Chirality & Odour Perception

Acyclics (Alcohols, Esters, Acids, Aldehydes)

by John C. Leffingwell, Ph.D.

Photo by permission of M. Roudintska - Art & Parfum

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones & Furanones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

Enantiomer & Odor Description
 Odour Threshold (PPB)

Acyclics (Alcohols, Esters, Acids, Aldehydes)

..

(2S)-(+)-2-Butanol - oily, wine-like (vinous)

59.1 µg/Liter in air

(2R)-(-)-2-Butanol - oily, wine-like (vinous)

41.8 µg/Liter in air

(R)-(+)-2-methylbutanol - fermented, fatty

NA

(S)-(-)-2-methylbutanol - ethereal, fresh

NA

(-)-(2R)-2-ethylhexanol - Odor description: heavy, earthy, and slightly floral

NA

(+)-(2S)-2-ethylhexanol - Odor description: a light, sweet floral fragrance

NA

(R)-4-methylhexanol - a green, fatty, and nut- and carrot-like odor

NA

(S)-4-methylhexanol - a spicy, nutty, slightly green, and sour note

NA

(S)-(+)-2-methylbutanal - pungent, fresh, fruity (Boelens, et. al.); Peculiar to burnt cocoa and coffee like, in high concentrations pungent (Bartschat et. al)

10 (in air)

(R)-(-)-2-methylbutanal - pungent, caprylic (Boelens, et. al.); Peculiar to burnt cocoa and coffee like (Bartschat et. al)

100 (in air)

(3S)-3-methylpentanal -Intensive green, fresh, in high concentrations sweet(y) & faint fruity; in low concentrations - a slightly pungent odor

30 (in air)

(3R)-3-methylpentanal - No fragrance impression at >2.5 ppm in air

>2500 (in air)

(4S)-4-methylhexanal - No fragrance impression at >0.25 ppm in air

>250 (in air)

(4R)-4-methylhexanal - Intensive, flowery, warm with a green & fresh note

30 (in air)

(S)-(+)-2-methylbutanoic acid - fruity, sweet

NA

(R)-(-)-2-methylbutanoic acid - cheesey, sweaty

NA

(R)-2-methylpentanoic acid - pleasant sweet, fruit note; also described as weak sweaty fruity

NA

(S)-2-methylpentanoic acid - sweet, pungent, heavy; also described as sweaty fruity

NA

R)-2-methylhexanoic acid - sweet, sweaty odor

NA

S)-2-methylhexanoic acid - sour, pungent, musty odor

NA

(S)-(-)-4-methylhexanoic acid - caprylic, slightly fatty; GC-O has confirmed both enantiomers to possess acidic, fatty notes, with the (R)-enantiomer being more potent (Dregus et al.).

NA

(R)-(+)-4-methylhexanoic acid - stronger than (S)-(-)-isomer, more fatty; GC-O has confirmed both enantiomers to possess acidic, fatty notes, with the (R)-enantiomer being more potent (Dregus et al.).

NA

(4S)-4-methyloctanoic acid - muttony, goaty, fresher than the (R)-enantiomer

<13 (in air)

(4R)-4-methyloctanoic acid - muttony, goaty, fusty

<25 in air

(S)-(-)-4-ethyloctanoic acid - goaty, reminiscent of fresh goat's milk cheese

<6 (in air)

(R)-(+)-4-ethyloctanoic acid - fusty, goaty-muttony

<13 (in air)

(4S)-4-methylnonanoic acid - more intensive than the (R)-enantiomer, reminiscent of mutton & goat

<250 (in air)

(4R)-4-methylnonanoic acid - weak, sweaty

<250 (in air)

Methyl (S)-(+)-2-methylbutanoate - fruity, apple-like

0.3 (perception) in water

Methyl (R)-(-)-2-methylbutanoate - fruity, dairy

~ 0.5 (perception) in water

Ethyl (S)-(+)-2-methylbutanoate - fresh fruity, apple-like; also described as an etheric, sweety, unspecific, pleasant apple note at extreme dilution (Amano, et al.)

0.006

Ethyl (R)-(-)-2-methylbutanoate - fruity, caprylic; also described as having a first medical-phenolic note and then a fruity-sweet but unspecific note (Amano, et al.)

