Delphinidin-3-O-rutinoside chloride - Moligand™,≥95% , CAS No.15674-58-5

CAS: 15674-58-5 Cat. No.: D769910 Molecular Weight: 646.99 EC Number: 805-269-5

GRADE & PURITY Moligand™, ≥95%

Synonyms

Delphinidin-3-O-rutinoside (chloride) | 3',4',5,5',7-Pentahydroxy-3-[(6-O-alpha-L-rhamnosyl-beta-D-glucosyl)oxy]flavylium chloride | 3-[[6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1-benzopyryli

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Delphinidin-3-O-rutinoside is a glycosylated anthocyanin that has been found in R. nigrum and has antioxidant activity. It inhibits loss of viability in isolated rat aortic smooth muscle cells (SMCs), but not MH1C1 hepatoma cells, induced by tert-butyl-hydroperoxide (TBHP) when used at a concentration of 100 µM. Delphinidin-3-O-rutinoside prevents TBHP-induced DNA damage, as well as inhibits TBHP-induced increases in malondialdehyde (MDA) levels, in SMCs. It displays a hydrogen peroxide-induced and pH-dependent chemiluminescence peak at pH 7.

Specifications

Synonyms

Delphinidin-3-O-rutinoside (chloride) | 3', 4', 5, 5', 7-Pentahydroxy-3-[(6-O-alpha-L-rhamnosyl-beta-D-glucosyl)oxy]flavylium chloride | 3-[[6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-5, 7-dihydroxy-2-(3, 4, 5-trihydroxyphenyl)-1-benzopyryli

Specifications & Purity

Moligand™, ≥95%

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC4=C(C=C(C=C4[O+]=C3C5=CC(=C(C(=C5)O)O)O)O)O)O)O)O)O)O)O.[Cl-]
• IUPAC Name: (2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol;chloride
• InChIKey: ZOQQFMKYEOHRMC-KFOCXKDFSA-N
• INCHI: 1S/C27H30O16.ClH/c1-8-18(32)21(35)23(37)26(40-8)39-7-17-20(34)22(36)24(38)27(43-17)42-16-6-11-12(29)4-10(28)5-15(11)41-25(16)9-2-13(30)19(33)14(31)3-9;/h2-6,8,17-18,20-24,26-27,32,34-38H,7H2,1H3,(H4-,28,29,30,31,33);1H/t8-,17+,18-,20+,21+,22-,23+,24+,26+,27+;/m0./s1
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC4=C(C=C(C=C4[O+]=C3C5=CC(=C(C(=C5)O)O)O)O)O)O)O)O)O)O)O.[Cl-]
• Alternate CAS: 15674-58-5
• MeSH Entry Terms: delphinidin-3-rutinoside
• Molecular Weight: 646.99

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Anthocyanins
            • Level7 Anthocyanidin-3-O-glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Flavonoid O-glycosides - Anthocyanins
• Direct Parent: Anthocyanidin-3-O-glycosides
• Alternative Parents: Flavonoid-3-O-glycosides 7-hydroxyflavonoids 5-hydroxyflavonoids 4'-hydroxyflavonoids 3'-hydroxyflavonoids Anthocyanidins O-glycosyl compounds Disaccharides 1-benzopyrans Pyrogallols and derivatives 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Oxanes Benzene and substituted derivatives Heteroaromatic compounds Secondary alcohols Polyols Oxacyclic compounds Acetals Organic zwitterions Organic chloride salts Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Anthocyanidin-3-o-glycoside - Flavonoid-3-o-glycoside - Hydroxyflavonoid - 7-hydroxyflavonoid - 5-hydroxyflavonoid - 4'-hydroxyflavonoid - 3'-hydroxyflavonoid - Anthocyanidin - O-glycosyl compound - Glycosyl compound - Disaccharide - 1-benzopyran - Benzopyran - Pyrogallol derivative - Benzenetriol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Benzenoid - Oxane - Monocyclic benzene moiety - Heteroaromatic compound - Secondary alcohol - Oxacycle - Organoheterocyclic compound - Polyol - Acetal - Organic oxygen compound - Hydrocarbon derivative - Organic chloride salt - Organic salt - Organic zwitterion - Organooxygen compound - Alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a 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: 647.000 g/mol
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 6
• Exact Mass: 646.13 Da
• Monoisotopic Mass: 646.13 Da
• Topological Polar Surface Area: 260.000 Ų
• Heavy Atom Count: 44
• Formal Charge: 0
• Complexity: 902.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• 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: 2

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