3,4,5-Tricaffeoylquinic acid

Base Information

• Chemical Name: 3,4,5-Tricaffeoylquinic acid
• CAS No.: 86632-03-3
• Molecular Formula: C₃₄H₃₀O₁₅
• Molecular Weight: 678.603
• DSSTox Substance ID: DTXSID701106486
• Nikkaji Number: J552.490C,J1.764.978G
• Wikidata: Q105188646,Q105188644
• Pharos Ligand ID: QRUHY7QGAFUS
• ChEMBL ID: CHEMBL499997
• Mol file: 86632-03-3.mol

Synonyms: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

Chemical Property of 3,4,5-Tricaffeoylquinic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 916oC at 760 mmHg
• PKA: 3.31±0.50(Predicted)
• Flash Point: 290.9oC
• PSA: 257.81000
• Density: 1.64g/cm3
• LogP: 2.70510
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 13
• Exact Mass: 678.15847025
• Heavy Atom Count: 49
• Complexity: 1200

Purity/Quality:

98%Min ^*data from raw suppliers

3,4,5-Tricaffeoylquinic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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
• 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

Technology Process of 3,4,5-Tricaffeoylquinic acid

There total 22 articles about 3,4,5-Tricaffeoylquinic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 58.0%

3,4,5-tri-O-(3,4-di-O-acetylcaffeoyl)-1,7-isopropylidene-quinide → 3,4,5-tri-O-caffeoyl-quinic acid (86632-03-3)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 264h;

DOI:10.1248/cpb.59.502

Reference yield: 16.1%

C37H34O17 → (3R,5R)-3,4,5-tris{[(2E)-3-(3,4-dihydroxyphenyl)-1-oxoprop-2-en-1-yl]oxy}1-hydroxycyclohexanecarboxylic acid (86632-03-3)

Guidance literature:

With pyridine; lithium iodide; at 120 ℃; for 4h; Inert atmosphere;

Reference yield:

trichloroethyl 1-carbotrichloroethoxy-3,4,5-tris(3,4-dicarbotrichloroethoxycaffeoyl)quinate → 3,4,5-tri-O-caffeoyl-quinic acid (86632-03-3)

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran; at 35 - 40 ℃; for 8h;

upstream raw materials:

D-(-)-quinic acid

3,4-diacetoxycinnamoyl chloride

3,4-O-dimethoxycarbonyl caffeic acid chloride

(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

Refernces

• 1、 -. "METHOD FOR MANUFACTURING 3,4,5-TRICAFFEOYLQUINIC ACID". . . Retrieved 2016/02/19.
• 2、 Karakoese, Hande,Jaiswal, Rakesh,Kuhnert, Nikolai. "Characterization and quantification of hydroxycinnamate derivatives in Stevia rebaudiana leaves by LC-MSn". experimental part. p. 10143 - 10150. Retrieved 2012/01/13.