Cynarine

Cynarine is a hydroxycinnamic acid derivative and a biologically active chemical constituent of artichoke (Cynara cardunculus).^[1]

Cynarine

Names
Preferred IUPAC name (1R,3R,4S,5R)-1,3-Bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxycyclohexane-1-carboxylic acid
Other names 1,5-Dicaffeoylquinic acid; Cynarin; Cinarin; Cinarine
Identifiers
CAS Number	212891-05-9^N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2105478^N
ChemSpider	4445082^N
PubChem CID	5281769
UNII	85D81U9JAV^N
InChI 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
SMILES 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
Chemical formula	C25H24O12
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). N verify (what is ^YN ?) Infobox references

Chemically, it is an ester formed from quinic acid and two units of caffeic acid.

See also

• Chlorogenic acid

References

1. 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. S2CID 4254603.