Bakuchiol
Synonym(s):(S)-Bakuchiol;4-[(1E,3S)-3-Ethenyl-3,7-dimethyl-1,6-octadien-1-yl]phenol
- CAS NO.:10309-37-2
- Empirical Formula: C18H24O
- Molecular Weight: 256.38
- MDL number: MFCD01707441
- EINECS: 685-515-4
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-06 15:28:16
What is Bakuchiol?
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.
The Uses of Bakuchiol
(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.
What are the applications of Application
Bakuchiol is a PTP1B and DNA polymerase inhibitor
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.
Properties of Bakuchiol
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 |
form | neat |
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. |
Safety information for Bakuchiol
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H332:Acute toxicity,inhalation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Bakuchiol
InChIKey | LFYJSSARVMHQJB-WYMLVPIESA-N |
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