ChemicalBook Product Catalog Natural Products Flavonoids 7,3',4'-Trihydroxyflavanone

7,3',4'-Trihydroxyflavanone

Product Name7,3',4'-Trihydroxyflavanone
CAS21913-99-5
MFC15H12O5
MW272.25
EINECS
MOL FileMol File

Chemical Properties

Boiling point	582.4±50.0 °C(Predicted)
Density	1.485±0.06 g/cm3(Predicted)
solubility	Acetonitrile: Soluble Methanol: Soluble
form	Solid
pka	7.69±0.40(Predicted)
color	Light yellow to light brown

Usage And Synthesis

Uses

Butin is a major biologically active flavonoid isolated from the heartwood of Dalbergia odorifera with oral activity, with strong antioxidant, antiplatelet and anti-inflammatory activities. Butin significantly alleviates myocardial infarction and improves heart function, together with prevents diabetes-induced cardiac oxidative damage in rat[1][2].

Definition

ChEBI: 2-(3,4-dihydroxyphenyl)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one is a member of flavanones.

in vivo

Butin (10-40 mg/kg, orally, twice a day, 15 days) can significantly reduce myocardial ischemia-reperfusion injury in diabetic mice, improve heart function, and increase the ability to resist oxidative stress^[1].
Butin (25-50 mg/kg, intraperitoneal injection, single dose) can reduce behavioral changes and neuronal conditions in rats with cerebral hemorrhage by reducing apoptosis and inflammatory responses^[2].

Animal Model:	C57/BL6J mice induced by STZ(HY-13753)^[1]
Dosage:	10, 20, 40 mg/kg; twice a day; 15 days
Administration:	Oral
Result:	Improved cardiac function, significant increases in LVSP, +dP/dtmax and -dP/dtmin, reduced myocardial infarction area, reduced caspase-3 activity and Bax/Bcl-2 ratio, reduced GSH-px, GSH, SOD, CAT and GR activity.

Animal Model:	Intracerebral hemorrhage rats^[2]
Dosage:	25, 50 mg/kg; single dose
Administration:	Intraperitoneal injection (i.p.)
Result:	Increased the neurological score, significantly reduced the volume of hemorrhagic lesions, significantly reduced the Bax/Bcl-2 ratio and caspase-3 protein expression, and significantly reduced brain tissue inflammatory mediators tumor necrosis factor-α (TNF-α) and interleukin. Reduced levels of 6 (IL-6).

References

[1] Duan J, et al. Protective effect of butin against ischemia/reperfusion-induced myocardial injury in diabetic mice: involvement of the AMPK/GSK-3β/Nrf2 signaling pathway. Sci Rep. 2017 Jan 27;7:41491. DOI:10.1038/srep41491
[2] Li P, et al. Butin Attenuates Brain Edema in a Rat Model of Intracerebral Hemorrhage by Anti Inflammatory Pathway. Transl Neurosci. 2018 May 8;9:7-12. DOI:10.1515/tnsci-2018-0002
[3] JINPENG LV . Synthesis and melanogenesis evaluation of 3′,4′,7-trihydroxyflavanone derivatives and characterization of flavanone–BODIPY[J]. Bioorganic & Medicinal Chemistry Letters, 2015, 25 7: Pages 1607-1610. DOI: 10.1016/j.bmcl.2015.01.072
[4] S. MILOSAVLJEVIC. Flavonoids of the Heartwood of Cotinus coggygria Scop. Showing Protective Effect on Human Lymphocyte DNA[J]. Natural Product Communications, 2021, 53 1. DOI: 10.1177/1934578x211067289
[5] BHARGAVA S K. Estrogenic and postcoital anticonceptive activity in rats of butin isolated from Butea monosperma seed[J]. Journal of ethnopharmacology, 1986, 18 1: Pages 95-101. DOI: 10.1016/0378-8741(86)90046-2

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