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Chicoric acid

Names
IUPAC name (2R,3R)-2,3-bis{oxy}butanedioic acid
Identifiers
CAS Number	6537-80-0
3D model (JSmol)	Interactive image
ECHA InfoCard	100.109.212
KEGG	C10437
PubChem CID	5281764
CompTox Dashboard (EPA)	DTXSID0033332
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
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
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 , 100 kPa). 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 . It has the chemical formula C₂₂H₁₈O₁₂.

Sources

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

Biological functions

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

References

1. Hall III, Clifford (2002), John Shi, G. Mazza, Marc Le Maguer (ed.), Functional Foods: Biochemical & Processing Aspects, vol. 2, CRC Press, p. 241, ISBN 1566769027, retrieved 2008-12-09 {{citation}}: Cite has empty unknown parameters: |laydate=, |nopp=, |separator=, |chapterurl=, |laysummary=, |month=, and |lastauthoramp= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)CS1 maint: multiple names: editors list (link)
2. 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. doi: 10.1023/a:1002888016985
3. Jungmin Lee (2010). Short communication “Caffeic acid derivatives in dried Lamiaceae and Echinacea purpurea products”. Journal of Functional Foods 2, 158-162. doi:10.1016/j.jff.2010.02.003
4. Mazza, G.; Oomah, B. Dave (2000), Herbs, Botanicals & Teas, CRC Press, p. 51, ISBN 1566768519, retrieved 2008-12-09
5. Miller, Sandra Carol; Yu, He-Ci (2004), Echinacea, CRC Press, p. 140, ISBN 0415288282, retrieved 2008-12-09

• Dicarboxylic acids
• Tartrates
• Cinnamates
• Catechols
• Hydroxycinnamic acids