Vaccarin - 10mM in DMSO , CAS No.53452-16-7

CAS: 53452-16-7 Cat. No.: V424572 Formula: C₃₂H₃₈O₁₉ Molecular Weight: 726.6 PubChem CID: 71307582

GRADE & PURITY 10mM in DMSO

Synonyms

6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one | s9230 | 6-(2-O-alpha-L-Arabinopyranosyl

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Vaccarin is a major flavonoid glycoside in Vaccariae semen, its biotransformation pathways involves methylation, hydroxylation, glycosylation and deglycosylation.

Specifications

Synonyms

6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one | s9230 | 6-(2-O-alpha-L-Arabinopyranosyl

Specifications & Purity

10mM in DMSO

Storage

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

Pubchem Sid

528767678

Canonical Smiles

C1C(C(C(C(O1)OC2C(C(C(OC2C3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC=C(C=C5)OC6C(C(C(C(O6)CO)O)O)O)O)CO)O)O)O)O)O

IUPAC Name

6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one

InChIKey

GYIKGLVKALOGDP-HLEFUGOVSA-N

INCHI

1S/C32H38O19/c33-7-17-23(40)26(43)30(51-31-27(44)21(38)14(37)9-46-31)29(49-17)20-13(36)6-16-19(24(20)41)12(35)5-15(48-16)10-1-3-11(4-2-10)47-32-28(45)25(42)22(39)18(8-34)50-32/h1-6,14,17-18,21-23,25-34,36-45H,7-9H2/t14-,17+,18+,21-,22+,23+,25-,26-,27+,28+,29-,30+,31-,32+/m0/s1

Isomeric SMILES

C1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2C3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC=C(C=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)CO)O)O)O)O)O

PubChem CID

71307582

Molecular Weight

726.6

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavonoid glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Flavonoid O-glycosides
• Alternative Parents: Flavonoid C-glycosides 5-hydroxyflavonoids 7-hydroxyflavonoids Flavones Phenolic glycosides Fatty acyl glycosides of mono- and disaccharides Alkyl glycosides C-glycosyl compounds Chromones Disaccharides O-glycosyl compounds Phenoxy compounds Phenol ethers 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Pyranones and derivatives Oxanes Heteroaromatic compounds Vinylogous acids Secondary alcohols Oxacyclic compounds Dialkyl ethers Polyols Acetals Primary alcohols Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid o-glycoside - Flavonoid-4p-o-glycoside - Flavonoid c-glycoside - Hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Flavone - Phenolic glycoside - Fatty acyl glycoside - Fatty acyl glycoside of mono- or disaccharide - Alkyl glycoside - O-glycosyl compound - Glycosyl compound - C-glycosyl compound - Chromone - Disaccharide - 1-benzopyran - Benzopyran - Phenol ether - Phenoxy compound - 1-hydroxy-2-unsubstituted benzenoid - 1-hydroxy-4-unsubstituted benzenoid - Pyranone - Monocyclic benzene moiety - Fatty acyl - Benzenoid - Oxane - Pyran - Vinylogous acid - Heteroaromatic compound - Secondary alcohol - Acetal - Oxacycle - Organoheterocyclic compound - Polyol - Dialkyl ether - Ether - Organic oxide - Organic oxygen compound - Primary alcohol - Alcohol - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as flavonoid o-glycosides. These are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
• 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: 726.600 g/mol
• XLogP3: -3.100
• Hydrogen Bond Donor Count: 12
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 8
• Exact Mass: 726.201 Da
• Monoisotopic Mass: 726.201 Da
• Topological Polar Surface Area: 315.000 Ų
• Heavy Atom Count: 51
• Formal Charge: 0
• Complexity: 1220.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 14
• 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