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435759

Sigma-Aldrich

(S)-(+)-Carvone

96%

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Synonym(s):
(+)-Carvone, (S)-5-Isopropenyl-2-methyl-2-cyclohexenone, p-Mentha-6,8-dien-2-one
Empirical Formula (Hill Notation):
C10H14O
CAS Number:
Molecular Weight:
150.22
Beilstein/REAXYS Number:
2042970
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

96%

form

liquid

optical activity

[α]23/D +55.0±7°, neat

refractive index

n20/D 1.497 (lit.)

bp

96-98 °C/10 mmHg (lit.)

density

0.96 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-/m0/s1

InChI key

ULDHMXUKGWMISQ-VIFPVBQESA-N

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1 of 4

This Item
W224928W22490179245
(S)-(+)-Carvone 96%

435759

(S)-(+)-Carvone

D-Carvone ≥96%, FG

W224928

D-Carvone

L-Carvone ≥97%, FCC, FG

W224901

L-Carvone

(+)-Carvone certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

79245

(+)-Carvone

refractive index

n20/D 1.497 (lit.)

refractive index

n20/D 1.497 (lit.)

refractive index

n20/D 1.497 (lit.)

refractive index

-

density

0.96 g/mL at 25 °C (lit.)

density

0.96 g/mL at 25 °C (lit.)

density

0.959 g/mL at 25 °C (lit.)

density

0.960 g/mL at 20 °C (lit.)

bp

96-98 °C/10 mmHg (lit.)

bp

96-98 °C/10 mmHg (lit.)

bp

227-230 °C (lit.)

bp

228-230 °C (lit.)

form

liquid

form

-

form

-

form

-

optical activity

[α]23/D +55.0±7°, neat

optical activity

-

optical activity

[α]20/D −61°, neat

optical activity

-

General description

(S)-(+)-Carvone, a monoterpene found mainly in caraway and dill seed oils, is used in cosmetic, food and pharmaceutical preparations.

Application

(S)-(+)-Carvone can be used as a starting material to synthesize:
  • (-)-Samaderine Y, a pentacyclic quassinoid.
  • (-)-Ambrox, a terpenoid responsible for the odor of ambergris.
  • 3β-Acetoxydrimenin (a sesquiterpene) via conjugated addition of potassium cyanide followed by base catalyzed Robinson annulation reaction.
  • Thapsigargin family members such as trilobolide, nortrilobolide, and thapsivillosin F.

Packaging

(S)-(+)-Carvone, a monoterpene found mainly in caraway and dill seed oils, is used in cosmetic, food and pharmaceutical preparations.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Skin Sens. 1A

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

204.1 °F - closed cup

flash_point_c

95.6 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


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A Route to the Thapsigargins from (S)-Carvone Providing a Substrate-Controlled Total Synthesis of Trilobolide, Nortrilobolide, and Thapsivillosin F
Oliver SF, et al.
Angewandte Chemie (International Edition in English), 42(48), 5996-6000 (2003)
Total synthesis of drimane sesquiterpenes from S-(+)-carvone (part 5)
Swarts HJ, et al.
Tetrahedron, 50(33), 10083-10094 (1994)
Influence of the chirality of (R)-(-)-and (S)-(+)-carvone in the central nervous system: A comparative study.
Chirality, 19(4), 264-268 (2007)
Total Synthesis of (-)-Samaderine Y from (S)-(+)-Carvone
Shing TKM and Yeung YY
Angewandte Chemie (International Edition in English), 117(48), 8195-8198 (2005)
Total synthesis of (-)-Ambrox from S-(+)-carvone (part 6)
Verstegen-Haaksma AA, et al.
Tetrahedron, 50(33), 10095-10106 (1994)

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