491-04-3

Basic information

• Product Name: 6-(isopropyl)-3-methylcyclohex-2-en-1-ol
• Synonyms: 6-(isopropyl)-3-methylcyclohex-2-en-1-ol;(Z)-piperitol,1-p-menthen-3-ol;2-Cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-;PARA-MENTH-1-EN-3-OL;(3R,4S)-p-Menth-1-en-3-ol;[1R,2S,(+)]-5-Methyl-2-(1-methylethyl)-5-cyclohexen-1-ol;d-cis-Piperitol;1-p-Menthen-3-ol
• CAS NO: 491-04-3
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.24932
• EINECS: 207-725-3
• Mol File: 491-04-3.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 237.64°C (rough estimate)
• Flash Point: 89.8°C
• Appearance: /
• Density: 0.9119
• Vapor Pressure: 0.0205mmHg at 25°C
• Refractive Index: 1.4729
• PKA: 14.70±0.60(Predicted)
• CAS DataBase Reference: 6-(isopropyl)-3-methylcyclohex-2-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(isopropyl)-3-methylcyclohex-2-en-1-ol(491-04-3)
• EPA Substance Registry System: 6-(isopropyl)-3-methylcyclohex-2-en-1-ol(491-04-3)

Safety Data

• Hazardous Substances Data: 491-04-3(Hazardous Substances Data)

Usage

Description

p-Menth-l-en-3-ol has a fresh pungent odor and taste. May be prepared by reduction of racemic piperitone with lithium aluminum hydride or aluminum isopropoxide; the d-form is isolated from natural sources.

Chemical Properties

p-Menth-1-en-3-ol has a fresh pungent odor and taste.

Occurrence

Reported found in pennyroyal and other mentha oils; originally isolated from the oil of Eucalyptus radiata. Also reported found in dill herb and lemon balm, black currant, ginger, myrtle, berry, nutmeg, rosemary, sweet marjoram.

Preparation

By reduction of racemic pipertone with lithium aluminum hydride or aluminum isopropoxide; the d-form is isolated from natural sources.

Aroma threshold values

Aroma characteristics at 1.0%: cooling impact, fresh and clean minty body, candy cane confection-like.

Taste threshold values

Taste characteristics at 15 ppm: slight latent cooling, trigeminal taste sensation, almost like sorbitol, but longer lasting.

InChI:InChI=1/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9-11H,4-5H2,1-3H3

Upstream product

• 89-81-6 piperitone 
• 4573-50-6 (S)-(+)-piperitone 
• 28582-40-3 trans-piperityl chloride 
• 4573-50-6 (-)-piperitone 
• 138-86-3 limonene. 
• 61585-35-1 p-menth-1-ene 
• 555-31-7 aluminum isopropoxide 
• 124-41-4 sodium methylate 
• 74-88-4 methyl iodide 
• 4221-98-1 (R)-5-isopropyl-2-methylcyclohexa-1,3-diene 
• 112068-28-7 (3R,4R)-1-methyl-4-(1-methylethyl)-cyclohex-1-en-3-yl acetate 

Downstream Products

• 116977-43-6 piperityl phloroglucinol 
• 906433-07-6 (+/-) linderatin 
• 106877-72-9 1-chloromenth-2-ene 
• 28582-40-3 trans-piperityl chloride 
• 28582-40-3 (+/-)-3-Chloro-p-menthen 
• 111806-71-4 3-Chloro-6-isopropyl-3-methyl-cyclohexene 
• 66767-24-6 (1R,2R,3R,4R)-4-isopropyl-1-methylcyclohexane-1,2,3-triol 
• 99-83-2 p-mentha-1,5-diene 
• 555-10-2 beta-phellandrene 
• 94281-61-5 (4-isopropyl-1-methyl-2-cyclohexenyl) methyl ether 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 

Relevant articles and documents

Linderapyrone: A Wnt signal inhibitor isolated from Lindera umbellata

Linderapyrone, a Wnt signal inhibitor was isolated from the methanolic extract of the stems and twigs of Lindera umbellata together with epi-(-)-linderol A. Linderapyrone inhibited TCF/β-catenin transcriptional activity that was evaluated using cell-based TOPFlash luciferase assay system. To evaluate the structure-activity relationship and mechanism, we synthesized linderapyrone and its derivatives from piperitone. As the results of further bioassay for synthesized compounds, we found both of pyrone and monoterpene moieties were necessary for inhibitory effect. cDNA microarray analysis in a linderapyrone derivative treated human colorectal cancer cells showed that this compound downregulates Wnt signaling pathway. Moreover, we successes to synthesize the derivative of linderapyrone that has stronger inhibitory effect than linderapyrone and ICG-001 (positive control).

Enantioselective Total Syntheses of (+)-Hostmanin A, (-)-Linderol A, (+)-Methyllinderatin and Structural Reassignment of Adunctin E

A one-step protocol has been developed for the enantioselective synthesis of hexahydrodibenzofuran derivatives using a modified Friedel-Crafts reaction. The developed method was applied to the synthesis of a series of natural products including (+)-hostmanin A, (+)-methyllinderatin, and (-)-linderol A. The synthetic and spectroscopic data investigations led to the structural reassignment of natural product adunctin E, which was further confirmed by single-crystal X-ray analysis. (Chemical Presented).

Enantiomeric differentiation of oxygenated p-menthane derivatives by 13C NMR using Yb(hfc)3

The 13C NMR behaviour of 21 p-menthanic terpene bearing an oxygenated function (alcohol, ketone, acetate) was examined in the presence of a chiral lanthanide shift reagent (Yb(hfc)3). For each monocyclic compound, we measured the lanthanide-induced shift (LIS) on the signals of the carbons and the splitting of signals allowing the enantiomeric differentiation. Some general features were found about their LIS behaviour: experimental data establishing distinct patterns for carvomenthone-like compounds and menthone-like compounds. The enantiomeric splitting was observed for the majority of signals in the spectrum of each compound. In the case of alcohols and acetates, the influence of the relative stereochemistry (cis vs trans) of isopropyl(ene) and the binding function was discussed. Copyright