Chlorogenic acid

Chlorogenic acid
Chlorogenic acid
Names
Preferred IUPAC name
(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
Other names
3-(3,4-Dihydroxycinnamoyl)quinate
3-(3,4-Dihydroxycinnamoyl)quinic acid
3-Caffeoylquinate
3-Caffeoylquinic acid
3-CQA
3-O-Caffeoylquinic acid
Chlorogenate
Chlorogenic acid
Heriguard
3-trans-Caffeoylquinic acid
5-O-Caffeoylquinic acid
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
KEGG
RTECS number
  • GU8480000
UNII
  • InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1 checkY
    Key: CWVRJTMFETXNAD-JUHZACGLSA-N checkY
  • InChI=1/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1
    Key: CWVRJTMFETXNAD-JUHZACGLBD
  • O=C(O)[C@]2(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)\C=C\c1ccc(O)c(O)c1)C2
Properties
C16H18O9
Molar mass 354.311 g·mol−1
Density 1.28 g/cm3
Melting point 207 to 209 °C (405 to 408 °F; 480 to 482 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability (yellow): no hazard codeSpecial hazards (white): no code
1
0
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Chlorogenic acid (CGA) is the ester of caffeic acid and (−)-quinic acid, functioning as an intermediate in lignin biosynthesis.[1] The term chlorogenic acids refers to a related polyphenol family of esters, including hydroxycinnamic acids (caffeic acid, ferulic acid and p-coumaric acid) with quinic acid.[2]

Despite the "chloro" of the name, chlorogenic acids contain no chlorine. Instead, the name comes from the Greek χλωρός (khloros, light green) and -γένος (genos, a suffix meaning "giving rise to"), pertaining to the green color produced when chlorogenic acids are oxidized.

  1. ^ Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Lignin biosynthesis". Annual Review of Plant Biology. 54: 519–546. doi:10.1146/annurev.arplant.54.031902.134938. PMID 14503002.
  2. ^ Clifford, M. N.; Johnston, K. L.; Knight, S.; Kuhnert, N. (2003). "Hierarchical Scheme for LC-MSn Identification of Chlorogenic Acids". Journal of Agricultural and Food Chemistry. 51 (10): 2900–2911. doi:10.1021/jf026187q. PMID 12720369.