W296236

Sigma-Aldrich

(−)-Isopulegol

≥98%

Synonym(s):
(1R,2S,5R)-2-Isopropenyl-5-methylcyclohexanol, (1R,3R,4S)-p-Menth-8-en-3-ol
Empirical Formula (Hill Notation):
C10H18O
CAS Number:
Molecular Weight:
154.25
FEMA Number:
2962
Beilstein/REAXYS Number:
1906573
EC Number:
Council of Europe no.:
2033
MDL number:
PubChem Substance ID:
Flavis number:
2.067
NACRES:
NA.21

Quality Level

biological source

synthetic

grade

Halal

assay

≥98%

optical activity

[α]20/D −21°, neat

refractive index

n20/D 1.471 (lit.)

bp

212 °C (lit.)

density

0.912 g/mL at 25 °C (lit.)

Documentation

see Safety & Documentation for available documents

Featured Industry

Flavors and Fragrances

Organoleptic

cooling; minty

food allergen

no known allergens

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-/m1/s1

InChI key

ZYTMANIQRDEHIO-KXUCPTDWSA-N

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General description

(−)-Isopulegol is a monoterpenic alcohol widely used in flavor and fragrance industry. It is also a key intermediate in the synthesis of the industrially important chemical, (−)-menthol.

Packaging

1 kg in glass bottle
9, 20 kg in poly drum

Other Notes

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pictograms

Exclamation mark

signalword

Warning

hazcat

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

Target Organs

Respiratory system

storage_class_code

10 - Combustible liquids

WGK Germany

WGK 1

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

Certificate of Analysis

Certificate of Origin

Cyclization of (+)-citronellal to (?)-isopulegol catalyzed by H 3 PW 12 O 40/SiO 2.
da Silva KA, et al.
Catalysis Communications, 5(8), 425-429 (2004)
David Olagnier et al.
Bioorganic & medicinal chemistry letters, 17(22), 6075-6078 (2007-10-02)
Pure natural monoterpenes were evaluated in vitro for their antiplasmodial activities against Plasmodium falciparum. Chemically modified terpenes were also tested to see whether the introduction of an alkyne, a cyclopropane, a diene, or a cyclopentenone moiety had an influence on...

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