Cichoric acid

Cichoric acid

Names
IUPAC name (2R,3R)-2,3-bis{[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
Other names 2R,3R-O-dicaffeoyltartaric acid
Identifiers
CAS Number	6537-80-0 Y
3D model (Jmol)	Interactive image
ChemSpider	4445078 N
ECHA InfoCard	100.164.046
KEGG	C10437 Y
PubChem CID	5281764
InChI InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1 N Key: YDDGKXBLOXEEMN-IABMMNSOSA-N N InChI=1/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1 Key: YDDGKXBLOXEEMN-IABMMNSOBV
SMILES O=C(O)[C@H](OC(=O)\C=C\c1ccc(O)c(O)c1)[C@@H](OC(=O)\C=C\c2cc(O)c(O)cc2)C(=O)O
Properties
Chemical formula	C22H18O12
Molar mass	474.371 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Cichoric acid is a hydroxycinnamic acid, an organic compound of the phenylpropanoid class and occurs in a variety of plant species. It is a derivative of both caffeic acid and tartaric acid.

As a suitable marker for the distinction of Echinacea species, it is often assayed using RP-HPLC and Thin layer chromatography (TLC) methods.

Cichoric acid has first been isolated from Cichorium intybus (chicory) but also occurs in significant amounts in Echinacea, in particular E. purpurea, dandelion leaves, basil, lemon balm, and aquatic plants, including algae and seagrasses.

Cichoric acid has been shown to stimulate phagocytosis in both in vitro and in vivo studies, to inhibit the function of hyaluronidase (an enzyme that breaks down hyaluronic acid in the human body), to protect collagen from damage due to free radicals, and to inhibit the function of HIV-1 integrase.