Cynarin

Category	Influenza Virus
CAS	30964-13-7
Description	Cynarin, phenolic compound, is an antichoke agent with a variety of biological activities including antioxidant, antihistamic and antiviral activities. Cynarin is used in weight loss and lipid-lowering formulas, liver protection and anti-alcoholic drugs, etc.

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Product Information

Synonyms	Cyclohexanecarboxylic acid, 1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxy-, (1R,3R,4S,5R)-; (1R,3R,4S,5R)-1,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxycyclohexanecarboxylic acid; Cinnamic acid, 3,4-dihydroxy-, 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester; Cyclohexanecarboxylic acid, 1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-4,5-dihydroxy-, (1R,3R,4S,5R)-; Cyclohexanecarboxylic acid, 1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-4,5-dihydroxy-, [1R-(1α,3α,4α,5β)]-; Cynarine; 1,3-Dicaffeoylquinic acid; 1,5-Dicaffeoylquinic acid; Cinarin; Cinarine
IUPAC Name	(1R,3R,4S,5R)-1,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
Molecular Weight	516.45
Molecular Formula	C25H24O12
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
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)/t19-,20-,23+,25-/m1/s1
InChIKey	YDDUMTOHNYZQPO-GCBRTHAASA-N
Boiling Point	819.9±65.0°C at 760 mmHg
Melting Point	225-227°C
Flash Point	278.1±27.8 °C
Purity	>98%
Density	1.64±0.1 g/cm3
Solubility	Soluble in Ethyl Acetate (Slightly), Methanol (Slightly)
Appearance	Off-white to Pale Yellow Solid
Storage	Store at -20°C
Complexity	887
Exact Mass	516.12677620
Index Of Refraction	1.719
In Vitro	Cynarin inhibits taste receptors, making water to be sweet. It has been shown to have some pharmacological properties including hypocholesterolemic, hepatoprotective, antiviral, antibacterial, and antihistamic effects. Cynarin has marked antioxidant, anticholinergic, reducing ability, radical-scavenging, and metal-binding activities. Cynarin demonstrates 87.72% inhibition of linoleic acid lipid peroxidation at 30 mg/mL concentration. Cynarin exhibits effective DMPD+, ABTS+, O2-, DPPH1, and H2O2 scavenging effects, reducing capabilities and Fe2+ chelating effects. IC50 and Ki of cynarin for acetylcholinesterase enzyme inhibition are 243.67nM and 39.34±13.88 nM, respectively. Cynarin is a potential immunosuppressant that blocks the interaction between the CD28 of T-cell receptor and CD80 of antigen presenting cells. Cynarin blocks about 87% of the CD28-dependent "signal 2" pathway of T-cell activation under the condition of one to one ratio of T-cell and B-cell. Cynarin binds to the "G-pocket" of CD28 and thus interrupts the site of interaction between CD28 and CD80.
PSA	211.28000
Target	Reactive Oxygen Species; Influenza Virus
Vapor Pressure	0.0±3.1 mmHg at 25°C
XLogP3-AA	1.5