Cynarine

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
CAS Number	30964-13-7^Y
ChEMBL	ChEMBL2105478^N
ChemSpider	4445082^N
Jmol interactive 3D	Image
PubChem	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	516.46 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

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.

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.

Types of hydroxycinnamic acids

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	3,4,5-Trihydroxycinnamic acid 3,4,6-Trihydroxycinnamic acid

O-methylated forms	Ferulic acid 5-Hydroxyferulic 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

Ferulic acid glucoside
p-Coumaric acid glucoside
1-Sinapoyl-D-glucose

Tartaric acid esters

Caftaric acid
Cichoric acid (dicaffeoyltartaric acid)
Coutaric acid
Fertaric acid
Grape reaction product (caftaric acid conjugated with glutathione)

Other esters
with caffeic acid

Caffeoylmalic acid
Ethyl caffeate
Methyl caffeate
Caffeic acid phenethyl ester (CAPE)
Rosmarinic acid (ester with 3,4-dihydroxyphenyllactic acid)

Caffeoyl phenylethanoid
glycoside (CPG)

Echinacoside
Calceolarioside A, B, C and F
Chiritoside A, B and C
Cistanoside A, B, C, D, E, F, G an 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	Triferulic acids : 5-5',8'-O-4"-Triferulic acid

Tetramers	Tetraferulic acids

Conjugates with
coenzyme A (CoA)

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Cynarine

See also

References