(1R,3R,4S,5R)-3,4-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,5-dihydroxycyclohexane-1-carboxylic acid

Base Information

• Chemical Name: (1R,3R,4S,5R)-3,4-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,5-dihydroxycyclohexane-1-carboxylic acid
• CAS No.: 57378-72-0
• Molecular Formula: C₂₅H₂₄O₁₂
• Molecular Weight: 516.458
• DSSTox Substance ID: DTXSID601312292
• Mol file: 57378-72-0.mol

Synonyms:4,5-Dicaffeoylquinic acid;SCHEMBL18317176;DTXSID601312292

Chemical Property of (1R,3R,4S,5R)-3,4-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,5-dihydroxycyclohexane-1-carboxylic acid

Chemical Property:

• Vapor Pressure: 8.9E-28mmHg at 25°C
• Melting Point: 140 °C
• Refractive Index: 1.719
• Boiling Point: 810.8 °C at 760 mmHg
• PKA: 3.70±0.50(Predicted)
• Flash Point: 274.9 °C
• PSA: 211.28000
• Density: 1.64 g/cm³
• LogP: 1.02960
• Storage Temp.: ?20°C
• 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:

98%, ^*data from raw suppliers

4,5-DicaffeoylquinicAcid ^*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)O
• Isomeric SMILES: C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O
• Description: 4,5-Dicaffeoylquinic acid (4,5-DCQA) is a polyphenol originally isolated from G. fagetorum and G. pseudomollugo that has diverse biological activities, including anti-HIV replication, antioxidative, anti-inflammatory, and anti-melanogenic properties. It inhibits HIV-1 integrase 3'' end processing, 3’ end joining, and disintegration with IC50 values of 0.13, 0.24, and 0.3 μg/ml, respectively. It also inhibits HIV-1 replication in MT-2 T lymphoblastoid cells with an EC50 value of 2 μg/ml. 4,5-DCQA scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay (IC50 = 19.8 μM) and inhibits superoxide production in human neutrophils activated by N-formyl-Met-Leu-Phe (fMLF; ) and cytochalasin B (; IC50 = 1.49 μM). It decreases prostaglandin E2 (PGE2; ) production in LPS-stimulated U937 cells when used at concentrations of 5 and 10 μg/ml but increases it when used at 200 μg/ml and increases production of TNF-α at concentrations ranging from 5 to 200 μg/ml. It inhibits the synthesis of MCP3 in U937 cells. 4,5-DCQA (25 μM) inhibits melanogenesis by 84% and decreases the levels of proteins involved in melanin biosynthesis, including tyrosinase, TRP-1, DCT, and MITF in B16F1 murine melanocytes.

Technology Process of (1R,3R,4S,5R)-3,4-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,5-dihydroxycyclohexane-1-carboxylic acid

There total 17 articles about (1R,3R,4S,5R)-3,4-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,5-dihydroxycyclohexane-1-carboxylic 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: 73.0%

1-O-(2,2,2,-trichloroethoxycarbonyl)-4,5-di-O-caffeoylquinic acid → 4,5-di-O-caffeoylquinic acid (14534-61-3,17912-89-9,89886-28-2,89886-29-3,89886-30-6,89886-31-7,102851-07-0,102851-08-1,136088-12-5,57378-72-0)

Guidance literature:

With acetic acid; zinc; at 20 ℃; for 26h;

DOI:10.1248/cpb.59.502

Reference yield: 56.0%

1-O-(2,2,2-trichloroethoxycarbonyl)-4,5-di-O-acetylcaffeoyl-1,5-quinide → 1-O-(2,2,2,-trichloroethoxycarbonyl)-4,5-di-O-caffeoylquinic acid + 4,5-di-O-caffeoylquinic acid (14534-61-3,17912-89-9,89886-28-2,89886-29-3,89886-30-6,89886-31-7,102851-07-0,102851-08-1,136088-12-5,57378-72-0)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 336h;

DOI:10.1248/cpb.59.502

Reference yield:

neochlorogenic acid (327-97-9,534-61-2,906-33-2,15016-60-1,15076-00-3,29587-84-6,32719-11-2,72690-58-5,77209-78-0,82659-69-6,82659-70-9,82659-71-0,82690-55-9,93451-45-7,93451-46-8) → 3-O-(cis-caffeoyl)quinic acid (32719-11-2) + (1S,3R,4R,5R)-5-[3-(3,4-dihydroxyphenyl)-2-hydroxypropanoyl]-1,4,5-trihydroxycyclohexanecarboxylic acid (1258222-08-0) + (1S,3R,4R,5R)-5-[3-(3,4-dihydroxyphenyl)-3-hydroxypropanoyl]-1,4,5-trihydroxycyclohexanecarboxylic acid (1258222-09-1) + caffeic acid (331-39-5,501-16-6) + D-(-)-quinic acid (77-95-2) + 4-O-caffeoylquinic acid (905-99-7,6049-17-8,17608-52-5,82638-22-0,82638-23-1,87099-76-1,87099-73-8) + 4,5-di-O-caffeoylquinic acid (14534-61-3,17912-89-9,89886-28-2,89886-29-3,89886-30-6,89886-31-7,102851-07-0,102851-08-1,136088-12-5,57378-72-0) + 3-caffeoylquinic acid (202650-88-2)

Guidance literature:

In water; at 200 ℃; for 0.166667h;

DOI:10.1021/jf103373t

upstream raw materials:

1-O-(2,2,2-trichloroethoxycarbonyl)-3,4-O-isopropyliden-1,5-γ-quinide

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

caffeic acid

di-O-acetylcaffeic acid

Downstream raw materials:

4-cis,5-cis-dicaffeoylquinic acid

methyl 3,4-dihydroxycinnamate

(1S,3R,4R,5R)-3,4-bis{[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxycyclohexane-1-carboxylic methyl ester

Refernces

• 1、 Dawidowicz, Andrzej L.,Typek, Rafal. "Thermal stability of 5-o-caffeoylquinic acid in aqueous solutions at different heating conditions". experimental part. p. 12578 - 12584. Retrieved 2011/10/30.