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Flavor Properties of FEMA GRAS List 26 flavor chemicals
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 Flavor Properties of FEMA GRAS List 26 flavor chemicals
(A preliminary assessment)

by John C. Leffingwell & Diane Leffingwell

(A version of this appeared in Perfumer & Flavorist, Vol. 39, No. 1, 26-37: 2014)



Glucosyl steviol glycosides; Stevia extract, enzymatically modified

Natural low calorie sweetener and flavor enhancer.

Glucosyl steviol glycosides is a complex mixture of glucosides prepared by enzymatically modifying stevia extract to increase/change the degree of glycosylation.

In United States Patent 8318459 (Nov. 27, 2012) by Avetik Markosyan entitled Glucosyl stevia composition (assigned to PureCircle USA) it is demonstrated that improved sweetness profiles can be achieved.

In WIPO Patent Application WO2012128775 by Siddhartha Purkayastha entitled GLUCOSYLATED STEVIOL GLYCOSIDE COMPOSITION AS A TASTE AND FLAVOR ENHANCER (assigned to PureCircle USA) and WIPO Patent Application WO2012129451 by Siddhartha Purkayastha entitled GLUCOSYLATED STEVIOL GLYCOSIDE COMPOSITION AS A FLAVOR MODIFIER (assigned to PureCircle USA) the used in modifying the flavor profiles of various products is described.



Isomenthol; dl-Isomenthol; (±)-Isomenthol

dl-Isomenthol alone is considerably less cooling than (-)-Menthol and posesses a somewhat musty, woody camphoric odor. But, in United States Patent 8496950 (July 30, 2013) by Klaus Sorge, Hubert Loges, Arnold Machinek, Ulrike Simchen & Horst Surburg entitled MIXTURE CONTAINING MENTHOL assigned to Symrise the use of dl-Isomenthol in various menthol mixtures has been shown to lower the melting point of such mixtures. In addition, at the levels used the organoleptic perception is acceptable or improved.



Ethyl S-(1-methoxyhexan-3-yl)carbonothioate; O-ethyl S-(1-methoxyhexan-3-yl) carbonothioate

Sulfury, blackcurrant, tropical, roasted coffee; effective in coffee

This material is the subject of WIPO Patent Application WO/2010/115920 entitled CARBONOTHIOATES AS FLAVOURS AND FRAGRANCES (10/14/2010) by Klaus Gassenmeier, assigned to Givaudan.
Flavour description: sulfury, blackcurrant, tropical, roasted coffee.
Odor description: mushroom, herbaceous, slightly cacao connation.



Cassyrane®; 2-tert-Butyl-5-methyl-2-propyl-2,5-dihydrofuran

In United States Patent 7,632,790 (Dec. 15, 2009) by Philip Kraft assigned to Givaudan, it is described as: Odor description: Blackcurrant, natural, rich, eucalyptus buds, anis, buchu leaves, slightly green.

Descriptions of the enantiomers can be found at http://www.leffingwell.com/chirality/cassyranes.htm



1,5-Octadien-3-ol; Octa-1,5-dien-3-ol

Mixture of E/Z stereoisomers: with 60-90 % (E)
Earthy, mushroom, green, geranium leaf, marine notes

Boelens indicates: dusty, somewhat earthy, mushroom-like odor (PMP 2001)
Estelle Delort, Alain Jaquier, Christian Chapuis, Mark Rubin, and Christian Starkenmann (Volatile Composition of Oyster Leaf (Mertensia maritima (L.) Gray), J. Agric. Food Chem., 2012, 60 (47), pp 11681–11690) have described (Z)-1,5-octadien-3-ol as:
Orthonasal odor: green, marine, slightly mushroom, strong
Retronasal odor (10 ppm): floral, green, geranium leaf, crustaceous, mushroom, metallic




Flavor description: fruity, tropical, guava, watercress, vegetal (at 0.5 ppm in 5% sugar solution)
Source: Regula Naef, Alain Velluz and Alain Jaquier, New Volatile Sulfur-Containing Constituents in a Simultaneous Distillation-Extraction Extract of Red Bell Peppers (Capsicum annuum), J. Agric. Food Chem., 2008, 56 (2), pp 517–527.

The flavor description is for the diastereomeric mixture.




At the time of this writing we have no definitive information on the flavor of this material.

From the structure, we would anticipate that the organoleptic character would approximate "roasted, fatty, aldehydic".

Primarily finds use in savory, meat & fish flavors.




