Bakuchiol

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Bakuchiol is derived from the Psoralea corylifolia plant, commonly known as babchi. This popular herb has long been used in both traditional Ayurvedic and Chinese medicine due to its ability to alleviate various skin conditions. This ancient herb has received a significant amount of scientific study which have deemed its empirical benefits verifiable. This vegan alternative to retinol appears to mimic the benefits of Vitamin A: preventing fine lines and wrinkles, and helping with pigmentation, elasticity, and firmness – without the periodic side effects of retinol.

  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3249905/
  • https://incidecoder.com/ingredients/bakuchiol
  • https://www.cosmeticsdesign.com/Article/2007/07/23/New-ingredient-for-the-repair-of-photoaged-skin
Bakuchiol (Wikipedia)

Bakuchiol is a meroterpene (a chemical compound having a partial terpenoid structure) in the class terpenophenol.

Bakuchiol
Chemical structure of bakuchiol
Names
Preferred IUPAC name
4-[(1E,3S)-3-Ethenyl-3,7-dimethylocta-1,6-dien-1-yl]phenol
Other names
(+)-Bakuchiol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.211.101 Edit this at Wikidata
EC Number
  • 685-515-4
UNII
  • InChI=1S/C18H24O/c1-5-18(4,13-6-7-15(2)3)14-12-16-8-10-17(19)11-9-16/h5,7-12,14,19H,1,6,13H2,2-4H3/b14-12+/t18-/m1/s1 checkY
    Key: LFYJSSARVMHQJB-QIXNEVBVSA-N checkY
  • InChI=1/C18H24O/c1-5-18(4,13-6-7-15(2)3)14-12-16-8-10-17(19)11-9-16/h5,7-12,14,19H,1,6,13H2,2-4H3/b14-12+/t18-/m1/s1
    Key: LFYJSSARVMHQJB-QIXNEVBVBX
  • Oc1ccc(/C=C/[C@@](\C=C)(C)CC\C=C(/C)C)cc1
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. Bakuchiol is a meroterpene phenol abundant in and mainly obtained from the seeds of the Psoralea corylifolia plant, which is widely used in Indian as well as in Traditional Chinese medicine to treat a variety of diseases. It has also been isolated from other plants, such as P. grandulosa, P. drupaceae, Ulmus davidiana, Otholobium pubescens, Piper longum and Aerva sangulnolenta Blum.

Even though the first complete synthesis of Bakuchiol has been described in 1973, 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.

It has been reported to have anticancer activity in preclinical models, possibly due to its structural similarity with resveratrol. One study in rats suggested that bakuchiol and ethanol extracts of the Chinese medicinal plant Psoralea corylifolia could protect against bone loss.

Bakuchiol possesses antioxidant, anti-inflammatory and anti-bacterial 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.

Despite having no structural resemblance to retinol, Bakuchiol was found to have retinol functionality through retinol-like regulation of gene expression. 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 photo-aging (wrinkles, hyperpigmentation) but has a better skin tolerance.

Bakuchiol has been found to possess antiandrogenic activity in prostate cancer cells, which inhibited cell proliferation.

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