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Cynarine
Names
IUPAC name
(1R ,3R ,4S ,5R )-1,3-bis[[(E )-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
Other names
1,5-Dicaffeoylquinic acid; Cynarin; Cinarin; Cinarine
Identifiers
ChEMBL
ChemSpider
UNII
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
N Key: YDDUMTOHNYZQPO-RVXRWRFUSA-N
N InChI=1/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
Key: YDDUMTOHNYZQPO-RVXRWRFUBT
C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O
Properties
C 25 H 24 O 12
Molar mass
516.455 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Cynarine is a hydroxycinnamic acid and a biologically active chemical constituent of artichoke (Cynara cardunculus ).[ 1]
Chemically, it is an ester formed from quinic acid and two units of caffeic acid .
It inhibits taste receptors, making water (and other foods and drinks) seem sweet.[ 2]
It is an ingredient of the drug Sulfad .
See also
References
^ Panizzi, Luigi; Scarpati, Maria Luisa (1954). "Constitution of Cynarine, the Active Principle of the Artichoke". Nature . 174 (4440): 1062–3. doi :10.1038/1741062a0 . PMID 13214078 .
^ Feifer, Jason (May 2011). "A Matter of Taste". Men's Health . 26 (4): 140.
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 estersOther 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 withcoenzyme A (CoA)
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