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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/REAXYS Number:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

172.4 °F - closed cup

flash_point_c

78 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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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Isomenthone

(±)-Citronellal ≥95.0% (GC)

Sigma-Aldrich

27470

(±)-Citronellal

(R)-(+)-Pulegone ≥90%

Sigma-Aldrich

W296309

(R)-(+)-Pulegone

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)
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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