~ 1

Propyl (R)-2-methylbutanoate - weak, unspecific (by GC-O)

NA

Propyl (S)-2-methylbutanoate - intensive, full-ripe apple-note (by GC-O)

NA

Methyl (R)-2-methylpentanoate - nearly odorless (by GC-O)

NA

Methyl (S)-2-methylpentanoate - fruity, sweet, apple-like (by GC-O)

NA

Ethyl (R)-2-methylpentanoate - fruity, sweet, apple-like (by GC-O)

NA

Ethyl (S)-2-methylpentanoate - very intensive, fruity, sweet, very pleasant apple note (by GC-O)

NA

Ethyl (S)-(+)-3-methyl-2-oxo-pentanoate - a typical walnut note, accompanied by a walnut-husk, pungent, ethereal, slightly fruity odor

NA

Ethyl (R)-(-)-3-methyl-2-oxo-pentanoate - typical walnut note, but its odor is more pungent, more dry, less powerful and does not possess the fruity-apple note present in the (S)-isomer

NA

(+)-Ethyl (2R)-2-(1,1-dimethylpropoxy)propanoate - a connotation of the chamomile type. This note is particularly distinct in the odor of the ethyl (R)-2-(1,1-dimethylpropoxy)propionate whose fruity note is also very strong.

NA

(-)-Ethyl (2S)-2-(1,1-dimethylpropoxy)propanoate - a more spicy note which also comprises a chamomile type under note and other notes reminiscent of ethyl 2-acetyl-4-methyl-4-pentanoate, the wine lees, linalool and also coriander

NA

(2S)-(+)-2-Butyl acetate - intensive fruity ester note, slightly volatile

NA

(2R)-(-)-2-Butyl acetate - musty, herbaceous, slightly volatile

NA

(2S)-(+)-2-Butyl butanoate - intensely fruity, sweet ester note

NA

(2R)-(-)-2-Butyl butanoate - flowery, musty, weaker than its enantiomer

NA

(2S)-(+)-2-Butyl hexanoate - intensive fruity penetrating note

NA

(2R)-(-)-2-Butyl hexanoate - herbaceous, weaker than its enantiomer

NA

(2S)-(+)-2-Butyl octanoate - distinct ester note

NA

(2R)-(-)-2-Butyl octanoate - first sweet, then smoky

NA

(S)-(+)-2-pentyl acetate - Fruity, apple, plum, metallic

NA

(R)-(-)-2-pentyl acetate - Fruity, Muscat, green, metallic, chemical

NA

(2S)-(+)-2-Pentyl butanoate - fruity, easily volatile, sweaty aftersmell

NA

(2R)-(-)-2-Pentyl butanoate - spicy, smoky

NA

(S)-(+)-2-pentyl hexanoate - pleasant, fruity note

NA

(R)-(-)-2-pentyl hexanoate - flowery fragrance like

(2S)-(+)-2-Pentyl octanoate - weak fruity

NA

(2R)-(-)-2-Pentyl octanoate - unspecific, very weak

NA

(S)-2-hexyl acetate - Sweaty, sour, fruity, plum, nectarine

NA

(R)-2-hexyl acetate- Sour, fruity, cherry, plum, strawberry

NA

(2S)-(+)-2-Hexyl butanoate - pure fruity

NA

(2R)-(-)-2-Hexyl butanoate - weak fruity, herbaceous

NA

(2S)-(+)-2-hexyl hexanoate - spicy

NA

(2R)-(-)-2-hexyl hexanoate - sweet, flowery

NA

(2S)-(+)-2-Hexyl octanoate - weak spicy

NA

(2R)-(-)-2-Hexyl octanoate - very weak sweet, flowery

NA

(S)-(+)-2-heptyl acetate - Mushroom, earthy, wild berry (Nozaki, et. al.); also described as weak, pure fruity (Mosandl & Deger)

NA

(R)-(-)-2-heptyl acetate - Green, fatty, banana, methyl ketone (Nozaki, et. al.); also described as penetrating, sweat note (Mosandl & Deger)

NA

(2S)-(+)-2-Heptyl butanoate - distinct fruity aroma note

NA

(2R)-(-)-2-Heptyl butanoate - fruity-sweet ketone note

NA

(2S)-(+)-2-Heptyl hexanoate - distinct fruity ester note

NA

(2R)-(-)-2-Heptyl hexanoate - fruity sweet ketone note

NA

(2S)-(+)-2-Heptyl octanoate - moldy, musty, unspecific

NA

(2R)-(-)-2-Heptyl octanoate - very weak herbaceous, unspecific

NA

S)-2-octyl acetate - Methyl ketone, fruity, plum, dusty

NA

(R)-2-octyl acetate - Methyl ketone, fatty burnt, boiled vegetable

NA

(2S)-(+)-2-Octyl butanoate - weak fruity

NA

(2R)-(-)-2-Octyl butanoate - weak flowery note

NA

(2S)-(+)-2-Octyl hexanoate - intensive pure fruit note, reminiscent of raspberries