(4Z,7Z)-Tridecadienal is a fatty flavor aldehyde originally discovered by Lever Bros. as useful in fatty, savory flavors. In Great Britain Patent 1,034,352, Dutch Pat. No. 139,102 and Swiss Pat No. 471545 it is reported in the claims that both cis-4-decenal and cis,cis-4,7-tridecadienal and other polyunsaturated aldehydes containing 11-17 carbon atoms are suitable for imparting a savory aroma that enhanced chicken meat flavor to foodstuffs.

In Japanese Patent JP2012034662 (Feb. 23, 2012) by Tsukasa Saito et al. entitled DRIED FISH FLAVOR IMPROVING AGENT (assigned to T. Hasegawa) the use of 2,4,7-tridecatrienal and/or 4,7-tridecadienal for producing dried fish flavors (specifically, dried bonito) is disclosed. At low levels they can also impart umami effects.



L-gamma-Glutamyl-L-2-aminobutyric acid; gamma-Glu-Abu

A Kokumi imparting agent.

In United States Patent Application 20120034364 (Feb. 9, 2012) by Fumie Futaki, Reiko Yasuda, Seiichi Sato, Takashi Miyaki, Naohiro Miyamura & Yuzuru Eto entitled USE OF PEPTIDES FOR IMPARTING KOKUMI, is described a substance that provides a kokumi-imparting agent consisting of gamma-Glu-Abu (L-gamma-glutamyl-L-2-amino-butyric acid). The kokumi-imparting agent of the present invention or gamma-Glu-Abu can also be used in combination with at least one additional ingredient for seasonings selected from the group consisting of amino acids such as sodium glutamate (MSG), nucleic acids such as inosine monophosphate (IMP), inorganic salts such as sodium chloride, organic acids such as citric acid, and various kinds of yeast extracts to thus provide a favorable seasoning composition which is improved in its kokumi, as compared with those obtained by the use of such additional ingredients for seasonings individually.



Glutamyl-norvalyl-glycine; N-(N-L-gamma-Glutamyl-L-norvalyl)-glycine; L-Glutamyl-L-norvalyl-glycine; gamma-Glu-Nva-Gly

A Kokumi flavor enhancer

In WIPO Patent Application WO2011081186 (July 7, 2011) by Takashi Miyaki et al. entitled FLAVOR-ENRICHING AGENT it is disclosed that gamma-Glu-Nva-Gly (L-gamma-glutamyl-L-norvaline-glycine) exhibits a potent flavor-enriching action, particularly with respect to middle tastes, and exhibits an improved stability.



Glutamyl-norvaline; L-gamma-Glutamyl-L-norvaline N-(N-L-gamma-Glutamyl)-L-norvaline; L-Glutamyl-L-norvaline; gamma-Glu-Nva

A Kokumi flavor enhancer

In United States Patent 8541379 (Sept.24, 2013) by Takashi Miyaki et al. entitled Kokumi-imparting agent (assigned to Ajinomoto) wherin gamma-Glu-Nva (L-gamma-glutamyl-L-norvaline) is the subject compound.

Examples are given of the kokumi effect of L-Glutamyl-L-norvalyline wherein the intensity of the kokumi-imparting activity observed for each test compound was determined as a value observed when blending 0.00001 to 0.5 g/dL of the corresponding test compound with the distilled water containing sodium glutamate (0.05 g/dL), inosinic acid monophosphate (0.05 g/dL), and sodium chloride (0.5 g/dL). The Kokumi effect was effective at a dose level of 0.0001 g/dl which was a significantly lower dose level than a number of other kokumi compounds tested.



N-(2,3-Dimethoxybenzyl)-N'-(2-(pyridin-2-yl)ethyl)oxalamide; N1-(2,3-dimethoxybenzyl)-N2-(2-(pyridin-2-yl)ethyl)oxalamide

Savory; umami flavor enhancer

This material is disclosed in United States Patent 7476399 (01/13/2009) entitled "Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof " by Catherine Tachdjian et al. (assigned to Senomyx) - and was identified as a umami compound.




In United States Patent 8,071,531 (Dec. 6, 2011) by Takashi Aida & Kenya Ishida entitled Flavor and fragrance composition (assigned to Takasago) this material is decribed as having an acetophenone-like odor with sweetness and having a "cool and refreshing feeling equivalent to 10 ppm of menthol at a concentration of 50 ppm; appearance of refreshing feeling is relatively rapid with clear refreshing feeling without unpleasant taste" in aqueous solution..

Synergetic Effect with Menthol:
A 70:30 mixture of l-menthol and (1R,2R,4R)-1-(2-hydroxy-4-methylcyclohexyl)ethanone showed about 40% stronger cool and refreshing feeling than that of menthol alone.



