BAKUCHIOL

Base Information

• Chemical Name: BAKUCHIOL
• CAS No.: 17015-60-0
• Molecular Formula: C₁₈H₂₄O
• Molecular Weight: 256.388
• Mol file: 17015-60-0.mol

Synonyms:Phenol,4-(3-ethenyl-3,7-dimethyl-1,6-octadienyl)-, (E)- (9CI); Phenol,4-(3-ethenyl-3,7-dimethyl-1,6-octadienyl)-, (E)-(?à)-; Phenol, p-(3,7-dimethyl-3-vinyl-1,6-octadienyl)-,(E)-(?à)- (8CI); (?à)-Bakuchiol

Chemical Property of BAKUCHIOL

Chemical Property:

• Vapor Pressure: 1.1E-06mmHg at 25°C
• Refractive Index: 1.554
• Boiling Point: 382.7oC at 760 mmHg
• PKA: 10.10±0.26(Predicted)
• Flash Point: 172.6oC
• PSA: 20.23000
• Density: 0.97g/cm3
• LogP: 5.34410

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BAKUCHIOL

There total 34 articles about BAKUCHIOL 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:

trans-geranyl bromide (6138-90-5) → bakuchiol (17015-60-0,93998-10-8,10309-37-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3,4,5-trifluoro-N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; chromium dichloride; zirconocene dichloride; cesium iodide; nickel dichloride; manganese / tetrahydrofuran / 10 h / -10 °C / Inert atmosphere

2.1: pyridine; methanesulfonyl chloride / 10 h / 20 °C

2.2: 5 h / 20 °C

3.1: methyl magnesium iodide / 0.17 h / 185 °C / Inert atmosphere

With pyridine; chromium dichloride; manganese; methyl magnesium iodide; zirconocene dichloride; 3,4,5-trifluoro-N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; methanesulfonyl chloride; nickel dichloride; cesium iodide; In tetrahydrofuran;

DOI:10.1021/acs.orglett.6b02540

Reference yield:

4-Methoxyphenylacetaldehyde (5703-26-4) → bakuchiol (17015-60-0,93998-10-8,10309-37-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3,4,5-trifluoro-N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; chromium dichloride; zirconocene dichloride; cesium iodide; nickel dichloride; manganese / tetrahydrofuran / 10 h / -10 °C / Inert atmosphere

2.1: pyridine; methanesulfonyl chloride / 10 h / 20 °C

2.2: 5 h / 20 °C

3.1: methyl magnesium iodide / 0.17 h / 185 °C / Inert atmosphere

With pyridine; chromium dichloride; manganese; methyl magnesium iodide; zirconocene dichloride; 3,4,5-trifluoro-N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; methanesulfonyl chloride; nickel dichloride; cesium iodide; In tetrahydrofuran;

DOI:10.1021/acs.orglett.6b02540

Reference yield:

(R,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene (1020108-61-5) → 4-[(1E,3R)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol (1020108-62-6) + bakuchiol (17015-60-0,93998-10-8,10309-37-2)

Guidance literature:

(R,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene; With methyl magnesium iodide; In diethyl ether;

at 185 ℃; for 0.166667h; optical yield given as %ee; Inert atmosphere;

DOI:10.1002/hlca.200890041

upstream raw materials:

(+/-)-bakuchiol methyl ether

6-Methyl-hept-5-en-2-on

3,7-dimethyl-oct-6-en-1-yn-3-yl methyl carbonate

Geraniol

Downstream raw materials:

7,8,16,17-tetrahydrobakuchiol

7,8-dihydrobakuchiol

4-(3-ethyl-3,7-dimethyloctyl)phenol

C₁₉H₂₄O₂

Refernces

• 1、 Huang, Meng-Yuan,Chen, Long,Li, Ruoxi,Ji, Xueshun,Hong, Ran. "Synthesis of (±)-Bakuchiol via a pot-economy approach". . p. 715 - 720. Retrieved 2014/11/08.
• 2、 Xu, Qian-Qian,Zhao, Qun,Shan, Guang-Sheng,Yang, Xi-Cheng,Shi, Qi-Yuan,Lei, Xinsheng. "A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol and ent-Bakuchiol". . p. 10739 - 10746. Retrieved 2013/12/04.