Naringin - Moligand™, ≥90%, from citrus fruit , CAS No.10236-47-2

CAS: 10236-47-2 Cat. No.: N431264 Formula: C₂₇H₃₂O₁₄ Peso molecolare: 580.53 Beilstein Registry Number: 102012 Numero EC: 233-566-4

GRADE & PURITY Moligand™, ≥90%, from citrus fruit

Synonyms

(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside | (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-betaD-glucopyranos

Storage

Room temperature

Panoramica

Naringin is a flavanone glycoside.

Application

Naringin has been used in a study to assess aldosterone production by a human adrenocortical cell line. Long-term naringin consumption reverses a glucose uptake defect and can be used to improve cognitive deficits of Alzheimer′s disease.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N1376.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit .com/metlin.

Specifications

Sinonimi

(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside | (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-betaD-glucopyranos

Specifiche e purezza

Moligand™, ≥90%, from citrus fruit

Meccanismi biochimici e fisiologici

Naringin, a flavanoid in grapefruit and other citrus fruits, potently inhibits intestinal organic anion-transporting polypeptide 1A2 (OATP1A2). Grapefruit juice thereby reduces bioavailability of many pharmacological agents taken at the same time.

Condizioni di conservazione di stoccaggio

Room temperature

Grado

Moligand™

Purezza

≥90%

Nomi e identificatori

Sorrisi canonici

CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O

IUPAC Name

(2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

InChIKey

DFPMSGMNTNDNHN-ZPHOTFPESA-N

INCHI

1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

Isomeri SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O

WGK Germania

3

RTECS

QN6340000

Peso molecolare

580.53

Beilstein

102012

Reaxy-Rn

25075985

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25075985&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Classe Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Flavonoid-7-O-glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Classe: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Flavonoid O-glycosides
• Direct Parent: Flavonoid-7-O-glycosides
• Alternative Parents: 4'-hydroxyflavonoids 5-hydroxyflavonoids Flavanones Phenolic glycosides Chromones Disaccharides O-glycosyl compounds Aryl alkyl ketones 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Oxanes Benzene and substituted derivatives Vinylogous acids Secondary alcohols Polyols Acetals Oxacyclic compounds Primary alcohols Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-7-o-glycoside - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - Flavanone - Hydroxyflavonoid - Flavan - Phenolic glycoside - Chromone - Disaccharide - Glycosyl compound - O-glycosyl compound - Chromane - Benzopyran - 1-benzopyran - Aryl alkyl ketone - Aryl ketone - Phenol - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - 1-hydroxy-4-unsubstituted benzenoid - Oxane - Benzenoid - Monocyclic benzene moiety - Vinylogous acid - Secondary alcohol - Ketone - Polyol - Acetal - Organoheterocyclic compound - Oxacycle - Ether - Primary alcohol - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Alcohol - Organooxygen compound - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
• External Descriptors: flavanones

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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Meccanismi d'azione

Proprietà chimiche e fisiche

• Rotazione specifica [α]: -84 ° (C=2, EtOH)
• Punto di fusione (°C): 166℃
• Peso molecolare: 580.500 g/mol
• XLogP3: -0.500
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 6
• Exact Mass: 580.179 Da
• Monoisotopic Mass: 580.179 Da
• Topological Polar Surface Area: 225.000 Ų
• Heavy Atom Count: 41
• Formal Charge: 0
• Complexity: 884.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 11
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1