(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
Hs Code.:
DSSTox Substance ID:DTXSID601312292
Mol file:57378-72-0.mol

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

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

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
4,5-DicaffeoylquinicAcid
2.5mg
$ 365.00

Sigma-Aldrich
4,5-Di-O-caffeoylquinic acid ≥85% (LC/MS-ELSD)
1mg
$ 352.00

Medical Isotopes, Inc.
4,5-DicaffeoylquinicAcid
2 mg
$ 190.00

DC Chemicals
IsochlorogenicacidC(4,5') >98%,StandardReferencesGrade
20 mg
$ 280.00

Chemenu
3,4-Dicaffeoylquinicacid 98%
10mg
$ 152.00

Cayman Chemical
4,5-Dicaffeoylquinic Acid
50mg
$ 1046.00

Cayman Chemical
4,5-Dicaffeoylquinic Acid
25mg
$ 593.00

Cayman Chemical
4,5-Dicaffeoylquinic Acid
10mg
$ 266.00

Cayman Chemical
4,5-Dicaffeoylquinic Acid
5mg
$ 140.00

Biosynth Carbosynth
4,5-Dicaffeoylquinic acid
2 mg
$ 60.00

Total 42 raw suppliers

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:

99% ^*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%