p-Menth-1-en-3-ol

Base Information

• Chemical Name: p-Menth-1-en-3-ol
• CAS No.: 491-04-3
• Molecular Formula: C10H18 O
• Molecular Weight: 154.252
• European Community (EC) Number: 207-725-3
• DSSTox Substance ID: DTXSID0052128
• Nikkaji Number: J6.049F
• Wikidata: Q81984934
• Mol file: 491-04-3.mol

Synonyms:p-Menth-1-en-3-ol;491-04-3;3-Carvomenthenol;2-Cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-;6-(Isopropyl)-3-methylcyclohex-2-en-1-ol;3-methyl-6-propan-2-ylcyclohex-2-en-1-ol;Piperitol (monoterpene);UNII-7UM0ILT6I7;1-Methyl-4-isopropyl-1-cyclohexen-3-ol;FEMA No. 3179;11063-75-5;HSDB 5666;3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-ol;3-HYDROXY-4-ISOPROPYL-1-METHYLCYCLOHEXENE;EINECS 207-725-3;UNII-BLT1PGO03M;UNII-G7666796PG;EINECS 240-775-4;EINECS 240-777-5;Piperitol?;7UM0ILT6I7;SCHEMBL1245098;DTXSID0052128;FEMA 3179;6-isopropyl-3-methyl-cyclohex-2-enol;AKOS025295367;6-Isopropyl-3-methyl-2-cyclohexen-1-ol;3-methyl-6-(propan-2-yl)cyclohex-2-en-1-ol;3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-ol, 9CI;Cyclohexane, 1-methyl-4-(1-methylethyl)-, didehydro monohydroxy deriv. (9CI)

Chemical Property of p-Menth-1-en-3-ol

Chemical Property:

• Vapor Pressure: 0.0205mmHg at 25°C
• Refractive Index: 1.4729
• Boiling Point: 222.7°Cat760mmHg
• PKA: 14.70±0.60(Predicted)
• Flash Point: 89.8°C
• PSA: 20.23000
• Density: 0.924g/cm³
• LogP: 2.35960
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC1=CC(C(CC1)C(C)C)O
• 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.

Technology Process of p-Menth-1-en-3-ol

There total 31 articles about p-Menth-1-en-3-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 59.0%

piperitone (89-81-6,6091-52-7) → (1R*,6S*)-6-isopropyl-3-methylcyclohex-2-en-1-ol (491-04-3,16721-38-3,16721-39-4,25437-28-9,34350-53-3,65733-27-9,65733-28-0,75363-64-3,75363-65-4) + trans-6-isopropyl-3-methylcyclohex-2-en-1-ol (491-04-3,16721-38-3,16721-39-4,25437-28-9,34350-53-3,65733-27-9,65733-28-0,75363-64-3,75363-65-4)

Guidance literature:

piperitone; With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; Cooling;

With hydrogenchloride; water; In diethyl ether;

DOI:10.1016/j.tetasy.2010.02.031

Reference yield: 59.0%

piperitone (89-81-6,6091-52-7) → (1R*,6S*)-6-isopropyl-3-methylcyclohex-2-en-1-ol (491-04-3,16721-38-3,16721-39-4,25437-28-9,34350-53-3,65733-27-9,65733-28-0,75363-64-3,75363-65-4) + trans-6-isopropyl-3-methylcyclohex-2-en-1-ol (491-04-3,16721-38-3,16721-39-4,25437-28-9,34350-53-3,65733-27-9,65733-28-0,75363-64-3,75363-65-4)

Guidance literature:

piperitone; With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; Cooling;

With hydrogenchloride; water; In diethyl ether;

DOI:10.1016/j.tetasy.2010.02.031

Reference yield: 50.0%

2-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → piperitol (491-04-3)

Guidance literature:

With dihydrogen peroxide; sodium hydroxide; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.9b00531

upstream raw materials:

piperitone

(R)-5-isopropyl-2-methylcyclohexa-1,3-diene

(-)-piperitone

aluminum isopropoxide

Downstream raw materials:

piperityl phloroglucinol

(+/-)-3-Chloro-p-menthen

3-Chloro-6-isopropyl-3-methyl-cyclohexene

(1R,2R,3R,4R)-4-isopropyl-1-methylcyclohexane-1,2,3-triol

Refernces

• 1、 Maza, Ricardo J.,Davenport, Elliot,Miralles, Núria,Carbó, Jorge J.,Fernández, Elena. "Transition-Metal-Free Allylic Borylation of 1,3-Dienes". supporting information. p. 2251 - 2255. Retrieved 2019/04/10.
• 2、 Winska, Katarzyna,Grudniewska, Aleksandra,Chojnacka, Anna,Bialonska, Agata,Wawrzenczyk, Czeslaw. "Enzymatic resolution of racemic secondary cyclic allylic alcohols". experimental part. p. 670 - 678. Retrieved 2010/08/07.