kakkalide

4H-1-benzopyran-4-one, 5-hydroxy-6-methoxy-3-(4-methoxyphenyl)-7-((6-O-b-D-xylopranosyl-b-D-glucopyranosyl)oxy)-

CAS: 58274-56-9 C28 H32 O15 MW: 608.55104000

Identification

Namekakkalide
IUPAC5-hydroxy-6-methoxy-3-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
CAS Number58274-56-9
FDA UNIISearch
Molecular FormulaC28 H32 O15
Molecular Weight608.55104000
Nikkaji NumberJ871.697H

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 902.02 °C. @ 760.00 mm Hg (est)
Flash Point 566.00 °F. TCC ( 296.90 °C. ) (est)
logP (o/w) -0.292 (est)
Soluble in water, 761.4 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for kakkalide usage levels up tonot for fragrance use.
Recommendation for kakkalide flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

4H-1- benzopyran-4-one, 5-hydroxy-6-methoxy-3-(4-methoxyphenyl)-7-((6-O-b-D-xylopranosyl-b-D-glucopyranosyl)oxy)- 5- hydroxy-6-methoxy-3-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one PubMed: Screening for in vitro metabolites of kakkalide and irisolidone in human and rat intestinal bacteria by ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry. PubMed: Metabolic profile of irisolidone in rats obtained by ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry. PubMed: Metabolism and excretion of kakkalide and its metabolites in rat urine, bile, and feces as determined by HPLC/UV and LC/MS/MS. PubMed: Kakkalide ameliorates endothelial insulin resistance by suppressing reactive oxygen species-associated inflammation. PubMed: Cloning and characterization of ginsenoside Ra1-hydrolyzing beta-D-xylosidase from Bifidobacterium breve K-110. PubMed: Metabolism of ginsenoside Rb1 by human intestinal microflora and cloning of its metabolizing β-D-glucosidase from Bifidobacterium longum H-1. PubMed: Pharmacokinetics of kakkalide and its main metabolites in rat plasma determined by HPLC-DAD and LC-MSn. PubMed: Kakkalide and its metabolite irisolidone ameliorate carrageenan-induced inflammation in mice by inhibiting NF-κB pathway. PubMed: [Primary studies on chemical constituents from butanol extraction of the thorny elaeagnus leaf and their cytotoxicity]. PubMed: Simultaneous analysis of isoflavones and saponins in Pueraria flowers using HPLC coupled to an evaporative light scattering detector and isolation of a new isoflavone diglucoside. PubMed: Inhibitory activity of isoflavones of Pueraria flowers on nitric oxide production from lipopolysaccharide-activated primary rat microglia. PubMed: Isolation and identification of urinary metabolites of kakkalide in rats. PubMed: Cardioprotective effect of 'methylamine irisolidone', a new compound, in hypoxia/reoxygenation injury in cultured rat cardiac myocytes. PubMed: Aldose reductase inhibitors from Viola hondoensis W. Becker et H Boss. PubMed: Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect. PubMed: Kakkalide and irisolidone: HMG-CoA reductase inhibitors isolated from the flower of Pueraria thunbergiana. PubMed: Anti-inflammatory mechanisms of isoflavone metabolites in lipopolysaccharide-stimulated microglial cells. PubMed: Estrogenic effect of main components kakkalide and tectoridin of Puerariae Flos and their metabolites. PubMed: Hepatoprotective effects of irisolidone on tert-butyl hyperoxide-induced liver injury. PubMed: Protective effects of kakkalide from Flos puerariae on ethanol-induced lethality and hepatic injury are dependent on its biotransformation by human intestinal microflora. PubMed: Study of substance changes in flowers of Pueraria thunbergiana Benth. during storage. PubMed: Effects of naturally occurring isoflavones on prostaglandin E2 production. PubMed: Pharmacological studies on Puerariae flos III: protective effects of kakkalide on ethanol-induced lethality and acute hepatic injury in mice.