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SMB00604

Sigma-Aldrich

Bakuchiol

≥95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C18H24O
CAS Number:
10309-37-2
Molecular Weight:
256.38
Beilstein:
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

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

363.2 °F - Pensky-Martens closed cup

Flash Point(C)

184 °C - Pensky-Martens closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘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
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
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