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Merck

124931

(R)-(−)-Carvone

98%

Synonym(s):

(−)-Carvone, (R)-5-Isopropenyl-2-methyl-2-cyclohexenone, p-Mentha-6,8-dien-2-one, Carvol

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About This Item

Empirical Formula (Hill Notation):
C10H14O
CAS Number:
6485-40-1
Molecular Weight:
150.22
UNSPSC Code:
12352115
NACRES:
NA.22
PubChem Substance ID:
24847635
EC Number:
229-352-5
Beilstein/REAXYS Number:
2206714
MDL number:
MFCD00001578
Assay:
98%
Form:
liquid

Key Documents

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InChI key

ULDHMXUKGWMISQ-SECBINFHSA-N

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

SMILES string

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

vapor density

5.2 (vs air)

vapor pressure

0.4 mmHg ( 20 °C)

assay

98%

form

liquid

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.)

functional group

ketone

Quality Level

100

Related Categories

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

(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.
Chiral starting material.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class

10 - Combustible liquids

flash_point_f

192.2 °F - closed cup

flash_point_c

89 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF8501V
WXBF6827V
WXBF1209V
WXBD7936V
MKCR7856

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Liebigs Ann. Chem., 403-403 (1993)
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)
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)
An improved synthesis of homochiral octalones from (-)-carvone.
Tenius BSM, et al.
Tetrahedron Asymmetry, 4(4), 633-636 (1993)
The plant terpenoid carvone is a chemotaxis repellent for C. elegans.
Clayton Ellington et al.
microPublication biology, 2020 (2020-06-19)
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