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W296236

Sigma-Aldrich

(−)-Isopulegol

≥98%

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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:
1906573
EC Number:
Council of Europe no.:
2033
MDL number:
PubChem Substance ID:
Flavis number:
2.067
NACRES:
NA.21

biological source

synthetic

Quality Level

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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This Item
W266590W266523W266507
(−)-Isopulegol ≥98%

Sigma-Aldrich

W296236

(−)-Isopulegol

L-Menthol ≥99%, FCC, FG

Sigma-Aldrich

W266590

L-Menthol

L-Menthol natural, ≥99%, FCC, FG

Sigma-Aldrich

W266523

L-Menthol

DL-Menthol ≥95%, FCC, FG

Sigma-Aldrich

W266507

DL-Menthol

grade

Halal

grade

FG, Kosher

grade

FG, Halal, Kosher, natural

grade

FG, Halal, Kosher

assay

≥98%

assay

≥99%

assay

≥99%

assay

≥95%

optical activity

[α]20/D −21°, neat

optical activity

[α]22/D −49°, c = 10 in 95% ethanol

optical activity

[α]20/D −49°, c = 10 in 95% ethanol

optical activity

-

refractive index

n20/D 1.471 (lit.)

refractive index

-

refractive index

-

refractive index

-

bp

212 °C (lit.)

bp

212 °C (lit.)

bp

212 °C (lit.)

bp

216 °C (lit.)

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.

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 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

Certificates of Analysis (COA)

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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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