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SMB00802

Sigma-Aldrich

Bavachin

from Psoralea coryfolia, ≥97% (HPLC)

Synonym(s):

(2S)-2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 4′,7-Dihydroxy 6-(3-methyl 2-butenyl)flavanone, Corylifolin

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About This Item

Empirical Formula (Hill Notation):
C20H20O4
CAS Number:
19879-32-4
Molecular Weight:
324.37
MDL number:
MFCD11617359
UNSPSC Code:
12352205
NACRES:
NA.28

Assay

≥97% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

InChI

1S/C20H20O4/c1-12(2)3-4-14-9-16-18(23)11-19(24-20(16)10-17(14)22)13-5-7-15(21)8-6-13/h3,5-10,19,21-22H,4,11H2,1-2H3

InChI key

OAUREGNZECGNQS-UHFFFAOYSA-N

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Biochem/physiol Actions

Bavachin is a flavonoid isolated from seeds of Psoralea corylifolia. It is a phytoestrogen that activates ERα and ERβ (EC50s = 320 and 680 nM, respectively), stimulates osteoblast proliferation and differentiation, and prevents bone loss following ovariectomy in rats.

Bavachin is an inhibitor of acyl coenzyme A: cholesterol acyltransferase (ACAT). The IC50 value of bavachin was reported to be 86.0 μM in ACAT assay system using rat liver microsome.

Bavachin is also reported to increase insulin-induced glucose uptake by differentiated adipocytes and myoblasts.

Physical properties

Bavachin is soluble in DMSO at 30 mg/mL. Bavachin is not water soluble.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

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Jung Ho Choi et al.
Archives of pharmacal research, 31(11), 1419-1423 (2008-11-22)
Acyl-coenzyme A: cholesterol acyltransferase (ACAT) catalyzes cholesterol esterification and plays important roles in intestinal absorption of cholesterol, hepatic production of lipoproteins and accumulation of cholesteryl ester within macrophages and smooth muscle cells. Ethanol extract of Psoralea corylifolia showed a significant
Hyejin Lee et al.
International journal of molecular sciences, 17(4), 527-527 (2016-04-14)
The fruit of Psoralea corylifolia L. (Fabaceae) (PC), known as "Bo-Gol-Zhee" in Korea has been used as traditional medicine. Ethanol and aqueous extracts of PC have an anti-hyperglycemic effect by increasing plasma insulin levels and decreasing blood glucose and total
Joonwoo Park et al.
Biomolecules & therapeutics, 20(2), 183-188 (2012-03-01)
In this study, we examined the estrogenic activity of bavachin, a component of Psoralea corylifolia that has been used as a traditional medicine in Asia. Bavachin was purified from ethanolic extract of Psoralea corylifolia and characterized its estrogenic activity by

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