[2S-[2alpha,5beta(R*)]]-tetrahydro-alpha,alpha,5-trimethyl-5-(4-methyl-3-cyclohexen-1-yl)furan-2-methanol

Base Information

• Chemical Name: [2S-[2alpha,5beta(R*)]]-tetrahydro-alpha,alpha,5-trimethyl-5-(4-methyl-3-cyclohexen-1-yl)furan-2-methanol
• CAS No.: 26184-88-3
• Molecular Formula: C₁₅H₂₆O₂
• Molecular Weight: 238.37
• Mol file: 26184-88-3.mol

Synonyms:2-Furanmethanol,tetrahydro-a,a,5-trimethyl-5-(4-methyl-3-cyclohexen-1-yl)-, [2S-[2a,5b(R*)]]-; (-)-Bisabolol oxide B; (-)-a-Bisabolol oxide B; Bisabololoxide II; a-Bisabolol oxide B

Chemical Property of [2S-[2alpha,5beta(R*)]]-tetrahydro-alpha,alpha,5-trimethyl-5-(4-methyl-3-cyclohexen-1-yl)furan-2-methanol

Chemical Property:

• Boiling Point: 326.4±35.0 °C(Predicted)
• PKA: 14.57±0.29(Predicted)
• Flash Point: 124.9oC
• PSA: 29.46000
• Density: 1.006±0.06 g/cm3(Predicted)
• LogP: 3.44140
• Storage Temp.: Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

BisabololOxideB ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Bisabolol Oxide B is a metabolite of (-)-α-Bisabolol. In the metabolic pathway was used Glomerella Cingulata, a pathogenic fungus. Bisabolol Oxide A and B are in the composition of chamomile flower.

Technology Process of [2S-[2alpha,5beta(R*)]]-tetrahydro-alpha,alpha,5-trimethyl-5-(4-methyl-3-cyclohexen-1-yl)furan-2-methanol

There total 7 articles about [2S-[2alpha,5beta(R*)]]-tetrahydro-alpha,alpha,5-trimethyl-5-(4-methyl-3-cyclohexen-1-yl)furan-2-methanol 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:

6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol (26560-22-5) → 3,4-dihydroxy bisabolol + bisabololoxide B (26184-88-3)

Guidance literature:

With plant peroxygenase from tomato (Solanum lycopersicum); dihydrogen peroxide; at 40 ℃; for 0.666667h;

DOI:10.1016/j.molcatb.2013.07.001

Reference yield:

(-)-α-bisabolol (515-69-5,23089-26-1,23178-88-3,25428-43-7,72059-10-0,72691-24-8,76738-75-5,78148-59-1,123877-54-3,26560-22-5) → α-bisabolol oxide B (26184-88-3) + 2-(1-hydroxy-1-methylethyl)-5-methyl-5-(1-methylcyclohex-1-en-4-yl)tetrahydrofuran (26184-88-3) + 2-[(2S,5S)-5-Methyl-5-((S)-6-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-tetrahydro-furan-2-yl]-propan-2-ol + 2-(1-hydroxy-1-methylethyl)-5-methyl-5-(6-methyl-7-oxabicyclo[4.1.0]hept-3-yl)tetrahydrofuran

Guidance literature:

With tert.-butylhydroperoxide; VOL₇(OEt); In chloroform; at 20 ℃; for 48h;

DOI:10.1002/ejoc.200200644

Reference yield:

(-)-α-bisabolol (515-69-5,23089-26-1,23178-88-3,25428-43-7,72059-10-0,72691-24-8,76738-75-5,78148-59-1,123877-54-3,26560-22-5) → α-bisabolol oxide B (26184-88-3) + 2-(1-hydroxy-1-methylethyl)-5-methyl-5-(1-methylcyclohex-1-en-4-yl)tetrahydrofuran (26184-88-3) + 2-[(2S,5S)-5-Methyl-5-((S)-6-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-tetrahydro-furan-2-yl]-propan-2-ol + 2-(1-hydroxy-1-methylethyl)-5-methyl-5-(6-methyl-7-oxabicyclo[4.1.0]hept-3-yl)tetrahydrofuran

Guidance literature:

With tert.-butylhydroperoxide; VOL₇(OEt); In chloroform; at 20 ℃; for 48h;

DOI:10.1002/ejoc.200200644

upstream raw materials:

(-)-α-bisabolol

6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol