Isoastilbin - ≥99% , CAS No.54081-48-0

CAS: 54081-48-0 Cat. No.: I649414 Molecular Weight: 450.4

GRADE & PURITY ≥99%

Synonyms

FT-0775723 | 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-3-(3,4,5-TRIHYDROXY-6-METHYL-OXA N-2-YL)OXY-CHROMAN-4-ONE | HMS3355O07 | Astilbin;Neoisoastilbin | FT-0775722 | 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2,3-dihydroc

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Isoastilbin is a dihydroflavonol glycoside compound in Rhizoma Smilacis glabrae and Astragalus membranaceus . Isoastilbin inhibits glucosyltransferase (GTase) with an IC 50 value of 54.3 μg/mL, and also inhibits tyrosinase activity. Isoastilbin shows neuroprotective, antioxidation, antimicrobial and anti-apoptotic properties and has the potential for Alzheimer’s disease research

Form:Solid

IC50& Target:IC50: 54.3 μg/mL (Glucosyltransferase (GTase)

Specifications

Synonyms

FT-0775723 | 2-(3, 4-DIHYDROXYPHENYL)-5, 7-DIHYDROXY-3-(3, 4, 5-TRIHYDROXY-6-METHYL-OXA N-2-YL)OXY-CHROMAN-4-ONE | HMS3355O07 | Astilbin;Neoisoastilbin | FT-0775722 | 2-(3, 4-dihydroxyphenyl)-5, 7-dihydroxy-3-(3, 4, 5-trihydroxy-6-methyloxan-2-yl)oxy-2, 3-dihydroc

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Isoastilbin is a dihydroflavonol glycoside compound in Rhizoma Smilacis glabrae and Astragalus membranaceus . Isoastilbin inhibits glucosyltransferase (GTase) with an IC 50 value of 54.3 μg/mL, and also inhibits tyrosinase activity. Isoastilbin shows neur

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

INHIBITOR

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CC1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2,3-dihydrochromen-4-one
• InChIKey: ZROGCCBNZBKLEL-UHFFFAOYSA-N
• INCHI: 1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3
• Isomeric SMILES: CC1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• Alternate CAS: 54141-72-9
• NSC Number: 245342
• MeSH Entry Terms: (2R-cis)-isomer of astilbin;(2S-cis)-isomer of astilbin;3-0-alpha-1-rhamnosyl-(2R,3R)-dihydroquercetin;astilbin;isoastilbin;neoisoastilbin
• Molecular Weight: 450.4
• Reaxy-Rn: 25248269
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25248269&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Flavonoid-3-O-glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Flavonoid O-glycosides
• Direct Parent: Flavonoid-3-O-glycosides
• Alternative Parents: 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Flavanonols Hexoses Chromones O-glycosyl compounds Catechols Aryl alkyl ketones 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Oxanes Vinylogous acids Secondary alcohols Oxacyclic compounds Acetals Polyols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-3-o-glycoside - Hydroxyflavonoid - Flavanonol - Flavanone - 7-hydroxyflavonoid - 5-hydroxyflavonoid - 4'-hydroxyflavonoid - 3'-hydroxyflavonoid - Flavan - Hexose monosaccharide - Chromone - O-glycosyl compound - Glycosyl compound - Benzopyran - 1-benzopyran - Chromane - Aryl alkyl ketone - Aryl ketone - Catechol - 1-hydroxy-4-unsubstituted benzenoid - Phenol - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Benzenoid - Oxane - Monosaccharide - Vinylogous acid - Secondary alcohol - Ketone - Ether - Polyol - Organoheterocyclic compound - Acetal - Oxacycle - Organic oxide - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-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

Chemical and Physical Properties

• Molecular Weight: 450.400 g/mol
• XLogP3: 0.400
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 3
• Exact Mass: 450.116 Da
• Monoisotopic Mass: 450.116 Da
• Topological Polar Surface Area: 186.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 676.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 7
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1