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Merck

124931

Sigma-Aldrich

(R)-(−)-Carvone

98%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C10H14O
Número de CAS:
Peso molecular:
150.22
Beilstein/REAXYS Number:
2206714
EC Number:
MDL number:
UNSPSC Code:
12352115
PubChem Substance ID:
NACRES:
NA.22

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.)

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

(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

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

192.2 °F - closed cup

flash_point_c

89 °C - closed cup

ppe

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


Certificados de análisis (COA)

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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)
Yoshiyuki Yamada et al.
Neuron, 93(5), 1198-1212 (2017-02-28)
Sensory information is translated into ensemble representations by various populations of projection neurons in brain circuits. The dynamics of ensemble representations formed by distinct channels of output neurons in diverse behavioral contexts remains largely unknown. We studied the two output
Liebigs Ann. Chem., 403-403 (1993)
An improved synthesis of homochiral octalones from (-)-carvone.
Tenius BSM, et al.
Tetrahedron Asymmetry, 4(4), 633-636 (1993)

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