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

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

(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

(R)-(+)-7-hydroxy-6,7-dihydrocitronellal - weak floral (lilley-of the-valley) green, leaf-like and minty notes

NA

(S)-(-)-7-hydroxy-6,7-dihydrocitronellal - fresh floral, sweet lily-of-the-valley notes

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

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

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