(±)-Naringenin - Moligand™, analytical standard , CAS No.67604-48-2

CAS: 67604-48-2 Cat. No.: R135669 Formula: C₁₅H₁₂O₅ Peso molecolare: 272.26 Beilstein Registry Number: 8503 Numero EC: 266-769-1

QUALITÀ & PUREZZA Analytical standard, Moligand™

Synonyms

4H-1-Benzopyran-4-one,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)- | EINECS 266-769-1 | NCGC00017346-04 | NCGC00095963-01 | GTPL10298 | Naringenin (NAR) | FT-0778247 | NSC34875 | NSC-34875 | naringenin

Storage

Store at 2-8°C

Shipped In

Wet ice

Panoramica

(±)-Naringenin is an antioxidant flavonoid. It has anti-inflammatory and antitumor properties. (±)-Naringenin induces apoptosis. It stimulates DNA repair following oxidative damage. (±)-Naringenin inhibits the activity of PI 3-kinase (PI(3)K).
A PI 3-kinase inhibitor.

Application：

(±)-Naringenin, a polyphenolic material, is used to prepare nickel(II) naringenin-oxime complex, which can be used as a catalyst for Mizoroki−Heck cross-coupling reaction.It has been used as a hypochlorite scavenger to prevent the formation of chloramines from oxidation of hypochlorite in the human serum albumin.It induces apoptosis in human pancreatic cancer SNU-213 cells.It also shows cytotoxic effects on various human cancer cells such as breast, cervix, stomach, colon and liver cancer cells.

Specifiche

Sinonimi

4H-1-Benzopyran-4-one,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)- | EINECS 266-769-1 | NCGC00017346-04 | NCGC00095963-01 | GTPL10298 | Naringenin (NAR) | FT-0778247 | NSC34875 | NSC-34875 | naringenin

Specifiche e purezza

analytical standard, Moligand™

Meccanismi biochimici e fisiologici

Citrus flavonoid. Antioxidant, anti-inflammatory. Affects various signaling pathways in vitro and in vivo . Crosses the blood-brain barrier.

Condizioni di conservazione di stoccaggio

Store at 2-8°C

Spedito in

Wet ice

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Grado

Moligand™, Standard analitico

Tipo di azione

AGONIST

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Nomi e identificatori

Pubchem Sid

528753460

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/528753460

Sorrisi canonici

C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

InChIKey

FTVWIRXFELQLPI-UHFFFAOYSA-N

INCHI

1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2

Isomeri SMILES

C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O

WGK Germania

3

CAS alternativo

480-41-1,67604-48-2

Numero NSC

11855

Termini MeSH

(2S)-naringenin;4',5,7-trihydroxyflavanone;BE 14348A;BE-14348A;naringenin;naringenin-7-sulfate

Peso molecolare

272.26

Beilstein

8503

Reaxy-Rn

280888

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=280888&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Classe Flavonoids
      • Subclass Flavans

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Classe: Flavonoids
• Subclass: Flavans
• Intermediate Tree Nodes: Not available
• Direct Parent: Flavanones
• Alternative Parents: 7-hydroxyflavonoids 5-hydroxyflavonoids 4'-hydroxyflavonoids Chromones Aryl alkyl ketones Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Vinylogous acids Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavanone - Hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Chromone - Benzopyran - Chromane - 1-benzopyran - Aryl alkyl ketone - Aryl ketone - 1-hydroxy-4-unsubstituted benzenoid - Phenol - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Benzenoid - Vinylogous acid - Ketone - Organoheterocyclic compound - Oxacycle - Ether - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as flavanones. These are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
• External Descriptors: trihydroxyflavanone

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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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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MCF7 (126967 Activities)

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DGAT1 Tclin Diacylglycerol O-acyltransferase 1 (1719 Activities)

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Meccanismi d'azione

Proprietà chimiche e fisiche

• Solubilità: Soluble in ethanol (50 mg/ml), DMSO, methanol, and ammonium hydroxide (50 mg/ml). Insoluble in water (almost).
• Punto di ebollizione (°C): 577.47 °C
• Punto di fusione (°C): 247-250°C
• Peso molecolare: 272.250 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 272.068 Da
• Monoisotopic Mass: 272.068 Da
• Topological Polar Surface Area: 87.000 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 363.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1