(2S)-6-Prenylnaringenin - ≥99% , CAS No.68236-13-5

CAS: 68236-13-5 Cat. No.: P650810 Molecular Weight: 340.37 PubChem CID: 155094

GRADE & PURITY ≥99%

Synonyms

(2S)-6-Prenylnaringenin | 5,7,4'-Trihydroxy-6-prenylflavanone | CHEBI:27566 | 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-6-(3-methyl-but-2-enyl)-1-benzopyran-4-one | (2S)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one |

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

(2S)-6-Prenylnaringenin is the most efficient compound in forebrain. (2S)-6-Prenylnaringenin acts as a GABA A positive allosteric modulator at α+β- binding interface.

In Vitro

(2S)-6-Prenylnaringenin (6-Prenylnaringenin) displays a modulatory activity at low micromolar concentrations. (2S)-6-Prenylnaringenin potentiates GABA-induced displacement of [ 3 H]EBOB binding in a concentration-dependent manner where the IC 50 value for this potentiation in native GABAA receptors is 3.7 μM, respectively. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

Specifications

Synonyms

(2S)-6-Prenylnaringenin | 5, 7, 4'-Trihydroxy-6-prenylflavanone | CHEBI:27566 | 5, 7-Dihydroxy-2-(4-hydroxy-phenyl)-6-(3-methyl-but-2-enyl)-1-benzopyran-4-one | (2S)-2, 3-dihydro-5, 7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one |

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

(2S)-6-Prenylnaringenin is the most efficient compound in forebrain. (2S)-6-Prenylnaringenin acts as a GABA A positive allosteric modulator at α+β- binding interface.

Storage

Protected from light, Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

AGONIST

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CC(=CCC1=C(C2=C(C=C1O)OC(CC2=O)C3=CC=C(C=C3)O)O)C
• IUPAC Name: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• InChIKey: YHWNASRGLKJRJJ-KRWDZBQOSA-N
• INCHI: 1S/C20H20O5/c1-11(2)3-8-14-15(22)9-18-19(20(14)24)16(23)10-17(25-18)12-4-6-13(21)7-5-12/h3-7,9,17,21-22,24H,8,10H2,1-2H3/t17-/m0/s1
• Isomeric SMILES: CC(=CCC1=C(C2=C(C=C1O)O[C@@H](CC2=O)C3=CC=C(C=C3)O)O)C
• Alternate CAS: 68236-13-5
• PubChem CID: 155094
• MeSH Entry Terms: 6-prenylnaringenin
• Molecular Weight: 340.37

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavans
        • Level5 6-prenylated flavans
          • Level6 6-prenylated flavanones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavans
• Intermediate Tree Nodes: 6-prenylated flavans
• Direct Parent: 6-prenylated flavanones
• Alternative Parents: Flavanones 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: 6-prenylated flavanone - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Flavanone - Hydroxyflavonoid - Chromone - Chromane - Benzopyran - 1-benzopyran - Aryl alkyl ketone - Aryl ketone - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Monocyclic benzene moiety - Benzenoid - Vinylogous acid - Ketone - Organoheterocyclic compound - Ether - Oxacycle - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-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

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (293.80 mM; Need ultrasonic)
• Molecular Weight: 340.400 g/mol
• XLogP3: 4.300
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 340.131 Da
• Monoisotopic Mass: 340.131 Da
• Topological Polar Surface Area: 87.000 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 504.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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