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(-) -3,5-Dicaffeoylquinic acid

CAT: 0931-TL0005-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0931-TL0005-01Size:1 mg
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CAS Number
89919-62-0
Target
Others
Related Pathways
Others
Purity
0.9972
Bioactivity
3,5-O-Dicaffeoylquinic acid (Isochlorogenic Acid A) is an isolated compound from Artemisia argyi; its ester derivatives exert anti-leucyl-tRNA synthetase of Giardia lamblia (GlLeuRS) and potential anti-giardial effects. 3,5-O-Dicaffeoylquinic acid (Isochlorogenic Acid A) as a neuraminidase inhibitory ligand in Flos Lonicerae, it has neuroprotective effects on SH-SY5Y cells and senescence-accelerated-prone mice 8 through the up-regulation of phosphoglycerate kinase-1. 3,5-O-Dicaffeoylquinic acid (Isochlorogenic Acid A) also has antioxidant and anti-complementary activities.
Smiles
O(C(/C=C/C1=CC(O)=C(O)C=C1)=O)[C@H]2[C@@H](O)[C@H](OC(/C=C/C3=CC(O)=C(O)C=C3)=O)C[C@@](C(O)=O)(O)C2
Molecular Formula
C25H24O12
Molecular Weight
516.45
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

isochlorogenic acid A

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, an antineoplastic agent and a hepatoprotective agent. It is a carboxylic ester and a cyclitol carboxylic acid. It is functionally related to a trans-caffeic acid and a (-)-quinic acid. It is a conjugate acid of a 3,5-di-O-caffeoyl quinate.

CAS Number89919-62-0
PubChem CID6474310
IUPAC Nametrans-(3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
Molecular FormulaC25H24O12
Molecular Weight516.4
XLogP1.5
Topological Polar Surface Area211
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count12
Rotatable Bond Count9
Heavy Atom Count37
Formal Charge0
Complexity825
SMILES
C1C(C[C@H](C([C@@H]1OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)(O)C(=O)O
InChI
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23?,25?/m1/s1
InChIKey
KRZBCHWVBQOTNZ-RDJMKVHDSA-N
Chemical Structure
2D Structure
2D structure of isochlorogenic acid A
CAS: 89919-62-0
CID: 6474310
Formula: C25H24O12
MW: 516.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight516.4
XLogP31.5
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count12
Rotatable Bond Count9
Exact Mass516.12677620
Monoisotopic Mass516.12677620
Topological Polar Surface Area211 Ų
Heavy Atom Count37
Formal Charge0
Complexity825
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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