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SMB00604

Sigma-Aldrich

Bakuchiol

≥95%

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C18H24O
CAS-Nummer:
10309-37-2
Molekulargewicht:
256.38
Beilstein:
3611720
MDL-Nummer:
MFCD01707441
UNSPSC-Code:
12352205
PubChem Substanz-ID:
329825075
NACRES:
NA.25

Qualitätsniveau

200

Assay

≥95%

Form

liquid

Anwendung(en)

metabolomics
vitamins, nutraceuticals, and natural products

Lagertemp.

−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

InChIKey

LFYJSSARVMHQJB-QIXNEVBVSA-N

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Allgemeine Beschreibung

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.

Anwendung

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

Biochem./physiol. Wirkung

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.

Piktogramme

Environment
GHS09

Signalwort

Warning

H-Sätze

H410

Gefahreneinstufungen

Aquatic Acute 1 - Aquatic Chronic 1

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 3

Flammpunkt (°F)

363.2 °F - Pensky-Martens closed cup

Flammpunkt (°C)

184 °C - Pensky-Martens closed cup

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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
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)
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.
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
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