498-71-5

Basic information

• Product Name: SOBREROL
• Synonyms: 1-P-MENTHENE-6,8-DIOL;AURORA KA-476;SOBREROL;5-hydroxy-alpha,alpha,4-trimethylcyclohex-3-ene-1-methanol;5-Hydroxy-α,α,4-trimethyl-3-cyclohexene-1-methanol;Pinol hydrate;1-METHANE-6,8-DIOL;p-menth-6-ene-2,8-diol
• CAS NO: 498-71-5
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• EINECS: 207-868-1
• Mol File: 498-71-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 130°C
• Boiling Point: 259.9°C (rough estimate)
• Flash Point: 120.9°C
• Appearance: /
• Density: 0.9581 (rough estimate)
• Refractive Index: 1.5130 (estimate)
• PKA: 14.69±0.60(Predicted)
• Water Solubility: 32g/L(15 oC)
• CAS DataBase Reference: SOBREROL(CAS DataBase Reference)
• NIST Chemistry Reference: SOBREROL(498-71-5)
• EPA Substance Registry System: SOBREROL(498-71-5)

Safety Data

• Hazardous Substances Data: 498-71-5(Hazardous Substances Data)

Usage

Originator

Sobrepin,Corvi,Italy,1970

Manufacturing Process

To 19 l of well-agitated distilled water plus 18 g of ditertiary-butyl-p-cresol was added 19.84 kg (130 mols) of pure α-pinene oxide that was about half racemic, half d-form. The temperature was maintained at 30°C to 50°C, first with ice bath cooling and then with tap water cooling. The addition of the pinene oxide required 1,5 hours. After the addition was complete and the exothermic reaction was about over, the mixture was stirred for 2,5 hours at about 30°C, and then centrifuged to separate the crude sobrerol from the liquid phase consisting of oil and water.The crude sobrerol was washed with naphtha and then air dried to yield 14.81 kg (87.5 mols) of pure sobrerol, [α]D 25 -77.0°. It was found that 1 liter of the aqueous phase from the reaction contained 22 g of sobrerol, so, therefore, the entire aqueous phase contained 0.42 kg (2.5 mols) of sobrerol.

Therapeutic Function

Mucolytic

InChI:InChI=1S/C10H18O2/c1-7-4-5-8(6-9(7)11)10(2,3)12/h4,8-9,11-12H,5-6H2,1-3H3

Upstream product

• 60661-95-2 1,6-dichloro-p-menthane-2,8-diol 
• 110202-13-6 1,2-dibromo-p-menthan-8-ol 
• 71697-84-2 (-)-trans-sobrerol 
• 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 
• 56423-45-1 (4R,8RS)-8,9-epoxy-p-menth-6-en-2-one 
• 80-26-2 terpinyl acetate 
• 1197-06-4 cis-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol 
• 80-56-8 Pinene 
• 98-55-5 terpineol 
• 1686-14-2 α-pinene epoxide 
• 99-49-0 Carvone 
• 80-56-8 rac-α-pinene 
• 58506-22-2 p-menthane-1,2,8-triol 

Downstream Products

• 68754-15-4 6,8-diacetoxy-p-menth-1-ene 
• 71697-84-2 (-)-trans-sobrerol 
• 38235-58-4 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 
• 106262-55-9 Octanoic acid 5-(1-hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enyl ester 
• 137821-91-1 (-)-(1S,5R)-sobrerol 

Relevant articles and documents

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.

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.

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.