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| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
3,4,5-Tricaffeoylquinic acid (3,4,5-triCQA) inhibits tumor necrosis factor-α-stimulated production of inflammatory mediators in keratinocytes via suppression of Akt- and NF-κB-pathways. 3,4,5-Tricaffeoylquinic acid induces cell cycle arrest at G0/G1, actin cytoskeleton organization, chromatin remodeling, neuronal differentiation, and bone morphogenetic protein signaling in human neural stem cells. 3,4,5-Tricaffeoylquinic acid has the potential for the research of aging-associated diseases.
In Vitro
3,4,5-Tricaffeoylquinic acid (0-50 μM) reduces TNF-α-induced production of cytokines in HEK001 keratinocytes. 3,4,5-Tricaffeoylquinic acid (15 μM, 35 min) inhibits TNF-α-induced IkBα phosphorylation and activation of NF-κB. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: Keratinocytes Concentration: 15, 25 and 50 μM Incubation Time: 24 hours Result: Cell death was cell ∼4-5% at 15 and 25 μM, ∼9% at 50 μM. Western Blot AnalysisCell Line: Keratinocytes Concentration: 15 μM Incubation Time: 20 min before 10 ng/mL TNF-α addition for 15 min Result: Decreased TNF-α-induced-IkBα phosphorylation of IkBα and levels of cytosolic NF-Κb p65, cytosolic NF-Κb p65.
Form:Solid
| Canonical Smiles | C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)OC(=O)C=CC4=CC(=C(C=C4)O)O |
|---|---|
| IUPAC Name | (3R,5R)-3,4,5-tris[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1-hydroxycyclohexane-1-carboxylic acid |
| InChIKey | OAFXTKGAKYAFSI-JFPZSYFPSA-N |
| INCHI | 1S/C34H30O15/c35-21-7-1-18(13-24(21)38)4-10-29(41)47-27-16-34(46,33(44)45)17-28(48-30(42)11-5-19-2-8-22(36)25(39)14-19)32(27)49-31(43)12-6-20-3-9-23(37)26(40)15-20/h1-15,27-28,32,35-40,46H,16-17H2,(H,44,45)/b10-4+,11-5+,12-6+/t27-,28-,32?,34?/m1/s1 |
| Isomeric SMILES | C1C(C[C@H](C([C@@H]1OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)O)(O)C(=O)O |
| Alternate CAS | 86632-03-3 |
| PubChem CID | 6440783 |
| MeSH Entry Terms | 1,5-O-dicaffeoylquinic acid;3,4,5-tri-caffeoylquinic acid;3,4,5-tricaffeoylquinic acid;3,4-O-dicaffeoylquinic acid;4,5-O-dicaffeoylquinic acid;caffeoylquinic acid;dicaffeoylquinic acid;TCQA cpd |
| Molecular Weight | 678.59 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Alcohols and polyols |
| Intermediate Tree Nodes | Cyclic alcohols and derivatives - Cyclitols and derivatives |
| Direct Parent | Quinic acids and derivatives |
| Alternative Parents | Tetracarboxylic acids and derivatives Coumaric acids and derivatives Cinnamic acid esters Styrenes Catechols Fatty acid esters Cyclohexanols 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Alpha hydroxy acids and derivatives Tertiary alcohols Enoate esters Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Tetracarboxylic acid or derivatives - Quinic acid - Cinnamic acid ester - Hydroxycinnamic acid or derivatives - Coumaric acid or derivatives - Cinnamic acid or derivatives - Styrene - Catechol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Fatty acid ester - Cyclohexanol - Fatty acyl - Benzenoid - Hydroxy acid - Monocyclic benzene moiety - Alpha-hydroxy acid - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Tertiary alcohol - Carboxylic acid ester - Carboxylic acid - Carboxylic acid derivative - Organic oxide - Hydrocarbon derivative - Carbonyl group - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as quinic acids and derivatives. These are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. |
| External Descriptors | Not available |
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Molecular Weight | 678.600 g/mol |
|---|---|
| XLogP3 | 3.500 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 15 |
| Rotatable Bond Count | 13 |
| Exact Mass | 678.158 Da |
| Monoisotopic Mass | 678.158 Da |
| Topological Polar Surface Area | 258.000 Ų |
| Heavy Atom Count | 49 |
| Formal Charge | 0 |
| Complexity | 1200.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 3 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 3 |
| Covalently-Bonded Unit Count | 1 |