13323-67-6

Basic information

• Product Name: 4-O-methylbutein
• Synonyms: 4-O-methylbutein;3,4',6'-Trihydroxy-4-methoxychalcone;3,2',4'-Trihydroxy-4-methoxychalcone
• CAS NO: 13323-67-6
• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28
• Mol File: 13323-67-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 198.5-200.5℃
• Boiling Point: 555.6°C at 760 mmHg
• Flash Point: 210.6°C
• Appearance: /
• Density: 1.369g/cm³
• Vapor Pressure: 5.97E-13mmHg at 25°C
• Refractive Index: 1.684
• PKA: 7.33±0.35(Predicted)
• CAS DataBase Reference: 4-O-methylbutein(CAS DataBase Reference)
• NIST Chemistry Reference: 4-O-methylbutein(13323-67-6)
• EPA Substance Registry System: 4-O-methylbutein(13323-67-6)

Safety Data

• Hazardous Substances Data: 13323-67-6(Hazardous Substances Data)

Usage

General Description

4-O-methylbutein is a natural compound found in the stems and leaves of the Fabaceae plant family, particularly in the bark and heartwood of Pterocarpus marsupium, Dalbergia sissoo, and Dalbergia latifolia. It belongs to the class of organic compounds known as biflavonoids, which are characterized by the presence of two flavonoid units connected through a central carbon bridge. 4-O-methylbutein has been researched for its potential pharmaceutical and medicinal properties, as it has been found to exhibit anti-inflammatory, antioxidative, and antidiabetic effects. These properties make it a promising candidate for the development of new drugs for the treatment of various diseases and disorders.

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

Upstream product

• 621-59-0 isovanillin 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 34123-66-5 O-isopropylisovanillin 
• 728911-59-9 2,4-diisopropoxyacetophenone 
• 1417453-13-4 2’,3,4’-triisopropoxy-4-methoxychalcone 

Downstream Products

• 54867-60-6 7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-benzo(b)pyran-4-one 
• 1657006-82-0 C₁₉H₁₈Br₂O₅ 
• 1657007-02-7 C₁₉H₁₈O₅ 

Relevant articles and documents

Identification of Interleukin-8-Reducing Lead Compounds Based on SAR Studies on Dihydrochalcone-Related Compounds in Human Gingival Fibroblasts (HGF-1 cells) in Vitro

Background: In order to identify potential activities against periodontal diseases, eighteen dihydrochalcones and structurally related compounds were tested in an established biological in vitro cell model of periodontal inflammation using human gingival fibroblasts (HGF-1 cells). Methods: Subsequently to co-incubation of HGF-1 cells with a bacterial endotoxin (Porphyromonas gingivalis lipopolysaccharide, pgLPS) and each individual dihydrochalcone in a concentration range of 1 μM to 100 μM, gene expression of interleukin-8 (IL-8) was determined by qPCR and cellular interleukin-8 (IL-8) release by ELISA. Results: Structure–activity analysis based on the dihydrochalcone backbone and various substitution patterns at its aromatic ring revealed moieties 20,4,40,60-tetrahydroxy 3-methoxydihydrochalcone (7) to be the most effective anti-inflammatory compound, reducing the pgLPS-induced IL-8 release concentration between 1 μM and 100 μM up to 94%. In general, a 2,4,6-trihydroxy substitution at the A-ring and concomitant vanilloyl (4-hydroxy-3-methoxy) pattern at the B-ring revealed to be preferable for IL-8 release inhibition. Furthermore, the introduction of an electronegative atom in the A,B-linker chain led to an increased anti-inflammatory activity, shown by the potency of 4-hydroxybenzoic acid N-vanillylamide (13). Conclusions: Our data may be feasible to be used for further lead structure designs for the development of potent anti-inflammatory additives in oral care products.