NA

(2R)-(-)-2-Octyl hexanoate - herbaceous, green

NA

(2S)-(+)-2-Octyl octanoate - first fine fruity, then intensive lovage note

NA

(2R)-(-)-2-Octyl octanoate - weak fruity, unspecific note

NA

(2S)-(+)-2-Nonyl acetate - typical fruity note

NA

(2R)-(-)-2-Nonyl acetate - flowery, more intense than its enantiomer

NA

(2S)-(+)-2-Nonyl butanoate - first unspecific, then somewhat spicy

NA

(2R)-(-)-2-Nonyl butanoate - unspecific, weak flowery

NA

(2S)-(+)-2-Nonyl hexanoate - flowery sweet

NA

(2R)-(-)-2-Nonyl hexanoate - weak fruity, slightly earthy note

NA

(2S)-(+)-2-Nonyl octanoate - weak unspecific note

NA

(2R)-(-)-2-Nonyl octanoate - weak unspecific note, but distinguishable

NA

(S)-3-Heptyl acetate - exhibits a rosy, fresh, agrest scent

NA

(R)-3-Heptyl acetate - exhibits a green, fruity pear scent

NA

(S)-2-pentanol - Heavy, wild berry, ripe, dusty, astringent

NA

(R)-2-pentanol - Light, seedy, sharp

NA

(S)-2-hexanol - Mushroom, green, ripe, berry, astringent, metallic

NA

(R)-2-hexanol - Mushroom, dusty, oily

NA

(S)-2-heptanol - Mushroom, oily, fatty, blue cheese, mouldy

NA

(R)-2-heptanol - Fruity, sweet, oily, fatty

NA

(S)-3-Heptanol - exhibits a lavender medicinal scent

NA

(R)-3-Heptanol - exhibits an earthy, mushroom scent

NA

(S)-2-octanol - Mushroom, oily, fatty, creamy, grape

NA

(R)-2-octanol - Creamy, cucumber, fatty, sour

NA

(-)-(1R,2S)-2-heptylcyclopropanecarboxylic acid - The enantiomers of the cis isomer give odour notes that can be described as follows: woody, balsamic, incense-like, green, herbal, pith-like and waxy; In addition, mixtures of the enantiomers of the cis isomers of 2-heptylcyclopropyl-1-carboxylic acid have a balsamic, peel-like but not aldehydic flavour note. However, the non-natural (1R,2S) cis enantiomer displays a very much weaker odour than the naturally occurring (1S,2R) enantiomer.

NA

(+)-(1S,2R)-2-heptylcyclopropanecarboxylic acid - The enantiomers of the cis isomer give odour notes that can be described as follows: woody, balsamic, incense-like, green, herbal, pith-like and waxy; In addition, mixtures of the enantiomers of the cis isomers of 2-heptylcyclopropyl-1-carboxylic acid have a balsamic, peel-like but not aldehydic flavour note. However, the natural (1S,2R) cis enantiomer displays a very much stronger odour than the non-naturally occurring (1R,2S) enantiomer.

NA

(S)-1-hexen-3-ol - Metallic, green, earthy

NA

(R)-1-hexen-3-ol - Top impact, acid, meat, stronger than the (S)-enantiomer

NA

(S)-1-hepten-3-ol - Fruity, earthy

NA

(R)-1-hepten-3-ol - Chemical, diffusible, green

NA

(S)-(+)-1-octen-3-ol - moldy, grassy, artificial; also desribed as herbaceous, green, musty

100 ppb in aqueous ethanol

(R)-(-)-1-octen-3-ol - fruity, genuine mushroom-like; also desribed as intensive mushroom note, fruity, soft

10 ppb in aqueous ethanol

(S)-1-nonen-3-ol - Heavy, metallic, aldehydic

NA

(R)-1-nonen-3-ol - Mushroom, cheesy, fruity

NA

(S)-1-decen-3-ol - Metallic, oily, waxy, earthy

NA

(R)-1-decen-3-ol - Heavy, aldehydic, lactone

NA

(R)-(-)-2-ethylhexanoic acid - herbaceous, earthy

NA

(S)-(+)-2-ethylhexanoic acid - sweet, herbaceous, faint musty

NA

(R)-(+)-2,5,6-trimethyl-2-heptanol - odor typical of white flowers, reminiscent of linalool, with a slight connotation of terpineol, and a lilac and fruity note

NA

(S)-(-)-2,5,6-trimethyl-2-heptanol - more floral and citrus-like, showing a note reminiscent of dimethyloctanol, a soapy and a slight aldehyde connotation

NA

(4S,5S)-(+)-epoxy-(E)-2-decenal - At 0.02 ppb in water - no smell, no taste (weakest enantiomer)

