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Chemical compound
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
ChEMBL
ChemSpider
ECHA InfoCard
100.109.212
KEGG
UNII
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
N Key: YDDGKXBLOXEEMN-IABMMNSOSA-N
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
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
C22 H18 O12
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).
Chemical compound
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]
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 .
[7]
[8]
See also
References
^ 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
Aglycones
Precursor Monohydroxycinnamic acids (Coumaric acids)
Dihydroxycinnamic acids Trihydroxycinnamic acids O -methylated formsothers
Esters
glycoside-likes
Esters of caffeic acid with cyclitols
Glycosides
Tartaric acid esters Other esters with caffeic acid Caffeoyl phenylethanoid glycoside (CPG)
Echinacoside
Calceolarioside A ,
B ,
C ,
F
Chiritoside A ,
B ,
C
Cistanoside A ,
B ,
C ,
D ,
E ,
F ,
G ,
H
Conandroside
Myconoside
Pauoifloside
Plantainoside A
Plantamajoside
Tubuloside B
Verbascoside (
Isoverbascoside ,
2′-Acetylverbascoside )
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 Tetramers
Conjugates with
coenzyme A (CoA)