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124931

Sigma-Aldrich

(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
Beilstein:
2206714
EC Number:
229-352-5
MDL number:
MFCD00001578
UNSPSC Code:
12352115
PubChem Substance ID:
24847635
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
GHS07

Signal Word

Warning

Hazard Statements

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class Code

10 - Combustible liquids

WGK

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

124931-VAR:
124931-5ML:
124931-25ML:
124931-100ML:
124931-BULK:
124931-500ML:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
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)
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