Chicoric acid

Chicoric acid
Names
	Preferred IUPAC name (2R,3R)-2,3-Bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
	Other names Cichoric acid; (2R,3R)-O-Dicaffeoyltartaric acid
Identifiers
CAS Number	6537-80-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL282731 ;
ChemSpider	4445078 ;
ECHA InfoCard	100.109.212
KEGG	C10437 ;
PubChem CID	5281764;
UNII	S4YY3V8YHD ;
CompTox Dashboard (EPA)	DTXSID0033332 ;
	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 Key: YDDGKXBLOXEEMN-IABMMNSOSA-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). verify (what is ?) Infobox references

Chicoric acid (also known as 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.^[1]

As a suitable marker for the distinction of Echinacea species, it is often assayed using RP-HPLC and Thin layer chromatography (TLC) methods.^[2]

Sources

Chicoric 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.^[3]^[4]^[5]^[6]

Chicoric 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.^[7]^[8]

^ John Shi; Giuseppe Mazza; Marc Le Maguer (27 February 2002). Functional Foods: Biochemical and Processing Aspects. CRC Press. pp. 241–. ISBN 978-1-4200-1287-3.
^ Bauer R, Khan IA, Wagner H. Echinacea-Drogen, Standardisierung mittels HPLC und DC. Deutsche Apotheker Zeitung, 1986, 126:1065–1070. Citation in WHO Monographs on Selected Medicinal Plants - Volume 1
^ Chkhikvishvili, I. D.; Kharebava, G. I. (2001). "Chicoric and Chlorogenic Acids in Plant Species from Georgia". Applied Biochemistry and Microbiology. 37 (2): 188–191. doi:10.1023/a:1002888016985. S2CID 6322156.
^ Lee, Jungmin (2010). "Caffeic acid derivatives in dried Lamiaceae and Echinacea purpurea products". Journal of Functional Foods. 2 (2): 158–162. doi:10.1016/j.jff.2010.02.003.
^ Lee, Jungmin; Scagel, Carolyn F. (2009). "Chicoric acid found in basil (Ocimum basilicum L.) leaves". Food Chemistry. 115 (2): 650–656. doi:10.1016/j.foodchem.2008.12.075.
^ Lee, Jungmin; Scagel, Carolyn F. (2013). "Chicoric acid: Chemistry, distribution, and production". Frontiers in Chemistry. 1: 40. Bibcode:2013FrCh....1...40L. doi:10.3389/fchem.2013.00040. PMC 3982519. PMID 24790967.
^ Mazza, G.; Oomah, B. Dave (2000), Herbs, Botanicals & Teas, CRC Press, p. 51, ISBN 1-56676-851-9, retrieved 2008-12-09
^ Miller, Sandra Carol; Yu, He-Ci (2004), Echinacea, CRC Press, p. 140, ISBN 0-415-28828-2, retrieved 2008-12-09