(2S)-Isoxanthohumol - 10mM in DMSO , CAS No.70872-29-6

CAS: 70872-29-6 Cat. No.: S425624 Molecular Weight: 354.4 EC Number: 805-345-8

GRADE & PURITY 10mM in DMSO

Synonyms

s9070 | CCG-268085 | DTXSID101045280 | (2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one | AC-35040 | (2S)-Isoxanthohumol | Isoxanthohumol, (-)- | (-)-Isoxanthohumol | (S)-7-Hydroxy-2-(4-hydroxyphenyl)-5-methoxy-

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Store at +4°C. The product can be stored for up to 12 months.

Specifications

Synonyms

s9070 | CCG-268085 | DTXSID101045280 | (2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2, 3-dihydrochromen-4-one | AC-35040 | (2S)-Isoxanthohumol | Isoxanthohumol, (-)- | (-)-Isoxanthohumol | (S)-7-Hydroxy-2-(4-hydroxyphenyl)-5-methoxy-

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Phytoestrogen. Induces apoptosis. Induces G 2 /M cell cycle arrest. Shows antitumor effects. Shows weakly estrogenic effects in vivo. Orally active.

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.

Names and Identifiers

• Canonical Smiles: CC(=CCC1=C2C(=C(C=C1O)OC)C(=O)CC(O2)C3=CC=C(C=C3)O)C
• IUPAC Name: (2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• InChIKey: YKGCBLWILMDSAV-SFHVURJKSA-N
• INCHI: 1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3/t18-/m0/s1
• Isomeric SMILES: CC(=CCC1=C2C(=C(C=C1O)OC)C(=O)C[C@H](O2)C3=CC=C(C=C3)O)C
• Molecular Weight: 354.4
• Reaxy-Rn: 325732
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=325732&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavans
        • Level5 8-prenylated flavans
          • Level6 8-prenylated flavanones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavans
• Intermediate Tree Nodes: 8-prenylated flavans
• Direct Parent: 8-prenylated flavanones
• Alternative Parents: 5-O-methylated flavonoids Flavanones 7-hydroxyflavonoids 4'-hydroxyflavonoids Chromones Aryl alkyl ketones Anisoles Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 8-prenylated flavanone - 5-methoxyflavonoid-skeleton - 4'-hydroxyflavonoid - 7-hydroxyflavonoid - Flavanone - Hydroxyflavonoid - Chromone - Chromane - Benzopyran - 1-benzopyran - Anisole - Aryl alkyl ketone - Aryl ketone - Phenol ether - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Monocyclic benzene moiety - Benzenoid - Ketone - Ether - Organoheterocyclic compound - Oxacycle - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.
• External Descriptors: Not available

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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Molecular Weight: 354.400 g/mol
• XLogP3: 4.100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 354.147 Da
• Monoisotopic Mass: 354.147 Da
• Topological Polar Surface Area: 76.000 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 518.000
• 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