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SMB00604

Sigma-Aldrich

Bakuchiol

≥95%

Sinónimos:

(S)-Bakuchiol, 4-[(1E,3S)-3-Ethenyl-3,7-dimethyl-1,6-octadien-1-yl]phenol

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About This Item

Fórmula empírica (notación de Hill):
C18H24O
Número de CAS:
10309-37-2
Peso molecular:
256.38
Beilstein/REAXYS Number:
3611720
MDL number:
MFCD01707441
UNSPSC Code:
12352205
PubChem Substance ID:
329825075
NACRES:
NA.25

Quality Level

200

assay

≥95%

form

liquid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

C\C(C)=C/CC[C@@](C)(C=C)\C=C\c1ccc(O)cc1

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

InChI key

LFYJSSARVMHQJB-QIXNEVBVSA-N

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General description

Bakuchiol (BAK) is a phenolic meroterpene compound extracted from the fruits and seeds of Psoralea corylifolia. It can also be found in other plants and flowers from the Leguminosae plant family.

Application

Bakuchiol has been used as a reference standard to detect its existence in Psoralea corylifolia L. (PC) using ultra-performance liquid chromatography.

Biochem/physiol Actions

Bakuchiol (BAK) has various pharmacological effects such as antioxidant, antiaging, anti-inflammatory, anti-bacterial, anti-diabetic, cardioprotective, and estrogen-like effects. It is known to have similar efficacy but to be better-tolerated than retinol in improving photoaging. Bakuchiol displays antimicrobial activity against oral microorganisms such as Streptococcus mutans. It is also a DNA polymerase inhibitor and showed anti-tumor activity in human lung adenocarcinoma A549 cells. Bakuchiol has displayed hepatoprotective activity against rat liver damage in both in vitro and in vivo.

pictograms

Environment
GHS09

signalword

Warning

hcodes

H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

363.2 °F - Pensky-Martens closed cup

flash_point_c

184 °C - Pensky-Martens closed cup

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Eun-Jeon Park et al.
Planta medica, 71(6), 508-513 (2005-06-23)
The aim of this study was to investigate the protective effect of (S)-bakuchiol isolated from the seed of Psoralea corylifolia, on liver injury. Primary rat hepatocyte intoxication was induced by tert-butyl hydroperoxide (tBH), carbon tetrachloride (CCl4) or D-galactosamine (D-GalN). Liver
S Dhaliwal et al.
The British journal of dermatology, 180(2), 289-296 (2018-06-28)
Bakuchiol is a phytochemical that has demonstrated cutaneous antiageing effects when applied topically. Early studies have suggested that bakuchiol is a functional analogue of topical retinoids, as both compounds have been shown to induce similar gene expression in the skin
H Katsura et al.
Antimicrobial agents and chemotherapy, 45(11), 3009-3013 (2001-10-16)
Bakuchiol was isolated from the seeds of Psoralea corylifolia, a tree native to China with various uses in traditional medicine, followed by extraction with ether and column chromatography combined with silica gel and octyldecyl silane. In this study, the antimicrobial
Youn-Chul Kim et al.
Planta medica, 71(1), 87-89 (2005-01-29)
Protein tyrosine phosphatase 1B plays a major role in the negative regulation of insulin signaling, and this establishes protein tyrosine phosphatase 1B as an attractive therapeutic target for diabetes. Bioassay-guided fractionation of the EtOAc-soluble extract of the seeds of Psoralea
Masaki Shoji et al.
The Journal of biological chemistry, 290(46), 28001-28017 (2015-10-09)
Influenza represents a substantial threat to human health and requires novel therapeutic approaches. Bakuchiol is a phenolic isoprenoid compound present in Babchi (Psoralea corylifolia L.) seeds. We examined the anti-influenza viral activity of synthetic bakuchiol using Madin-Darby canine kidney cells.
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