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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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20 MG
$322.00

$322.00

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20 MG
$322.00

About This Item

Empirical Formula (Hill Notation):
C18H24O
CAS Number:
10309-37-2
Molecular Weight:
256.38
Beilstein/REAXYS Number:
3611720
MDL number:
MFCD01707441
UNSPSC Code:
12352205
PubChem Substance ID:
329825075
NACRES:
NA.25

$322.00

Available to ship onApril 07, 2025Details

Request a Bulk Order

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.[1] It can also be found in other plants and flowers from the Leguminosae plant family.[2]

Application

Bakuchiol has been used as a reference standard to detect its existence in Psoralea corylifolia L. (PC) using ultra-performance liquid chromatography.[3]

Biochem/physiol Actions

Bakuchiol (BAK) has various pharmacological effects such as antioxidant, antiaging, anti-inflammatory, anti-bacterial, anti-diabetic, cardioprotective, and estrogen-like effects.[1] It is known to have similar efficacy but to be better-tolerated than retinol in improving photoaging.[2] Bakuchiol displays antimicrobial activity against oral microorganisms such as Streptococcus mutans.[4] It is also a DNA polymerase inhibitor and showed anti-tumor activity in human lung adenocarcinoma A549 cells.[5] Bakuchiol has displayed hepatoprotective activity against rat liver damage in both in vitro and in vivo.[6]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000379926
0000347904
0000347904
0000379926
0000279024

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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
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.
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
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
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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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