Vitamin-A-säure
TRETINOIN · ATRA · ALL-TRANS-RETINOIC ACID · VITAMIN A ACID · Retinoic · (2E,4E,6E,8E)-3,7-DiMethyl-9-(2,6,6-triMethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid · retinic acid · retin-a
Identifikatoren & physikalische Daten
| CAS No. | 302-79-4 |
|---|---|
| Summenformel | C20H28O2 |
| Durchschnittliche Molmasse | 300,4 g/mol |
| Monoisotopische Masse | 300,20893013 g/mol |
| SMILES | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CCC1 |
| InChIKey | SHGAZHPCJJPHSC-YCNIQYBTSA-N |
| PubChem CID | 444795 |
| ChEMBL | CHEMBL38 |
| ChEBI | CHEBI:15367 |
| EC No. | 206-129-0 |
| DTXSID | DTXSID7021239 |
| Lokaler Name | Vitamin-A-säure |
Chemische & physikalische Eigenschaften
| XLogP | 6,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 22 |
| Formalladung | 0 |
| Komplexität | 567 |
| Schmelzpunkt | 180-181 °C (lit.) |
| Siedepunkt | 381.66°C (rough estimate) |
| Dichte | 1.0597 (rough estimate) |
| Brechungsindex | 1.4800 (estimate) |
| Lagerbedingungen | -20°C |
| Löslichkeit | Practically insoluble in water, soluble in methylene chloride, slightly soluble in ethanol (96 per cent). |
| pKa (Säurekonstante) | 4.73±0.33(Predicted) |
| Aggregatzustand | powder |
| Farbe | yellow |
| Biologische Quelle | synthetic (organic) |
| Merck | 14,8165 |
| BRN | 2057223 |
| Stabilität | Store Dry in Freezer at -20°C for up to 1 yearin Solution at -20°C for up to 3 Months. |
| 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+ |
| InChIKey | SHGAZHPCJJPHSC-ZVCIMWCZSA-N |
| SMILES | CC1=C(\C=C\C(C)=C\C=C\C(C)=C\C(O)=O)C(C)(C)CCC1 |
| LogP (Verteilungskoeffizient) | 6.300 |
| CAS Datenbank | 302-79-4(CAS DataBase Reference) |
| EPA chemische Informationen | Retinoic acid (302-79-4) |
Sicherheit & Vorschriften
| F | 7-8-16-23 |
|---|---|
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 3249 |
| Zollcode | 29362100 |
| RTECS-Nr. | VH6475000 |
| R-Sätze (R) | 22-63-38-20/21/22-51/53 |
| Toxizität | LD50 (10 day) in mice, rats (mg/kg): 790, 790 i.p.2200, 2000 orally (Kamm) |
| Gefahrensymbole | T,Xn,N |
| Sicherheitshinweise (S) | 53-26-36/37/39-45-36/37-61-24/25 |
| Gefahrenklasse | 6.1(b)Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Repr. 1BSkin Irrit. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 302-79-4(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
all-trans Retinoic acid is a metabolite of vitamin A and a ligand for retinoic acid receptors (RARs) with IC50 values of 9, 3, and 10 nM for RARα, RARβ, and RARγ, respectively, in radioligand binding assays. It induces expression of a luciferase reporter in COS-7 cells expressing RARα, RARβ, or RARγ (EC50s = 169, 9, and 2 nM, respectively). all-trans Retinoic acid (17 nmol) reduces papilloma formation induced by phorbol 12-myristate 13-acetate (TPA; ) in mice. It reduces bile duct proliferation, hydroxyproline levels, and liver inflammation in a rat model of α-naphthylisothiocyanate-induced chronic cholestasis and reduces plasma levels of alkaline phosphatase and bile salts in the Mdr2-/- mouse model of cholestasis. all-trans Retinoic acid also reduces hepatic fat accumulation, triglycerides, body weight, and serum glucose levels in mice with Western diet-induced obesity.
Verwenden
Physiological metabolite of vitamin A. Effects gene expression via nuclear retinoic acid receptors (RAR); mediates cellular growth and differentiation