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{{short description|Chemical compound}}
{{chembox {{chembox
| Verifiedfields = changed
| ImageFile = Cichoric acid.png
| Watchedfields = changed
| verifiedrevid = 404187058
| ImageFile = Chicoric acid.svg
| ImageFile2 = Cichoric acid-3D-balls.png
| ImageSize = | ImageSize =
| IUPACName =(2''R'',3''R'')-2,3-bis{oxy}butanedioic acid | PIN =(2''R'',3''R'')-2,3-Bis{oxy}butanedioic acid
| OtherNames = Cichoric acid; (2''R'',3''R'')-''O''-Dicaffeoyltartaric acid
| OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| Abbreviations = | Abbreviations =
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 6537-80-0 | CASNo = 6537-80-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = S4YY3V8YHD
| EINECS = | EINECS =
| PubChem = 5281764 | PubChem = 5281764
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4445078
| SMILES =O=C(O)(OC(=O)\C=C\c1ccc(O)c(O)c1)(OC(=O)\C=C\c2cc(O)c(O)cc2)C(=O)O | SMILES =O=C(O)(OC(=O)\C=C\c1ccc(O)c(O)c1)(OC(=O)\C=C\c2cc(O)c(O)cc2)C(=O)O
| InChI =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 | 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 = | RTECS =
| MeSHName = | MeSHName =
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = | ChEBI =
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 282731
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C10437 | KEGG = C10437
}}
| ATCCode_prefix =
|Section2={{Chembox Properties
| ATCCode_suffix =
| ATC_Supplemental =}}
| Section2 = {{Chembox Properties
| Formula = C<sub>22</sub>H<sub>18</sub>O<sub>12</sub> | Formula = C<sub>22</sub>H<sub>18</sub>O<sub>12</sub>
| MolarMass = 474.371 g/mol | MolarMass = 474.371 g/mol
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| Density = | Density =
| MeltingPt = | MeltingPt =
| Melting_notes = | MeltingPt_notes =
| BoilingPt = | BoilingPt =
| Boiling_notes = | BoilingPt_notes =
| Solubility = | Solubility =
| SolubleOther = | SolubleOther =
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| pKa = | pKa =
| pKb = }} | pKb = }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| EUClass =
| EUIndex =
| MainHazards = | MainHazards =
| NFPA-H = | NFPA-H =
| NFPA-F = | NFPA-F =
| NFPA-R = | NFPA-R =
| NFPA-O = | NFPA-S =
| RPhrases =
| SPhrases =
| RSPhrases =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
| ExploLimits = | ExploLimits =
| PEL = }} | PEL = }}
}} }}
'''Cichoric acid''' is a ], an organic compound of the ] class and occurs in a variety of plant species. It is a derivative of both ] and ] '''Chicoric acid''' (also known as '''cichoric acid''') is a ], an organic compound of the ] class and occurs in a variety of plant species. It is a derivative of both ] and ].<ref name="func">{{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–}}</ref>

<ref name="func">
As a suitable marker for the distinction of '']'' species, it is often assayed using ] and ] (TLC) methods.<ref>Bauer R, Khan IA, Wagner H. Echinacea-Drogen, Standardisierung mittels HPLC und DC. Deutsche Apotheker Zeitung, 1986, 126:1065–1070. Citation in </ref>
{{Citation
|last= Hall III
|first= Clifford
|authorlink=
|coauthors= Jurgen G. Schwarz
|editor= John Shi, G. Mazza, Marc Le Maguer
|title= Functional Foods: Biochemical & Processing Aspects
|url= http://books.google.com/?id=rEr8g-phGHAC
|format=
|accessdate= 2008-12-09
|edition=
|series=
|volume= 2
|date= 2002
|year=
|month=
|publisher= CRC Press
|location=
|language=
|isbn= 1566769027
|oclc=
|doi=
|id=
|page=241
|pages=
|nopp=
|chapter=
|chapterurl=
|quote=
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}}
</ref>.
It has the ] ]<sub>22</sub>]<sub>18</sub>]<sub>12</sub>.


==Sources== ==Sources==
Cichoric acid has first been isolated from ] (chicory) but also occurs in significant amounts in ], particularly ], ] leaves, ], ] and in ], including ] and ]. <ref>I.D. Chkhikvishvili and G.I. Kahrebava (2001). “Cichoric and Chlorogenic Acids in Plant Species from Georgia”. ''Applied Biochemistry and Microbiology'', 37 (2): 188-191. </ref> <ref>Jungmin Lee (2010). Short communication “Caffeic acid derivatives in dried Lamiaceae and Echinacea purpurea products”. ''Journal of Functional Foods'' 2, 158-162. </ref> Chicoric acid has first been isolated from '']'' (chicory) but also occurs in significant amounts in '']'', in particular ], ] leaves, ], ], and ], including ] and ].<ref>{{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}}</ref><ref>{{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 }}</ref><ref>{{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. }}</ref><ref>{{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 }}</ref>


==Biological functions== ==Biological functions==
Cichoric acid has been shown to stimulate ] in both ] and ] studies, to inhibit the function of ] (an enzyme which breaks down ] in the human body), protect ] from damage due to ]s, and inhibit the function of ]-1 ] Chicoric acid has been shown to stimulate ] in both '']'' and '']'' studies, to inhibit the function of ] (an enzyme that breaks down ] in the human body), to protect ] from damage due to ]s, and to inhibit the function of ]-1 ].<ref name="herb">
<ref name="herb">
{{Citation {{Citation
| last =Mazza | last1 =Mazza
| first =G. | first1 =G.
| author-link = | author-link =
| last2 =Oomah | last2 =Oomah
| first2 =B. Dave | first2 =B. Dave
| author2-link = | author2-link =
| publication-date = | publication-date =
| date = | year = 2000
| title =Herbs, Botanicals & Teas
| year = 2000
| edition =
| title =Herbs, Botanicals & Teas
| edition = | volume =
| volume = | series =
| series = | location =
| publication-place = | place =
| publisher = CRC Press
| place =
| publisher = CRC Press | pages = 51
| pages = 51 | id =
| isbn =1-56676-851-9
| id =
| isbn =1566768519 | doi =
| doi = | oclc =
| url= https://books.google.com/books?id=Au1HLD7eyZQC
| oclc =
| accessdate = 2008-12-09
| url= http://books.google.com/?id=Au1HLD7eyZQC
| accessdate = 2008-12-09
}} }}
</ref> </ref><ref name="ech">
<ref name="ech">
{{Citation {{Citation
| last =Miller | last1 =Miller
| first =Sandra Carol | first1 =Sandra Carol
| author-link = | author-link =
| last2 =Yu | last2 =Yu
| first2 =He-Ci | first2 =He-Ci
| author2-link = | author2-link =
| publication-date = | publication-date =
| date = | year = 2004
| year = 2004 | title =Echinacea
| edition =
| title =Echinacea
| edition = | volume =
| volume = | series =
| series = | location =
| publication-place = | place =
| publisher = CRC Press
| place =
| publisher = CRC Press | pages = 140
| pages = 140 | id =
| isbn =0-415-28828-2
| id =
| isbn =0415288282 | doi =
| doi = | oclc =
| url= https://books.google.com/books?id=WMGlDuGhKq8
| oclc =
| accessdate = 2008-12-09
| url= http://books.google.com/?id=WMGlDuGhKq8
| accessdate = 2008-12-09
}} }}
</ref>. </ref>

== See also ==
* ] (monocaffeyltartaric acid)


==References== == References ==
<references/> <references/>
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==External links== -->


{{Hydroxycinnamic acid}} {{Hydroxycinnamic acid}}


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