Group Title: Citrus Station mimeo report - Florida Citrus Experiment Station ; CES 65-8
Title: Analysis of some recovered natural flavor enhancement materials
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Permanent Link: http://ufdc.ufl.edu/UF00072429/00001
 Material Information
Title: Analysis of some recovered natural flavor enhancement materials
Series Title: Citrus Station mimeo report
Physical Description: 3, 3 leaves : ; 28 cm.
Language: English
Creator: Wolford, R. W
Citrus Experiment Station (Lake Alfred, Fla.)
Florida Citrus Commission
Publisher: Florida Citrus Experiment Station :
Florid Citrus Commission
Place of Publication: Lake Alfred FL
Publication Date: 1964
 Subjects
Subject: Citrus -- Quality -- Florida   ( lcsh )
Genre: government publication (state, provincial, terriorial, dependent)   ( marcgt )
non-fiction   ( marcgt )
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Statement of Responsibility: R.W. Wolford ... et al..
General Note: Caption title.
General Note: "October 6, 1964."
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Bibliographic ID: UF00072429
Volume ID: VID00001
Source Institution: University of Florida
Rights Management: All rights reserved by the source institution and holding location.
Resource Identifier: oclc - 75969830

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Citrus Station Mimeo Report CES 65-8
October 6, 1964


Analysis of Some Recovered Natural Flavor Enhancement Materials

R. W. Wolford, J. A. Attaway, G. E. Alberding, and C. D. Atkins
Florida Citrus Commission
Lake Alfred, Florida


Much apparent interest has been aroused among citrus processors during the
past few years on the subject of flavor and quality in processed citrus products.
Quality control efforts have been increased and emphasis has been placed on
standardization of products. However, flavor maintenance has become more diffi-
cult with industry expansion, greater production, and present processing economics.
Significant problems.have resulted from the utilization of wider ranges of fruit
varieties, increased yield of juice per box of fruit, and the employment of
methods for improving the physical stability of these products. Both favorable
and unfavorable results have been experienced in attaining the overall objectives
of good flavor and quality.

Economic expediency is largely attributable in the rash of investigations
into the use of many modifying techniques and methods for furnishing the natural
orange flavor to concentrated and processed citrus juice. The time-honored
method using cutback juice and coldpressed oil has, in the course of time, been
beset by some of the problems mentioned above. Thus, the development of materials
of different sorts, having origin in the juice or peel of the fruit, which might
be used as a substitute for or to compliment the use of cutback and oil were ex-
plored. Among the several flavor enhancement procedures for addition of flavor
to evaporator concentrate "pump-out" has been the successful employment of freeze-
concentrated cutback juice. More recently, investigations in several facets of
the industry have been toward the development and use of recovered essences, cen-
trifuged juice oils, and centrifuged juice emulsions. It has been observed that
only relatively limited testing and evaluation, on a comparative basis, has been
made in the utilization of these materials in frozen orange concentrate pro-
duction. Each of the materials has its own merits but will require extensive
evaluation to determine its desirable flavor enhancement qualities, as well as
product stability, and flavor acceptance by the consumer.

Efforts to obtain some basic information concerning chemical composition
resulted in analyses of the various flavor enhancement materials as a part of
our continuing research toward characterizing the flavor of citrus juices. Some
of the comparative results, although quite preliminary, will be presented. It
should be pointed out that it is not the intent of this discussion to make
recommendations relative to any of these flavor enhancing materials. However,
the results will be presented as objectively as possible for your consideration.
The fundamental aspects in the application of these materials as related to the
flavor of orange juices remain as points for continued study.


Florida Citrus Commission and
Florida Citrus Experiment Station,
Lake Alfred, Florida.
400-10/6/64 RWW











These studies were divided roughly as follows: (1) continued basic identi-
fication of volatile flavor components in orange juices via recovered essences;
(2) gas chromatographic comparative studies using highly sensitive systems in
analyses of the various flavor enhancement materials; and (3) the use of each of
the materials in production of frozen orange concentrates.

