prunin
4H-1-benzopyran-4-one, 7-(β-D-glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-
Identification
| Name | prunin |
| 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 Number | 529-55-5 |
| EINECS | 208-464-8 |
| FDA UNII | Search |
| Molecular Formula | C21 H22 O10 |
| Molecular Weight | 434.39834000 |
| MDL Number | MFCD00210548 |
| Nikkaji Number | J182.295K |
| Beilstein | 066743 |
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 SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
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Potential Uses
Natural Occurrence
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 6â³-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.