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439053

Sigma-Aldrich

(+)-Isopulegol

99%

Synonym(s):

(1S,2R,5S)-2-Isopropenyl-5-methylcyclohexanol, (1S,3S,4R)-p-Menth-8-en-3-ol

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About This Item

Empirical Formula (Hill Notation):
C10H18O
CAS Number:
Molecular Weight:
154.25
Beilstein:
4659691
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

liquid

optical activity

[α]20/D +22°, neat

refractive index

n20/D 1.469 (lit.)

bp

91 °C/12 mmHg (lit.)

density

0.912 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m0/s1

InChI key

ZYTMANIQRDEHIO-AEJSXWLSSA-N

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General description

Isopulegol is a monoterpene alcohol, which is generally found in essential oils of various plants. It is widely used as a fragrance ingredient in cosmetics, shampoos and toilet soaps. Isopulegol is also a key intermediate in the synthesis of (−)-menthol.

Application

(+)-Isopulegol can be used as a starting material to synthesize:
  • A natural product (−)-isopiperitenone.
  • Medicinally important octahydro-2H-chromen-4-ol derivatives by reacting with benzaldehydes.
  • Antituberculosis diterpenoid named 12-epi-ileabethoxazole.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

172.4 °F - closed cup

Flash Point(C)

78 °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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Central nervous system activity of acute administration of isopulegol in mice
Silva MIG, et al.
Pharmacology, Biochemistry, and Behavior, 88(2), 141-147 (2007)
Chemoenzymatic synthesis of the intermediates in the peppermint monoterpenoid biosynthetic pathway
Cheallaigh AN, et al.
Journal of Natural Products, 81(7), 1546-1552 (2018)
Fragrance material review on isopulegol
Bhatia SP, et al.
Food And Chemical Toxicology, 46(11), S185-S189 (2008)
One-step, stereoselective synthesis of octahydrochromanes via the Prins reaction and their cannabinoid activities
Slater S, et al.
Tetrahedron Letters, 59(9), 807-810 (2018)
Total Synthesis of Ileabethoxazole, Pseudopteroxazole, and seco-Pseudopteroxazole
Yang M, et al.
Angewandte Chemie (International ed. in English), 55(8), 2851-2855 (2016)

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