| Identification | Back Directory | [Name]
CYNARIN | [CAS]
19870-46-3 | [Synonyms]
1,3-Dicaffeoylquinic acid
Dicaffeoylquinic Acid, 1,5-
1,5-di-O-Caffeoylquinic acid
(1S,3R,4R,5R)-1,3-Bis[3-(3,4-dihydroxyphenyl)acryloyloxy]-4,5-dihydroxycyclohexanecarboxylic acid
(1S,3R,4R,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylicaci
(1S,3R,4R,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
Cyclohexanecarboxylic acid, 1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxy-, (1S,3R,4R,5R)- | [EINECS(EC#)]
214-655-7 | [Molecular Formula]
C25H24O12 | [MDL Number]
MFCD00075714 | [MOL File]
19870-46-3.mol | [Molecular Weight]
516.45 |
| Chemical Properties | Back Directory | [Boiling point ]
819.9±65.0 °C(Predicted) | [density ]
1?+-.0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [solubility ]
soluble5mg/mL, clear, colorless to light yellow | [form ]
neat | [pka]
2.50±0.50(Predicted) | [color ]
white to off-white | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [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.1,2 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.2 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; Item No. 21495) in a dose-dependent manner.1 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.3 | [Chemical Properties]
White crystalline powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from artichoke leaves, artichoke, forest senecio herb, and honeysuckle. | [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. | [in vivo]
1,3-Dicaffeoylquinic acid (32.0 mg/kg, p.o.) and 1-O-ABL are absorbed very quickly in Wistar rats. The maximum plasma concentrations for 1,3-Dicaffeoylquinic acid and 1-O-ABL are 44.5 ± 7.1 and 19.1 ± 6.9 ng/mL, respectively[1]. | [IC 50]
PI3K | [storage]
Store at -20°C, protect from light | [References]
[1] J HEILMANN M W I Merfort. Radical scavenger activity of different 3’,4’-dihydroxyflavonols and 1,5-dicaffeoylquinic acid studied by inhibition of chemiluminescence.[J]. Planta medica, 1995, 61 5: 435-438. DOI: 10.1055/s-2006-958131
[2] W E ROBINSON. Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase.[J]. Molecular Pharmacology, 1996, 50 4: 846-855.
[3] XU CAO . 1, 5-Dicaffeoylquinic acid-mediated glutathione synthesis through activation of Nrf2 protects against OGD/reperfusion-induced oxidative stress in astrocytes[J]. Brain Research, 2010, 1347: Pages 142-148. DOI: 10.1016/j.brainres.2010.05.072 |
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