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(S)-(+)-Carvone

Name: (<I>S</I>)-(+)-Carvone
Brand: ALDRICH

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:

2244-16-8

Molecular Weight:

150.22

Beilstein:

2042970

EC Number:

218-827-2

MDL number:

MFCD00062997

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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Chiral Catalysts & Ligands

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

GHS07

Signal Word

Warning

Hazard Statements

H317

Precautionary Statements

P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364

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

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Total synthesis of drimane sesquiterpenes from S-(+)-carvone (part 5)

Swarts HJ, et al.

Tetrahedron, 50(33), 10083-10094 (1994)

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)

Are vectors able to learn about their hosts? A case study with Aedes aegypti mosquitoes.

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

Influence of the chirality of (R)-(-)-and (S)-(+)-carvone in the central nervous system: A comparative study.

Chirality, 19(4), 264-268 (2007)