Lactone & Furanone Odorants
by John C. Leffingwell, Ph.D.
Photo by permission of M. Roudintska - Art & Parfum
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Ionones, Irones, Damascones & Structurally Related Odorants |
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Lactones |
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(R)-(+)-4-methylbutan-4-olide - faint sweet |
20000 |
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(S)-(-)-4-methylbutan-4-olide - faint |
NA |
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(R)-(+)-4-ethylbutan-4-olide - faint, sweet coconut, hatty, herbaceous, hay note |
NA |
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(S)-(-)-4-ethylbutan-4-olide - sweet, creamy coconut, woody aspects |
NA |
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(R)-(+)-4-propylbutan-4-olide - sweet, spicy, herbaceous, hay note, coumarin-like |
700 ppb in water |
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(S)-(-)-4-propylbutan-4-olide - fatty, coconut-note, fruity-sweet aspects |
890 ppb in water |
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(R)-(+)-4-butylbutan-4-olide - spicy-green, coconut note, with almond notes (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips) |
300 ppb in water |
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(S)-(-)-4-butylbutan-4-olide - fatty coconut note, less intense than (R)-isomer (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips) |
130 ppb in water |
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(R)-(+)-4-pentylbutan-4-olide - strong, sweet, soft coconut with fatty-milky aspects (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips) |
220 ppb in water |
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(S)-(-)-4-pentylbutan-4-olide - fatty, moldy, weak coconut note, less intense than (R)-isomer (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips) |
150 ppb in water |
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(R)-(+)-4-hexylbutan-4-olide - strong, fatty-sweet fruity note, some reminiscence to coconut, caramel (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips); Bourdineaud et. al. describe this as: Fatty, animalic top note. Upon evaporation clearly different from the racemate with regard to the acidic and animalic base notes; In particular suitable for flavours. |
34 ppb in red wine |
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(S)-(-)-4-hexylbutan-4-olide - soft, sweet coconut note with fruity-fatty aspects (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips); Bourdineaud et. al. describe this as: Fruity, banana like, lactonic and jasmonic like floral top note. Base note is closest to that of the racemate with more volume, less sweet and floral, but heavier and more lactonic. |
47 ppb in red wine |
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(R)-(+)-4-heptylbutan-4-olide - strong, fatty-sweet, reminiscent of peach, with some bloomy aspects (Mosandl & Gunther); strong, sweet, coconut (Yamamoto) |
4 ppb in water |
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(S)-(-)-4-heptylbutan-4-olide - fatty-sweet aldehyde note less intense than its enantiomer (Mosandl & Gunther); sweet, coconut (Yamamoto) |
12 ppb in water |
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(R)-(+)-4-octylbutan-4-olide - strong, fruity-sweet, bloomy note with aldehyde and woody aspects (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips) |
8 ppb in red wine |
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(S)-(-)-4-octylbutan-4-olide - fatty-fruity, milky note, less intense than (R)-isomer (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips) |
39 ppb in red wine |
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(3S,4S)-(-)-cis-3,4-Dimethylbutanolide - Faint, fatty-nutty, moldy odor |
NA |
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(3R,4R)-(+)-cis-3,4-Dimethylbutanolide - Faint, sweet hay note |
NA |
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(3R,4S)-(-)-trans-3,4-Dimethylbutanolide - Faint spicy, fatty-fruity note |
NA |
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(3S,4R)-(+)-trans-3,4-Dimethylbutanolide - Faint, fatty, spicy note |
NA |
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(3R,4S)-(-)-4-butyl-3-methylbutan-4-olide -strong coconut note, reminiscent of celery |
305-330 ppb in white wine |
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(3S,4R)-(+)-4-butyl-3-methylbutan-4-olide - piquant celery note, faint coconut note, green walnut note |
140-172 ppb in white wine |
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(3R,4R)-(+)-4-butyl-3-methylbutan-4-olide - sweet woody, bright fresh coconut note |
132 ppb in white wine |
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(3S,4S)-(-)-4-butyl-3-methylbutan-4-olide - faint coconut note, faint musty, earthy, remeniscant of hay |
20-24
ppb in white wine |
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(3S,4S)-(-)-3-Methyl-4-decanolide - Top note has a strong matured fruity smell. Middle note has a waxy and milky scent. The overall tonality is a good long lasting aroma with a strong matured fruity and a little bit of milky scent. |
