Chicoric acid: Difference between revisions

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	'''Cichoric acid''' is a ], an organic compound of the ~~phenylpropanoids~~ class and occurs in a variety of plant species. It is a derivative of both ] and ]		'''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 ]
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Revision as of 17:18, 25 December 2010

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

Chemical compound

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.

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.

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 .

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)
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
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
Mazza, G.; Oomah, B. Dave (2000), Herbs, Botanicals & Teas, CRC Press, p. 51, ISBN 1566768519, retrieved 2008-12-09
Miller, Sandra Carol; Yu, He-Ci (2004), Echinacea, CRC Press, p. 140, ISBN 0415288282, retrieved 2008-12-09

Aglycones

Precursor	Cinnamic acid
Monohydroxycinnamic acids (Coumaric acids)	p-Coumaric acid o-Coumaric acid m-Coumaric acid
Dihydroxycinnamic acids	Caffeic acid (3,4-dihydroxycinnamic acid) Umbellic acid (2,4-dihydroxycinnamic acid) 2,3-Dihydroxycinnamic acid 2,5-Dihydroxycinnamic acid 3,5-Dihydroxycinnamic acid
Trihydroxycinnamic acids	2,4,5-Trihydroxycinnamic acid 3,4,5-Trihydroxycinnamic acid
O-methylated forms	Ferulic acid 5-Hydroxyferulic acid Isoferulic acid Sinapinic acid
others	Plicatin A Plicatin B

Esters

glycoside-likes

Esters of
caffeic acid
with cyclitols

esters of quinic acid	Chlorogenic acid (3-caffeoylquinic acid) Cryptochlorogenic acid (4-O-caffeoylquinic acid) Neochlorogenic acid (5-O-Caffeoylquinic acid) Cynarine (1,5-dicaffeoylquinic acid) 3,4-dicaffeoylquinic acid 3,5-dicaffeoylquinic acid
esters of shikimic acid	Dactylifric acid (3-O-caffeoylshikimic acid)

Glycosides

Other esters
with caffeic acid

Caffeoyl phenylethanoid
glycoside (CPG)

Oligomeric forms

Dimers	Diferulic acids (DiFA) : 5,5′-Diferulic acid, 8-O-4′-Diferulic acid, 8,5′-Diferulic acid, 8,5′-DiFA (DC), 8,5′-DiFA (BF), 8,8′-Diferulic acid
Trimers	Triferulic acids : 5-5′,8′-O-4″-Triferulic acid
Tetramers	Tetraferulic acids

Conjugates with
coenzyme A (CoA)