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

Base Information

Chemical Name:(1S,3R,4R,5R)-1,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
CAS No.:19870-46-3
Molecular Formula:C₂₅H₂₄O₁₂
Molecular Weight:516.458
Hs Code.:
European Community (EC) Number:815-081-5
DSSTox Substance ID:DTXSID30872474
Mol file:19870-46-3.mol

Synonyms:1,3-dicaffeoylquinic acid

Suppliers and Price of (1S,3R,4R,5R)-1,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-4,5-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
1,3-DicaffeoylquinicAcid
5mg
$ 185.00

Sigma-Aldrich
1,5-Dicaffeoylquinic acid analytical standard
5mg
$ 561.00

Matrix Scientific
1,3-O-Dicaffeoylquinic acid 95+%
1g
$ 4631.00

CSNpharm
1,3-O-DicaffeoylquinicAcid
5mg
$ 153.00

Crysdot
1,3-O-Dicaffeoylquinicacid 95+%
100mg
$ 489.00

Crysdot
1,3-O-Dicaffeoylquinicacid 95+%
1g
$ 1955.00

Crysdot
1,3-O-Dicaffeoylquinicacid 95+%
250mg
$ 782.00

ChemScene
1,3-Dicaffeoylquinicacid 98.85%
25mg
$ 600.00

ChemScene
1,3-Dicaffeoylquinicacid 98.85%
10mg
$ 300.00

ChemScene
1,3-Dicaffeoylquinicacid 98.85%
5mg
$ 180.00

Total 44 raw suppliers

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

Chemical Property:

Boiling Point:819.9 °C at 760 mmHg
PKA:2.50±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.:soluble5mg/mL, clear, colorless to light 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:

98% ^*data from raw suppliers

1,3-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)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=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O)O
Description 1,5-Dicaffeoylquinic acid (1,5-DCQA) has been found in A. montana and is an HIV-1 integrase inhibitor and free radical scavenger. 1,5-DCQA inhibits HIV-1 integrase 3'' end processing, end joining, and disintegration with IC50 values of 0.35, 0.56, and 0.84 μg/ml, respectively. It also inhibits HIV-1 replication in MT-2 T lymphoblastoid cells with an ED50value of 2 μg/ml. 1,5-DCQA (0.25-1 μM) reduces the level of free radicals released from human polymorphonuclear (PMN) cells stimulated by N-formyl-Met-Leu-Phe (fMLP; ) in a dose-dependent manner. It also dose-dependently increases cell survival and glutathione (GSH) levels and decreases reactive oxygen species (ROS) production and lactate dehydrogenase (LDH) release in an oxygen-glucose deprivation/reperfusion assay in rat cerebral astrocytes when used at concentrations ranging from 5 to 100 μM.
Uses 1,5-Dicaffeoylquinic Acid acts as an anti-hyperlipidemic agent. In addition, acts as a neuroprotective agent against amyloid-β toxicity in the treatement of Alzheimer’s.

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

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

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

Guidance literature:: Photolyse von Cynarin;

Reference yield:

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

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