NA |
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(3R,4R)-(+)-3-Methyl-4-decanolide - Top note has lactone notes with a little bit of a fatty smell. Middle note has lactone notes along with a little stimulant green scent. The overall tonality is a good long lasting aroma with lactone-like, greeny smell. |
NA |
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(R)-(+)-5-pentylpentan-5-olide - sweet, fruity, milk note; Bourdineaud et. al. describe this as: Top note: alpha-allyl-ionone; heavier, more lactonic and tuberose than racemate. Floral notes stronger than in the S-(-)-enantiomer. |
NA |
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(S)-(-)-5-pentylpentan-5-olide - sweet, fruity, peach note, fatty, butter-like; Bourdineaud et. al. describe this as: Fruity top note; heavier, milder and more coumarin but less tuberose than racemate. The more the sample is enriched in the R-(+)-enantiomer the more the floral notes are important; inversely, the more enriched in the S-(-)-enantiomer, the more the sample is intense and lactonic. |
NA |
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(R)-(-)-delta-Jasmolactone - Exhibits a floral coconut note which is fresher and more rising than in the S-(+)-enantiomer; the fruity note is more marked than that of the racemate. Base' note is coconut without the fatty aspect. |
NA |
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(S)-(+)-delta-Jasmolactone - Exhibits a heavy woody coconut note with the spicy celery-jasmone aspect of the racemate; the base note is creamy tuberose like. |
NA |
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(R)-(-)-massoialactone - Heavy tonka like top note and less fruity than (S)-(+)-enantiomer. Base note is strongly coconut like with fatty aspects. This enantiomer exhibits a more pleasant character with more volume than the racemate. |
NA |
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(S)-(+)-massoialactone - Fatty fruity (a bit tuberose like) top note, which is more intense than that of the (R)-(-)-enantiomer. upon evaporation the fatty aspects disappear in favor of a milky, coconut, tonka and a strong coumarin note. |
NA |
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(R)-(-)-Tuberolactone - Fruity, coconut, tonka note with metallic and slightly fatty aspects. Base note, which is essentially tuberose lactonic, has less volume than (S)-(+)-enantiomer. In comparison to the racemate this enantiomer is more pleasant with regard to the tuberose note, but has less volume. |
NA |
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(S)-(+)-Tuberolactone - Heavy fatty and less fruity top note. Upon evaporation becomes clearly lactonic, tuberose and tonka. In general much more volume than the (R)-(-)-enantiomer. Less pleasant general floral note, but more voluminous than the racemate. |
NA |
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(R)-(+)-5-hexylpentan-5-olide - Fruity, sweet, creamy |
100 |
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(S)-(-)-5-hexylpentan-5-olide - Fruity, sweet, milky |
30 |
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(R)-(+)-5-heptylpentan-5-olide - Fruity, sweet, apricot |
500 |
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(S)-(-)-5-heptylpentan-5-olide - Fruity, sweet |
50 |
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(4S,5S)-(+)-cis-4-methyl-5-decanolide or (4S,5S)-(-)-cis-Aerangis lactone - reminiscent of certain aspects of the smell of the flower of the tuberose (Polianthes tuberosa) and gardenia varieties and on the other hand is reminiscent of caramel, condensed milk and coconut, especially coconut milk |
0.13 ng |
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(4R,5R)-(+)-cis-4-methyl-5-decanolide or (4R,5R)-(+)-cis-Aerangis lactone - reminiscent of delta-decalactone and coconut, and with a fragrance intensity much lower than the (4S,5S)-isomer |
30 ng |
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(4S,5R)-trans-4-methyl-5-decanolide or (4S,5R)-trans-aerangis lactone - reminiscent of delta-decalactone and cocos, with similar intensity to the cis-(4R,5R)-enantiomer and higher than the trans-(4R,5S)-enantiomer |
50 ng |
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(4R,5S)-trans-4-methyl-5-decanolide or (4R,5S)-trans-aerangis lactone - showed slightly lactonic fragrance, with the lowest fragrance intensity of all the stereoisomers |
100 ng |
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(S)-(+)-(Z)-7-gamma-decenolactone - creamy, milky, soft, caramel, fruity gamma-decalactone-like, weakly peach-like |
NA |
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(R)-(-)-(Z)-7-gamma-decenolactone - racemate-like, fruity, intensive peach-like, coconut, distinctly stronger than (S)-(+) -antipode |
NA |
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(S)-(+)-(Z)-7-delta-decenolactone - fatty, creamy, less intensive than racemate |
NA |
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(R)-(-)-(Z)-7-delta-decenolactone - milky, coconut, fruity, less intensive than racemate, distinctly stronger than (S)-(+) -antipode |
