19879-32-4

Basic information

• Product Name: BAVACHIN
• Synonyms: BAVACHIN;(S)-2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one;(2S)-2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
• CAS NO: 19879-32-4
• Molecular Formula: C20H20O4
• Molecular Weight: 324.37
• Mol File: 19879-32-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 558.3oC at 760 mmHg
• Flash Point: 202.1oC
• Appearance: /
• Density: 1.244
• Vapor Pressure: 4.52E-13mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: ≤20mg/ml in ethanol;30mg/ml in DMSO;50mg/ml in dimethyl formamide
• PKA: 8.27±0.40(Predicted)
• CAS DataBase Reference: BAVACHIN(CAS DataBase Reference)
• NIST Chemistry Reference: BAVACHIN(19879-32-4)
• EPA Substance Registry System: BAVACHIN(19879-32-4)

Safety Data

• Hazardous Substances Data: 19879-32-4(Hazardous Substances Data)

Usage

Description

Bavachin is a flavonoid first isolated from seeds of P. corylifolia. It is a phytoestrogen that activates the estrogen receptors ERα and ERβ (EC50s = 320 and 680 nM, respectively). Through this action, bavachin stimulates osteoblast proliferation and differentiation and prevents bone loss following ovariectomy in rats. Bavachin less potently inhibits acyl-coenzyme A:cholesterol acyltransferase (IC50 = 86 μM).

Uses

Bavachin has therapeutic potential for type 2 diabetes by activating insulin signaling pathways. Also, it has anabolic and potent anticatabolic biological effects on chondrocytes. Strong inhibitor of human UDP-glucuronosyltransferase (UGT1A1)

references

[1] choi j h, rho m c, lee s w, et al. bavachin and isobavachalcone, acyl-coenzyme a: cholesterol acyltransferase inhibitors from psoralea corylifolia[j]. archives of pharmacal research, 2008, 31(11): 1419-1423.[2] park j, kim d h, ahn h n, et al. activation of estrogen receptor by bavachin from psoralea corylifolia[j]. biomolecules & therapeutics, 2012, 20(2): 183-188.[3] lee h, li h, noh m, et al. bavachin from psoralea corylifolia improves insulin-dependent glucose uptake through insulin signaling and ampk activation in 3t3-l1 adipocytes[j]. international journal of molecular sciences, 2016, 17(4): 527.

InChI:InChI=1/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

Upstream product

• 934247-88-8 7,4'-dimethoxymethoxy-6-(3,3-dimethylallyl)-flavanone 
• 948307-21-9 2-hydroxy-4,4’-dimethoxy methyl ether-5-isopentenyl chalcone 
• 1314539-20-2 2'-prenyloxy-4'-methoxymethoxyacetophenone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 128961-13-7 (E)-1-(2-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one 
• 128961-25-1 1-(4-methoxy-2-((3-methylbut-2-en-1-yl)oxy)phenyl)ethan-1-one 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 1092462-95-7 4'-methoxy-4-methoxymethoxy-2'-prenyloxychalcone 
• 78316-24-2 7,4'-di(methoxymethoxy)flavan-4-one 
• 124775-22-0 1-<2-Hydroxy-4-(methoxymethoxy)phenyl>-3-<4-(methoxymethoxy)phenyl>prop-2-en-1-on 
• 65490-08-6 2-hydroxy-4-(methoxymethoxy)acetophenone 
• 870-63-3 prenyl bromide 
• 99217-72-8 2-hydroxy-5-(3,3-dimethylallyl)-4-methoxymethyloxyacetophenone 

Related news

Determination of BAVACHIN (cas 19879-32-4) and isobavachalcone in Fructus Psoraleae by high‐performance liquid chromatography with electrochemical detection09/28/2019

A simple, sensitive and selective method of high‐performance liquid chromatography with electrochemical detection (HPLC‐ECD) has been developed for simultaneous determination of bavachin and isobavachalcone in Fructus Psoraleae. At optimized conditions, bavachin and isobavachalcone could be we...detailed

Separation of isomeric BAVACHIN (cas 19879-32-4) and isobavachalcone in the Fructus Psoraleae by capillary electrophoresis–mass spectrometry10/01/2019

Bavachin and isobavachalcone are the isomeric compounds in the Fructus Psoraleae. The ion trap mass spectrometric fragmentation pathways of the bavachin and isobavachalcone in negative ion mode were elucidated for the identification. A novel method for determination of isomeric bavachin and isob...detailed

Microbial transformation of BAVACHIN (cas 19879-32-4) by Absidia coerulea09/27/2019

Microbial transformation of bavachin (1), one of the major bioactive components of Psoralea corylifolia L., was performed by using Absidia coerulea. Three oxidized metabolites were obtained in the biotransformation of 1, and their structures were elucidated as bavachinone A (2), (2S)-4′-hydroxy...detailed

Phytoestrogen BAVACHIN (cas 19879-32-4) mediates anti-inflammation targeting IκB kinase-IκBα-NF-κB signaling pathway in chondrocytes in vitro09/26/2019

The pro-inflammatory cytokine interleukin-1beta (IL-1β) plays critical roles in pathogenesis of osteoarthritis. Although estrogen is protective for cartilage in osteoarthritis patients, it also potentially increases the risk of stroke and cancer. Phytoestrogens acting as natural estrogen recept...detailed

BAVACHIN (cas 19879-32-4) and isobavachalcone, acyl-coenzyme A: Cholesterol acyltransferase inhibitors from Psoralea corylifolia09/25/2019

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 Psor...detailed

Relevant articles and documents

Flavonoids as vasorelaxant agents: Synthesis, biological evaluation and quantitative structure activities relationship (QSAR) studies

A series of 2-(2-diethylamino)-ethoxychalcone and 6-prenyl(or its isomers)-flavanones 10a,b and 11a-g were synthesized and evaluated for their vasorelaxant activities against rat aorta rings pretreated with 1 μM phenylephrine (PE). Several compounds showe

Synthesis of four natural prenylflavonoids and their estrogen-like activities

Four prenylflavonoids, bavachin 1, isobavachin 2, 7,4′-dihydroxy-8- prenylflavone 3, and 8-prenylapigenin 4 were synthesized and recognized for possessing estrogen-like activity in MCF-7/BOS cells, as evaluated by an estrogen-screening assay. All compound