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Safety Information

439061

Sigma-Aldrich

(−)-Isopulegol

99%

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:
Molecular Weight:
154.25
Beilstein:
1906573
EC Number:
MDL number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

liquid

optical activity

[α]20/D −22°, neat

refractive index

n20/D 1.471 (lit.)

bp

212 °C (lit.)

density

0.912 g/mL at 25 °C (lit.)

functional group

hydroxyl

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 monoterpene alcohol, a useful ingredient for the production of fragrances in perfume industries. It is also used as a starting material in the manufacture of menthol by the hydrogenation process. Menthol is an important component in cosmetics, pharmaceuticals, and toothpaste.

Application

(−)-Isopulegol can be used as a starting material for the enantioselective preparation of:      
  • 8-arylmenthols by Smiles-Truce rearrangement of aryl sulfonates.,·        
  • Stereoisomers of 5,9-dimethylpentadecane.
  • Octahydro-2H-chromen-4-ol by Prins cyclization with vanillin in the presence of montmorillonite clay as the catalyst.     
  • p-menthane-3,8,9-triol by catalytic Sharpless dihydroxylation.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

439061-1ML:
439061-5ML:
439061-VAR:
439061-BULK:


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Synthesis and Absolute Configuration at C (8) of `p-Menthane-3, 8, 9-triol?Derived from (-)-Isopulegol
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Helvetica Chimica Acta, 87(10), 2602-2607 (2004)
Green synthesis of (-)-isopulegol from (+)-citronellal: application to essential oil of citronella
Jacob RG, et al.
Tetrahedron Letters, 44(18), 3605-3608 (2003)
Synthesis of octahydro-2H-chromen-4-ol from vanillin and isopulegol over acid modified montmorillonite clays: Effect of acidity on the Prins cyclization
Timofeeva MN, et al.
J. Mol. Catal. A: Chem., 398, 26-34 (2015)
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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