439061

(−)-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: 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

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302,H315,H319,H335
• pcodes: P261 - P264 - P270 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• 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