5502-74-9

Basic information

• Product Name: 4-(2-hydroxy-2-propyl)cyclohexene-1-methanol
• Synonyms: 4-(2-hydroxy-2-propyl)cyclohexene-1-methanol;4-(1-Hydroxy-1-methylethyl)-1-cyclohexene-1-methanol;p-Menth-1-ene-7,8-diol
• CAS NO: 5502-74-9
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.24872
• EINECS: 226-838-9
• Mol File: 5502-74-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 276.1°Cat760mmHg
• Flash Point: 127.1°C
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 0.000614mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: 4-(2-hydroxy-2-propyl)cyclohexene-1-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-hydroxy-2-propyl)cyclohexene-1-methanol(5502-74-9)
• EPA Substance Registry System: 4-(2-hydroxy-2-propyl)cyclohexene-1-methanol(5502-74-9)

Safety Data

• Hazardous Substances Data: 5502-74-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H18O2/c1-10(2,12)9-5-3-8(7-11)4-6-9/h3,9,11-12H,4-7H2,1-2H3

Upstream product

• 6931-54-0 β-pinene oxide 
• 15719-64-9 methylammonium carbonate 
• 80-26-2 terpinyl acetate 
• 149194-95-6 2-(1-Oxa-spiro[2.5]oct-6-yl)-propan-2-ol 
• 149194-96-7 2-(1-Oxa-spiro[2.5]oct-6-yl)-propan-2-ol 
• 7299-42-5 δ-terpineol 
• 154843-77-3 (r-1,c-4)-7-bromo-p-menthane-1,8-diol 
• 154843-76-2 (r-1,t-4)-7-bromo-p-menthane-1,8-diol 
• 154843-84-2 (r-1,c-4)-1,7-dibromo-p-menthan-8-ol 
• 177698-19-0 Beta-pinene 

Relevant articles and documents

New sustainable synthetic routes to cyclic oxyterpenes using the ecocatalyst toolbox

Cyclic oxyterpenes are natural products that are mostly used as fragrances, flavours and drugs by the cosmetic, food and pharmaceutical industries. However, only a few cyclic oxyterpenes are accessible via chemical syntheses, which are far from being ecofriendly. We report here the synthesis of six cyclic oxyterpenes derived from ?-pinene while respecting the principles of green and sustainable chemistry. Only natural or biosourced catalysts were used in mild conditions that were optimised for each synthesis. A new generation of ecocatalysts, derived from Mn-rich water lettuce, was prepared via green processes, characterised by MP-AES, XRPD and TEM analyses, and tested in catalysis. The epoxidation of ?-pinene led to the platform molecule, ?-pinene oxide, with a good yield, illustrating the efficacy of the new generation of ecocatalysts. The opening ?-pinene oxide was investigated in green conditions and led to new and regioselective syntheses of myrtenol, 7-hydroxy-α-terpineol and perillyl alcohol. Successive oxidations of perillyl alcohol could be performed using no hazardous oxidant and were controlled using the new generation of ecocatalysts generating perillaldehyde and cuminaldehyde.

Selective Catalytic Isomerization of β-Pinene Oxide to Perillyl Alcohol Enhanced by Protic Tetraimidazolium Nitrate

A series of tetraimidazolium salts with different anions was prepared and applied in the isomerization of β-pinene oxide. After examining the activity of different catalysts, a remarkable enhancement of the selectivity of perillyl alcohol (47 %) was obtained over [PEimi][HNO3]4 under mild reaction conditions and using DMSO as the solvent. Furthermore, noncovalent interactions between solvent molecules and the catalyst were found by FT-IR spectroscopy and confirmed by computational chemistry. The homogeneous catalyst showed excellent stability and was reused up to six times without significant loss.

Iron-catalyzed epoxidation of aromatic olefins and 1,3-dienes

The combination of iron(III) chloride, pyridine-2,6-dicarboxylic acid and formamidine ligands allows for the epoxidation of styrenes and conjugated dienes in excellent chemoselectivity and yields.