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132465-11-3

132465-11-3 Structure

132465-11-3 Structure
IdentificationBack Directory
[Name]

CDC
[CAS]

132465-11-3
[Synonyms]

CDC
CDC 5-LO inhibitor
CDC lipoxygenase inhibitor
-3,4-dihydroxy-α-cyanocinnamate
Cinnamyl-3,4-dihydroxy-α-cyanocinnamate
CINNAMYL-3,4-DIHYDROXY-ALPHA-CYANOCINNAMATE
Cinnamyl 3,4-dihydroxy-alpha-cyanocinnamate CDC
1-Cyclohexy1-3-(3-dimethylamino proply)carbodilimide methiodide
(E,Z)-2-Cyano-3-(3,4-dihydroxyphenyl)-2-propenoic acid 3-phenyl-2-propenyl ester
2-Propenoic acid, 2-cyano-3-(3,4-dihydroxyphenyl)-, 3-phenyl-2-propen-1-yl ester, (2E)-
[Molecular Formula]

C19H15NO4
[MDL Number]

MFCD00210839
[MOL File]

132465-11-3.mol
[Molecular Weight]

321.33
Chemical PropertiesBack Directory
[Boiling point ]

583.9±50.0 °C(Predicted)
[density ]

1.326±0.06 g/cm3(Predicted)
[storage temp. ]

room temp
[solubility ]

DMSO: ≥15mg/mL
[form ]

powder
[pka]

8.75±0.10(Predicted)
[color ]

light yellow to yellow
[InChI]

1S/C19H15NO4/c20-13-16(11-15-8-9-17(21)18(22)12-15)19(23)24-10-4-7-14-5-2-1-3-6-14/h1-9,11-12,21-22H,10H2/b7-4+,16-11+
[InChIKey]

XGHYFEJMJXGPGN-UYHGDYIZSA-N
[SMILES]

Oc1ccc(cc1O)\C=C(/C#N)C(=O)OC\C=C\c2ccccc2
Safety DataBack Directory
[Symbol(GHS) ]

GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS09
[Signal word ]

Warning
[Hazard statements ]

H317-H410
[Precautionary statements ]

P261-P272-P273-P280-P302+P352-P333+P313
[Hazard Codes ]

Xi,N
[Risk Statements ]

43-50/53
[Safety Statements ]

36/37-60-61
[RIDADR ]

UN 3077 9 / PGIII
[WGK Germany ]

3
[HazardClass ]

9
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Aquatic Acute 1
Aquatic Chronic 1
Skin Sens. 1
Hazard InformationBack Directory
[Uses]

CDC is an inhibitor of 5-LO, 12-LO, and 15-LO.
[Biological Activity]

Cinnamyl-3,4-dihydroxy-α-cyanocinnamate (CDC) is a potent and direct inhibitor of 5-LO (5-Lipoxygenase) th at reduces 5-LO activity in cell-free assays. CDC also inhibits 12-LO and 15-LO
[in vivo]

The high glucose and 12(S)-hydroxyeicosatetraenoic acid (HETE) could alter vascular endothelial (VE)-cadherin and β‐catenin phosphorylation levels, but did not alter total protein expression. However, the 12/15-LO inhibitor, Cinnamyl-3,4-dihydroxy-α-cyanocinnamate (CDC), antagonized the effect of high glucose on protein phosphorylation to mitigate destruction of the endothelial cell barrier, and the mouse diabetes mellitus model further confirmed these conclusions[1].

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