NA

(4R,5R)-(-)-epoxy-(E)-2-decenal - At 0.02 ppb in water - faint smell, mild metallic taste (strongest enantiomer)

NA

(-)-(E,R)-Filbertone [(-)-(E,R)-5-methyl-2-hepten-4-one] - hazelnut, soft, butter, chocolate, metallic, weaker impact (at 25 ppb in water)

see comments

(+)-(E,S)-Filbertone [(+)-(E,S)-5-methyl-2-hepten-4-one] - hazelnut, metallic, fatty, pyidine, stronger impact (at 25 ppb in water)

see comments

(R)-(+)-3-hydroxy-3-methylhexanoic acid - Cumin spice like odor, weaker than racemic body; also described by Hasegawa et. al. as having a weak animalic odor

NA

(S)-(-)-3-hydroxy-3-methylhexanoic acid - Armpit odor like and cumin spice like odor; also described by Hasegawa et. al. as having a strong spicy odor

NA

(-)-(S)-Undecavertol (ee = 75%) - Weaker enantiomer, fruity-green, pinefir balsam note with aspects of tea, not so typical of Undecavertol.

4.7 ng/L air

(+)-(R)-Undecavertol (ee = 93%) - Typical Undecavertol odour, floral, green, fresh, violet leaves, stronger and greener than the racemic commercial material, with aspects of cucumber and Neofolione (methyl non-2-enoate).

0.31 ng/L air

(4R)-4-hydroxypentan-2-one - a rather musty odour, but with some reminiscense of the (S)-enantiomer.

NA

(4S)-4-hydroxypentan-2-one - fresh herbaceous, grassy notes.

NA

(R)-8-Methyldecanal - Green, fresh (stronger than (S)-form), lack of Yuzu-like note

NA

(S)-8-Methyldecanal - Fresh, green, bitter odor, reminiscent of Yuzu

NA

(R)-6-Methyloctanal - Oily, lacking citrusy character, weak

NA

(S)-6-Methyloctanal - Fresh, green, sweet, citrus-like

NA

(R)-Ethyl 2-methylpentanoate - Top note: Etheric, phenolic; Middle~Last note: Dusty

NA

(S)-Ethyl 2-methylpentanoate - Fruity (apple, pear, star fruit, pineapple-like), sweet and full-flavored

NA

Methyl (2R,3R)-2-hydroxy-3-methylpentanoate - Odor quality perceived at the sniffing port during GC-O = Not available

>200 ng/L in air

Methyl (2S,3S)-2-hydroxy-3-methylpentanoate - Odor quality perceived at the sniffing port during GC-O = fruity

10 ng/L in air

Methyl (2S,3R)-2-hydroxy-3-methylpentanoate - Odor quality perceived at the sniffing port during GC-O = fruity

110 ng/L in air

Methyl (2R,3S)-2-hydroxy-3-methylpentanoate - Odor quality perceived at the sniffing port during GC-O = fruity

11 ng/L in air

4-((2R)-6-methylheptan-2-yloxy)butanal - Aldehydic, floral, citrus, muguet, lower intensity than the racemate

NA

4-((2S)-6-methylheptan-2-yloxy)butanal - Aldehydic, floral, green, watery, more intensive and diffusive than the racemate

NA

3-((2'R)-6-methylheptan-2'-yloxy)-(2RS)-2-methylpropanal - Aldehydic, citrus

NA

3-((2'S)-6-methylheptan-2'-yloxy)-(2RS)-2-methylpropanal - Aldehydic, citrus, marine

NA

Methyl (R)-(-)-3-hydroxyhexanoate - sweet, woody, fruity

2.1 ng/L in air

Methyl (S)-(+)-3-hydroxyhexanoate - weak and aldehyde-like

4380 ng/L in air

Ethyl (R)-(-)-3-hydroxyhexanoate - sweet, woody, fruity.

2.1 ng/L in air

Ethyl (S)-(+)-3-hydroxyhexanoate - weak fruity and aldehyde-like.

264.5 ng/L in air

(R)-2-Methylundecanal - similar to its enantomer in description and intensity; the racemate is describe as having a dry, slight fruity odor reminiscent of ambergris and incense with floral waxy notes (Givaudan) and a strong "fatty, green, citrus odor with fatty citrus taste" (Leffingwell, Flavor-Base 2007)

NA

(S)-2-Methylundecanal - similar to its enantomer in description and intensity

NA

(+)-(2S,3S)-2,3-Methano-3,7-dimethyl-6-octen-1-ol - Woody rosy odor with sweetness of nerol; similar to, but more woody than the racemate.

