Cyanidin 3-O-Rutinoside - analytical standard , CAS No.18719-76-1

CAS: 18719-76-1 Cat. No.: C135322 Molecular Weight: 630.98 EC Number: 242-528-6

GRADE & PURITY Analytical standard

Synonyms

Keracyanin chloride|KERACYANIN|Antirrhinin|18719-76-1|Sambucin|Prunicyanin|Cyaninoside|cyanidin 3-O-rutinoside chloride|Cyanidin 3-rutinoside|Keracyaninum|Keraciannai|Keracyanine|Meralop|Cyanidin 3-rhamnoglucoside|Rutinosyl-3-cyanidine|Cyanidine 3-rutinos

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

A polyphenolic anthocyanin.

Specifications

Synonyms

Keracyanin chloride | KERACYANIN | Antirrhinin | 18719-76-1 | Sambucin | Prunicyanin | Cyaninoside | cyanidin 3-O-rutinoside chloride | Cyanidin 3-rutinoside | Keracyaninum | Keraciannai | Keracyanine | Meralop | Cyanidin 3-rhamnoglucoside | Rutinosyl-3-cyanidine | Cyanidine 3-rutinos

Specifications & Purity

analytical standard

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Analytical standard

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.[Cl-]
• IUPAC Name: (2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol;chloride
• InChIKey: ADZHXBNWNZIHIX-XYGAWYNKSA-N
• INCHI: 1S/C27H30O15.ClH/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10;/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31);1H/t9-,18+,19-,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.[Cl-]
• Alternate CAS: 28338-59-2
• Molecular Weight: 630.98

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 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Anthocyanidins Disaccharides O-glycosyl compounds 1-benzopyrans Catechols 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Oxanes Heteroaromatic compounds Secondary alcohols Acetals Oxacyclic compounds Polyols Organic chloride salts Organic zwitterions 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 - Disaccharide - Glycosyl compound - O-glycosyl compound - Benzopyran - 1-benzopyran - Catechol - Phenol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Oxane - Benzenoid - Monocyclic benzene moiety - Heteroaromatic compound - Secondary alcohol - Polyol - Acetal - Organoheterocyclic compound - Oxacycle - Organic oxygen compound - Organooxygen compound - Alcohol - Organic zwitterion - Organic salt - Organic chloride salt - Hydrocarbon derivative - 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: Anthocyanidins and anthocyanins

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

• Solubility: Soluble in water, and alcohol.
• Molecular Weight: 631.000 g/mol
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 6
• Exact Mass: 630.135 Da
• Monoisotopic Mass: 630.135 Da
• Topological Polar Surface Area: 240.000 Ų
• Heavy Atom Count: 43
• Formal Charge: 0
• Complexity: 882.000
• 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

XLogP3

References

1. Jun Wang, Bocheng Wei, Jing Xu, Han Jiang, Yifei Xu, Chuyan Wang.  (2024)  Influence of lactic acid fermentation on the phenolic profile, antioxidant activities, and volatile compounds of black chokeberry (Aronia melanocarpa) juice.  JOURNAL OF FOOD SCIENCE,  89  (2): (834-850).  [PMID:38167751] [10.1111/1750-3841.16899]