(±)-6-Methoxy-2,6-dimethylheptanal; Methoxymelonal

Citrus, floral, fruity notes with a watery melon character

First reported in United States Patent 4311617 (Jan. 19, 1982) by Hifzur R. Ansari, Benjamin O. Isaac & Horst R. Wagner, entitled Perfumery compositions. It has long been used in fragrances.

Michael Zviely (Perfumer & Flavorist, Vol. 35, October 2010, pp. 22-23) reports it has "a light floral odor, slightly fruity note with a watery citrus character. It is fresh, herbaceous and slightly fruity with melon connotations".




Odor as described by Sungim Im, Fumiyo Hayakawa and Tadao Kurata, Identification and Sensory Evaluation of Volatile Compounds in Oxidized Porcine Liver, J. Agric. Food Chem., 2004, 52 (2), pp 300–305:
(E,Z)-3,5-undecadien-2-one - "Fatty, fried" by GC-O
(E,E)-3,5-undecadien-2-one - "Fatty, fried" by GC-O

3,5-undecadien-2-one was also described as "Fatty, fried" by H. T. Badings, Neth. Milk Dairy J., 24, 147-257 (1970) as referenced by David A. Forss, ODOR AND FLAVOR COMPOUNDS FROM LIPIDS in Progress in the Chemistry of Fats and other Lipids, Pergamon Press, 1975, p. 236)



(±)-2,5-Undecadien-1-ol; Undeca-2,5-dien-1-ol

The author is unfamiliar with this material, but by analogy expects it to have a somewhat fatty, waxy character.
The related 2,4-undecadien-1-ol has been described by both Bedoukian and Boelens as a "mild, fatty odor"

(Z,Z)-2,5-undecadien-1-ol is found in Noni (Morinda citrifolia L.)



Triethylthialdine; 2,4,6-Triethyl-1,3,5-dithiazinane; 5,6-Dihydro-2,4,6-triethyl-4H-1,3,5-dithiazine

Sulfurous, fried onion, leek, meaty, savory, seafood

Boelens indicates - narcotic, sulfurous- and amine-like; seafood note (FRM 2001)

Treatt indicates - Sulphurous, savoury; ‘cooked leek’. Used in flavours for oils and fats at 0.35-3.5 ppm; in meat and dairy flavours for snack foods and sauces at 3-6 ppm; and in soups and seasonings, at 4-8 ppm. Also described as a powerful "fried onion" note.

Also described as weak raw pumpkin, white part of Allium plants (at pH 7.3) and green, leek at lower pH by Tetsuo Kawai, J. Agric. Food Chem. 1985, 33, 393-397.



4-methylpentyl 4-methylpentanoate; 4-methylpentyl 4-methylvalerate; Isohexyl isohexanoate

Sweet, fruity, waxy, soapy, slightly herbal

Considered sensorially relevant to capsicum peppers.

Primarily used in fruit flavors



cis-3-Hexenyl salicylate; (Z)-3-Hexenyl salicylate; (Z)-Hex-3-enyl salicylate

Sweet, green, floral, woody, balsamic

Used as a modifier in floral & fruit flavors




Savory; umami flavor enhancer

This material is disclosed in United States Patent 7476399 (01/13/2009) entitled "Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof " by Catherine Tachdjian et al. (assigned to Senomyx) - and was identified as a umami compound.



Acetyl glutamate; N-Acetyl-L-glutamate; N-Acetyl-L-glutamic acid; alpha-(N-Acetyl)-L-glutamic acid

Flavor enhancer, umami like

In WIPO Patent Application WO2013010991 (Jan. 24, 2013) by Xiaogen Yang et al. entitled FLAVOUR MODIFYING COMPOUNDS (assigned to Givaudan) it is disclosed that N-acetyl glutamic acid can modify the taste or flavour, in particular the salt taste, umami taste, or savoury flavour, of a flavour composition or consumable product .



1,3-Propanediol; 1,3-Propylene glycol; Zemea® propanediol

A certified natural product replacement for 1,2-propylene glycol; can be used to replace glycols such as propylene glycol (1,2-propanediol), butylene glycol (1,3-/1,4-butanediol) or glycerin.



Ethyl melilotate; Ethyl 3-(2-hydroxyphenyl)propanoate; Ethyl 3-(2-hydroxyphenyl)propionate

Adds sweetness, extends vanilla character, sweet-cream-vanilla notes.

