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Sigma-Aldrich

(+)-Dihydrocarvone

mixture of isomers

Synonym(s):

(2R,5R)-5-Isopropenyl-2-methylcyclohexanone

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About This Item

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

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.)

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

Related Categories

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.

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

Certificates of Analysis (COA)

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Oxidized dihydrocarvone as a renewable multifunctional monomer for the synthesis of shape memory polyesters.
Lowe JR, et al.
Biomacromolecules, 10(7), 2003-2008 (2009)
Dan Jin et al.
Scientific reports, 10(1), 3309-3309 (2020-02-26)
Cannabis research has historically focused on the most prevalent cannabinoids. However, extracts with a broad spectrum of secondary metabolites may have increased efficacy and decreased adverse effects compared to cannabinoids in isolation. Cannabis's complexity contributes to the length and breadth
The structure and antimalarial activity of dispiro-1, 2, 4, 5-tetraoxanes derived from (+)-dihydrocarvone.
Dong Y, et al.
Bioorganic & Medicinal Chemistry Letters, 20(22), 6359-6361 (2010)
Insecticidal activity of sesquiterpenes skeleton synthesized by the conventional Robinson annulations reaction on Drosophila melanogaster.
Alarcon J, et al.
Industrial Crops and Products, 42, 268-272 (2013)
Redife Aslihan Ucar et al.
Food microbiology, 91, 103454-103454 (2020-06-17)
This research determined the concentration of trehalose, xylose and l-citrulline in fresh and fermented cucumbers and their utilization by Lactobacillus pentosus, Lactobacillus plantarum, Lactobacillus brevis and Lactobacillus buchneri. Targeted compounds were measured by HPLC and the ability of the lactobacilli
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