71697-84-2

Basic information

• Product Name: trans-Sobrerol
• Synonyms: (3S,5R)-2-Methyl-3β-hydroxy-5α-(1-hydroxy-1-methylethyl)cyclohexene;[1R,5S,(-)]-5-Hydroxy-α,α,4-trimethyl-3-cyclohexene-1-methanol;4β-(1-Hydroxy-1-methylethyl)-1-methyl-1-cyclohexene-6α-ol
• CAS NO: 71697-84-2
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.24872
• Mol File: 71697-84-2.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 270.5°Cat760mmHg
• Flash Point: 120.9°C
• Appearance: /
• Density: 1.051g/cm³
• CAS DataBase Reference: trans-Sobrerol(CAS DataBase Reference)
• NIST Chemistry Reference: trans-Sobrerol(71697-84-2)
• EPA Substance Registry System: trans-Sobrerol(71697-84-2)

Safety Data

• Hazardous Substances Data: 71697-84-2(Hazardous Substances Data)

Upstream product

• 498-71-5 sobrerol 
• 10482-56-1 (-)-(S)-α-terpineol 
• 108-05-4 vinyl acetate 
• 32226-54-3 trans-sobrerol 
• 80-56-8 rac-α-pinene 
• 60661-95-2 1,6-dichloro-p-menthane-2,8-diol 
• 80-56-8 Pinene 
• 99-49-0 Carvone 
• 1197-06-4 cis-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol 
• 80-26-2 terpinyl acetate 
• 7785-26-4 (-)-α-pinene 
• 7785-70-8 (+)-α-pinene 
• 772-36-1 (1R,5R)-5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-enol 
• 1686-14-2 (1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.^2,4]octane 

Downstream Products

• 68754-15-4 6,8-diacetoxy-p-menth-1-ene 
• 106262-55-9 Octanoic acid 5-(1-hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enyl ester 
• 38235-58-4 trans-sobrerol 
• 151-01-9 O-ethyl hydrogen dithiocarbonate 
• 7712-46-1 5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enone 
• 454-77-3 5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-enol 
• 498-71-5 (1SR,5RS)-5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-enol 
• 772-36-1 (1R,5R)-5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-enol 
• 38223-90-4 p-menthane-1,2,6,8-tetraol 
• 137821-91-1 (-)-(1S,5R)-sobrerol 
• 4436-81-1 homoterpenylmethylketone 
• 34182-03-1 (R)-5-(1-hydroxy-1-methylethyl)2-methylcyclohex-2-enone 

Relevant articles and documents

Chemo-enzymatic pathways toward pinene-based renewable materials

Sobrerol methacrylate (SobMA) was synthesized and subsequently polymerized using different chemical and enzymatic routes. Sobrerol was enzymatically converted from α-pinene in a small model scale by a Cytochrome P450 mutant from Bacillus megaterium. Conve

Hot water-promoted SN1 solvolysis reactions of allylic and benzylic alcohols

During the studies of hydrolysis of epoxides in water, we found that the hydrolysis of (-)-α-pinene oxide at 20 °C gave enantiomerically pure trans-(-)-sobrerol, whereas the same reaction in water heated at reflux unexpectedly gave a racemic mixture of trans- and cis-sobrerol (trans/cis=6:4). We have examined this remarkable difference in detail and found that hot water, whose behavior is quite different compared with room- or high-temperature water, could promote SN1 solvolysis reactions of allylic alcohols and thus caused the racemization of trans-(-)-sobrerol. The effect of reaction temperature, the addition of organic co-solvent, and the concentration of the solute on the rate of the racemization of trans-(-)-sobrerol were further examined to understand the role that hot water played in the reaction. It was proposed that the catalytic effects of hot water are owing to its mild acidic characteristic, thermal activation, high ionizing power, and better solubility of organic reactant. Further investigation showed that the racemization of other chiral allylic/benzylic alcohols could efficiently proceed in hot water.

Unique salt effect on the high yield synthesis of acid-labile terpene oxides using hydrogen peroxide under acidic aqueous conditions

Acid-labile epoxides such as -pinene oxide are (effectively) synthesized in high yield from the epoxidation of terpenes with aqueous H2O 2 catalyzed by Na2WO4, [Me(n-C 8H17)3N]HSO4, and PhP(O)(OH) 2 in the presence of Na2SO4 as an auxiliary additive under organic solvent-free conditions at ambient temperature. Origin of the salt effect is considered that the addition of a saturated amount of Na2SO4 to aqueous H2O2 strongly inhibited the undesired hydrolysis of the acid-labile epoxide products, despite the highly acidic reaction conditions. Georg Thieme Verlag Stuttgart · New York.