Bakuchiol
Chemical compound
From Wikipedia, the free encyclopedia
Bakuchiol is a meroterpenoid (a chemical compound having a partial terpenoid structure) in the class terpenophenol.[1]
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| Names | |
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| Preferred IUPAC name
4-[(1E,3S)-3-Ethenyl-3,7-dimethylocta-1,6-dien-1-yl]phenol | |
| Other names
(+)-Bakuchiol | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.211.101 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C18H24O | |
| Molar mass | 256.389 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It was first isolated in 1966 by Mehta et al. from Psoralea corylifolia seed and was called Bakuchiol based on the Sanskrit name of the plant, Bakuchi.[2] Bakuchiol is a meroterpene phenol abundant in[3] and mainly obtained from the seeds of the Psoralea corylifolia plant,[4][5][6] which is widely used in Indian Ayurveda[7] to treat a variety of diseases.[8] It has also been isolated from other plants, such as P. grandulosa,[9][10] P. drupaceae,[11] Ulmus davidiana,[12] Otholobium pubescens,[13] Piper longum[14] and Aerva sangulnolenta Blum.[15]
Even though the first complete synthesis of Bakuchiol was described in 1973,[16] its first commercial use in topical applications did not occur until 2007 when it was introduced to the market under the trade name Sytenol A by Sytheon Ltd.[17]
It has been reported to have anticancer activity in preclinical models, possibly due to its structural similarity with resveratrol.[18] One study in rats suggested that Bakuchiol and ethanol extracts of the Chinese medicinal plant Psoralea corylifolia could protect against bone loss.[19]
Bakuchiol possesses antioxidant,[20][21] anti-inflammatory (in mice),[22][23] and in vitro antibacterial [24] properties. Bakuchiol isolated from P. corylifolia has shown activity against numerous Gram-positive and Gram-negative oral pathogens. It was able to inhibit the growth of Streptococcus mutans under a range of sucrose concentrations, pH values and in the presence of organic acids in a temperature-dependent manner and also inhibited the growth of cells adhered to a glass surface.[25]
Despite having no structural resemblance to retinol,[26] Bakuchiol was found to have retinol functionality through retinol-like regulation of gene expression.[27][28] In 2018, a randomized, double-blind, 12-week clinical study with 44 volunteers demonstrated that Bakuchiol is comparable with retinol in its ability to improve photoaging (wrinkles, hyperpigmentation) but has a better skin tolerance.[29]
Bakuchiol has been found to possess antiandrogenic activity in prostate cancer cells, which inhibited cell proliferation.[30]