3-caffeoylquinic acid (chlorogenic acid)
Compound Structure: |
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Synonyms: | CHLOROGENIC ACID;327-97-9;3-O-Caffeoylquinic acid;Heriguard;Chlorogenate;3-(3,4-Dihydroxycinnamoyl)quinic acid;3-Caffeoylquinic acid;Hlorogenic acid;trans-Chlorogenic acid;CP chlorogenic acid;Caffeoyl quinic acid;Chlorogenicacid | ||||||||||||||||||||||||||||||||||||||||||||
Compound ID: | NMPC-341 | ||||||||||||||||||||||||||||||||||||||||||||
PubChem ID: | |||||||||||||||||||||||||||||||||||||||||||||
Molecular Formula: | C16H18O9 | ||||||||||||||||||||||||||||||||||||||||||||
Canonical SMILES: | C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O | ||||||||||||||||||||||||||||||||||||||||||||
InChIKey: | CWVRJTMFETXNAD-JUHZACGLSA-N | ||||||||||||||||||||||||||||||||||||||||||||
About the compound: | Chlorogenic acid is a cinnamate ester formed through the formal condensation of trans-caffeic acid's carboxy group with quinic acid's 3-hydroxy group. This compound plays a crucial role as an intermediate in lignin biosynthesis. It serves dual functions as a plant metabolite and a component found in various foods. Chlorogenic acid is categorized as a cinnamate ester and is also classified as a tannin. It shares functional associations with (-)-quinic acid and trans-caffeic acid and can be considered the conjugate acid of a chlorogenate. Chlorogenic acid, often abbreviated as CGA, has been explored in clinical trials for its potential in treating advanced cancer and impaired glucose tolerance. This natural compound, Chlorogenic Acid, can be naturally found in organisms such as Pavetta indica, Fragaria nipponica, and others. Furthermore, it's important to note that the name "chlorogenic acids" might be misleading, as it contains no chlorine. Instead, the name is derived from the Greek words "khloros" (meaning light green) and "-γένος" (a suffix indicating "giving rise to"), which relates to the green color produced when chlorogenic acids undergo oxidation. Chlorogenic acid (CGA) is essentially the ester formed by the combination of caffeic acid and (−)-quinic acid and is a representative of the broader polyphenol family of esters known as chlorogenic acids, which includes hydroxycinnamic acids like caffeic acid, ferulic acid, and p-coumaric acid, combined with quinic acid. GHS Hazard Statements • H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] • H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] • H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] |
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Properties: |
Chemical
and Physical Properties
Source: PubChem |
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Source Species: |
Echinacea purpurea Eichhornia crassipes Ficus capensis Newbouldia laevis Raphia hookeri Solanum aethiopicum Luffa cylindrica Talinum triangulare |