NA

(-)-(2R,3R)-2,3-Methano-3,7-dimethyl-6-octen-1-ol - Woody rosy odor close to the racemate, a little bit more woody

NA

(+)-(2R,3S)-2,3-Methano-3,7-dimethyl-6-octen-1-ol - Woody rosy odor with aromatic aspect reminiscent of sulfrol found in the top note of sandalwood oil

NA

(-)-(2S,3R)-2,3-Methano-3,7-dimethyl-6-octen-1-ol - Nerol-like odor (floral-rosy), but less intensive than the racemate.

NA

(+)-(2R,3S)-2,3-Methano-1-pentanol - Difusive ether green odor, close to nor-leaf alcohol, more green than the racemate or its enantiomer

NA

(-)-(2S,3R)-2,3-Methano-1-pentanol - Weak rosy odor without characteristic green aspect found in the racemate

NA

(-)-(R)-1,2-Methano-3-octanol - Sweet matsutake-like (mushroom-like) odor, close to natural (R)-matsutakeol (natural 1-octen-3-ol)

NA

(+)-(S)-1,2-Methano-3-octanol - Humid mossy rosy odor, no mushroom character as found in the racemate

NA

(-)-(S)-1-isopropoxy-1-oxopropan-2-yl pivalate - possesses an odor having a floral, rosy/geranium type note having also a linalool, citronellol, geranyl acetate aspect, as well as a fruity, citrusy type note having lemon, bergamot aspects. The overall hedonic effect is an interesting rosy/geranium and fruity impression.

NA

(+)-(R)-1-isopropoxy-1-oxopropan-2-yl pivalate - possesses an odor similar to the one of the S enantiomer but distinguishing itself by a slightly more pronounced fruity note and being less raising than the S enantiomer.

NA

(2S)-3-mercapto-2-methylpropan-1-ol - Weaker than the (2R)-enantiomer. Although both of the enantiomers are characterized by the same broth and sweat odour, they have very different odour strength and thresholds.

35-40 ppb

(2R)-3-mercapto-2-methylpropan-1-ol - Stronger than than the (2S)-enantiomer. Although both of the enantiomers are characterized by the same broth and sweat odour, they have very different odour strength and thresholds.

3-7 ppb

3R)-3-mercaptohexan-1-ol - In dilution, the (R)-enantiomer is distinctly weaker, showing only sulfury and herbaceous odor impressions - (description of Werkhoff, et. al.); The two enantiomers have quite different aromas; Tominaga et. al. (2006) indicates "The R form is fruitier, with a zesty aroma reminiscent of grapefruit, while the S form smells more of passion fruit".

0.08 ng/L in air

(3S)-3-mercaptohexan-1-ol - In dilution, posseses interesting exotic and tropical fruit notes - (description of Werkhoff, et. al.); Werkhoff, et. al. described the 3-mercaptohexanols as fruity, juicy, tropical fruits, grapefruit, black currant, buccu, mango, guava; Tominaga et. al. (2006) indicates "The R form is fruitier, with a zesty aroma reminiscent of grapefruit, while the S form smells more of passion fruit".

0.07 ng/L in air

(3R)-(-)-3-mercaptohexyl acetate - In dilution, posseses attractive tropical fruity notes (for the (3R)-3-mercaptohexyl acetate and (3R)-3-mercaptohexyl butanoate) - (description of Werkhoff, et. al.); Werkhoff, et. al. described the 3-mercaptohexyl acetates as grapefruit, black currant, buccu, mango, passion fruit, guava

0.10 ng/L in air

(3S)-(+)-3-mercaptohexyl acetate - In dilution, posseses insignificant sulfury, herbaceous and oniony characteristics (for the (3S)-3-mercaptohexyl acetate and (3S)-3-mercaptohexyl butanoate) - (description of Werkhoff, et. al.)

0.03 ng/L in air

(3R)-3-mercaptohexyl butanoate - In dilution, posseses attractive tropical fruity notes (for the (3R)-3-mercaptohexyl butanoate) and (3R)-3-mercaptohexyl acetate - (description of Werkhoff, et. al.); Werkhoff, et. al. described the 3-mercaptohexyl butanoates as fruity, grapefruit, black currant, buccu, tropical fruits, mango

NA

(3S)-3-mercaptohexyl butanoate - In dilution, posseses insignificant sulfury, herbaceous and oniony characteristics (for the (3S)-3-mercaptohexyl butanoate) and (3S)-3-mercaptohexyl acetate - (description of Werkhoff, et. al.)

