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

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

Uses

Used in Pharmaceutical Industry:
4-O-methylbutein is used as a pharmaceutical candidate for the development of new drugs for the treatment of various diseases and disorders due to its anti-inflammatory, antioxidative, and antidiabetic effects.
Used in Medicinal Applications:
4-O-methylbutein is used as a medicinal compound for the treatment of various diseases and disorders, including inflammation, oxidative stress, and diabetes, due to its potential therapeutic properties.

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

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

Downstream Products

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

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.

Reactivity assessment of chalcones by a kinetic thiol assay

The electrophilic nature of chalcones (1,3-diphenylprop-2-en-1-ones) and many other α,β-unsaturated carbonyl compounds is crucial for their biological activity, which is often based on thiol-mediated regulation processes. To better predict their biological activity a simple screening assay for the assessment of the second-order rate constants (k2) in thia-Michael additions was developed. Hence, a clear structure-activity relationship of 16 differentially decorated hydroxy-alkoxychalcones upon addition of cysteamine could be established. Moreover, amongst other naturally occurring α,β-unsaturated carbonyl compounds k2 values for curcumin and cinnamaldehyde were gained while cinnamic acids or esters gave no or very slow reactions.