32226-54-3

Upstream product

• 58506-22-2 p-menthane-1,2,8-triol 
• 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 
• 1686-14-2 α-pinene epoxide 
• 110202-13-6 1,2-dibromo-p-menthan-8-ol 
• 98-55-5 terpineol 
• 1686-14-2 (1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.^2,4]octane 
• 80-26-2 terpinyl acetate 
• 75957-19-6 hydroperoxy-6 hydroxy-8 p-menthene-1 ⁽²⁾ trans 
• 17177-64-9 (+/-)-trans-sobrenol diacetate 
• 56423-45-1 (4S,8RS)-8,9-epoxy-p-menth-6-en-2-one 
• 7664-93-9 sulfuric acid 

Downstream Products

• 68754-15-4 6,8-diacetoxy-p-menth-1-ene 
• 38235-58-4 trans-sobrerol 
• 137821-91-1 (-)-(1S,5R)-sobrerol 
• 106262-55-9 Octanoic acid 5-(1-hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enyl ester 
• 71697-84-2 (-)-trans-sobrerol 
• 38223-90-4 p-menthane-1,2,6,8-tetraol 
• 7712-46-1 5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enone 
• 127104-12-5 (+/-)-trans-1-methyl-4-<1-methyl-1-(trimethylsiloxy)ethyl>-6-(trimethylsiloxy)cyclohex-1-ene 
• 98-55-5 terpineol 
• 34182-03-1 (R)-5-(1-hydroxy-1-methylethyl)2-methylcyclohex-2-enone 
• 34182-03-1 (+/-)-5-(1-hydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one 
• 111323-96-7 C₁₇H₂₄N₂O₃S 
• 17177-64-9 (+/-)-trans-sobrenol diacetate 

Relevant academic research and scientific papers

Biomimetic conversion of α-pinene with H2O2 to sobrerol over V2O5: Dihydroxylation by a peroxo vanadium peracid vectoring gentle synergistic oxidation

In this communication, we report the gentle preparation of sobrerol from dihydroxylation of α-pinene synergistically catalyzed by V2O5-H2O2 under benign conditions. It was proposed that a “peroxo vanadium acid”, VVO(OH)(OOH), was formed by HOO? insertion and proton transfer between V2O5 and H2O2. Theoretical DFT calculations that using the dimer?vanadium peracid as a model of the catalytically active species revealed that peroxo vanadium acid exhibited bifunctional catalytic capabilities resembling epoxidation of α-pinene by peracetic acid and then open-ring hydration with an acetic media.

Heteropoly acid catalysts in upgrading of biorenewables: Synthesis of para-menthenic fragrance compounds from α-pinene oxide

The isomerization of α-pinene oxide in the presence of Cs2.5H0.5PW12O40 (CsPW) heteropolysalt as solid acid catalyst is reported. The reactions were performed in various solvents, which allowed to obtain trans-carveol, trans-sobrerol and pinol in 60–80% yield each, which exceed the yields reported so far. The CsPW catalyst could be recovered and reused without loss of its activity and selectivity.

A simple strategy toward the substitution of styrene by sobrerol-based monomers in unsaturated polyester resins

Sobrerol acrylate (SobAcr) and sobrerol methacrylate (SobMet) were synthesized for the first time through the functionalization of sobrerol with double bonds. Sobrerol was obtained by a green route that involved the hydration of α-pinene oxide in the presence of CO2. As unsaturated monomers (UMs) with rigid structures and extremely low volatilities, these new monomers are interesting alternatives for styrene (Sty) replacement in unsaturated polyester resin (UPR) formulations. The impact of the substitution of Sty by the new Sob-based monomers was studied using three different unsaturated polyesters (UPs): one commercially available and two fully bio-based that are synthesized in this work. The Sob-based monomers were able to fully dissolve the three UPs. Although UPRs with SobAcr showed higher thermal stability than SobMet-based materials, SobMet-based formulations presented higher glass transition temperatures (Tg) and storage moduli (E′). Overall, both Sob-based monomers exhibited promising properties to be used as low-volatile, bio-based effective Sty substitutes, and by that means mitigate a serious environmental issue concerning human exposure to toxic, volatile organic compounds (VOCs).

Mild and selective deprotection of tert -butyl(dimethyl)silyl ethers with catalytic amounts of sodium tetrachloroaurate(III) dihydrate

A simple and mild method for the removal of tert-butyl(dimethyl)silyl (TBS) protecting groups with catalytic amounts of sodium tetrachloroaurate(III) dihydrate is described. The procedure permits selective deprotection of aliphatic TBS ethers in good to excellent yields in the presence of aromatic TBS ethers, aliphatic triisopropylsilyl ethers, aliphatic tert-butyl(diphenyl)silyl ethers, or sterically hindered aliphatic TBS ethers. Additionally, TBS ethers can also be transformed into 4-methoxybenzyl ethers or methyl ethers in one pot by using larger quantities of the catalyst and a higher reaction temperature.

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 highly selective synthesis of acid-labile terpene and styrene oxides with a tungsten/Hcatalytic system under acidic aqueous conditions

Acid-labile epoxides such as terpene and styrene oxides are effectively synthesized in high yields with good selectivities using tungsten-catalyzed hydrogen peroxide epoxidation in the presence of NaO The salt effect is thought to originate with the addition of a saturated amount of NaOto aqueous H this addition strongly inhibited the undesired hydrolysis of the acid-labile epoxy products, despite the biphasic conditions of substrate as oil phase and Has acidic aqueous phase.

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.

Mechanism of the aerobic oxidation of α-Pinene

A combined experimental and theoretical approach is used to study the thermal autoxidation of α-pinene. Four different types of peroxyl radicals are generated; the verbenyl peroxyl radical being the most abundant one. The peroxyl radicals propagate a long

Comparative autoxidation of 3-Carene and α-Pinene: Factors governing regioselective hydrogen abstraction reactions

Autoxidation reactions of 3-Carene 1 and α-Pinene 2 were performed using various homogeneous catalysts. Different product and regio- selectivities were observed. The factors that promote hydrogen abstraction (HA) reactions in both molecules are discussed, and it is proposed that the difference in the product selectivities is due to the lack of 'cyclic activation' in 2. Oxidation of 1 produced mainly 3-carene-5-one 3, while 2 yielded 2,3-epoxypinane 6 as the major product.

A reagent for selective deprotection of alkyl acetates

The use of magnesium methoxide for selective deprotection of alkyl esters is described. By adjusting the equivalents of the magnesium methoxide reagent, it is possible to selectively cleave primary acetate in the presence of secondary and tertiary acetate and to cleave secondary acetate in the presence of tertiary acetate. A high selectivity can also be obtained for the same primary acetates if the β-positions of the acetates render a different steric bulkiness. This mild reagent has been successfully applied to the selective deprotection of many natural-occurring molecules including hydroxycitronnellol diacetate, trans-sobrerol diacetate, betulin diacetate, and baccatin III.