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W296236

Sigma-Aldrich

(−)-Isopulegol

≥98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H18O
CAS Number:
89-79-2
Molecular Weight:
154.25
FEMA Number:
2962
Beilstein:
1906573
EC Number:
201-940-6
Council of Europe no.:
2033
MDL number:
MFCD00134655
UNSPSC Code:
12164502
PubChem Substance ID:
24901422
Flavis number:
2.067
NACRES:
NA.21

biological source

synthetic

Quality Level

400

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.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

Organoleptic

minty; cooling

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.

Disclaimer

For R&D or non-EU Food use. Not for retail sale.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(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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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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