Cynarin (Cynarine) is a phytochemical from artichoke that has a variety of pharmacological properties, including free radical scavenging, antioxidant, antihistidine, and antiviral activity. Cynarin blocks the interaction between CD28 of the T-cell receptor and CD80 of the antigen-presenting cell. Cynarin triggers nuclear translocation of Nrf2, restores the balance of glutathione (GSH) and reactive oxygen species (ROS), and inhibits mitochondrial depolarization.

 

Brand: BCM

 

Target: Antioxidant; Antiviral; Influenza Virus; Reactive Oxygen Species

 

Signaling Pathways: Immunology/Inflammation; Metabolism; Microbiology/Virology; NF-κB; oxidation-reduction

 

In Vitro: 1,5-Dicaffeoylquinic acid has protective effects against MPP~+ induces neurotoxicity of PC12 Cells, it (50 umol/L) pretreatment can inhibit the MPP+-induced up-regulation of the expression of α-synuclein mRNA and protein.1, 5-diCQA has antioxidant signaling properties that upregulate GSH synthesis by stimulating the Nrf2 pathway in astrocytes and protects them from cell death in an in vitro model of ischemia/reperfusion[1].1,5-Dicaffeoylquinic acid 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

 

Melting Point: 225-227°C

 

Boiling Point: 819.9±65.0 °C(Predicted)

 

Specific Rotation: D25 -59° (c = 2 in methanol)

 

pKa: 2.58±0.50(Predicted)

 

Solubility: Soluble in DMSO; soluble in Ethanol. Insoluble in Water.

 

Stability: Hygroscopic

 

GHS: GHS07

 

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  

 

InChIKey: YDDUMTOHNYZQPO-RVXRWRFUSA-N  

 

InChI: InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1

 

Attribute
[Chem Name]	(1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
[Synonym]	Cynarin; Cynarine
[CAS No.]	30964-13-7
[EINECS]	214-655-7
[MDL No.]	MFCD00867168
[Formula]	C25H24O12
[Molecular]	516.45
[Form]	Faint yellow to yellow powder
[Storage]	Sealed in dry, 2-8°C

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