Previous papers, presented at these meetings in the past, concerning the
volatile flavor components of citrus juices have contained summary lists of
identified volatile flavor components. Table 1 provides an updated list of 60
components, 50 of which have now been positively identified and 10 components
which have received strong tentative identification. In the course of these
studies, a compilation of retention data for some 55 compounds was prepared for
use in interpreting the analytical results obtained for the various flavor en-
hancement materials. In addition, in Table 2 are shown the criteria for identi-
fication of compounds isolated from orange essences.

In the gas chromatographic analyses of these materials two types of de-
tection systems were employed simultaneously. These systems consisted of the
flame ionization (FI) and the electron capture (EC) detectors. The GC column
effluent was split at a ratio of 31/5.6 to the FI and EC detectors, respectively.
The latter system, a highly sensitive and selective type of detector and one of
the more recent advances in the art of gas chromatography, was used successfully
in analyzing each of the materials. The chromatographic presentations and
comparisons for these various flavor materials using combined EC and FI provided
entirely new exploratory information concerning the volatile flavor components.
The EC response is considered as having some relationship to the aroma and flavor
of orange juices. Also, it may be closely associated with distinctive character-
istics of the aroma and flavor of fresh juice, possibly providing secondary flavor-
ing characteristics. It was interesting that the EC peaks, of which at least 25
have been observed had virtually no retention coincidence with the component peaks
from the FI detector. Also, some differences in the EC chromatograms were observed
for each of the materials studied.

The analyses were conducted using three column stationary phases, Carbowax
20M, 4% w/w on Gas-Chrom Z, 60-80 mesh; Apiezon L, 8% w/w on Chromosorb W,
80-100 mesh; and Estrex P4-S, 10% w/w on Gas-Chrom Z, 60-80 mesh. Columns were
1/8" copper ranging from 6' to 12' in length. Each of the stationary phases
gave similar results in the total number of peaks and differed primarily in
elution order depending upon the polarity of the column used. The Estrex column
was found to be somewhat superior to Carbowax in the separation of EC components.
Most of the results to be presented were obtained using the GC separations ob-
tained on the Estrex column.

The identification of individual EC components has to date been confined to
obtaining some chemical classification for those components exhibiting electron
affinity, a major requirement of electron capture detection. One of the major
components may be a sulfur compound as shown by its Mass Spectral indication at
mass 35 and 32. In addition, some subtractive chemical studies directed toward
organic sulfides caused removal of six of the EC components.


Florida Citrus Commission and
Florida Citrus Experiment Station,
Lake Alfred, Florida.
400- 10/6/64 RWW







-3-


Some interesting differences were also observed in FI chromatograms, particu-
larly in comparisons between the oxygenated fractions of juice oil, coldpressed
oil, and that of juice emulsions. It was shown, however, that experimentally re-
covered orange essences from the pilot plant system contained a reasonably good
balance of components from both the oils and emulsions.

As a third step in these investigations, each of the materials, CES pilot
plant recovered orange essences, commercially prepared orange juice emulsions
(Centrico), and juice oils (DeLaval) were employed in the preparation of frozen
concentrates in the pilot plant. Some of the organoleptic evaluations will be
presented in the subsequent paper by Dr. F. W. Wenzel.

In summary, investigation into the basic and applied aspects of some
relatively new recovered natural materials, having potential flavor enhancement
characteristics, has been discussed. In these preliminary studies of less than
one years time, every effort has been made to provide some objective results and
evaluation for each of the materials. Two varieties of orange juices, Pineapple
and Valencia, and their counter parts in recovered flavor materials were utilized.
New methods of analysis have been introduced, including the chemical oxygen demand
(ppm COD/ml) as a measure for the water-soluble volatile constituents of citrus
juices and products, as discussed by Mr. Dougherty in the previous paper, and the
electron capture detection system, which has provided a new and possibly first
time look at some different chemical factors related to aroma and flavor of
orange juices.

There remain a number of questions concerning the use of any one of the
materials introduced for flavor enhancement in the processing of citrus juices.
If a fresh-like flavor is to be achieved in processed citrus products, then in
light of present production procedures and with a view toward using recovered
natural flavor materials as enhancers a carefully balanced material would be a
basic requirement.