NA |
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(4S)-gamma-Hexathionolactone - green, grassy, mint, burnt |
NA |
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(4R)-gamma-hexathionolactone - green, grassy |
NA |
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(4S)-gamma-Octathionolactone - mushroom-like odor, hay-like odor, pungent |
NA |
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(4R)-gamma-Octathionolactone - mushroom-like odor, hay-like odor |
NA |
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(4S)-gamma-Decathionolactone - sweet, fruity |
NA |
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(4R)-gamma-Decathionolactone - fruity |
NA |
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(4S)-delta-Hexathionolactone - maggi-like odor, sulfurous, burnt |
NA |
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(4R)-delta-Hexathionolactone - maggi-like odor, spicy, burnt |
NA |
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(4S)-delta-Octathionolactone - mushroom-like odor, grassy, hay like odor, sulfurous |
NA |
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(4R)-delta-Octathionolactone - mushroom-like odor, grassy, green |
NA |
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(4S)-delta-decathionolactone - sweet, fruity |
NA |
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(4R)-delta-Decathionolactone - green, slightly sweet, slightly fruity |
NA |
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(3R)-Butylphthalide - Celery stem odor, heavy, somewhat spicy. Less intense in fresh celery odor than (S)-enantiomer. |
0.37 ppm |
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(3S)-Butylphthalide - Celery stem odor, strong, fresh, with aspects of celery leaf |
0.07 ppm |
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(3S,3aS,7aR)-3-Butylhexahydrophthalide - sweet, warm, heavy, slightly medicinal (by GC-O); also described as “sweet and sickly” |
0.13 ng |
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(3R,3aR,7aS)-3-Butylhexahydrophthalide - odorless by GC-O at 125 ng |
>125 ng |
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(3S,3aR,7aS)-3-Butylhexahydrophthalide - odorless by GC-O at 125 ng |
>125 ng |
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(3R,3aS,7aR)-3-Butylhexahydrophthalide - odorless by GC-O at 125 ng |
>125 ng |
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(3S,3aR,7aR)-3-Butylhexahydrophthalide - reminiscent of dry celery leaves by GC-O; also described as “celery, fruity" |
25 ng |
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(3R,3aS,7aS)-3-Butylhexahydrophthalide - herbaceous, like celery by GC-O; also described as “celery, fruity" |
12.5 ng |
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(3S,3aS,7aS) -3-Butylhexahydrophthalide - herbaceous, like celery by GC-O; also described as “celery, fruity" |
25 ng |
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(3R,3aR,7aR)-3-Butylhexahydrophthalide - odorless by GC-O at 125 ng |
>125 ng |
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(-)-(3S,3aR)-Sedanolide - 99.9% ee - Natural celery leaf odor, herbal, and strong bitter. |
1.3x10-2 ppm |
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(+)-(3R,3aS)-Sedanolide - 99.4% ee - Celery seed odor, heavy, and spicy. Weak impression of celery. |
2.7x10-1 ppm |
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(+)-(3R,3aR)-Sedanolide - 99.1% ee - Natural celery stem odor, herbal, and bitter. |
1.6 ppm |
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(-)-(3S,3aS)-Sedanolide - 99.6% ee - Very weak odor. No impression of celery. |
1.9 ppm |
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(-)-(S)-Sedanenolide - Celery stem odor, strong, fresh, with aspects reminiscent of celery fibers. |
0.14 ppm |
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(+)-(R)-Sedanenolide - Celery stem odor, bitter, Less intense in fresh celery odor than (S)-(-)-enantiomer |
0.60 ppm |
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(+)-(3R,3aS,6R,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - very powerful coumarinic odor notes, sweet with a caramel type character (Gaudin); also described as coconut like by GC-O (Katja Buhr) |
>100 ng/l in air |
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(-)-(3S,3aR,6S,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone (87% pure) - Odor: butyric, rancid, coumarinic, lactonic, sulfury, powerful. |
>100 ng/l in air |
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(-)-(3S,3aS,6R,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone (98% pure) - coumarinic, lactonic, cold tobacco side (Gaudin); also described as coconut like by GC-O (Katja Buhr) |
0.000001 ng/l in air |
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(+)-(3R,3aR,6S,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - coumarinic, hay, earthy, lactonic (Gaudin); also described as coconut like by GC-O (Katja Buhr) |
>100 ng/l in air |
