586-82-3

Basic information

• Product Name: 4-(isopropyl)-1-methylcyclohex-3-en-1-ol
• Synonyms: 4-(isopropyl)-1-methylcyclohex-3-en-1-ol;3-terpinen-1-ol,1-methyl-4-(1-methylethyl)-3-cyclohexen-1-ol,p-menth-3-en-1-ol,1-terpinenol,1-terpineol;3-Cyclohexen-1-ol, 1-methyl-4-(1-methylethyl)-;PARA-MENTH-3-EN-1-OL;1-METHYL-4-(PROPAN-2-YL)CYCLOHEX-3-EN-1-OL;1-Methyl-4-(1-methylethyl)-3-cyclohexen-1-ol;1-Terpineol;p-Mentha-3-ene-1-ol
• CAS NO: 586-82-3
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.24932
• EINECS: 209-585-9
• Mol File: 586-82-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 215.3°Cat760mmHg
• Flash Point: 87.7°C
• Appearance: /
• Density: 0.933g/cm³
• Vapor Pressure: 0.0325mmHg at 25°C
• Refractive Index: 1.484
• PKA: 15.05±0.40(Predicted)
• CAS DataBase Reference: 4-(isopropyl)-1-methylcyclohex-3-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(isopropyl)-1-methylcyclohex-3-en-1-ol(586-82-3)
• EPA Substance Registry System: 4-(isopropyl)-1-methylcyclohex-3-en-1-ol(586-82-3)

Safety Data

• Hazardous Substances Data: 586-82-3(Hazardous Substances Data)

Usage

Description

p-Menth-3-en-l-ol has a dry, woody, somewhat musty odor.

Chemical Properties

p-Menth-3-en-1-ol has a dry, woody, somewhat musty odor. This ingredient is considered an undesirable component of commercial terpineol.

Occurrence

Reported found in camphor essential oil, grapefruit juice, mandarin, lemon and lime peel oil, ginger, cognac, white wine, cocoa, tea, plum, cardamom, Roman chamomile oil and mastic gum fruit oil.

InChI:InChI=1/C10H18O/c1-8(2)9-4-6-10(3,11)7-5-9/h4,8,11H,5-7H2,1-3H3

Upstream product

• 38651-65-9 (1R,5S)-(+)-nopinone 
• 917-54-4 methyllithium 
• 138-86-3 limonene. 
• 590-86-3 isovaleraldehyde 
• 99180-72-0 1-methoxy-4-(1'-methylethyl)cyclohexa-1,4-diene 
• 57422-87-4 (E)-1-(3-methylbut-1-en-1-yl)piperidine 
• 5259-66-5 isopropyl-4 cyclohexene-3 one-1 
• 74-88-4 methyl iodide 
• 17699-09-1 2(S)-methyl-5(R)-(2-propenyl)cyclohexan-1(R)-ol 
• 1195-92-2 (+/-)-(1R,2S,4S)-limonene oxide 
• 1195-92-2 trans-1-methyl-4-isopropenyl-7-oxabicyclo<4.1.0>heptane 
• 80-53-5 terpin hydrate 
• 98-55-5 terpineol 
• 562-74-3 TERPINEN-4-OL 

Downstream Products

• 25570-96-1 1,4-dibromo-p-menthane 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 27621-71-2 1,4-dichloro-p-menthane 
• 7599-88-4 1,2,4-trihydroxy paramenthane 
• 118723-78-7 Phenyl-carbamic acid 4-isopropyl-1-methyl-cyclohex-3-enyl ester 
• 118723-64-1 Isopropyl-carbamic acid 4-isopropyl-1-methyl-cyclohex-3-enyl ester 
• 89-81-6 piperitone 
• 10458-14-7 Menthone 
• 118723-72-1 tert-Butyl-carbamic acid 4-isopropyl-1-methyl-cyclohex-3-enyl ester 
• 25570-95-0 1,4-dichloro-trans-p-menthane 

Relevant articles and documents

Synthesis of (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus, its racemate, (1R,4R)- and (1S,4S)-isomers

(S)-Perillyl alcohol was converted to (R)-cryptone (91.5-93% ee) in six steps, which was then treated with methyllithium to give (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus. The racemic pheromone was also prepared by methylation of (±)-cryptone. Both (1R,4R)- and (1S,4S)-isomers (98% ee) of the pheromone were synthesized from the enantiomers of dihydrolimonene oxide.

HYDROGENOLYSE EN PHASE LIQUIDE SUR Pd/C DES EPOXYDES DU CARVOMENTHENE ET DU LIMONENE

Hydrogenolysis over Pd/C of cis and trans epoxides of carvomenthene and limonene give a mixture of hydrocarbons, secondary and tertiary alcohols, and ketones in proportions dependent upon the nature of the starting material.In the limonene epoxides, the extracyclic double bond plays an important role in the opening of the oxirane ring through a common unsaturated tertiary alcohol intermediate by double bond migration, hydrogenation of which leads to the products.For the carvomenthene epoxides the results are similar to those found in the 4-t-butyl series with competition between cis addition and trans addition of hydrogen.The presence of the isopropenyl group leads to slower reaction rates in comparison with t-butyl analogues.