Carvone

Carvone
Compound Structure:
Synonyms: CARVONE;99-49-0;2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone;Karvon;1-Carvone;p-Mentha-6,8-dien-2-one;dl-Carvone;2-Methyl-5-isopropenyl-2-cyclohexenone;Carvol;Carvone (natural);Carvone [ISO];D-Cavone;limonen-6-one
Compound ID: NMPC-727
PubChem ID:

7439

Molecular Formula: C10H14O
Canonical SMILES: CC1=CCC(CC1=O)C(=C)C
InChIKey: ULDHMXUKGWMISQ-UHFFFAOYSA-N
About the compound:

Carvone, a type of p-menthane monoterpenoid, is composed of a cyclohex-2-enone ring with methyl and isopropenyl groups at the 2nd and 5th positions, respectively. It plays a role as an allergen and belongs to the carvone family, known for its anti-fungal properties in plants. Naturally occurring in various species like Tanacetum vulgare and Lindera erythrocarpa, carvone is also produced by Saccharomyces cerevisiae, a type of yeast. This compound is part of the larger terpenoid family and is predominantly found in essential oils, especially those extracted from caraway seeds, spearmint, and dill. Carvone has significant applications in the food and flavor industry. R-(−)-Carvone, for instance, is utilized in air fresheners and various aromatherapy and alternative medicine products due to its presence in essential oils. S-(+)-Carvone has been observed to reduce weight gain in mice on high-fat diets. In the realm of food, carvone is crucial for the distinctive flavors of caraway, dill, and spearmint, and has been used in culinary practices for thousands of years. Notable examples include Wrigley's Spearmint Gum and spearmint-flavored Life Savers, which use natural spearmint oil from Mentha spicata. Caraway seed, extracted with alcohol, is a key ingredient in the European beverage Kümmel. In agriculture, S-(+)-Carvone is applied to deter premature sprouting in stored potatoes, particularly in the Netherlands where it's sold under the brand name Talent. For insect control, R-(−)-Carvone has gained approval from the U.S. Environmental Protection Agency as a mosquito repellent.

GHS Hazard Statements

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

150.22 g/mol

XLogP3-AA

2.4

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

1

Exact Mass

150.104465066 g/mol

Monoisotopic Mass

150.104465066 g/mol

Topological Polar Surface Area

17.1Ų

Heavy Atom Count

11

Formal Charge

0

Complexity

223

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

1

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Colorless or pale yellowish liquid; [Hawley] White powder;

 

Boiling Point

230-231 °C

Melting Point

MP: 25.2 °C

Solubility 

Soluble in alcohol, ether, chloroform, propylene glycol, mineral oils; insoluble in glycerol

Vapor Pressure

0.16 [mmHg]

Source: PubChem

Source Species: Boswellia dalzielii
Eucalyptus tereticornis
Eucalyptus torelliana
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