37275

(+)-Dihydrocarvone

mixture of isomers

• Synonym(s): (2R,5R)-5-Isopropenyl-2-methylcyclohexanone
• Empirical Formula (Hill Notation): C₁₀H₁₆O
• CAS Number: 5524-05-0
• Molecular Weight: 152.23
• Beilstein: 2044615
• EC Number: 226-872-4
• MDL number: MFCD00001636
• UNSPSC Code: 12352115
• PubChem Substance ID: 57649710
• NACRES: NA.22

Properties

• form: liquid
• optical activity: [α]20/D +20±2°, neat
• composition: n-(+)-dihydrocarvone, ~77% ; iso-(+)-dihydrocarvone, ~20%
• refractive index: n20/D 1.471
• density: 0.928 g/mL at 20 °C (lit.)
• functional group: ketone
• SMILES string: CC1CCC(CC1=O)C(C)=C
• InChI: 1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3
• InChI key: AZOCECCLWFDTAP-UHFFFAOYSA-N

Description

General description

(+)-Dihydrocarvone, a monoterpenoid compound found in caraway oil, is a key building block to synthesize sesquiterpenes. It is generally produced either by the hydrogenation of carvone or oxidation of limonene.

Application

(+)-Dihydrocarvone may be used in the following processes:

• Synthesis of dispiro 1,2,4,5-tetraoxanes, which show potent anti-malarial activity.
• Synthesis of an epoxylactone by oxidation, which can undergo copolymerization with ε-caprolactone to form cross-linked copolymers with shape memory properties.
• Synthesis of α-Cyperone, a eudesmane type sesquiterpenoid compound with potent insecticidal activity.

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): 215.6 °F - closed cup
• Flash Point(C): 102 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves