116719-38-1

Basic information

• Product Name: 2H-1-Benzopyran-7,8-diol,3,4-dihydro-3-(4-hydroxyphenyl)-
• Synonyms: Zy 16681
• CAS NO: 116719-38-1
• Molecular Formula: C15H14 O4
• Molecular Weight: 258.274
• Mol File: 116719-38-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran-7,8-diol,3,4-dihydro-3-(4-hydroxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-7,8-diol,3,4-dihydro-3-(4-hydroxyphenyl)-(116719-38-1)
• EPA Substance Registry System: 2H-1-Benzopyran-7,8-diol,3,4-dihydro-3-(4-hydroxyphenyl)-(116719-38-1)

Safety Data

• Hazardous Substances Data: 116719-38-1(Hazardous Substances Data)

Usage

Chemical Family

Flavonoids

Source

Naturally occurring compounds found in various plants

Derived From

Hydroxylation of the flavone, apigenin

Therapeutic Properties

Antioxidant
Anti-inflammatory
Anti-cancer effects

Biological Activities

Scavenging free radicals
Reducing oxidative stress in the body

Mechanism of Action

Interaction with various enzymes and signaling pathways in the body

Potential Applications

Further research
Pharmaceutical development

Upstream product

• 87-66-1 2-hydroxyresorcinol 
• 14191-95-8 4-cyanomethylphenol 
• 77316-95-1 2-(4-hydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)ethanone 
• 75187-63-2 8-hydroxydaidzein 

Relevant articles and documents

Enzymatic studies of isoflavonoids as selective and potent inhibitors of human leukocyte 5-lipo-oxygenase

Continuing our search to find more potent and selective 5-LOX inhibitors, we present now the enzymatic evaluation of seventeen isoflavones (IR) and nine isoflavans (HIR), and their in vitro and in cellulo potency against human leukocyte 5-LOX. Of the 26 compounds tested, 10 isoflavones and 9 isoflavans possessed micromolar potency, but only three were selective against 5-LOX (IR-2, HIR-303, and HIR-309), with IC50 values at least 10 times lower than those of 12-LOX, 15-LOX-1, and 15-LOX-2. Of these three, IR-2 (6,7-dihydroxy-4-methoxy-isoflavone, known as texasin) was the most selective 5-LOX inhibitor, with over 80-fold potency difference compared with other isozymes; Steered Molecular Dynamics (SMD) studies supported these findings. The presence of the catechol group on ring A (6,7-dihydroxy versus 7,8-dihydroxy) correlated with their biological activity, but the reduction of ring C, converting the isoflavones to isoflavans, and the substituent positions on ring B did not affect their potency against 5-LOX. Two of the most potent/selective inhibitors (HIR-303 and HIR-309) were reductive inhibitors and were potent against 5-LOX in human whole blood, indicating that isoflavans can be potent and selective inhibitors against human leukocyte 5-LOX in vitro and in cellulo. Of the 26 compounds tested, 10 isoflavones and 9 isoflavans possessed micromolar potency, but only three were selective against 5-LOX (IR-2, HIR-303, and HIR-309), with IC50 values at least 10 times lower than those of 12-LOX, 15-LOX-1, and 15-LOX-2. Docking and steered molecular dynamics were performed to determinate the structure-activity relationship.

Benzopyrans and use thereof in treating vascular diseases

Isoflavans of the formula I STR1 wherein the groups OR, R', R" and ring B are as defined in the specification, exhibit valuable pharmacological properties, especially for the treatment of vascular diseases. They are prepared by methods known per se.