NA

(3R)-3-mercaptohexyl hexanoate - herbaceous, fresh sulfur note

NA

(3S)-3-mercaptohexyl hexanoate - sulfurous, burnt

NA

(3R)-(-)-3-mercaptoheptyl acetate - 3-mercaptoheptyl acetate (as the racemate) possesses a relatively weak top note reminding of a peach, citrus and tea tonality

NA

(3S)-(+)-3-mercaptoheptyl acetate - Amongst said enantiomers the most appreciated is the (S) one, which has a taste very close to the one of the racemate, although its grapefruit type note is weaker than the one of the racemate.

NA

(3R)-3-acetylthiohexanol - fruity, grapefruit, sulfurous

NA

(3S)-3-acetylthiohexanol - sulfurous, roasted, rubberlike

NA

(3R)-3-mercaptohexanal - sulfurous, rubberlike

NA

(3S)-3-mercaptohexanal - green, citrus peel, fruity

NA

(3R)-3-acetylthiohexanal - sulfurous, roasted, citrus peel

NA

(3S)-3-acetylthiohexanal - fruity, sweet, grapefruit

NA

(R)-3-methylthiobutanal - exhibits the odour typical of cooked potatoes.

NA

(S)-3-methylthiobutanal - odourless

NA

(S)-(+)-3-(methylthio)-hexan-1-ol - exotic, fruity; also described as exotic and tropical fruit

NA

(R)-(-)-3-(methylthio)-hexan-1-ol - herbaceous, weak; also described as weaker, sulfury and herbaceous

NA

(3R)-3-(methylthio)hexyl acetate - fruity

NA

(3S)-3-(methylthio)hexyl acetate - intensive sulfurous, herbaceous

NA

(3R)-3-(methylthio)hexyl butyrate - very weak, unspecific fruity

NA

(3S)-3-(methylthio)hexyl butyrate - oniony, later weak fruity

NA

(3R)-3-(methylthio)hexyl hexanoate - very weak, unspecific fruity

NA

(3S)-3-(methylthio)hexyl hexanoate -weak oniony, roasty

NA

(2R,3S)-3-mercapto-2-methyl-pentane-1-ol - broth-like, sweaty, leek-like

0.04

(2S,3R)-3-mercapto-2-methyl-pentane-1-ol - broth-like, sweaty, leek-like

0.03

(2S,3S)-3-mercapto-2-methyl-pentane-1-ol - broth-like, sweaty, leek-like

>30

(2R,3R)-3-mercapto-2-methyl-pentane-1-ol - broth-like, sweaty, leek-like

> 12

(3S)-(-)-3-mercapto-3-methylhexan-1-ol - The (S)-isomer exhibits herbaceous, agrestic and green notes; Also described as sweat and onion-like (Troccaz, et.al); also described by Hasegawa et. al. as having a strong meaty, fruity note wth a charachteristic sulfury odor

NA

3R)-(+)-3-mercapto-3-methylhexan-1-ol - The (R)-isomer can be described as grapefruit/passion fruit, black currant and onion-like; Also described as fruity and grapefruit-like (Troccaz, et.al); also described by Hasegawa et. al. as having a green fruity note

NA

(-)-(2S)-Heptane-2-thiol - bell pepper, fruity, vegetable at lower concentrations; at higher concentrations (100-1000 times the threshold) - sulfury, onion, with some mushroom note; No differences in odor note and threshold value were observed for the enantiomeric forms.

10

(+)-(2R)-Heptane-2-thiol - bell pepper, fruity, vegetable at lower concentrations; at higher concentrations (100-1000 times the threshold) - sulfury, onion, with some mushroom note

10

(+)-(3S)-1-Methoxyhexane-3-thiol - In addition to the herbaceous and (clary) sage odor tonalities it has strong connotations of burnt sulfur and alliaceous notes and evokes associations with human olfactory axillary perspiration.

0.04 x 10-3 ng/liter air

(-)-(3R)-1-Methoxyhexane-3-thiol - sulfury, herbaceous and onion-like and definitely lacks the unique clary-sage signal.

1.09 x 10-3 ng/liter air

(-)-(S)-1-methoxyheptane-3-thiol - a nice natural black-currant note accompanied by green and tropical fruit notes.

NA

(+)-(R)-1-methoxyheptane-3-thiol - 1-methoxyheptane-3-thiol (racemic) imparts a floral, green gardenia note recalling the floral-fruity odor of styrallyl acetate, whereas 1-ethoxyhexane-3-thiol is able to impart a berry, blackberry type and vegetable note.

NA

(-)-S-methyl (2R)-2-methylbutanethioate - A beautiful, fresh, highly-taste, unique, strong odor which reminds a strong, fresh passion fruit. As seen, the S-methyl (R)-2-methylbutanethioate used in the flavor composition or fragrance composition of the present invention had a beautiful, fresh, highly-taste, unique, strong flavor and fragrance which reminded (of) a strong, fresh passion fruit.

