chicoric acid

{{short description|Chemical compound}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 404187058

| ImageFile = Chicoric acid.svg

| ImageFile2 = Cichoric acid-3D-balls.png

| ImageSize =

| PIN =(2R,3R)-2,3-Bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

| OtherNames = Cichoric acid; (2R,3R)-O-Dicaffeoyltartaric acid

|Section1={{Chembox Identifiers

| Abbreviations =

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 6537-80-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = S4YY3V8YHD

| EINECS =

| PubChem = 5281764

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4445078

| 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

| 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

| InChIKey = YDDGKXBLOXEEMN-IABMMNSOBV

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = YDDGKXBLOXEEMN-IABMMNSOSA-N

| RTECS =

| MeSHName =

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI =

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 282731

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C10437

}}

|Section2={{Chembox Properties

| Formula = C22H18O12

| MolarMass = 474.371 g/mol

| Appearance =

| Density =

| MeltingPt =

| MeltingPt_notes =

| BoilingPt =

| BoilingPt_notes =

| Solubility =

| SolubleOther =

| Solvent =

| pKa =

| pKb = }}

|Section7={{Chembox Hazards

| ExternalSDS =

| MainHazards =

| NFPA-H =

| NFPA-F =

| NFPA-R =

| NFPA-S =

| FlashPt =

| AutoignitionPt =

| ExploLimits =

| PEL = }}

}}

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.{{cite book|author1=John Shi|author2=Giuseppe Mazza|author3=Marc Le Maguer|title=Functional Foods: Biochemical and Processing Aspects|url=https://books.google.com/books?id=r2jLBQAAQBAJ&pg=PA241|date=27 February 2002|publisher=CRC Press|isbn=978-1-4200-1287-3|pages=241–}}

As a suitable marker for the distinction of Echinacea species, it is often assayed using RP-HPLC and Thin layer chromatography (TLC) methods.Bauer R, Khan IA, Wagner H. Echinacea-Drogen, Standardisierung mittels HPLC und DC. Deutsche Apotheker Zeitung, 1986, 126:1065–1070. Citation in [https://web.archive.org/web/20100123044246/http://apps.who.int/medicinedocs/es/d/Js2200e/15.html WHO Monographs on Selected Medicinal Plants - Volume 1]

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.{{Cite journal | title = Chicoric and Chlorogenic Acids in Plant Species from Georgia | doi = 10.1023/a:1002888016985| year = 2001| last1 = Chkhikvishvili| first1 = I. D.| journal = Applied Biochemistry and Microbiology| volume = 37| issue = 2| pages = 188–191| last2 = Kharebava| first2 = G. I.| s2cid = 6322156}}{{Cite journal | doi = 10.1016/j.jff.2010.02.003 | title = Caffeic acid derivatives in dried Lamiaceae and Echinacea purpurea products | journal = Journal of Functional Foods | volume = 2 | issue = 2 | pages = 158–162 | year = 2010 | last1 = Lee | first1 = Jungmin }}{{Cite journal | doi = 10.1016/j.foodchem.2008.12.075 | title = Chicoric acid found in basil (Ocimum basilicum L.) leaves | journal = Food Chemistry | volume = 115 | issue = 2 | pages = 650–656 | year = 2009 | last1 = Lee | first1 = Jungmin | last2 = Scagel | first2 = Carolyn F. }}{{Cite journal | doi = 10.3389/fchem.2013.00040 | pmid = 24790967 | pmc = 3982519 | title = Chicoric acid: Chemistry, distribution, and production | journal = Frontiers in Chemistry | volume = 1 | pages = 40 | year = 2013 | last1 = Lee | first1 = Jungmin | last2 = Scagel | first2 = Carolyn F. | bibcode = 2013FrCh....1...40L | doi-access = free }}

Biological functions

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.

{{Citation

| last1 =Mazza

| first1 =G.

| author-link =

| last2 =Oomah

| first2 =B. Dave

| author2-link =

| publication-date =

| year = 2000

| title =Herbs, Botanicals & Teas

| edition =

| volume =

| series =

| location =

| place =

| publisher = CRC Press

| pages = 51

| id =

| isbn =1-56676-851-9

| doi =

| oclc =

| url= https://books.google.com/books?id=Au1HLD7eyZQC

| accessdate = 2008-12-09

}}

{{Citation

| last1 =Miller

| first1 =Sandra Carol

| author-link =

| last2 =Yu

| first2 =He-Ci

| author2-link =

| publication-date =

| year = 2004

| title =Echinacea

| edition =

| volume =

| series =

| location =

| place =

| publisher = CRC Press

| pages = 140

| id =

| isbn =0-415-28828-2

| doi =

| oclc =

| url= https://books.google.com/books?id=WMGlDuGhKq8

| accessdate = 2008-12-09

}}

See also

References