(E,E)-3,5-Di-O-caffeoylquinic acid CAS#: 89919-62-0

(E,E)-3,5-Di-O-caffeoylquinic acid Basic information

Product Name:

(E,E)-3,5-Di-O-caffeoylquinic acid

Synonyms:

(E,E)-3,5-Di-O-caffeoylquinic acid
(-)-3,5-Dicaffeoyl quinic acid
(1S,3R,4S,5R)-3,5-Bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)-oxy)-1,4-dihydroxycyclohexanecarboxyl
(3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
Cyclohexanecarboxylicacid,3,5-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,4-dihydroxy-,(1a,3R,4a,5R)-
3, 5-O-Dicaffeoylquinic acid
Cyclohexanecarboxylic acid, 3,5-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,4-dihydroxy-, (1α,3R,4α,5R)-
(1S,3R,4S,5R)-3,5-Bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4-dihydroxycyclohexanecarboxylic acid

CAS:

89919-62-0

MF:

C25H24O12

MW:

516.46

Mol File:

89919-62-0.mol

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(E,E)-3,5-Di-O-caffeoylquinic acid Chemical Properties

Boiling point:: 826.2±65.0 °C(Predicted)
Density: 1.64
storage temp.: 2-8°C
pka: 3.52±0.50(Predicted)
form: Solid
color: White to off-white
InChIKey: KRZBCHWVBQOTNZ-XLDUFQNVNA-N
SMILES: O([C@@H]1C[C@@](O)(C(=O)O)C[C@@H](OC(=O)/C=C/C2C=CC(O)=C(O)C=2)[C@@H]1O)C(=O)/C=C/C1C=CC(O)=C(O)C=1 |&1:1,3,9,23,r|

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(E,E)-3,5-Di-O-caffeoylquinic acid Usage And Synthesis

Uses

3,5-O-Dicaffeoylquinic acid reverses Trimethyltin-induced learning and memory deficits[1].

Definition

ChEBI: 3,5-di-O-caffeoyl quinic acid is a carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities. It has a role as a metabolite, a hepatoprotective agent and an antineoplastic agent. It is a cyclitol carboxylic acid and a carboxylic ester. It is functionally related to a (-)-quinic acid and a trans-caffeic acid.

References

[1] Kang JY, et al. Reversal of Trimethyltin-Induced Learning and Memory Deficits by 3,5-Dicaffeoylquinic Acid.?Oxid Med Cell Longev. 2016;2016:6981595. DOI:10.1155/2016/6981595

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