Substance
ID:178551
Names and Identifiers
Synonyms
Isotretinoin13-cis-Retinoic acid
IUPAC name
(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
IUPAC Traditional name
isotretinoin
Properties
Pharmacology Properties
Gene Information
human ... NOS2(4843), RARA(5914), RARB(5915)
Safety Information
European Hazard Symbols
Toxic (T)GHS Precautionary statements
P201-P261-P305+P351+P338-P308+P313
RTECS
VH6440000
Storage Temperature
-20°C
GHS Signal Word
Danger
GHS Hazard statements
H315-H319-H335-H360
German water hazard class
3
GHS Pictograms
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
Respiratory sensitization, category 1
Germ cell mutagenicity, categories 1A,1B,2
Carcinogenicity, categories 1A,1B,2
Reproductive toxicity, categories 1A,1B,2
Specific Target Organ Toxicity – Single exposure, categories 1,2
Specific Target Organ Toxicity – Repeated exposure, categories 1,2
Aspiration Hazard, category 1
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
Safety Statements
53-26-36/37/39-45
Risk Statements
61-36/37/38
Physical Property
Melting Point
172-175 °C(lit.)
Product Information
Purity
≥98% (HPLC)
Molecule Details
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.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R3255.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
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.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R3255.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Molecular Spectra
No Data Available
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References
No Data Available
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