439436
13-cis-Retinoic acid
98%
Synonym(s):
Isotretinoin
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About This Item
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
Molecular Weight:
300.44
EC Number:
225-296-0
UNSPSC Code:
12352103
MDL number:
InChI key
SHGAZHPCJJPHSC-XFYACQKRSA-N
InChI
1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-
SMILES string
[H]\C(C(O)=O)=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C
assay
98%
mp
172-175 °C (lit.)
Biochem/physiol Actions
13-cis-Retinoic acid (RA) has anti-inflammatory and anti-tumor action. The action of RA is mediated through RAR-β and RAR-α receptors. RA attenuates iNOS expression and activity in cytokine-stimulated murine mesangial cells. It induces mitochondrial membrane permeability transition, observed as swelling and as a decrease in membrane potential, and stimulates the release of cytochrome c implicating mechanisms through the apoptosis pathway. These activities are reversed by EGTA and cyclosporin A. RA also increases MMP-1 protein expression partially via increased transcription.
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