Bakuchiol

Base Information

• Chemical Name: Bakuchiol
• CAS No.: 10309-37-2
• Molecular Formula: C₁₈H₂₄O
• Molecular Weight: 256.388
• Hs Code.: 2907199090
• NSC Number: 671195
• UNII: OT12HJU3AR
• DSSTox Substance ID: DTXSID401035664
• Nikkaji Number: J15.045B
• Wikipedia: Bakuchiol
• Wikidata: Q4849590
• RXCUI: 1368134
• Metabolomics Workbench ID: 129903
• ChEMBL ID: CHEMBL262344
• Mol file: 10309-37-2.mol

Synonyms:bakuchiol

Chemical Property of Bakuchiol

Chemical Property:

• Appearance/Colour: white-off solid or colorless liquid
• Vapor Pressure: 1.1E-06mmHg at 25°C
• Refractive Index: 1.554
• Boiling Point: 391.4°Cat760mmHg
• PKA: 10.10±0.26(Predicted)
• Flash Point: 176.6°C
• PSA: 20.23000
• Density: 0.963g/cm³
• LogP: 5.34410
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 20 mg/ml)
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 256.182715385
• Heavy Atom Count: 19
• Complexity: 328

Purity/Quality:

(S)-Bakuchiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(C)(C=C)C=CC1=CC=C(C=C1)O)C
• Isomeric SMILES: CC(=CCC[C@@](C)(C=C)/C=C/C1=CC=C(C=C1)O)C
• Recent ClinicalTrials: Comparison of the Cosmetic Effects of Bakuchiol and Retinol
• Description: Bakuchiol (10309-37-2) is a natural terpenoid antioxidant.It has the follow effects: 1.Inhibits oxidative stress-induced decrease in mitochondrial membrane potential and associated release of pro-apoptotic factors.2.Protects against acute lung injury.3.Displays neuroprotective and anti-inflammatory effects.
• Uses: (S)-Bakuchiol is a meroterpen found in the medicinal resinous shrub Psoralea glandulosa. An analogue of Resveratrol (R150000) with antifungal and anti-tumor effects. Studies have shown that Bakuchiol is a potent cytotoxic agent that exhibiting concentration dependent growth inhibition against leukemia cancer cells.

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:

bakuchiol ethyl ether

(S,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-propoxybenzene

C₁₉H₂₄O₂

(S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-2-nitrophenol

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.
• 2、 Xiong, Yang,Zhang, Guozhu. "Enantioselective Synthesis of Quaternary Stereocenters via Chromium Catalysis". . p. 5094 - 5097. Retrieved 2016/10/14.
• 3、 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.