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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:
89-79-2
Molecular Weight:
154.25
Beilstein:
1906573
EC Number:
201-940-6
MDL number:
MFCD00134655
UNSPSC Code:
12352205
PubChem Substance ID:
24867323
NACRES:
NA.22

Quality Level

100

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.)

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
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)

172.4 °F

Flash Point(C)

78 °C

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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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)
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)
Green synthesis of (-)-isopulegol from (+)-citronellal: application to essential oil of citronella
Jacob RG, et al.
Tetrahedron Letters, 44(18), 3605-3608 (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
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)
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