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Sigma-Aldrich

(R)-(+)-Pulegone

≥90%

Synonym(s):

(+)-Pulegone, (R)-2-Isopropylidene-5-methylcyclohexanone, (R)-p-Menth-4(8)-en-3-one, p-Menth-4(8)-en-3-one

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About This Item

Empirical Formula (Hill Notation):
C10H16O
CAS Number:
89-82-7
Molecular Weight:
152.23
Beilstein:
2040703
EC Number:
201-943-2
MDL number:
MFCD00063000
UNSPSC Code:
12352200
PubChem Substance ID:
24863438
NACRES:
NA.22

vapor pressure

138 mmHg ( 25 °C)

Assay

≥90%

form

liquid

optical activity

[α]20/D +23.5°, neat

refractive index

n20/D 1.486 (lit.)

bp

224 °C (lit.)

density

0.937 g/mL at 25 °C (lit.)

SMILES string

C[C@@H]1CC\C(=C(\C)C)C(=O)C1

InChI

1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1

InChI key

NZGWDASTMWDZIW-MRVPVSSYSA-N

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General description

(R)-(+)-Pulegone, a monoterpene ketone found in the essential oil of pennyroyal, can induce abortion.

Application

(R)-(+)-Pulegone may be used as a starting material to synthesize:
  • (2S,4R,6R,8S)-2,4,8-trimethyl-1,7-dioxaspiro[5.5]undecane, a spiroketal
  • (R)-(+)-citronellic acid, an intermediate to prepare leucine-d3
  • (+)-fawcettidine, a lycopodium alkaloid

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

179.6 °F - closed cup

Flash Point(C)

82 °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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Total Synthesis of (+)-Fawcettidine.
Kozak JA and Dake GR.
Angewandte Chemie (International Edition in English), 47(22), 4221-4223 (2008)
Metabolism of (R)-(+)-pulegone in F344 rats.
Chen LJ, et al.
Drug Metabolism and Disposition, 29(12), 1567-1577 (2001)
From (R)-(+)-pulegone to (2S,4R,6R,8S)-2,4,8-trimethyl-1,7-dioxaspiro[5.5]undecane-A unique spiroacetal from the insect Kingdom.
Tu YQ, et al.
Tetrahedron Asymmetry, 6(2), 397-400 (1995)
Synthesis of (2S, 4S)-and (2S, 4R)-[5,5,5-2H3] leucine from (R)-pulegone.
Hill RK, et al.
Canadian Journal of Chemistry, 72(1), 110-113 (1994)
Feng Li et al.
Chemical research in toxicology, 24(5), 744-751 (2011-04-08)
A predominant pathway of xenobiotic-induced toxicity is initiated by bioactivation. Characterizing reactive intermediates will provide information on the structure of reactive species, thereby defining a potential bioactivation mechanism. Because most reactive metabolites are not stable, it is difficult to detect
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