What molecule am I?
November is flavor and aroma month at MOTW!
Like limonene, the Molecule of the Week for November 1, 2021, carvone is a monoterpene that exists in nature as two enantiomers: (R)-carvone [aka (鈥�)-carvone, L-carvone] and (S)-carvone [aka (+)-carvone, D-carvone]. The (R)-isomer is shown here.
Both enantiomers have well-recognized flavors and aromas. (R)-carvone has the flavor and aroma of mint; it is the dominant compound in spearmint oil. Like (R)-limonene, (S)-carvone1 is a key component of caraway and dill seed oils.
In 1841, Swiss chemist Eduard Schweizer isolated what eventually became known as (S)-carvone from oil extracted from caraway seeds (Carum carvi), from which carvone gets its name. Fifty years later, German chemist W. Kwaenick discovered its enantiomer in the oils of spearmint (Mentha spicata) and kuromoji (Lindera umbellata, a deciduous Asian shrub). In 1905, H. Waldbaum and O. H眉thig at what is now Technische Universit盲t Dresden (Germany) reported that both isomers exist in gingergrass (Paspalum distichum) oil.
Both carvones are commercial products used in a variety of industries, primarily for their flavors and aromas. Natural (R)-carvone is used to flavor chewing gum and mint candies and to provide aromas in personal-care products, air fresheners, and aromatherapy oils. In 2009, the US Environmental Protection Acency registered it for use in insect repellents.
(S)-Carvone has fewer uses. Its presence in caraway oil adds to the flavor of k眉mmel, a liqueur popular in Europe. It is used in agriculture to prevent the premature sprouting of potatoes. Both isomers are used as starting materials for synthesizing complex terpenoids.
At 3800 t/year, the worldwide market for (R)-carvone is much larger than that of its (S)-isomer (10 t/year). Much (R)-carvone is extracted from natural mint, but about half of the commercial product is synthesized from (R)-limonene.
1. CAS Reg. No. 2244-16-8.
(R)-Carvone hazard information
| Hazard class* | GHS code and hazard statement | |
|---|---|---|
| Flammable liquids, category 4 | H227鈥擟ombustible liquid |  |
| Acute toxicity, oral, category 4 | H302鈥擧armful if swallowed |  |
| Skin sensitization, category 1 | H317鈥擬ay cause an allergic skin reaction | |
| Short-term (acute) aquatic hazard, category 2 | H401鈥擳oxic to aquatic life | |
*Globally Harmonized System (GHS) of Classification and Labeling of Chemicals.聽
This molecule was suggested by a reader. We present聽almost all of the molecules suggested by our readers.聽If you have a molecule you would like us to consider, please send us a message. And thank you for your interest in Molecule of the Week! 鈥擡d.
(R)-Carvone 聽fast facts
| CAS Reg. No. | 6485-40-1 |
nomenclature | 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5R)- |
| Empirical formula | C10H14O |
| Molar mass | 150.22 g/mol |
| Appearance | Colorless to pale yellow liquid |
| Boiling point | 228鈥�230掳 C |
| Water solubility | 1.3 g/L |
, the most authoritative and comprehensive source for chemical information.
Molecule of the Week needs your suggestions!
If your favorite molecule is not in our聽archive, please send us a message. The molecule can be notable for its current or historical importance or for any quirky reason. Thank you!
Stay Ahead of the Chemistry Curve
Learn how ACS can help you stay ahead in the world of chemistry.
