439061

Sigma-Aldrich

(−)-Isopulegol

99%

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
Beilstein/REAXYS Number:
1906573
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

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.)

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.

Packaging

1 mL in glass bottle

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

Enantioselective synthesis of three stereoisomers of 5, 9-dimethylpentadecane, sex pheromone component of Leucoptera coffeella, from (-)-isopulegol
Moreira JA and Correa AG
Tetrahedron Asymmetry, 14(23), 3787-3795 (2003)
Steven W M Crossley et al.
Organic letters, 18(11), 2620-2623 (2016-05-14)
Hydrogen atom transfer (HAT) circumvents a disfavored Friedel-Crafts reaction in the derivatization of the inexpensive monoterpene isopulegol. A variety of readily prepared aryl and heteroaryl sulfonates undergo a formal hydroarylation to form 8-arylmenthols, privileged scaffolds for asymmetric synthesis, as typified...
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)
Green synthesis of (-)-isopulegol from (+)-citronellal: application to essential oil of citronella
Jacob RG, et al.
Tetrahedron Letters, 44(18), 3605-3608 (2003)
Synthesis and Absolute Configuration at C (8) of `p-Menthane-3, 8, 9-triol?Derived from (-)-Isopulegol
Yuasa Y and Yuasa Y
Helvetica Chimica Acta, 87(10), 2602-2607 (2004)

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