| Identification | Back Directory | [Name]
BAVACHIN | [CAS]
19879-32-4 | [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 | [Molecular Formula]
C20H20O4 | [MDL Number]
MFCD11617359 | [MOL File]
19879-32-4.mol | [Molecular Weight]
324.37 |
| Chemical Properties | Back Directory | [Boiling point ]
558.3±50.0 °C(Predicted) | [density ]
1.244 | [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [solubility ]
≤20mg/ml in ethanol;30mg/ml in DMSO;50mg/ml in dimethyl formamide | [form ]
crystalline solid | [pka]
8.27±0.40(Predicted) | [color ]
White | [InChI]
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/t19-/m0/s1 | [InChIKey]
OAUREGNZECGNQS-IBGZPJMESA-N | [SMILES]
[C@H]1(C2=CC=C(O)C=C2)OC2=CC(O)=C(C/C=C(/C)\C)C=C2C(=O)C1 | [CAS DataBase Reference]
19879-32-4 |
| Hazard Information | Back Directory | [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).1,2 Through this action, bavachin stimulates osteoblast proliferation and differentiation and prevents bone loss following ovariectomy in rats.3,4 Bavachin less potently inhibits acyl-coenzyme A:cholesterol acyltransferase (IC50 = 86 μM).5 | [Chemical Properties]
Pale yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the fruit of Psoralea corylifolia Linn. | [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) | [target]
NF-kB | p65 | IkB | VEGFR | IL Receptor | AP-1 | AMPK | PPAR | GLUT | Akt | IKK | Estrogen receptor α | Estrogen receptor β | [storage]
Store at -20°C | [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. |
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