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(-)-(3R,3aR,6R,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone - coumarinic, flouve, hay, sulfur, rubbery (Gaudin); also described as coconut like by GC-O (Katja Buhr) |
0.4 ng/l in air |
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(+)-(3S,3aS,6S,7aR)-Perhydro-3,6-dimethyl-2-benzo[b]furanone - coconut like by GC-O (Katja Buhr) |
0.5 ng/l in air |
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(+)-(3S,3aS,6R,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - tonka, beans, hay, flouve type characters are best represented whose coumarinic character is more marked in the bottom note than in the top note, and is accompanied of a metallic side (Gaudin); also described as coconut like by GC-O (Katja Buhr) |
0.15 ng/l in air |
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(-)-(3R,3aR,6S,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone - description not given (Gaudin); described as coconut like by GC-O (Katja Buhr) |
0.003 ng/l in air |
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(-)-(3S,3aR,6R,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone - coumarinic, flouve, hay, vaguely sulphury odor. |
>100 ng/l in air |
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(+)-(3R,3aS,6S,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - description not given |
>100 ng/l in air |
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(3R,3aR,6R,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - no odor description given |
>100 ng/l in air |
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(3S,3aR,6R,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - coconut like |
30 ng/l in air |
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(3R,3aS,6S,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone - coconut like |
0.0075 ng/l in air |
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(3R,3aS,6R,7aS)-perhydro-3,6-dimethyl-2-benzo[b]furanone - coconut like |
7.5 ng/l in air |
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(3S,3aR,6S,7aR)-perhydro-3,6-dimethyl-2-benzo[b]furanone - no description given |
>100 ng/l in air |
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(+)-(3aS,6R,7aR)-perhydro-6-methyl-3-methylene-2-benzo[b]furanone - coumarinic, lactonic, tonka, daffodil, very powerful.; perhydro-6-methyl-3-methylene-2-benzo[b]furanone possesses a very powerful odor of the coumarinic, fat, lactonic type, with a balsamic bottom note reminiscent of the odor of daffodil. This is an odor note which is very close to that of coumarin and which is best represented in (+)-(3aS,6R,7aR)-perhydro-6-methyl-3-methylene-2-benzo[b ]furanone, a preferred compound of the invention |
NA |
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(-)-(3aR,6S,7aS)-perhydro-6-methyl-3-methylene-2-benzo[b]furanone - Not available |
NA |
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(3aS,6R,7aS)-perhydro-6-methyl-3-methylene-2-benzo[b]furanone - coumarinic, lactonic, tonka |
NA |
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(3aR,6S,7aR)-perhydro-6-methyl-3-methylene-2-benzo[b]furanone - not available |
NA |
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(+)-(6R)-3(RS)-3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran-2(3H)-one - it develops a phenolic/coumarin-like odour, making it a useful alternative to coumarin. It also has a completely original, minty odoriferous note much appreciated by perfumers |
NA |
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(-)-(6S)-3(RS)-3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran-2(3H)-one - not available |
NA |
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(-)-(3aS,6R,7aS)-perhydro-3,3,6-trimethyl-2-benzo[b]furanone - lactonic, fruity, coumarinic |
NA |
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(+)-(3aR,6S,7aR)-perhydro-3,3,6-trimethyl-2-benzo[b]furanone - not available |
NA |
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(3S,3aS,7aR)-Wine lactone - intense sweet and coconut-like (coumarinic); this is the naturally occurring enantiomer |
0.00001-0.00004 ng/l in air |
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(3R,3aR,7aS)-Wine lactone - description not available |
>1000 ng/l in air |
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(3S,3aR,7aR)-Wine lactone - coconut like |
0.05 - 0.2 ng/l in air |
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(3R,3aS,7aS)-Wine lactone - coconut like |
8-16 ng/l in air |
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(3R,3aS,7aR)-Wine lactone - coconut like |
>1000 ng/l in air; also reported as 0.25 ng/l in air |
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(3S,3aR,7aS)-Wine lactone - coconut like |
80-160 ng/l in air |
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(3S,3aS,7aS)-Wine lactone - coconut like |
0.007-0.014 ng/l in air |
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(3R,3aR,7aR)-Wine lactone - coconut like |
14-28 ng/l in air |
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(-)-(5S,8R)-4,4,8-trimethyl-1-oxaspiro[4.5]dec-6-en-2-one - coconut odor |
NA |
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NA |