NA

(+)-S-methyl (2S)-2-methylbutanethioate - S-methyl 2-methylbutanethioate (as the racemic form) has an odor which is natural but is low in strength and has slight other smells. Meanwhile, all the perfumers or flavorists pointed out that the racemic S-methyl2-methylbutanethioate had an odor which was natural but was low in strength and had slight other smells.

NA

D-Methionine - "moldy", "old potatoes" and "rotten dairy products" (panelists spontaneous comments) for both D- & L-methionine

1.5 ppm

L-Methionine - "moldy", "old potatoes" and "rotten dairy products" (panelists spontaneous comments) for both D- & L-methionine

11.9 ppm

D-Cysteine - "sulfur" and "rotten eggss" (panelists spontaneous comments) for both D- & L-cysteine

26.7 ppm

L-Cysteine - "sulfur" and "rotten eggss" (panelists spontaneous comments) for both D- & L-cysteine

24.2 ppm

L-Proline - smell of "semen", "sperm", and "chlorine" (panelists spontaneous comments) for both D- & L-proline

11513 ppm

D-Proline - smell of "semen", "sperm", and "chlorine" (panelists spontaneous comments) for both D- & L-proline

8635 ppm

(2R,3R)-3-((dimethyl(2,3-dimethylbutan-2-yl)silyl)methyl)butan-2-ol - camphoraceous-earthy and green odor, slightly sweaty and somewhat floral

NA

(2S,3S)-3-((dimethyl(2,3-dimethylbutan-2-yl)silyl)methyl)butan-2-ol - more earthy-mouldy than camphoraceous, with fruity green-metallic nuances

NA

4-{[(1R)-1,5-dimethylhexyl]oxy}butanal - Aldehydic, floral, citrus, muguet, lower intensity than racemate

NA

4-{[(1S)-1,5-dimethylhexyl]oxy}butanal - Aldehydic, floral, green, watery, more intensive and diffusive than racemate

NA

3-{[(1R)-1,5-dimethylhexyl]oxy}-2-methylpropanal - Aldehydic, citrus

NA

3-{[(1S)-1,5-dimethylhexyl]oxy}-2-methylpropanal - Aldehydic, citrus, marine

NA

Ethyl (2S)-2-hydroxy-4-methylpentanoate - fresh blackberry aroma. Both enantiomers have quite similar aromatic nuances.

55 ppb

Ethyl (2R)-2-hydroxy-4-methylpentanoate - fresh blackberry aroma. Both enantiomers have quite similar aromatic nuances.

126 ppb

(3R)-3-Hydroxy-2-octanone - a mushroom-like, fresh grass odour.

NA

(3S)-3-Hydroxy-2-octanone - a mushroom-like, earthy note

NA

(4R)-4-acetylthio-2-pentanone - more unpleasant (catty, sulfury) descriptions for the (R)-enantiomer (by GC-O)

230 ng/L air

(4S)-4-acetylthio-2-pentanone - more fruity-pleasant (grapefruit, blackcurrant) notes for the (S)-enantiomer (by GC-O)

110 ng/L air

(4R)-4-acetylthio-2-hexanone - more unpleasant (catty, sulfury) descriptions for the (R)-enantiomer (by GC-O)

1800 ng/L air

(4S)-4-acetylthio-2-hexanone - more fruity-pleasant (grapefruit, blackcurrant) notes for the (S)-enantiomer (by GC-O)

350 ng/L air

(4R)-4-acetylthio-2-heptanone - more unpleasant (catty, sulfury) descriptions for the (R)-enantiomer (by GC-O)

22 ng/L air

(4S)-4-acetylthio-2-heptanone - more fruity-pleasant (grapefruit, blackcurrant) notes for the (S)-enantiomer (by GC-O)

21 ng/L air

(4R)-4-acetylthio-2-octanone - more unpleasant (catty, sulfury) descriptions for the (R)-enantiomer (by GC-O)

24 ng/L air

(4S)-4-acetylthio-2-octanone - more fruity-pleasant (grapefruit, blackcurrant) notes for the (S)-enantiomer (by GC-O)

57 ng/L air

(4R)-4-acetylthio-2-nonanone - more unpleasant (catty, sulfury) descriptions for the (R)-enantiomer (by GC-O)

200 ng/L air

(4S)-4-acetylthio-2-nonanone - more fruity-pleasant (grapefruit, blackcurrant) notes for the (S)-enantiomer (by GC-O)

