Chirality & Odour Perception

Acyclic Terpenoid Odorants

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)

Acyclic Terpenoid Odorants

 .

(S)-(+)-linalool - sweet, floral; odor reminiscent of petitgrain and lavender

7.4

(R)-(-)-linalool - floral, woody lavender note

0.8

(S)-(-)-citronellol - floral, rose-like odor, reminiscent of geranium oil; Described by Yamamoto et. al.. as very fresh light and clean rosy-leafy, petal-like

40-50

(R)-(+)-citronellol - citronella oil-like; Described by Yamamoto et. al.., as slightly oily light rosy-leafy, petal like odor with irritating top note

50

(6S)-(-)-6,7-epoxygeraniol - lactone like-rosy

NA

(6R)-(+)-6,7-epoxygeraniol - metallic-rosy

NA

(2S,3S)-(+)-Epoxygeraniol - green-rosy

NA

(2R,3R)-(-)-Epoxygeraniol - floral-rosy

NA

(3S)-(-)-citronellal - powerful, fresh, bright clean, herbaceous-citrusy

25

(3R)-(+)-citronellal - powerful, fresh, herbaceous-citrusy

25

(3S)-(-)-citronellyl acetate - fresh lime citrus odor with camphoraceous note

250

(3R)-(+)-citronellyl acetate - fresh citrus lime odor with dirty aldehyde note

250

(3RS)-citronellyl (2R)-lactate - a flowery character of lily of the valley type, warm and rich and more natural than rosy alcohols (Rosilial PlusTM); this enantiomer (2-diastereomers) was introduced into commerce by Rhodia in early 2003 and is described in their literature as "Rosy floral note with a citrus facet. It brings a natural effect."

NA

(3RS)-citronellyl (2S)-lactate - a flowery honeysuckle character closer to citronellol, which gives it a less natural effect than the (3RS)-citronellyl (2R)-lactate.

NA

(3S)-(-)-citronellyl ethyl ether - clean sweet rosy odor , powerful fresh topnote

500

(3R)-(+)-citronellyl ethyl ether - floral rosy odor

250

(3S)-(+)-citronellyl nitrile - strong citrus odor with aldehyde note

75

(3R)-(-)-citronellyl nitrile - mild fresh citrus

100

(3S)-(-)-dihydrocitronellal - floral odor with sweet rosy note

5

(3R)-(+)-dihydrocitronellal - powerful rosy odor with irritative green note

5

(3S)-(-)-dihydrocitronellol - floral odor like clean rose

250

(3R)-(+)-dihydrocitronellol - chemical, waxy and dry rosy

100

(3S)-(-)-dihydrocitronellyl acetate - clean citrus and muguet floral

250

(3R)-(+)-dihydrocitronellyl acetate - sweet citrus and muguet floral

250

(3RS)-dihydrocitronellyl (2R)-lactate - citronella-like, grassy, woody character

NA

(3RS)-dihydrocitronellyl (2S)-lactate - rosy, woody, lemony character

NA

(3S)-(-)-dihydrocitronellyl ethyl ether - clean, rosy

1000

(3R)-(+)-dihydrocitronellyl ethyl ether - fresh rosy odor with clean fatty topnote

500

(3S)-(+)-dihydrocitronellyl nitrile - citrus floral with fatty and herbal topnote

50

(3R)-(-)-dihydrocitronellyl nitrile - floral and slightly citrus odor with natty and fatty topnote

75

(3S)-(+)-2-methylene-citronellal - clean citrus odor like bergamot

250

(3R)-(-)-2-methylene-citronellal - citrus odor with citronellal-like side note

250

(3S)-(+)-2-methylene-citronellol - fresh citrus peel

500

(3R)-(-)-2-methylene-citronellol - citrus odor with aliphatic aldehyde

1000

(3R)-(+)-7-hydroxy-6,7-dihydrocitronellal - weak floral (liley-of the-valley) green, leaf-like and minty notes (Skorianetz et al.); also described as "powerful irritating, rosy, liley-of the-valley" (Yamamato)

NA

(3S)-(-)-7-hydroxy-6,7-dihydrocitronellal - fresh floral, sweet lily-of-the-valley notes (Skorianetz et al.); also described as "clean, green, lily-of-the-valley and is superior in fine fragrance to its (3R)-(+)- antipode" (Yamamato)

NA

(3S,6E)- (-)-2,3-dihydrofarnesol - a clean, graceful and long-lasting fragrance similar to cyclamen

NA

(3R,6E)-(+)-2,3-dihydrofarnesol - a weak fragrance with a somewhat metallic and balsamic side note

NA

(3E,6R)-2,6-dimethylocta-3,7-diene-2,6-diol - citrus, sweet, powdery

NA

(3E,6S)-2,6-dimethylocta-3,7-diene-2,6-diol - herbal green

NA

(3R)-(-)-3,7-Dimethyl-2-methylene-6-octen-1-al - a somewhat crude citronellal-like perfume

NA

(3S)-(+)-3,7-Dimethyl-2-methylene-6-octen-1-al - an extremely fresh green bergamot-like citrus-based fragrance

NA

(-)-(2S)-5-methyl-2-[(1S)-1-methylprop-2-enyl]hex-4-en-1-ol - possesses a floral rosy, natural note, very fine, presenting multiple aspects, slightly rosinol and green, reminding a little of rose oxide. It provokes indeed odor notes of the family of roses and geranium, with an extremely refined character which evokes the best fractions of rose oil.

NA

(+)-(2R)-5-methyl-2-[(1R)-1-methylprop-2-enyl]hex-4-en-1-ol - develops a floral odorant note, rosy, with a dimension of Rosacène (floral composition; origin: Firmenich SA), tea rose - more pronounced than that of its (S,S)-isomer to which the odor is however closer to that of citronellol.

NA

(R)-Lavandulol - weak floral, herbal odor with slightly lemon-like, fresh citrus fruity nuance

NA

(S)-Lavandulol - very weak odor

NA

(3S)-(+)-Hotrienol - Green fresh flower aroma, graceful and sweet

NA

(3R)-(-)-Hotrienol - Citrus fruit-juice aroma with a pure sweet flower aroma

NA

(S)-(+)-Sulcatol - Both enantiomers of sulcatol were odoriferous to the human nose and smelled like geraniol with almost no difference in the odor as tested by the noses of the author (Mori) and his students

NA

(R)-(-)-Sulcatol - Both enantiomers of sulcatol were odoriferous to the human nose and smelled like geraniol with almost no difference in the odor as tested by the noses of the author (Mori) and his students

NA

(3R)-(+)-Aurantiol - an orange flower fragrance that is not much different from those (prepared from) the other isomeric (d- or dl) forms of hydroxycitronellal, but a more irritating odor, less clean, and less (or none) of the green note as compared to the laevo form. (Yamamato)

NA

(3S)-(-)-Aurantiol - an orange flower fragrance that is not much different from those (prepared from) the other isomeric (d- or dl) forms of hydroxycitronellal, but with a less irritating odor and imparts a clean and green note note as compared to the dextro or racemic forms; therefore, the impression of this substance was that it was of higher quality than the other forms. (Yamamato)

NA

HOME

Telephone: 01-770-8895111 - Email: leffingwell@mindspring.com
Copyright © Leffingwell & Associates
TERMS OF SERVICE.............PRIVACY POLICY