94344-54-4

Basic information

• Product Name: sappanchalcone
• Synonyms: sappanchalcone;(2E)-3-(3,4-Dihydroxyphenyl)-1-(4-hydroxy-2-Methoxyphenyl)-2-propen-1-one;3-(3,4-Dihydroxyphenyl)-1-(4-hydroxy-2-Methoxyphenyl)prop-2-en-1-one
• CAS NO: 94344-54-4
• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.27936
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 94344-54-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 581.673 °C at 760 mmHg
• Flash Point: 221.031 °C
• Appearance: /
• Density: 1.369 g/cm³
• Vapor Pressure: 3.96E-14mmHg at 25°C
• Refractive Index: 1.684
• Storage Temp.: Refrigerator
• Solubility: Acetone (Slightly), Methanol (Slightly)
• CAS DataBase Reference: sappanchalcone(CAS DataBase Reference)
• NIST Chemistry Reference: sappanchalcone(94344-54-4)
• EPA Substance Registry System: sappanchalcone(94344-54-4)

Safety Data

• Hazardous Substances Data: 94344-54-4(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Definition

ChEBI: A member of the class of chalcones that consists of trans-chalcone substituted by hydroxy groups at positions 3, 4 and 4' and a methoxy group at position 2'. Isolated from Caesalpinia sappan, it exhibits neuroprotective and cy oprotective activity.

InChI:InChI=1/C16H14O5/c1-21-16-9-11(17)4-5-12(16)13(18)6-2-10-3-7-14(19)15(20)8-10/h2-9,17,19-20H,1H3/b6-2+

Upstream product

• 493-33-4 1-(4-hydroxy-2-methoxy-phenyl)ethanone 
• 139-85-5 3,4-dihydroxybenzaldehyde 

Relevant articles and documents

Synthesis and evaluation of butein derivatives for in vitro and in vivo inflammatory response suppression in lymphedema

Herein, we demonstrate that butein (1) can prevent swelling in a murine lymphedema model by suppressing tumor necrosis factor α (TNF-α) production. Butein derivatives were synthesized and evaluated to identify compounds with in vitro anti-inflammatory activity. Among them, 20 μM of compounds 7j, 7m, and 14a showed 50percent suppression of TNF-α production in mouse peritoneal macrophages after lipopolysaccharide stimulation. Compound 14a, exhibited the strongest potency with an in vitro IC50 of 14.6 μM and suppressed limb volume by 70percent in a murine lymphedema model. The prodrug strategy enabled a six-fold increase in kinetic solubility of compound 1 and five-fold higher levels of active metabolite in the blood for compound 14a via oral administration in the pharmacokinetics study. We suggest that the compound 14a could be developed as a potential therapeutic agent targeting anti-inflammatory activity to alleviate lymphedema progression.