500 ng/L air

(4R)-4-acetylthio-2-decanone - more unpleasant (catty, sulfury) descriptions for the (R)-enantiomer (by GC-O)

7600 ng/L air

(4S)-4-acetylthio-2-decanone - more fruity-pleasant (grapefruit, blackcurrant) notes for the (S)-enantiomer (by GC-O)

8300 ng/L air

(4R)-4-mercapto-2-pentanone - more unpleasant (catty, sulfury) descriptions for the (R)-enantiomer (by GC-O)

1.2 ng/L air

(4S)-4-mercapto-2-pentanone - more fruity-pleasant (grapefruit, blackcurrant) notes for the (S)-enantiomer (by GC-O)

0.99 ng/L air

(4R)-4-mercapto-2-hexanone - more unpleasant (catty, sulfury) descriptions for the (R)-enantiomer (by GC-O)

69 ng/L air

(4S)-4-mercapto-2-hexanone - more fruity-pleasant (grapefruit, blackcurrant) notes for the (S)-enantiomer (by GC-O)

0.45 ng/L air

(4R)-4-mercapto-2-heptanone - more unpleasant (catty, sulfury) descriptions for the (R)-enantiomer (by GC-O)

0.79 ng/L air

(4S)-4-mercapto-2-heptanone - more fruity-pleasant (grapefruit, blackcurrant) notes for the (S)-enantiomer (by GC-O)

0.22 ng/L air

(4R)-4-mercapto-2-octanone - more unpleasant (catty, sulfury) descriptions for the (R)-enantiomer (by GC-O)

0.09 ng/L air

(4S)-4-mercapto-2-octanone - more fruity-pleasant (grapefruit, blackcurrant) notes for the (S)-enantiomer (by GC-O)

0.04 ng/L air

(4R)-4-mercapto-2-nonanone - more unpleasant (catty, sulfury) descriptions for the (R)-enantiomer (by GC-O)

0.86 ng/L air

(4S)-4-mercapto-2-nonanone - more fruity-pleasant (grapefruit, blackcurrant) notes for the (S)-enantiomer (by GC-O)

0.76 ng/L air

(4R)-4-mercapto-2-decanone - more unpleasant (catty, sulfury) descriptions for the (R)-enantiomer (by GC-O)

36 ng/L air

(4S)-4-mercapto-2-decanone - more fruity-pleasant (grapefruit, blackcurrant) notes for the (S)-enantiomer (by GC-O)

36 ng/L air

(2S,4R)-4-mercapto-2-heptanol - sulfury, savory, meaty (by GC-O)

0.2 ng/L air

(2R,4S)-4-mercapto-2-heptanol - sulfury, green, dill (by GC-O)

0.3 ng/L air

(2R,4R)-4-mercapto-2-heptanol - sulfury, fruity, flowery (by GC-O)

0.1 ng/L air

(2S,4S)-4-mercapto-2-heptanol - sulfury, onion, sweet (by GC-O)

0.05 ng/L air

(2S,4R)-4-mercapto-2-heptyl acetate - sulfury, passion fruit (by GC-O)

0.2 ng/L air

(2R,4S)-4-mercapto-2-heptyl acetate - sulfury, grapefruit (by GC-O)

6.1 ng/L air

(2R,4R)-4-mercapto-2-heptyl acetate - sulfury, sweet (by GC-O)

2.1 ng/L air

(2S,4S)-4-mercapto-2-heptyl acetate - sulfury, onion (by GC-O)

0.03 ng/L air

(2S,4R)-4-acetylthio-2-heptyl acetate - sulfury, grapefruit (by GC-O)

0.3 ng/L air

(2R,4S)-4-acetylthio-2-heptyl acetate - sulfury, green (by GC-O)

1.3 ng/L air

(2R,4R)-4-acetylthio-2-heptyl acetate - sulfury, fruity, fresh (by GC-O)

5.5 ng/L air

(2S,4S)-4-acetylthio-2-heptyl acetate - sulfury, onion, fruity (by GC-O)

0.09 ng/L air

(2S,4R)-4-acetylthio-2-heptanol - grapefruit, refreshing (by GC-O)

0.2 ng/L air

(2R,4S)-4-acetylthio-2-heptanol - grapefruit, fruity, sweet (by GC-O)

4.9 ng/L air

(2R,4R)-4-acetylthio-2-heptanol - savory, sweet (by GC-O)

17.2 ng/L air

(2S,4S)-4-acetylthio-2-heptanol - sulfury, onion, sweet (by GC-O)

0.03 ng/L air

Prenyl (2S)-2-methylpentanoate - Odor - reminiscent of black currant

Prenyl (2R)-2-methylpentanoate - Odor - musty, sweety, fruity, weak chemical

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