37275
(+)-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:
Molecular Weight:
152.23
UNSPSC Code:
12352115
NACRES:
NA.22
PubChem Substance ID:
EC Number:
226-872-4
Beilstein/REAXYS Number:
2044615
MDL number:
Form:
liquid
InChI key
AZOCECCLWFDTAP-UHFFFAOYSA-N
InChI
1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3
SMILES string
CC1CCC(CC1=O)C(C)=C
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
Quality Level
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
10 - Combustible liquids
wgk
WGK 3
flash_point_f
215.6 °F - closed cup
flash_point_c
102 °C - closed cup
ppe
Eyeshields, Gloves
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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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