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Merck
CN

SMB00604

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
UNSPSC Code:
12352205
NACRES:
NA.25
PubChem Substance ID:
329825075
MDL number:
MFCD01707441
Beilstein/REAXYS Number:
3611720

Key Documents

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Product Name

Bakuchiol, ≥95%

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

SMILES string

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

assay

≥95%

form

liquid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

Quality Level

200

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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.

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.

pictograms

Environment
GHS09

signalword

Warning

hcodes

H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000486043
0000486043
0000379926
0000347904
0000347904

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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)
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.
Zhenlong Xin et al.
Pharmacological research, 141, 208-213 (2019-01-06)
Bakuchiol (BAK), [(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadien-1-yl]phenol is a prenylated phenolic monoterpene extracted from the fruit of Psoralea corylifolia L., which belongs to the Leguminosae plant family. Previous research has shown that BAK exerts a variety of pharmacological effects, including antioxidant, antibacterial, anti-inflammatory, antiaging
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