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(3aR,5R,7aR)-5-isopropenyl-7a-methylhexahydro-1-benzofuran-2(3H)-one - moderately intense, agreeable, herbaceous odor with lupine flower and parsley root notes |
NA |
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(3aS,5S,7aS)-5-isopropenyl-7a-methylhexahydro-1-benzofuran-2(3H)-one - faint, mushroomy, and moldy with a floral note. |
NA |
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(-)-(S)-4,8-dimethylnon-7-en-4-olide - fresh fruity lactone odour with peach and/or pear-like nuances It also has green and floral notes. |
0.65 ppb (in water) |
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(+)-(R)-4,8-dimethylnon-7-en-4-olide - an oily and heavy lactone odour which is expressed rather milky and coconut-like. |
0.16 ppb (in water) |
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(4R)-Solerone - weak, fruity |
NA |
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(4S)-Solerone - fruity, wine-like |
NA |
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(4R,5R)-Solerole - fruity, sweet |
NA |
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(4S,5S)-Solerole - musty, earthy |
NA |
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(4R,5S)-Solerole - weak, fruity |
NA |
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(4S,5R)-Solerole - unspecific, musty |
NA |
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(5R)-Demethylmarmelo lactone - butter cake smell |
NA |
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(5S)-Demethylmarmelo lactone - milky almond smell |
NA |
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(4S)-(+)-(2Z,6Z)-2,6-Nonadien-4-olide - weak odor described as "powdery and coumarin-like lactonic" |
NA |
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(4R)-(-)-(2Z,6Z)-2,6-Nonadien-4-olide - strong odor described to be "waxy and jasmin-like lactonic" |
NA |
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(R)-cis-6-gamma-dodecenolactone - flowery, fruity, coconut-, peach- and apricot-like. The odor of the (R)-enanantiomer was described as being significantly weaker than the (S)-enantiomer, although no sensory differences in odor quality were noted. |
12.2 pg (in air) |
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(S)-cis-6-gamma-dodecenolactone - flowery, fruity, coconut-, peach- and apricot-like. The odor of the (S)-enanantiomer was described as being significantly stronger than the (R)-enantiomer, although no sensory differences in odor quality were noted. |
4.6 pg (in air) |
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(+)-(2R)-Furaneol® - obviously strong, sugary, jammy, sweet |
NA |
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(-)-(2S)-Furaneol® - extremely weak |
NA |
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(+)-(2R)-Mesifuran - burnt, intensive caramel |
NA |
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(-)-(2S)-Mesifuran - lactone, coumarin like, no caramelic odor |
NA |
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(S)-(-)-4-Acetoxyfuraneol - weak caramelic odor |
NA |
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(R)-(+)-4-Acetoxyfuraneol - burnt, intense caramel odor |
NA |
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(2R)-(+)-Homofuraneol I - strong roast sweet |
NA |
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(2S)-(-)-Homofuraneol I - weak, roast sweet lactone like |
NA |
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(2R)-(+)-Homofuraneol II - weak, clear sweet less roasted odor |
NA |
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(2S)-(-)-Homofuraneol II - weak, clear sweet less roasted odor |
NA |
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(+)-(S)-Sotolone - curry, walnut (strongly caramelic) |
0.8 ppb |
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(-)-(R)-Sotolone - walnut, rancid. Although the aromatic nuances of both enantiomers were quite similar, the perception threshold of (S)-sotolon in dilute alcohol solution (12% vol) was >100 times lower than that of (R)-sotolon. |
0.89 ppb |
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(S)-(-)-Maple furanone - less intense than the (R)-(+)-Maple furanone enantiomer. |
NA |
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(R)-(+)-Maple furanone - possessed a significantly intense maple syrup-like odor at 100 ppt solution in H2O, while (S)-(-)-Maple furanone was less intense. |
NA |
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(4S)-(+)-Dihydrobovolide - deep green tea notes (a metallic, spicy, green tea note) |
3.7 ppm |
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(4R)-(-)-Dihydrobovolide - light green tea notes (a light and spicy green tea note) |
1.6 ppm |
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(R)-6-Carbomethoxyethyl-6-Methyl-epsilon-caprolactone - pleasant almond-like aroma, sweet notes |
NA |
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(S)-6-Carbomethoxyethyl-6-Methyl-epsilon-caprolactone - low intensity, described as floral, oily notes |
NA |
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