Sobrerol

Base Information

• Chemical Name: Sobrerol
• CAS No.: 498-71-5
• Deprecated CAS: 5947-39-7,6252-24-0
• Molecular Formula: C10H18O2
• Molecular Weight: 170.252
• Hs Code.: 2906199090
• European Community (EC) Number: 255-780-7,250-966-4,207-868-1
• NSC Number: 408849,74541,43652
• DSSTox Substance ID: DTXSID90871701
• Nikkaji Number: J6.110G
• Wikipedia: Sobrerol
• Wikidata: Q105194289
• Metabolomics Workbench ID: 127391
• ChEMBL ID: CHEMBL2228862
• Mol file: 498-71-5.mol

Synonyms:1-methyl-4-(2-hydroxyisopropyl)cyclohex-1,2-en-6-ol;1-methyl-alpha-hydroxyisopropylcyclohexenol-6;Sobrepin;sobrerol;sobrerol, (+-)-isomer

Chemical Property of Sobrerol

Chemical Property:

• Melting Point: 130°C
• Refractive Index: 1.5130 (estimate)
• Boiling Point: 270.5°Cat760mmHg
• PKA: 14.69±0.60(Predicted)
• Flash Point: 120.9°C
• PSA: 29.46000
• Density: 1.051g/cm³
• LogP: 2.12920
• Water Solubility.: 32g/L(15 oC)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 170.130679813
• Heavy Atom Count: 12
• Complexity: 194

Purity/Quality:

98%,99%, ^*data from raw suppliers

SOBEROL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC(CC1O)C(C)(C)O
• Therapeutic Function: Mucolytic

Technology Process of Sobrerol

There total 36 articles about Sobrerol 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: 94.0%

α-pinene epoxide (1686-14-2,25488-94-2) → sobrerol (498-71-5,454-77-3,772-36-1,32226-54-3,38235-58-4,42370-41-2,54164-89-5,60687-00-5,71697-84-2)

Guidance literature:

ruthenium trichloride; In water; for 0.0833333h;

DOI:10.1016/S0040-4020(97)10319-2

Reference yield: 75.0%

(1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.2,4]octane (1686-14-2,25488-94-2) → (1SR,5RS)-5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-enol (498-71-5) + 5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-enol (454-77-3,498-71-5,772-36-1,32226-54-3,38235-58-4,42370-41-2,54164-89-5,60687-00-5,71697-84-2)

Guidance literature:

With water; at 60 ℃; for 8h; Overall yield = 75 %;

DOI:10.1002/chem.201202886

Reference yield: 51.0%

(1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.2,4]octane (1686-14-2,25488-94-2) → 5-Isopropenyl-2-methyl-cyclohex-2-enol (99-48-9,22567-18-6,20307-86-2) + (1SR,5RS)-5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-enol (498-71-5) + trans-sobrerol (32226-54-3)

Guidance literature:

With water; at 100 ℃; for 1h;

DOI:10.1002/chem.201202886

upstream raw materials:

p-menthane-1,2,8-triol

rac-α-pinene

1,6-dichloro-p-menthane-2,8-diol

Pinene

Downstream raw materials:

(-)-trans-sobrerol

trans-sobrerol

p-menthane-1,2,6,8-tetraol

5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-cyclohex-2-enone

Refernces

• 1、 Xu, Zhao-Bing,Qu, Jin. "Hot water-promoted SN1 solvolysis reactions of allylic and benzylic alcohols". . p. 314 - 323. Retrieved 2013/03/13.
• 2、 Hachiya, Houjin,Kon, Yoshihiro,Ono, Yutaka,Takumi, Kiyoshi,Sasagawa, Naoki,Ezaki, Yoichiro,Sato, Kazuhiko. "Unique salt effect on the high yield synthesis of acid-labile terpene oxides using hydrogen peroxide under acidic aqueous conditions". scheme or table. p. 2819 - 2822. Retrieved 2012/01/02.