1,3-Dicaffeoylquinic acid

Base Information

• Chemical Name: 1,3-Dicaffeoylquinic acid
• CAS No.: 30964-13-7
• Molecular Formula: C₂₅H₂₄O₁₂
• Molecular Weight: 516.458
• Hs Code.: 29182900
• European Community (EC) Number: 815-081-5,845-639-3
• Nikkaji Number: J489.718H,J93.939K
• Wikipedia: Cynarine
• Wikidata: Q105346691
• NCI Thesaurus Code: C81041
• Metabolomics Workbench ID: 137767
• ChEMBL ID: CHEMBL478574
• Mol file: 30964-13-7.mol

Synonyms:1,5-dicaffeoylquinic acid;1-carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate);cinarin;cinarina;cinarine;Cynarex;cynarin;cynarin, (1alpha,3alpha,4alpha,5beta)-isomer;cynarine;cynarix;listricol;listrocol;nivellipid;phemocil

Chemical Property of 1,3-Dicaffeoylquinic acid

Chemical Property:

• Melting Point: 225-227°
• Boiling Point: 819.9 °C at 760 mmHg
• PKA: 2.58±0.50(Predicted)
• Flash Point: 278.1 °C
• PSA: 211.28000
• Density: 1.64 g/cm³
• LogP: 1.02960
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble5mg/mL, clear, light yellow to yellow
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 9
• Exact Mass: 516.12677620
• Heavy Atom Count: 37
• Complexity: 887

Purity/Quality:

5%10% ^*data from raw suppliers

1,3-Dicaffeoylquinic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(C(CC1(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O)O
• Isomeric SMILES: C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O
• Description: 1,3-Dicaffeoylquinic acid is a polyphenol that has been found in C. scolymus. It decreases the expression and protein levels of inducible nitric oxide synthase (iNOS) when used at a concentration of 10 μM in human coronary artery smooth muscle cells (HCASMCs) treated with a cytokine mixture. 1,3-Dicaffeoylquinic acid decreases protein levels of tyrosinase and microphthalmia-associated transcription factor (MITF) in B16F1 murine melanocytes. It inhibits melanogenesis in B16F1 cells and decreases tyrosinase activity in cell lysates when used at a concentration of 25 μM. 1,3-Dicaffeoylquinic acid (20 and 40 μM) reduces triglyceride levels in sodium oleate-induced hyperlipidemic HepG2 cells compared to hyperlipidemic control cells.
• Uses: Cynarin is used on MDR cells in anti-cancer therapy as an inhibitor of P-glycoprotein-mediated transport.
• Therapeutic Function: Choleretic, Antihyperlipidemic

Technology Process of 1,3-Dicaffeoylquinic acid

There total 4 articles about 1,3-Dicaffeoylquinic 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:

→ 1,5-dicaffeoylquinic acid (1884-24-8,19870-46-3,30964-13-7,30964-14-8,30964-15-9,30964-16-0,97415-78-6)

Guidance literature:

Photolyse von Cynarin;

Reference yield:

→ 1,5-di-O-caffeoylquinic acid (1884-24-8,19870-46-3,30964-13-7,30964-14-8,30964-15-9,30964-16-0,97415-78-6)

Guidance literature:

(Chinasaeure-4,5-isopropylidenether)-methylester-1,3-bis-(3,4-carbonyldioxy-cinnamat)/Acn., wss.NaOH (RT), dann 80percentig.Eg (Δ);

Reference yield:

→ (1S,3S,4R,5S)-1,3-Bis-[(Z)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-4,5-dihydroxy-cyclohexanecarboxylic acid (1884-24-8,19870-46-3,30964-13-7,30964-14-8,30964-15-9,30964-16-0,97415-78-6)

Guidance literature:

Photolyse von Cynarin;