3-caffeoylquinic acid (chlorogenic acid)

3-caffeoylquinic acid (chlorogenic acid)
Compound Structure:
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:

1794427

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]


Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

354.31 g/mol

XLogP3-AA

-0.4

Hydrogen Bond Donor Count

6

Hydrogen Bond Acceptor Count

9

Rotatable Bond Count

5

Exact Mass

354.09508215 g/mol

Monoisotopic Mass

354.09508215 g/mol

Topological Polar Surface Area

165Ų

Heavy Atom Count

25

Formal Charge

0

Complexity

534

Isotope Atom Count

0

Defined Atom Stereocenter Count

4

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

1

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Solid

Melting Point

205 - 209 °C

Solubility 

40 mg/mL at 25 °C

Source: PubChem                                                         

Source Species: Echinacea purpurea
Eichhornia crassipes
Ficus capensis
Newbouldia laevis
Raphia hookeri
Solanum aethiopicum
Luffa cylindrica
Talinum triangulare
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