In WIPO Patent Application WO2013000595 (Jan. 3, 2013) by Estelle Delort & Erik Decorzant entitled FLAVORING COMPOUND (assigned to Firmenich) Ethyl 3-(2-hydroxyphenyl)propanoate is disclosed as a flavoring ingredient to impart or reinforce a coumarine and/or vanilla tonality.



Toscanol®; 1-(Cyclopropylmethyl)-4-methoxybenzene; 1-Cyclopropylmethyl-4-methoxybenzene; p-(Cyclopropylmethyl)anisole

Strong anisic, estragole, anethole, sassafras, cresolic

Givaudan indicates for Toscanol® - Odor: Anisic, Green, Liqueur like, Herbaceous
Use: Powerful and linear anisic, sweet-spicy note of estragole (methyl chavicol), Licorice and Sassafras oil character with a touch of Saffron, Myrtle, Opopanax and Carvi Seeds. Toscanol can be used in all kind of accords to add anisic agrestic and aromatic character.

See also - United States Patent 7704942 (April 27, 2010) entitled Fragrance and flavour compositions by Andreas Goeke (assigned to Givaudan).



S-Prenyl thioisobutyrate; S-(3-Methylbut-2-enyl) 2-methylpropanethioate

Boelens indicates - sulfurous, fruity, tropical fruit connotation, durian, passion fruit odor (PMP 2001)
Primary use is probably vegetable, savory, tropical fruit, and pineapple flavors.

Found in Agathosma oils related to buchu.



S-Prenyl thioisovalerate; S-3-Methylbut-2-enyl 3-methylbutanethioate; S-Prenyl thioisopentanoate; S-(3-methylbut-2-en-1-yl) 3-methylbutanethioate

Sulfurous, fruity, tropical fruit connotation, durian, passion fruit notes.
Primary use is probably vegetable, savory, tropical fruit, and pineapple flavors.

Found in Agathosma oils related to buchu.



(-)-Matairesinol; (8R,8'R)-(-)-Matairesinol; (3R,4R)-Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone; (3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

Reduces bitterness and astringency.

In European Patent Application EP2517574 (Oct. 31, 2012) by Michael Backes et al. entitled Specific vanillyl lignanes and their use as taste enhancers (assigned to Symrise) the use of (-)-Matairesinol has been shown to reduce both bitter impressions and astrigency at levels of about 25-100 ppm.



Stevioside; Steviosin; (4,alpha)-13-[(2-O-beta-D-Glucopyranosyl-alpha-D-glucopyranosyl)oxy]kaur-16-en-18-oic acid beta-D-glucopyranosyl ester

Natural low calorie sweetener

Steviol glycosides are responsible for the sweet taste of the leaves of the stevia plant (Stevia rebaudiana Bertoni). These compounds range in sweetness from 40 to 300 times sweeter than sucrose.

The four major steviol glycosides found in the stevia plant tissue are:
5–10% stevioside (250–300X of sugar)
2–4% rebaudioside A — most sweet (350–450X of sugar) and least bitter
1–2% rebaudioside C
½–1% dulcoside A.




Sweetness enhancer, bitterness reducer.

In United States Patent Application 20080113073 (May 15, 2008) by Jakob Ley, Gunter Kindel, Susanne Paetz & Gerhard G.E. Krammer entitled HYDROXYDEOXYBENZOINS AND THE USE THEREOF TO MASK A BITTER TASTE, this material was demonstrated to enhance sweetness of sucrose and reduce bitterness (of caffeine).



Ethyl 5-(formyloxy)decanoate; Ethyl 5-formyloxydecanoate

delta-decalactone precursor; dairy like

This material forms delta-decalactone when heated or under enzymatic conditions.
Useful in dairy flavors or wherever delta-decalactone might be employed.



3-[3-(2-Isopropyl-5-methyl-cyclohexyl)ureido]butyric acid ethyl ester; Ethyl 3-(3-(menthyl)ureido)butyrate; Ethyl 3-(3-(2-isopropyl-5-methylcyclohexyl)ureido)butanoate

Salty, metallic, umami

In United States Patent Application 20090311401 (Dec. 17, 2009) by Jakob Peter Ley, Heiko Oertling, Michael Backes & Tobias Vossing entitled Neo-Menthyl Derivatives as Flavor Materials (assigned to Symrise) discloses a series of ureas, thioureas, carbamates, thiocarbamates and guanidines based on the neomenthyl structure as flavor materials or flavor material mixtures for producing, imparting, modifying and/or enhancing savory flavor notes.
The racemic mixture of 3-[3-((1S,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)ureido]-butyric acid ethyl ester (compound 7) and 3-[3-((1R,2R,5S)-2-Isopropyl-5-methyl-cyclohexy1)-ureido]-butyric acid ethyl ester (compound 8) had a flavor profile of: bitter, salty, metallic, umami



