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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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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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DrugBank | |
ECHA InfoCard | 100.211.101 |
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PubChem CID |
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CompTox Dashboard (EPA) |
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Properties | |
C18H24O | |
Molar mass | 256.38 g/mol |
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] as well as in Traditional Chinese medicine[8] to treat a variety of diseases.[9] It has also been isolated from other plants, such as P. grandulosa,[10][11] P. drupaceae,[12] Ulmus davidiana,[13] Otholobium pubescens,[14] Piper longum[15] and Aerva sangulnolenta Blum.[16]
Even though the first complete synthesis of Bakuchiol was described in 1973,[17] 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.[18]
It has been reported to have anticancer activity in preclinical models, possibly due to its structural similarity with resveratrol.[19] One study in rats suggested that Bakuchiol and ethanol extracts of the Chinese medicinal plant Psoralea corylifolia could protect against bone loss.[20]
Bakuchiol possesses antioxidant,[21][22] anti-inflammatory,[23][24] and antibacterial[25] 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.[26]
Despite having no structural resemblance to retinol,[27] Bakuchiol was found to have retinol functionality through retinol-like regulation of gene expression.[28][29] 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.[30]
Bakuchiol has been found to possess antiandrogenic activity in prostate cancer cells, which inhibited cell proliferation.[31]
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