ChemicalBook Product Catalog Natural Products Flavonoids kaempferol-3-O-galactoside

kaempferol-3-O-galactoside

Product Namekaempferol-3-O-galactoside
CAS23627-87-4
MFC21H20O11
MW448.38
EINECS200-258-5
MOL File23627-87-4.mol

Chemical Properties

Melting point	245-246℃
Boiling point	823.2±65.0 °C(Predicted)
Density	1.79±0.1 g/cm3 (20 ºC 760 Torr)
storage temp.	-20°C
solubility	Ethanol: soluble
form	A solid
pka	6.20±0.40(Predicted)
color	Off-white to light yellow
Major Application	cell analysis clinical research general analytical life science and biopharma metabolomics
InChIKey	JPUKWEQWGBDDQB-DTGCRPNFSA-N
SMILES	O=C1C=2C(OC(=C1O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)C4=CC=C(O)C=C4)=CC(O)=CC2O

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Uses

Kaempferol 3-O-β-D-galactopyranoside (Trifolin) is an orally active flavonoid derivative that can be found in the aerial parts of Consolida oliverana. Kaempferol 3-O-β-D-galactopyranoside exhibits antitumor and cardioprotective effects[1][2][3].

Definition

ChEBI: A beta-D-galactoside compound with a 4',5,7-trihydroxychromen-3-yl group at the anomeric position.

in vivo

Kaempferol 3-O-β-D-galactopyranoside (0.1–10.0 mg/kg, p.o., once daily for 4 weeks) improves cardiac function and reduces cardiomyocyte apoptosis in Angiotensin II (AngII) (HY-13948)-induced hypertensive cardiac injury C57BL/6 mice model^[3].

Animal Model:	Angiotensin II (AngII) (HY-13948)-induced hypertensive cardiac injury C57BL/6 mice model^[3]
Dosage:	0.1, 1.0, and 10.0 mg/kg
Administration:	Oral gavage (p.o.), once daily for 4 weeks
Result:	Improved left ventricular ejection fraction (LVEF) and fractional shortening (LVFS). Alleviated inflammatory cell infiltration and pathological damage in cardiac tissue. Reduced cardiomyocyte apoptosis and regulated Bax, Bcl-2, and cleaved caspase-3 protein expression

References

[1] da Silva I, et al. Structure determination of monohydrated trifolin (kaempferol 3-O-β-D-galactopyranoside) from laboratory powder diffraction data. J Pharm Sci. 2011;100(4):1588-1593. DOI:10.1002/jps.22379
[2] Kim MJ, et al. Trifolin induces apoptosis via extrinsic and intrinsic pathways in the NCI-H460 human non-small cell lung-cancer cell line. Phytomedicine. 2016 Sep 15;23(10):998-1004. DOI:10.1016/j.phymed.2016.05.009
[3] Zhang F, et al. Trifolin Attenuates Hypertension-Mediated Cardiac Injury by Inhibiting Cardiomyocyte Apoptosis: Mechanistic Insights and Therapeutic Potential. Eur J Pharmacol. 2024 Nov 9:177125. DOI:10.1016/j.ejphar.2024.177125

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