DAIDZIN
Synonyms. Daidzin; 7-(beta-D-Glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 7-(beta-D-Glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one; Daidzein 7-O-glucoside; Daidzein 7-glucoside; Daidzoside; 4',7-Dihydroxyisoflavone; Other RN: 1329-08-4. 28572-56-7

DAIDZIN
 

PRODUCT IDENTIFICATION

CAS RN

 552-66-9

EINECS RN

  

FORMULA

 C21H20O9

MOLE WEIGHT

 416.38

H.S CODE

 2938.90.0000

SMILES

 c1(=O)c2ccc(cc2occ1c1ccc(cc1)O)O[C@@H]1O[C@@H]([C @@H](O) [C@@H](O)[C@H]1O)CO

CLASSIFICATION

Alcohol deterrent, Enzyme inhibitor, Isoflavone

EXTRA NOTES

 A potent, selective, and reversible inhibitor of human mitochondrial aldehyde dehydrogenase
Daidzin is an isoflavone reported to have anti-oxidant, anti-carcinogenic, and anti-artherosclerotic activities. Daidzin is the major active component of the traditional Chinese medicine (TCM) derived from radix puerariae (Kudzu) that is commonly used to treat alcohol abuse. Daidzin is a potent and selective inhibitor of mitochondrial aldehyde dehydrogenase 2 (ALDH-2).  

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

white powder

MELTING POINT

 234 - 242 C (Decomposes)

BOILING POINT

  

DENSITY

 

SOLUBILITY IN WATER

 Insoluble
SOLVENT SOLUBILITY Soluble in DMSO or dilute aqueous base

VAPOR DENSITY

 

log P(octanol-water)

  

VAPOR PRESSURE

  

AUTOIGNITION TEMP

  
pH

 

REFRACTIVE INDEX

 

FLASH POINT

 

 
STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong Oxidizing agents
POLYMERIZATION

Has not been reported

NFPA RATINGS

Health hazard: 0, Flammability: 0, Physical hazards: 0

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

Drug Information Portal (U.S. National Library of Medicine) - Daidzin

PubChem Compound Summary - Daidzin

Drug Bank -  Daidzin

KEGG (Kyoto Encyclopedia of Genes and Genomes) -  Daidzin

http://www.ebi.ac.uk/ -  Daidzin

http://www.ncbi.nlm.nih.gov/ - Daidzin

http://pubs.acs.org/
Structure of Daidzin, a Naturally Occurring Anti-Alcohol-Addiction Agent, in Complex with Human Mitochondrial Aldehyde Dehydrogenase

http://www.pnas.org/
Daidzin, a major active principle of an ancient Chinese herbal treatment (Radix puerariae) for alcohol abuse, selectively suppresses ethanol intake in all rodent models tested. It also inhibits mitochondrial aldehyde dehydrogenase (ALDH-2). Studies on ethanol intake suppression and ALDH-2 inhibition by structural analogs of daidzin established a link between these two activities and suggested that daidzin may suppress ethanol intake by inhibiting ALDH-2. ALDH-2 is a principal enzyme involved in serotonin (5-HT) and dopamine (DA) metabolism. Thus, daidzin may act by inhibiting 5-HT and DA metabolism. To evaluate this possibility, we have studied the effect of daidzin and its analogs on 5-HT and DA metabolism in isolated hamster and rat liver mitochondria. Daidzin potently inhibits the formation of 5-hydroxyindole-3-acetic acid (5-HIAA) and 3,4-dihydroxyphenylacetic acid (DOPAC) from their respective amines in isolated mitochondria. Inhibition is concentrationdependent and is accompanied by a concomitant accumulation of 5-hydroxyindole-3-acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. Daidzin analogs that suppress hamster ethanol intake also inhibit 5-HIAA and DOPAC formation. Comparing their effects on mitochondria-catalyzed 5-HIAA or DOPAC formation and hamster ethanol intake reveals a positive correlation—the stronger the inhibition on 5-HIAA or DOPAC formation, the greater the ethanol intake suppression. Daidzin and its active analogs, at concentrations that significantly inhibit 5-HIAA formation, have little or no effect on mitochondria-catalyzed 5-HT depletion. It appears that the antidipsotropic action of daidzin is not mediated by 5-HT (or DA) but rather by its reactive intermediates 5-hydroxyindole-3-acetaldehyde and, presumably, 3,4-dihydroxyphenylacetaldehyde as well, which accumulates in the presence of daidzin.

http://extension.agron.iastate.edu/
Isoflavones are biologically-active, nonnutritive compounds that are present in relatively large amounts in soybean and soyfoods. Soybeas contain two main types of isoflavones; daidzein and genistein. These compounds are part of a larger group of plant chemicals, called flavenoids, that are common in many fruits, vegetables, and legumes. Soybean are by far the most concentrated source of isoflavones in the human diet. Isoflavones are produced by the soybean plant as part of their defense mechanism against insects and diseases such as Phytophthora, and in response to environmental stresses such as drought. Isoflavones also play an important role in the growing soybean plant by stimulating nodule formation by nitrogen-fixing Rhizobium bacteria.

 

SALES SPECIFICATION

APPEARANCE

white powder

ASSAY

98.0% min
LOSS ON DRYING

0.5% max
MELTING POINT

236 - 242 C
SOURCE Pueraria lobata (Willd.) Ohwi

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

Not regulated

HAZARD SYMBOL

  
PACKING GROUP  

 

SAFETY INFORMATION

HAZARD OVERVIEW

Not known
HAZARD CODES

 

RISK PHRASES

 36/38

SAFETY PHRASES

 26-36