4H-1-benzopyran-4-one, 7-(β-D-glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-

CAS: 529-55-5 C21 H22 O10 MW: 434.39834000

Identification

Nameprunin
IUPAC(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
CAS Number529-55-5
EINECS208-464-8
FDA UNIISearch
Molecular FormulaC21 H22 O10
Molecular Weight434.39834000
MDL NumberMFCD00210548
Nikkaji NumberJ182.295K
Beilstein066743

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 802.40 °C. @ 760.00 mm Hg (est)
Flash Point 544.00 °F. TCC ( 284.60 °C. ) (est)
logP (o/w) 0.820 (est)
Soluble in water, 2170 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
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 prunin usage levels up tonot for fragrance use.
Recommendation for prunin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

peach pinus spp. tomato

Synonyms

4H-1- benzopyran-4-one, 7-(β-D-glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)- 4',5- dihydroxy-7-glucosyloxyflavanone (2S)-7-(b-D- glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (S)-7-(b-D- glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (S)-7-(beta-dextro- glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (2S)-5- hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl b-D-glucopyranoside (S)-5- hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl b-D-glucopyranoside (2S)-5- hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one (-)- naringenin 7-b-D-glucoside naringenin 7-O-b-D-glucopyranoside naringenin 7-O-b-D-glucoside naringenin 7-O-glucoside 4',5,7- trihydroxyflavanone 7-O-b-D-glucopyranoside PubMed: [Quantitative analysis of six flavonoids of hongzhu capsule by QAMS]. PubMed: Two new dihydroamentoflavone glycosides from Cycas revoluta. PubMed: Computer-guided approach to access the anti-influenza activity of licorice constituents. PubMed: [Identification and characterization of Aspergillus aculeatus JMUdb058 for naringinase production]. PubMed: Development and evaluation of an HPLC method for accurate determinations of enzyme activities of naringinase complex. PubMed: Conformational epitope mapping of Pru du 6, a major allergen from almond nut. PubMed: Prunin- and hesperetin glucoside-alkyl (C4-C18) esters interaction with Jurkat cells plasma membrane: consequences on membrane physical properties and antioxidant capacity. PubMed: Isolation of Prunin from the fruit shell of Bixa orellana and the effect of β-cyclodextrin on its binding with calf thymus DNA. PubMed: Alpha-L-rhamnosidase from Aspergillus clavato-nanicus MTCC-9611 active at alkaline pH. PubMed: Updates on naringinase: structural and biotechnological aspects. PubMed: Enzymatic Synthesis of the Flavone Glucosides, Prunin and Isoquercetin, and the Aglycones, Naringenin and Quercetin, with Selective α-L-Rhamnosidase and β-D-Glucosidase Activities of Naringinase. PubMed: Cloning, expression and patient IgE reactivity of recombinant Pru du 6, an 11S globulin from almond. PubMed: A microarray approach to identify genes involved in seed-pericarp cross-talk and development in peach. PubMed: Antibacterial activity of naringin derivatives against pathogenic strains. PubMed: Molecular characterization and enzymatic hydrolysis of naringin extracted from kinnow peel waste. PubMed: α-Rhamnosidase and β-glucosidase expressed by naringinase immobilized on new ionic liquid sol-gel matrices: Activity and stability studies. PubMed: Antimicrobial properties of prunin, a citric flavanone glucoside, and its prunin 6″-O-lauroyl ester. PubMed: Effects of unripe Citrus hassaku fruits extract and its flavanone glycosides on blood fluidity. PubMed: Crystal structure of prunin-1, a major component of the almond (Prunus dulcis) allergen amandin. PubMed: Metabolism of saikosaponin c and naringin by human intestinal bacteria. PubMed: Purification, crystallization and preliminary X-ray characterization of prunin-1, a major component of the almond (Prunus dulcis) allergen amandin. PubMed: Protein changes between dormant and dormancy-broken seeds of Prunus campanulata Maxim. PubMed: Stereoisomeric separation of flavanones and flavanone-7-O-glycosides by capillary electrophoresis and determination of interconversion barriers. PubMed: Inhibition of uropathogenic Escherichia coli by cranberry juice: a new antiadherence assay. PubMed: Fractionation of the naringinase complex from Aspergillus terreus by dye affinity chromatography. PubMed: Chiral separation of diastereomeric flavanone-7-O-glycosides in citrus by capillary electrophoresis. PubMed: Thermal inactivation and product inhibition of Aspergillus terreus CECT 2663 alpha-L-rhamnosidase and their role on hydrolysis of naringin solutions. PubMed: Purification and characterization of a beta-glucosidase from Citrus sinensis var. Valencia fruit tissue. PubMed: Chiral separation of six diastereomeric flavanone-7-O-glycosides by capillary electrophoresis and analysis of lemon juice. PubMed: The thermostable alpha-L-rhamnosidase RamA of Clostridium stercorarium: biochemical characterization and primary structure of a bacterial alpha-L-rhamnoside hydrolase, a new type of inverting glycoside hydrolase. PubMed: Purification, characterization, and substrate specificity of a novel highly glucose-tolerant beta-glucosidase from Aspergillus oryzae. PubMed: Purification and characterization of beta-glucosidase from Bacteroides JY-6, a human intestinal bacterium. PubMed: A linkage map with RFLP and isozyme markers for almond. PubMed: Disruption of the cytokeratin cytoskeleton and inhibition of hepatocytic autophagy by okadaic acid. PubMed: Protection by naringin and some other flavonoids of hepatocytic autophagy and endocytosis against inhibition by okadaic acid. PubMed: Molecular characterization of cDNAs corresponding to genes expressed during almond (Prunus amygdalus Batsch) seed development. PubMed: UDP-rhamnose:flavanone-7-O-glucoside-2''-O-rhamnosyltransferase. Purification and characterization of an enzyme catalyzing the production of bitter compounds in citrus. PubMed: Improvement of hyperglycemia and hyperlipemia in streptozotocin-diabetic rats by a methanolic extract of Prunus davidiana stems and its main component, prunin. PubMed: Antihyperlipidemic effect of flavonoids from Prunus davidiana. PubMed: Flavanone-specific 7-O-glucosyltransferase activity in Citrus paradisi seedlings: purification and characterization. PubMed: Inhibition of growth and xylogenesis and promotion of vacuolation in prunus callus by the flavanone prunin. PubMed: A rapid method for the determination of naringin, prunin, and naringenin applied to the assay of naringinase. PubMed: Induction and characterization of a microsomal flavonoid 3'-hydroxylase from parsley cell cultures. PubMed: Microbial transformation of flavonoids. PubMed: Prunin identification, biological activity and quantitative change in comparison to naringenin in dormant peach buds.