5-O-Caffeoylshikimic acid - ≥98% , CAS No.73263-62-4

CAS: 73263-62-4 Cat. No.: O692256 PubChem CID: 5281762

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifications & Purity

≥98%

Storage

Room temperature

Purity

≥98%

Names and Identifiers

Canonical Smiles

C1C(C(C(C=C1C(=O)O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O

IUPAC Name

(3R,4R,5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxycyclohexene-1-carboxylic acid

InChIKey

QMPHZIPNNJOWQI-GDDAOPKQSA-N

INCHI

1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1

Isomeric SMILES

C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O

Alternate CAS

1656981-79-1,73263-62-4

PubChem CID

5281762

MeSH Entry Terms

5-O-caffeoylshikimic acid

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Cinnamic acids and derivatives
      • Subclass Hydroxycinnamic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Cinnamic acids and derivatives
• Subclass: Hydroxycinnamic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Coumaric acids and derivatives
• Alternative Parents: Cinnamic acid esters Styrenes Catechols Fatty acid esters 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Dicarboxylic acids and derivatives Cyclitols and derivatives Enoate esters Secondary alcohols 1,2-diols Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Coumaric acid or derivatives - Cinnamic acid ester - Catechol - Styrene - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Fatty acid ester - Phenol - Cyclitol or derivatives - Monocyclic benzene moiety - Fatty acyl - Benzenoid - Dicarboxylic acid or derivatives - Alpha,beta-unsaturated carboxylic ester - Enoate ester - 1,2-diol - Secondary alcohol - Carboxylic acid ester - Carboxylic acid derivative - Carboxylic acid - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Alcohol - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
• External Descriptors: Caffeate derivatives

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: 336.290 g/mol
• XLogP3: 0.200
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 336.085 Da
• Monoisotopic Mass: 336.085 Da
• Topological Polar Surface Area: 145.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 540.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1