EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

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

Supplier Sponsors

Name:(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 Number: 529-55-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:208-464-8
FDA UNII: Search
Nikkaji Web:J182.295K
Beilstein Number:066743
MDL:MFCD00210548
XlogP3-AA:0.60 (est)
Molecular Weight:434.39834000
Formula:C21 H22 O10
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Naringenin-7-O-glucoside 98%
BOC Sciences
For experimental / research use only.
Prunin >98%
Odor: characteristic
Use: Prunin is a flavanone glycoside found in immature citrus fruits and in tomatoes. Its aglycone form is called naringenin. Prunin can not only inhibit protein tyrosine phosphatase 1B (PTP1B) but also stimulate glucose uptake in insulin-resistant HepG2 cell anti-diabetic
Coompo
For experimental / research use only.
Prunin from Plants ≥96%
ExtraSynthese
For experimental / research use only.
Prunin (HPLC) ≥99%
Sigma-Aldrich: Sigma
For experimental / research use only.
Prunin ≥95% (LC/MS-ELSD)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for prunin usage levels up to:
 not for fragrance use.
 
Recommendation for prunin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :92794
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(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
Chemidplus:0000529555
 
References:
 (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
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):92794
Pubchem (sid):135049939
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09099
HMDB (The Human Metabolome Database):Search
FooDB:FDB016683
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 peach
Search Trop Picture
 pinus spp.
Search Trop Picture
 tomato
Search Trop Picture
 
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
 

Articles:

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.
 
Notes:
a legumin-like type of globulin.
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