10309-37-2

Basic information

• Product Name: 4-(3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-PHENOL
• Synonyms: 4-(3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-PHENOL;BAKUCHIOL;P-(3,7-DIMETHYL-3-VINYLOCTA-TRANS-1,6-DIMETHYL) PHENOL;7-dimethyl-1,6-octadienyl)-4-(3-ethenyl-(s-(e))-pheno;BACTRIS GASIPAES FRUIT JUICE;BAKUCHIOL(RG);Backuchiol;(S)-Bakuchiol
• CAS NO: 10309-37-2
• Molecular Formula: C₁₈H₂₄O
• Molecular Weight: 256.38
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 10309-37-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 391℃
• Flash Point: 177℃
• Appearance: white-off solid or colorless liquid
• Density: 0.963
• Vapor Pressure: 1.1E-06mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: -20°C
• Solubility: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 20 mg/ml)
• PKA: 10.10±0.26(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
• BRN: 3611720
• CAS DataBase Reference: 4-(3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-PHENOL(10309-37-2)
• EPA Substance Registry System: 4-(3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-PHENOL(10309-37-2)

Safety Data

• WGK Germany: 3
• RTECS: SL3785000
• Hazardous Substances Data: 10309-37-2(Hazardous Substances Data)

Usage

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.

Safety Profile

Poison by intravenous andintraperitoneal routes. Moderately toxic by ingestion.When heated to decomposition it emits acrid smoke andfumes.

References

1) Adhikari et al. (2007), Physico-chemical studies on the evaluation of the antioxidant activity of herbal extracts and active principles of some Indian medicinal plants; J. Clin. Biochem. Nutr., 40 174 2) Kim et al. (2013), Protective effects of the compounds isolated from the seed of Psoralea corylifolia on oxidative stress-induced retinal damage; Toxicol. Appl. Pharmacol., 269 109 3) Zhang et al. (2017), Bakuchiol protects against acute lung injury in septic mice; Inflammation, 40 351 4) Kim et al. (2016), Quantitative Analysis of Psoralea corylifolia Linne and its Neuroprotective and Anti-Neuroinflammatory Effects in HT22 Hippocampal Cells and BV-2 Microglia; Molecules, 21 E1076

InChI:InChI=1/C18H24O/c1-5-18(4,13-6-7-15(2)3)14-12-16-8-10-17(19)11-9-16/h5,7-12,14,19H,1,6,13H2,2-4H3/b14-12+/t18-/m1/s1

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Downstream Products

• 1026776-51-1 C₁₉H₂₄O₂ 
• 1026776-58-8 (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-2-nitrophenol 
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• 1361320-43-5 (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)phenyl decanoate 
• 1361320-41-3 4-(3,7-dimethyl-3-vinylocta-1,6-dienyl)phenyl hexanoate 
• 1361320-40-2 4-(3,7-dimethyl-3-vinylocta-1,6-dienyl)phenyl pentanoate 
• 1361320-38-8 (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)phenyl propionate 
• 1361320-56-0 2,6-dibromo-4-(3-ethyl-3,7-dimethyloctyl)phenol 
• 1361320-55-9 1-methoxy-[4-{3-(4-methoxystyryl)-3,7-dimethylocta-1,6-dienyl}]benzene 
• 1361320-45-7 4-(3-ethyl-3,7-dimethyloctyl)-2-iodophenol 

Relevant articles and documents

A short synthesis of (+)-bakuchiol

The concise enantioselective total synthesis of (+)-bakuchiol has been achieved using an asymmetric 1,4-addition to construct its all-carbon chiral quaternary center based on the induction of chirality by the (2′S)-2′-phenyloxazolidinone auxiliary, followed by a one-pot transformation under aldol reaction conditions. The synthesis was completed in four steps from (E)-geranic acid in an overall yield of 53%. Georg Thieme Verlag Stuttgart · New York.

Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated claisen rearrangement and total synthesis of (+)-Bakuchiol

An asymmetric Claisen rearrangement using Oppolzer's camphorsultam was developed. Under thermal conditions, a geraniol-derived substrate underwent the rearrangement with good stereoselectivity. The absolute configuration of the newly formed all-carbon quaternary stereocenter was confirmed by the total synthesis of (+)-bakuchiol from the rearrangement product.