90-29-9

Basic information

• Product Name: PSEUDOBAPTIGENIN
• Synonyms: 7-HYDROXY-3',4'-(METHYLENEDIOXY)-ISOFLAVONE;AKOS 213-29;PSEUDOBAPTIGENIN;psi-baptigenin;3-(1,3-Benzodioxol-5-yl)-7-hydroxy-4H-1-benzopyran-4-one;3',4'-(Methylenedioxy)-7-hydroxyisoflavone;ψ-Baptigenin;PRUNETIN(P)
• CAS NO: 90-29-9
• Molecular Formula: C₁₆H₁₀O₅
• Molecular Weight: 282.25
• Product Categories: Iso-Flavones
• Mol File: 90-29-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 296～297℃
• Boiling Point: 510.6°C at 760 mmHg
• Flash Point: 197.8°C
• Appearance: /
• Density: 1.494g/cm³
• Vapor Pressure: 4.76E-11mmHg at 25°C
• Refractive Index: 1.69
• PKA: 6.93±0.20(Predicted)
• CAS DataBase Reference: PSEUDOBAPTIGENIN(CAS DataBase Reference)
• NIST Chemistry Reference: PSEUDOBAPTIGENIN(90-29-9)
• EPA Substance Registry System: PSEUDOBAPTIGENIN(90-29-9)

Safety Data

• Hazardous Substances Data: 90-29-9(Hazardous Substances Data)

Usage

Uses

Pseudobabtigen, has been shown to be a Lipoxygenases (LOXs) directed anti-inflammatory and anti-cancerous secondary metabolite. Lipoxygenases (LOXs), key enzymes involved in the biosynthesis of leukotrienes, are well known to participate in the inflammatory and immune responses.

Definition

ChEBI: A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone and in which the phenyl group at position 3 is replaced by a 1,3-benzodioxol-5-yl group.

InChI:InChI=1/C16H10O5/c17-10-2-3-11-14(6-10)19-7-12(16(11)18)9-1-4-13-15(5-9)21-8-20-13/h1-7,17H,8H2

Upstream product

• 5653-25-8 α-(1,3-benzodioxol-5-yl)-2,4-dihydroxyacetophenone 
• 122-51-0 orthoformic acid triethyl ester 
• 860741-88-4 1-benzo[1,3]dioxol-5-yl-2-(3-hydroxy-phenoxy)-ethanone 
• 63347-43-3 pseudobaptigenin 7‐O‐β‐D‐glucoside 
• 1186-70-5 bis(dimethylamino)methoxymethane 
• 4253-03-6 O-benzyl ψ-baptigenin 
• 4439-02-5 3,4-methylenedioxyphenylacetonitrile 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 
• 108-46-3 recorcinol 
• 124-63-0 methanesulfonyl chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 935659-67-9 3',4'-methylenedioxy-7-(tetrahydropyran-2-yloxy)isoflavone 
• 40288-65-1 1-(benzo[1,3]dioxol-5-yl)-2-bromoethanone 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 

Downstream Products

• 4253-04-7 7-methoxy-3',4'-methylenedioxyisoflavone 
• 4737-28-4 7-(3-methyl-2-butenyloxy)-3-(3,4-methylenedioxyphenyl)benzopyran-4-one: maxima substance-B 
• 142751-46-0 Dimethyl-thiocarbamic acid O-(3-benzo[1,3]dioxol-5-yl-4-oxo-4H-chromen-7-yl) ester 
• 64-18-6 formic acid 
• 5574-40-3 3-(benzo[d][1,3]dioxol-5-yl)-4-oxo-4H-chromen-7-yl acetate 
• 1208066-20-9 7-(allyloxy)-3-(benzo[d][1,3]dioxol-5-yl)-4H-chromen-4-one 
• 62502-14-1 3-(3,4-methylenedioxyphenyl)-8,8-dimethyl-4-oxo-4H,8H-benzo[1,2-b:3,4-b']dipyran 
• 1137423-90-5 2-{[3-(1,3-benzodioxol-5-yl)-4-oxo-4H-1-benzopyran-7-yl]oxy}acetic acid 
• 93261-50-8 3-(1,3-benzodioxol-5-yl)-7-hydroxy-4-oxo-4H-1-benzopyran-8-carboxaldehyde 
• 1124174-23-7 3-(2,4-dihydroxyphenyl)-4-(3,4-methylenedioxyphenyl)-1H-pyrazole 
• 142751-51-7 Dimethyl-thiocarbamic acid S-(3-benzo[1,3]dioxol-5-yl-4-oxo-4H-chromen-7-yl) ester 

Relevant articles and documents

Novel daidzein analogs and their in vitro anti-influenza activities

A series of novel isoflavonoids were synthesized based on structural modifications of daidzein, an active ingredient of traditional Chinese medicine (TCM) and evaluated for their anti-influenza activity, in vitro, against H1N1 Tamiflu-resistant (H1N1 TR) virus in the MDCK cell line. Among them, 4-oxo-4H-1-benzopyran-8-carbaldehydes 11a-11g were most promising, and they demonstrated better activities and selectivities comparable to those the reference ribarivin, a nucleoside antiviral agent. 3-(4-Bromophenyl)-7-hydroxy-4-oxo-4H-1-benzopyran-8-carboxaldehyde (11c) displayed the best inhibitory activity (EC50, 29.0 μM) and selectivity index (SI>10.3). Analysis of the structure￡activity relationships (SAR) indicated that both the non-naturally-occurring Br-substituted B-ring and appropriate CHO and OH groups on the A-ring might be critical for the activity and selectivity against H1N1 TR influenza viruses.

The synthesis and evaluation of flavone and isoflavone chimeras of novobiocin and derrubone

The natural products novobiocin and derrubone have both demonstrated Hsp90 inhibition and structure-activity relationships have been established for each scaffold. Given these compounds share several key structural features, we hypothesized that incorporation of elements from each could provide insight to structural features important for Hsp90 inhibition. Thus, chimeric analogues of novobiocin and derrubone were constructed and evaluated. These studies confirmed that the functionality present at the 3-position of the isoflavone plays a critical role in determining Hsp90 inhibition and suggests that the bicyclic ring system present in both novobiocin and derrubone do not share similar modes of binding.

7-Hydroxy-benzopyran-4-one derivatives: A novel pharmacophore of peroxisome proliferator-activated receptor α and -γ (PPARα and γ) dual agonists

Design, synthesis, and in vitro bioevaluation of a new class of potential dual PPARα and γ agonists discovered through a structure-driven design paradigm are described. The 7-hydroxy-benzopyran-4-one moiety (includes flavones, flavanones, and isoflavones) is the key pharmacophore of these novel molecules, exhibiting similarity to the core structure of both fibrates and thiazolidinediones. New lead PPAR ligands were identified from "natraceuticals" and synthetic analogues. In total, 77 molecules, including chalcones, flavones, flavanones, isoflavones, and pyrazole derivatives, were screened and structure-activity relationship studies of the dual agonists undertaken. Compounds 68, 70, 72, and 76 were identified as novel and potent dual PPARα and γ agonists. These novel molecules may have the potential to be the future leads in PPAR-related disorders, including type II diabetes mellitus and metabolic syndrome. 2009 American Chemical Society.