(-)-Chicoric acid

C22H18O12CAS 70831-56-0474.37 g/mol

Open in Covalent MOL file
OOHHOOOHOOOOHOHOHO
AlkeneCarboxylic acidEsterPhenol

Properties

Molecular formula
C22H18O12
Molar mass
474.37 g/mol
Exact mass
474.0798 Da
Melting point
206 °C
Boiling point
46–47 °C
logP
1.23Crippen estimate
Polar surface area
208.1 Ų
H-bond donors / acceptors
6 / 10
Rotatable bonds
9
Stereocentres
R, Rin SMILES atom order
Double bonds
E, EE/Z, in SMILES order

Hazards

Danger
Irritant (GHS07)Health Hazard (GHS08)

Aggregated from 39 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P321, P330, P333+P317, P342+P316, P362+P364, P403, P501

Identifiers

CAS number
70831-56-0
SMILES
O=C(/C=C/c1ccc(O)c(O)c1)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/c1ccc(O)c(O)c1)C(=O)O
InChIKey
YDDGKXBLOXEEMN-IABMMNSOSA-N
InChI
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

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

9 names
  • Butanedioic acid, 2,3-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-, (2R,3R)-
  • Butanedioic acid, 2,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, [R-[R*,R*-(E,E)]]-
  • Butanedioic acid, 2,3-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (2R,3R)-
  • (2R,3R)-2,3-Bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]butanedioic acid
  • Chicoric acid, (-)-
  • l-Chicoric acid
  • (-)-L-Chicoric acid
  • NSC 99173
  • trans-Caffeoyltartaric acid

Work with (-)-Chicoric acid

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Boiling point under vacuumAt any pressure, from its normal boiling point Isotope patternExact mass and the mass spectrum pattern

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

Chicoric acid6537-80-0Stereoisomer

Similar compounds

Caftaric acid67879-58-785 % similar Rosmarinic acid20283-92-570 % similar α-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3,4-dihydroxybenzenepropanoic acid537-15-570 % similar Methyl caffeate3843-74-162 % similar 3,5-Dicaffeoylquinic acid2450-53-558 % similar Ethyl caffeate102-37-458 % similar Caffeic acid phenethyl ester104594-70-956 % similar Caffeic acid331-39-556 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue.

All similar compounds

Elsewhere

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