2-Isopropyl-4-methyl-3-thiazoline; 2-Isopropyl-4-methyl-2,5-dihydrothiazole; 2,5-dihydro-2-isopropyl-4-methylthiazole

Flavor enhancer for fruit flavors, brown flavors & Savory flavors

In European Patent Application EP2289351 (Mach 2, 2011) by Kathryn A. Bardsley, Kenneth J. Kraut, Linda Psota-Kelty & LaurenceTrinnaman entitlted Use of thiazoline compounds in flavor applications (assigned to IFF) the flavor use of 2-Isopropyl-4-methyl-3-thiazoline is disclosed.
Detection Threshold: 10 ppb (slightly fruity, tropical, peach, berry)
At 50 ppm: rubber, phenolic, mushroom



Adoxal (Givaudan); 2,6,10-trimethyl-9-undecenal

Fresh, aldehydic, powerful, floral, rosy, ozonic-marine.

Givaudan indicates: Olfactive note - Fresh, Aldehydic, Powerful, Floral, Rosy, Marine
Description - Adoxal blends extremely well with floral notes such as muguet and cyclamen, as well as with fruity and woody compositions. It can also be seen as having a typical "fresh linen" odour and a natural, ozonic aspect.



5-Mercapto-5-methyl-3-hexanone; Sauvignone 100 (Takasago)

Sparkling citrus, grape, fruity, watery, tropical notes

Takasago indicates - Odor Description: Sparkling Citrus, Grape
Very effective in watery applications where traces provide interesting effects, obviously in fruity notes.



Rubescenamine; (E)-N-[2-(1,3-Benzodioxol-5-yl)ethyl]-3-(3,4-dimethoxyphenyl)prop-2-enamide

Umami flavor enhancer

In United States Patent Application 20120308703 (Dec. 6, 2012) by Jakob Peter Ley,Katharina Reichelt, Susanne Paetz, Michael Backes & Katja Obst entitled CINNAMAMIDES AS SAVORY FLAVORINGS (assigned to Symrise), Rubescenamine (along with a number of structurally similar compounds) is disclosed as an excellent savory flavor ingredient.
Rubescenamine at 5 mg/kg test concentration is characterized by an umami taste that is very similar to that of monosodium glutamate (MSG), which above all enhances the mouth-fill and meaty character and the mouth-watering effect significantly, without tasting unpleasantly sweet.



4-amino-5-(3-(isopropylamino)-2,2-dimethyl-3-oxopropoxy)-2-methylquinoline-3-carboxylic acid; 5-(2-(isopropylcarbamoyl)-2-methylpropoxy)-4-amino-2-methylquinoline-3-carboxylic acid

Sweetness enhancer / modifier

This material is covered by the claims in Senomyx United States Patent Application 20110245353 (Oct. 6, 2011) entitled Sweet Flavor Modifier and specifically mentioned in Senomyx United States Patent Application 20120041078 (Feb. 16, 2012) entitled METHOD OF IMPROVING STABILITY OF SWEET ENHANCER AND COMPOSITION CONTAINING STABILIZED SWEET ENHANCER



Ebanol®; 3-Methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol

Sandalwood, Musk aspect, Powerful

Givaudan indicates - Olfactive note: Sandalwood, Musk aspect, Powerful
Description: Ebanol has a very rich, natural sandalwood odour. It is powerful and intense, bringing volume and elegance to woody accords and a diffusive sandalwood effect to compositions. Ebanol is highly substantive on all supports.

The enantiomers of Ebanol are described at http://www.leffingwell.com/chirality/ebanol.htm



Javanol®; (1-Methyl-2-(1,2,2-trimethylbicyclo[3.1.0]-hex-3-ylmethyl)cyclopropyl)methanol (Mixture of diastereoisomers)

Sandalwood, creamy, rosy, powerful odor

This material is one of the most powerful and best of the sandalwood replacements.

Givaudan indicates - Olfactive note: Sandalwood, Creamy, Rosy, Powerful
Description: Javanol is a new-generation sandalwood molecule with unprecedented power and substantivity. It has a rich, natural, creamy sandalwood note like beta santalol. With its exceptonal low threshold, it is approximately 8x more effective in wash tests on a weight basis than the most powerful known product.

Cassyrane®, Ebanol®, Javanol® and Toscanol® are trademarks of Givaudan SA

We look forward to receiving additional insights and descriptors for these materials - email: leffingwell@mindspring.com