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

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

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

Upstream product

• 17015-63-3 (+/-)-bakuchiol methyl ether 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 104846-78-8 3,7-dimethyl-oct-6-en-1-yn-3-yl methyl carbonate 
• 106-24-1 Geraniol 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 105460-59-1 methyl 2-{4-[(tert-butyldimethylsilyl)oxy]phenyl}acetate 
• 65071-54-7 3,7-dimethyl-1,2,6-octatriene 
• 498548-56-4 2-(4-((tert-butyldimethylsilyl)-oxy)phenyl)acetaldehyde 
• 17015-63-3 (S,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene 
• 1201917-34-1 (R)-(-)-3-vinyl-3,7-dimethyloct-6-enal 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 58558-13-7 (2E)-3,7-dimethyl-2,6-octadienoyl chloride 
• 4698-08-2 (E)-geranic acid 
• 1473417-84-3 C₁₉H₂₃NO₃ 

Downstream Products

• 43010-52-2 7,8,16,17-tetrahydrobakuchiol 
• 43010-50-0 7,8-dihydrobakuchiol 
• 10309-38-3 4-(3-ethyl-3,7-dimethyloctyl)phenol 
• 43010-46-4 (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)phenyl acetate 
• 17015-63-3 (S,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene 
• 74921-91-8 bakuchiol ethyl ether 
• 74921-92-9 (S,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-propoxybenzene 
• 74921-97-4 2-hydroxybakuchiol methyl ether 

Relevant articles and documents

Synthesis of (±)-Bakuchiol via a pot-economy approach

A rapid synthetic route toward (±)-Bakuchiol is presented in 29% overall yield. After the sole all-carbon quaternary carbon center is created via allylboration of 2-aryl acetaldehyde, a “Pot-Economy” approach including mesylation, elimination, and desilylation was realized in the presence oftBuOK under ambient temperature to provide (±)-Bakuchiol.

Enantioselective Synthesis of Quaternary Stereocenters via Chromium Catalysis

Asymmetric allylation of aldehydes with γ-disubstituted allyl halides has been achieved in the presence of a sulfonamide/oxazoline chromium complex. A variety of synthetically useful α-homoallylic alcohols with two consecutive stereogenic centers, including one quaternary carbon, can be accessed in a highly diastereoselective and enantioselective manner.

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.

A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol and ent-Bakuchiol

A facile asymmetric synthesis of Δ3-2-Hydroxybakuchiol, Bakuchiol, and ent-Bakuchiol is described through one common intermediate bearing a chiral all-carbon quaternary carbon center, which involves stereoselectively unconjugated alkylation of the α,β-unsaturated imide bearing Evans' auxiliary, Takai-Utimoto reaction, Negishi reaction, and Heck reaction as key steps.

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.

Stereoselective total synthesis of natural (S)-bakuchiol and its enantiomer

A practical stereoselective synthesis of (S)-bakuchiol (1) and its enantiomer is reported. The important intermediate, (R)-configured β-siloxy aldehyde 5, was obtained in three steps from the easily available material geraniol (2) via the key step of Yamamoto's rearrangement of epoxy silyl ethers. (S)-Bakuchiol (1) and its enantiomer, (R)-bakuchiol (17), were finally obtained in different synthetic sequences with overall yields of 51% (ten steps) and 40% (nine steps) from geraniol (2), respectively.

Efficient construction of a chiral all-carbon quaternary center by asymmetric 1,4-addition and its application to total synthesis of (+)-bakuchiol

The conjugate addition of lithium divinylcuprate to (4S,2′E)-3-(6′-TBDPS-3′-methylhex-2′-enoyl)-4-phenyloxazolidin-2-one proceeded efficiently to create a chiral all-carbon quaternary center with a high diastereoselectivity (R:S = 95:5). The absolute configuration of the newly generated chiral center was confirmed by applying this methodology to the total synthesis of (+)-bakuchiol.

Synthesis and structure-immunosuppressive activity relationships of bakuchiol and its derivatives

A series of derivatives of bakuchiol were synthesized and tested in vitro for their cytotoxicity, and inhibition of T cell proliferation and B cell proliferation. The data obtained provided preliminary structure-activity relationships of the compounds as immunosuppressive activity.

Pharmaceutical compounds for treating copd

Use of an MPO inhibitor for the treatment of COPD.

Enantiocontrolled synthesis of natural (+)-bakuchiol

(+)-Bakuchiol (1), an irregular phenolic monoterpene of Psoralea corylifolia L., has been first synthesized in natural forms starting from (S)-O-benzylglycidol (2).