Grundinformationen
- Standard-SMILES
CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CCC1- InChIKey
SHGAZHPCJJPHSC-YCNIQYBTSA-N- Summenformel
- C20H28O2
- Durchschnittliche Molmasse
- 300,4 g/mol
- Monoisotopische Masse
- 300,20893013
Namen und Bezeichner
- Bevorzugter Name
- Retinoic Acid
- IUPAC
- (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
- Lokaler Name
- Vitamin-A-säure
- Englischer Name
- Retinoic acid
- Summenformel
- C20H28O2
- Molmasse
- 300.44
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
302-79-4、97950-17-9- PubChem CID
- 444795
- DTXSID
DTXSID7021239- ChEMBL
CHEMBL38- ChEBI
CHEBI:15367- UNII
- 5688UTC01R
- EC Number
- 206-129-0
- Nikkaji
- J1.313.469C、J1.518K、J2.378.058E、J494.243D、J690.379G、J970.183D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 6,3
- Polarare Oberfläche (TPSA)
- 37,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 567
Physikochemische Eigenschaften
- Schmelzpunkt
- 180 · 180-181 °C (lit.)
- Siedepunkt
- 381.66 °C · 381.66°C (rough estimate)
- Dichte
- 1.0597 · 1.0597 (rough estimate)
- Brechungsindex
- 1.48 · 1.4800 (estimate)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- Practically insoluble in water, soluble in methylene chloride, slightly soluble in ethanol (96 per cent).
- pka
- 4.73 · 4.73±0.33(Predicted)
- Aggregatzustand
- powder
- Farbe
- yellow
- Biologische Quelle
- synthetic (organic)
- Wasserlöslichkeit
- insoluble
- Merck
- 14 · 14,8165
- BRN
- 2057223 · 2057223
- Stabilität
- -20 °C · Store Dry in Freezer at -20°C for up to 1 year; in 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
- 6.3 · 6.300
- CAS Datenbank
- 302 · 302-79-4(CAS DataBase Reference)
- EPA chemische Informationen
- Retinoic acid (302-79-4)
Sicherheit und Regulatorisches
Sicherheitsdaten
- F
- 7-8-16-23
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- 3249
- hs_code
- 29362100
- RTECS-Nr.
- VH6475000
- risk_code
- 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)
- hazard_code
- T,Xn,N
- safety_code
- 53-26-36/37/39-45-36/37-61-24/25
- hazard_class
- 6.1(b)
- packing_group
- III
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Giftige Stoffe Daten
- 302-79-4(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Repr. 1BSkin Irrit. 2
Chemie und Industrie
Anwendungen
Beschreibungall-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.
VerwendenPhysiological metabolite of vitamin A. Effects gene expression via nuclear retinoic acid receptors (RAR); mediates cellular growth and differentiation
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Ergänzende Hinweise
DefinitionChEBI: Retinoic acid is a retinoid in which all four exocyclic double bonds have E- (trans-) geometry. It is a naturally occurring derivative of vitamin A (retinol). Retinoids such as tretinoin are important regulators of cell reproduction, proliferation, and differentiation and are used to treat acne and photodamaged skin and to manage keratinization disorders such as ichthyosis and keratosis follicularis.
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