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Bakuchiol

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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
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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℃
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Safety Information

WGK Germany 
3
RTECS 
SL3785000
Toxicity
LD50 orl-mus: 2560 mg/kg MZHUDX 42,646,80
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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.

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