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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:
3611720
Número MDL:
MFCD01707441
Código UNSPSC:
12352205
ID de la sustancia en PubChem:
329825075
NACRES:
NA.25

Nivel de calidad

200

Ensayo

≥95%

Formulario

liquid

aplicaciones

metabolomics
vitamins, nutraceuticals, and natural products

temp. de almacenamiento

−20°C

cadena SMILES

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

Clave InChI

LFYJSSARVMHQJB-QIXNEVBVSA-N

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Descripción general

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.

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Pictogramas

Environment
GHS09

Palabra de señalización

Warning

Frases de peligro

H410

Consejos de prudencia

P273 - P391 - P501

Clasificaciones de peligro

Aquatic Acute 1 - Aquatic Chronic 1

Código de clase de almacenamiento

10 - Combustible liquids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

363.2 °F - Pensky-Martens closed cup

Punto de inflamabilidad (°C)

184 °C - Pensky-Martens closed cup

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Certificados de análisis (COA)

Lot/Batch Number
0000379926
0000347904
0000379926
0000279024
0000210314

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In vitro protein tyrosine phosphatase 1B inhibitory phenols from the seeds of Psoralea corylifolia.
Kim YC, Oh H, Kim BS, Kang TH, Ko EK, Han YM, Kim BY, Ahn JS.
Planta Medica, 71(1), 87-89 (2005)
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.
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
N J Sun et al.
Journal of natural products, 61(3), 362-366 (1998-04-17)
An ethanol extract of Psoralea corylifolia caused strong DNA polymerase inhibition in a whole cell bioassay specific for inhibitors of DNA replication enzymes. Bioassay-directed purification of the active compounds led to the isolation of the new compound corylifolin (1) and
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