3,4,5-Tricaffeoylquinic acid - ≥98% , CAS No.86632-03-3

CAS: 86632-03-3 Cat. No.: T646562 Molecular Weight: 678.59 PubChem CID: 6440783
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GRADE & PURITY ≥98%
Synonyms
AKOS025402173 | 3,4,5-tricaffeoylquinic acid | SCHEMBL17466763 | (1alpha,3R,4alpha,5R)-3,4,5-Tris[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1-hydroxycyclohexanecarboxylic acid | Caffeoylquinic acid der. | NCGC00169736-01 | ACon1_001037 | (1S,
Storage
Protected from light,Store at -20°C
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Status
Price
Qty
1mg
T646562-1mg
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Why this grade

≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Protected from light,Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Overview

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

Specifications

Synonyms
AKOS025402173 | 3, 4, 5-tricaffeoylquinic acid | SCHEMBL17466763 | (1alpha, 3R, 4alpha, 5R)-3, 4, 5-Tris[[(2E)-3-(3, 4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1-hydroxycyclohexanecarboxylic acid | Caffeoylquinic acid der. | NCGC00169736-01 | ACon1_001037 | (1S,
Specifications & Purity
≥98%
Biochemical and Physiological Mechanisms
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, acti
Storage
Protected from light, Store at -20°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Action Type
INHIBITOR
Purity
≥98%
Names and Identifiers
Canonical SmilesC1C(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
InChIKeyOAFXTKGAKYAFSI-JFPZSYFPSA-N
INCHI1S/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

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

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✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

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📊 Datasheet

Quick-reference summary of product specifications and applications.

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🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

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Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassAlcohols and polyols
Intermediate Tree Nodes Cyclic alcohols and derivatives - Cyclitols and derivatives
Direct ParentQuinic 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 FrameworkAromatic 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
DescriptionThis 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
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
APP Tclin Amyloid-beta A4 protein (8510 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mechanisms of Action
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
Molecular Weight678.600 g/mol
XLogP33.500
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count15
Rotatable Bond Count13
Exact Mass678.158 Da
Monoisotopic Mass678.158 Da
Topological Polar Surface Area258.000 Ų
Heavy Atom Count49
Formal Charge0
Complexity1200.000
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds3
Covalently-Bonded Unit Count1
Solution Calculators
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