Cynarine

Cynarine


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
CAS number	30964-13-7^Y
PubChem	5281769
ChEMBL	CHEMBL487258^N
Jmol-3D images	Image 1
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
Molecular formula	C₂₅H₂₅O₁₂
Molar mass	517.46 g mol⁻¹
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cynarine is a hydroxycinnamic acid and a biologically active chemical constituent of artichoke.^[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]

References

^ Panizzi, Luigi; Scarpati, Maria Luisa (1954). "Constitution of Cynarine, the Active Principle of the Artichoke". Nature 174 (4440): 1062. doi:10.1038/1741062a0. PMID 13214078.
^ Feifer, Jason (May 2011). "A Matter of Taste". Men's Health 26 (4): 140.

Types of hydroxycinnamic acids

Hydroxycinnamic acids	Caffeic acid \| Cichoric acid \| Cinnamic acid \| Coumaric acid \| Diferulic acid \| Ferulic acid \| Plicatins A and B \| Sinapinic acid

Glycosides	Chlorogenic acid \| Cynarine

Tartaric acid esters	Caftaric acid \| Coutaric acid \| Fertaric acid

Others	Grape reaction product