Acknowledgments

The authors wish to thank Mr. Adolf Distelkamp and Centrico, Inc.; also,
Mr. Omar McDuff, Adams Packing Assn. for supplying the centrifuged juice
emulsions for these studies. In addition the authors express appreciation to
those companies: Adams Packing Association, Minute Maid Company, Pasco Packing
Company, Ben Hill Griffin Concentrates, and Stokely-Bordo who cooperated in the
production of the juice emulsions used in these studies.

The authors wish to also thank Mr. J. W. Kesterson, Citrus Experiment
Station for supplying the coldpressed oils and (DeLaval) centrifuged juice
oils and the companies who cooperated in their production.






Florida Citrus Commission and
Florida Citrus Experiment Station,
Lake Alfred, Florida.
400-10/6/64 RWW












Table 1
Volatile Flavor Components in Recovered Orange Essence
(Confirmed Identifications Unless Noted )


Aldehydes and Ketones
Acetone
Acetaldehyde
n-Hexanal
2-Hexenal
n-Octanal
n-Nonanal
n-Decanal
Neral
Geranial
Carvone
2-Octenal
Furfural*
Methyl heptenone


Alcohols
Methanol
Ethanol
n-Propanol
Isobutanol
n-Butanol
Isopentanol
n-Pentanol
n-Hexanol
3-Hexen-l-ol
Methyl heptenol
Linalool
n-Octanol
Terpinen-4-ol
n-Nonanol
alpha-Terpineol
n-Decanol
Citronellol
Nerol
Geraniol
Carveol
Isohexanol*


Acids
Formic
Acetic
Propionic
Butyric
Caproic
Capric
Isovaleric*
Valeric
Isocaproic*
Caprylic*


Terpene Hydrocarbons
alpha-Pinene
beta-Pinene
d-Limonene
Myrcene
gamma-Terpinene
alpha-Terpinene
delta-3-Carene*
Terpinolene*
p-Cymene*
alpha-Phellandrene*
beta-Phellandrene*


Esters
Ethyl butyrate
Ethyl caproate
Ethyl caprylate
Linalyl acetate
Terpinyl format
Citronellyl butyrate


Strong tentative identification lacks confirmation.


Florida Citrus Commission and
Florida Citrus Experiment Station,
Lake Alfred, Florida.
400-10/6/64 RWW








Critej

Compound
Ethyl butyrate
Butyl butyrate?
Ethyl caproate?
Ethyl caprylate
Linalyl acetate
Cedryl acetate
Terpinyl format
Citronellyl butyrate
alpha-Pinene
beta-Pinene?
Myrcene
d-Limonene
p-Cymene
Acetaldehyde
Acetone
n-Hexanal
2-Hexenal
Octanal
Methyl heptenone
Nonanal
Citronellal
Decanal
Neral
Geranial
Carvone
Methanol
Ethanol
Propanol
Isobutanol
n-Butanol
Isopentanol
n-Pentanol
n-Hexanol
3-Hexen-l-ol
Methyl heptenol
Linalool
n-Octanol
Terpinen-4-ol
n-Nonanol
alpha-Terpineol


Table 2
ria for Identification of Compounds Isolated from Orange Essence
GLC Study GLC-FI Derivative Infrared
on 2 columns Rechromatography Study TLC Spectrum
+ + +


+ +


+ +






Table 2 (Continued)


n-Decanol + +
Citronellol + + + +
Nerol + + +
Geraniol + + +
Carveol + + +
Formic acid +1 +2
Acetic acid + +
Propionic acid + +
Butyric acid + +
Caproic acid + +
Capric + +


Acids were studied on one column phase after removing neutral components.
2
Acid derivatives were diethylamine salts studied paper chromatographically.



Table taken from publication entitled "Isolation and Identification of Volatile Flavor
Components in Recovered Orange Essences Using Gas Chromatography" by John A. Attaway and
Richard W. Wolford, presented at the Fifth International Symposium on Gas Chromatography,
Brighton, England, September 8-10, 1964.











Florida Citrus Commission and
Florida Citrus Experiment Station,
Lake Alfred, Florida.
400-10/6/64 RWW




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