Bakuchiol Chemical Properties

Boiling point:

391℃

Density 

0.963

vapor pressure 

0Pa at 25℃

refractive index 

1.4500 (estimate)

Flash point:

177℃

storage temp. 

Inert atmosphere,Store in freezer, under -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)

form 

Liquid

color 

Oil

optical activity

[α]/D +24.0 to +30.0°, c = 0.1 in chloroform

BRN 

3611720

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.

InChIKey

LFYJSSARVMHQJB-WYMLVPIESA-N

LogP

5.09 at 20℃ and pH6.31

Surface tension

43.92mN/m at 1g/L and 20℃

Safety Information

WGK Germany 

3

RTECS 

SL3785000

Toxicity

LD50 orl-mus: 2560 mg/kg MZHUDX 42,646,80

Bakuchiol Usage And Synthesis

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.

Chemical Properties

Bakuchiol (Bakuchiol) is the main component of the volatile oil of the commonly used traditional Chinese medicine Bakuchiol, accounting for more than 60% of its volatile oil, is an isoprenoid-based phenolic terpenoid. It is easily oxidized and has the property of overflowing with water vapor. Soluble in methanol, ethanol, DMSO and other organic solvents, from the seeds of PsoraleacorylifoliaLinn. It is light yellow oily liquid at room temperature, with strong fat solubility.

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.

Biological Activity

Bakuchiol (BAK) has various pharmacological effects such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, antidiabetic, cardioprotective, and estrogen-like effects. BAK exhibits antimicrobial activity against oral microorganisms such as Streptococcus mutans. It is also a DNA polymerase inhibitor and showed anti-tumour activity in human lung adenocarcinoma A549 cells. BAK showed hepatoprotective activity in vitro and in vivo against liver injury in rats.

Safety Profile

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

Synthesis

General procedure for the synthesis of (E)-4-(3,7-dimethyl-3-vinyl-octa-1,6-dien-1-yl)phenol from the compound (CAS: 17015-63-3): to a 5 mL solution of ether (Et2O) containing 151 mg (0.56 mmol) of the raw material, 0.28 mL (0.84 mmol, 3.0 M in Et2O ) of methylmagnesium iodide (MeMgI) ether solution. After completion of the reaction, the solvent was removed under reduced pressure and the residue was heated at 180 °C for 10 min under argon (Ar) protection. After the reaction mixture was cooled to room temperature, the reaction was quenched with 10 mL of saturated aqueous ammonium chloride (NH4Cl). Subsequently, the product was extracted with ethyl acetate (AcOEt, 10 mL x 3). The organic phases were combined, washed with brine and dried over anhydrous sodium sulfate (Na2SO4). The solvent was removed by concentration under reduced pressure and the crude product was purified by column chromatography (eluent: petroleum ether/ethyl acetate = 15:1) to afford psoralen as a colorless oil (129 mg, 90% yield). Thin layer chromatography (TLC) showed an Rf value of 0.53 (Expander: petroleum ether/ethyl acetate = 10:1). The specific optical rotation [α]D27.5 was +24.9 (c 0.98, CHCl3). Nuclear magnetic resonance hydrogen spectrum (1H NMR, 400 MHz, CDCl3) δ: 7.24 (d, J=8.5 Hz, 2H), 6.76 (d, J=8.5 Hz, 2H), 6.25 (d, J=16.2 Hz, 1H), 6.05 (d, J=16.2 Hz, 1H), 5.88 (dd, J=17.2,10.8 Hz, 1H ), 5.11 (t, J=7.1 Hz, 1H), 5.02 (m, 2H), 1.95 (m, 2H), 1.67 (s, 3H), 1.58 (s, 3H), 1.49 (m, 2H), 1.19 (s, 3H). Nuclear magnetic resonance carbon spectrum (13C NMR, 100 MHz, CDCl3) δ: 154.5, 145.9, 135.7, 131.3, 130.7, 127.3, 126.4, 124.7, 115.3, 111.8, 42.4, 41.2, 25.6, 23.2, 23.1, 17.6. electrospray mass spectrometry (ESI- MS): calculated value C18H25O+ [M+H]+: 257.1, measured value: 257.2.

Mode of action

The research found that BAK upregulates the expression of the antiapoptotic molecule Bcl2 and downregulates the expression of the proapoptotic molecules Bax and caspase-3 by activating the silent information regulator 1 (SIRT1) signaling pathway and thereby inhibits mitochondrial damage and ameliorates myocardial IRI. BAK promotes apoptosis in hepatic astrocytes through the caspase-3-dependent pathway and inhibits liver fibrosis. In addition, BAK exerts a protective effect against hepatotoxicity induced by tert-butyl hydroperoxide (tBH), tetrachloromethane (CCl4), and d-galactosamine (D-GalN). BAK (60?mg/kg) treatment significantly reduces edema and pathological changes in lung tissues by inhibiting intense inflammation and exerting protective effects in the lung under sepsis conditions[5-6].

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
[5] Zhenlong Xin . “Bakuchiol: A newly discovered warrior against organ damage.” Pharmacological research 141 (2019): Pages 208-213.
[6] Jianyu Feng. “Bakuchiol attenuates myocardial ischemia reperfusion injury by maintaining mitochondrial function: the role of silent information regulator 1.” Apoptosis 71 1 (2016): 532–545.

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