 11.9

30.0 12.5

30.0 11.7

39.0 11.7
















TAB


Cc
Date
Juice A

3-11-52

6-1-51

7-1-51 42.4

8-1-51 47.6

9-1-51 43.6

10-1-51 47.6

Tahiti Limes are seedless.


LE 16.-DISTRIBUTION AND DRY SOLIDS CONTENT OF THE COMPONENT PARTS OF
TAHITI LIME.

imponent Parts of Fruit-% \I Dry Solids-%o


I I Rag and
lbedo I Flavede 1 Pulp


Seeds


SRag and
Juice Albedo Flavedo Pulp


Whole
Seeds Fruit


....... 24.8
.... ........ 16.8

9.2 .... ........ 14.7

8.7 .. 26.1 16.4 13.8

8.1 .... 21.7 14.5 12.5

8.0 .... 20.8 15.8 12.5










TABLE 17.-DISTRIBUTION AND DRY SOLIDS CONTENT OF THE COMPONENT PARTS OF
DANCY TANGERINE.


Component Parts of Fruit-%
I Albedo
Juice Albedo Flavedo Rag and
Pulp


Date



5-27-52

7-1-51

8-1-51

9-1-51

10-1-51

11-1-51

12-1-51

1-1-52

2-1-52

3-1-52


40.7

33.9

38.8

44.5

58.8

54.1

63.5


Seeds








5.4

4.2

3.2

2.0

1.6

1.8

2.4


Dry Solids-%
Albedo
Juice Albedo Flavedo Rag and
SPulp







8.8 29.4 19.6

8.3 27.9 17.2

8.9) 25.6 15.0

9.7 25.7 16.8

10.1 23.2 15.2

11.9 27.8 18.4

13.5 .... 30.1 21.2


16.7

16.5

14.2

11.7

10.8

10.1

6.9


Seeds








30.0

30.0

28.0

33.0

33.0

41.0

37.0


Whole
Fruit

37.0

25.6

20.8

17.8

15.5

14.3

15.2

14.9

17.5

20.1











TABLE 18.-DISTRIBUTION AND DRY SOLIDS CONTENT OF THE COMPONENT PARTS OF
ORLANDO TANGELO.


Component Parts of Fruit-%
Date IRag and
SJuice Albedo Flavedo Pulp

5-13-52 ....


13.6 12.7

18.1 9.5

11.6 10.0

14.4 10.0

19.9 8.3

17.9 7.8

17.5 8.1

16.4 8.2


27.5

21.9

21.4

24.2

18.9

19.0

23.4

21.5


Dry Solids-%
Rag and
Seeds Juice Albedo Flavedo Pulp








2.6 9.3 28.1 26.0 17.6

2.5 8.6 21.2 29.9 17.4

1.5 9.9 23.3 24.6 17.4

1.3 11.0 24.2 26.5 16.7

1.1 12.0 23.3 26.1 16.9

1.6 13.1 25.8 27.8 19.0

1.0 13.8 25.0 27.8 18.4

1.2 15.0 26.7 29.4 20.2


Whole
Seeds Fruit

34.8

30.0

23.0

.. 19.4


6-1-51

7-1-51

8-1-51

9-1-51

10-1-51

11-1-51

12-1-51

1-1-52

2-1-52

3-1-52

4-1-52


S 43.6

S 48.0

55.5

50.1

51.8

53.7

50.0

S 52.7








TABLE 19.-DISTRIBUTION AND DRY SOLIDS CONTENT OF THE COMPONENT PARTS OF
TEMPLE ORANGE.

Component Parts of Fruit-% I Dry Solids-%
I Rag and Rag and
Juice Albedo Flaved-o Pulp Seeds Juice Albedo Flavedo Pulp


Date


5-13-52

6-1-51

7-1-51

8-1-51

9-1-51

10-1-51

11-1-51

12-1-51

1-1-52

2-1-52

3-1-52

4-1-52


24.8

26.3

21.7

23.7

22.0

26.4

25.9

27.2


24.5

22.7

24.8

25.9

25.4

29.8

28.3

31.0
...


17.1

17.4

16.1

16.6

16.1

18.4

19.9

19.4


Whole
Seeds Fruit

S 33.4

.... 24.8

19.5

16.2

30.0 16.4

30.0 15.3

42.0 15.2

46.0 16.5

47.0 16.6

42.0 18.8

51.0 19.5

46.0 20.2


15.1 11.4 25.5

11.9 12.1 19.7

11.9 10.3 21.0

12.7 10.2 22.8

14.6 9.5 23.6

14.0 9.1 21.2

14.8 9.4 20.7

15.4 8.4 23.4




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