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435759

Sigma-Aldrich

(S)-(+)-Carvone

96%

Synonym(s):

(+)-Carvone, (S)-5-Isopropenyl-2-methyl-2-cyclohexenone, p-Mentha-6,8-dien-2-one

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About This Item

Empirical Formula (Hill Notation):
C10H14O
CAS Number:
2244-16-8
Molecular Weight:
150.22
Beilstein:
2042970
EC Number:
218-827-2
MDL number:
MFCD00062997
UNSPSC Code:
12352115
PubChem Substance ID:
24867255
NACRES:
NA.22

Quality Level

100

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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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
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1A

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

204.1 °F - closed cup

Flash Point(C)

95.6 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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)
Wladimir J Alonso et al.
Memorias do Instituto Oswaldo Cruz, 98(5), 665-672 (2003-09-16)
The way in which vectors distribute themselves amongst their hosts has important epidemiological consequences. While the role played by active host choice is largely unquestioned, current knowledge relates mostly to the innate response of vectors towards stimuli signalling the presence
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)
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