Bakuchiol
Bakuchiol Basic information
- Product Name:
- Bakuchiol
- Synonyms:
-
- 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
- (S)-Bakuchiol
- 4-[(1E,3S)-3,7-Dimethyl-3-vinyl-1,6-octadienyl]phenol
- 4-[(1E,3S)-3-Vinyl-3,7-dimethyl-1,6-octadienyl]phenol
- 4-[(S,E)-3-Ethenyl-3,7-dimethyl-1,6-octadienyl]phenol
- CAS:
- 10309-37-2
- MF:
- C18H24O
- MW:
- 256.38
- EINECS:
- 685-515-4
- Product Categories:
-
- chemical reagent
- pharmaceutical intermediate
- phytochemical
- reference standards from Chinese medicinal herbs (TCM).
- standardized herbal extract
- Mol File:
- 10309-37-2.mol
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)
- form
- Liquid
- pka
- 10.10±0.26(Predicted)
- 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℃
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.
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.
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.
BakuchiolSupplier
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