246Trihydroxychalcone

Product Name246Trihydroxychalcone
CAS4197-97-1
MFC15H12O4
MW256.25
EINECS
MOL File4197-97-1.mol

Chemical Properties

Melting point	189.9℃
Boiling point	487.9±45.0 °C(Predicted)
Density	1.384±0.06 g/cm3(Predicted)
storage temp.	4°C, away from moisture and light
form	Solid
pka	6.86±0.40(Predicted)
color	Light yellow to yellow
InChI	InChI=1S/C15H12O4/c16-11-8-13(18)15(14(19)9-11)12(17)7-6-10-4-2-1-3-5-10/h1-9,16,18-19H
InChIKey	LOYXTWZXLWHMBX-UHFFFAOYSA-N
SMILES	C(C1=C(O)C=C(O)C=C1O)(=O)C=CC1=CC=CC=C1

Usage And Synthesis

Uses

Pinocembrin chalcone (2',4',6'-Trihydroxychalcone) is an antibacterial compound from Helichrysum Trilineatum. Pinocembrin chalcone facilitates AMP-activated protein kinase (AMPK) activation, improves glucose tolerance, increases muscle FAO and reduces fat accumulation in the liver and skeletal muscles in high-fat diet-induced (HFD) diabetic mice. Pinocembrin chalcone is promising for research of gastric ulcers and diabetes[1][2].

Definition

ChEBI: Pinocembrin chalcone is a member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2', 4' and 6' respectively. It has a role as a plant metabolite and an antifungal agent. It is functionally related to a trans-chalcone.

in vivo

Pinocembrin chalcone (30 mg/kg, oral gavage, daily for 3 weeks) improves glucose tolerance and fat accumulation through fatty acid oxidation rate increase in skeletal muscle, which is mainly mediated by AMPK activation in HFD-induced diabetic mice^[2].

Animal Model:	HFD-induced diabetic mice^[2]
Dosage:	30 mg/kg
Administration:	oral gavage, daily for 3 weeks
Result:	Reduced the circulating FFA levels and fat accumulation in the liver and muscles by increasing FAO, which improved glucose tolerance in HFD-induced diabetic mice.

References

[1] P D Bremner, et al. Pinocembrin Chalcone: An Antibacterial Compound From Helichrysum Trilineatum. Planta Med. 1998 Dec;64(8):777. DOI:10.1055/s-2006-957585
[2] Shin J, et al. Antidiabetic effects of trihydroxychalcone derivatives via activation of AMP-activated protein kinase[J]. Journal of Industrial and Engineering Chemistry, 2018, 60: 177-184.