124931

Sigma-Aldrich

(R)-(−)-Carvone

98%

Synonym(s):
p-Mentha-6,8-dien-2-one, (−)-Carvone, (R)-5-Isopropenyl-2-methyl-2-cyclohexenone, Carvol
Empirical Formula (Hill Notation):
C10H14O
CAS Number:
Molecular Weight:
150.22
Beilstein/REAXYS Number:
2206714
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

vapor density

5.2 (vs air)

vapor pressure

0.4 mmHg ( 20 °C)

assay

98%

optical activity

[α]20/D −61°, neat

refractive index

n20/D 1.497 (lit.)

bp

227-230 °C (lit.)

density

0.959 g/mL at 25 °C (lit.)

SMILES string

CC(=C)[C@@H]1CC=C(C)C(=O)C1

InChI

1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1

InChI key

ULDHMXUKGWMISQ-SECBINFHSA-N

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General description

(R)-(−)-Carvone is a monoterpenoid. Its ozonolysis in the gaseous phase has been proposed. Aldehydes (formaldehyde) and biradicals were obtained as the major products. It participates in the diastereoselective synthesis of homochiral octalones.

Application

Chiral starting material.
(R)-(−)-Carvone may be employed as starting reagent for the synthesis of enantiopure (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1, a useful intermediate formed during the synthesis of terpenoids. It may be employed as starting reagent for the synthesis of differently protected (4S,6R,7R)-trihydroxy-1-octyne derivatives.

Packaging

5 mL in glass bottle
100, 500 mL in poly bottle

pictograms

Exclamation mark

signalword

Warning

hazcat

Acute Tox. 4 Oral - Skin Sens. 1

storage_class_code

10 - Combustible liquids

WGK Germany

WGK 1

Flash Point F

192.2 °F - closed cup

Flash Point C

89 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

An improved synthesis of homochiral octalones from (-)-carvone.
Tenius BSM, et al.
Tetrahedron Asymmetry, 4(4), 633-636 (1993)
Liebigs Ann. Chem., 403-403 (1993)
Gas-phase ozonolysis of the monoterpenoids (S)-(+)-carvone,(R)-(-)-carvone,(-)-carveol, geraniol and citral.
Nunes FMN, et al.
Atmospheric Environment, 39(40), 7715-7730 (2005)
Bryostatin: A novel asymmetric synthesis of the C27-C34 fragment starting from (R)-carvone as chiral template.
De Brabander J, et al.
Tetrahedron Asymmetry, 8(11), 1721-1724 (1997)
Leandro de C Alves et al.
Organic & biomolecular chemistry, 13(28), 7633-7642 (2015-05-23)
A route to enantiopure (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1, an intermediate for terpenoids, has been developed and includes a highly chemo- and regioselective Tiffeneau-Demjanov reaction. Starting from readily available (R)-(-)-carvone, this robust sequence is available on a deca-gram scale and uses flow chemistry for...

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