4-Oxoretinoic acid
Grundinformationen
- CAS
38030-57-8- Standard-SMILES
CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CCC1=O- InChIKey
GGCUJPCCTQNTJF-FRCNGJHJSA-N- Summenformel
- C20H26O3
- Durchschnittliche Molmasse
- 314,4 g/mol
- Monoisotopische Masse
- 314,18819469
Überblick
All-trans-4-oxoretinoic acid is a retinoid that consists of all-trans-retinoic acid bearing an oxo substituent at position 4 on the cyclohexenyl ring. It has a role as a human xenobiotic metabolite. It is a retinoid and an enone. It is functionally related to an all-trans-retinoic acid.
Namen und Bezeichner
- Bevorzugter Name
- 4-Oxoretinoic acid
- IUPAC
- (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
- Englischer Name
- (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid
- Summenformel
- C20H26O3
- Molmasse
- 314.42
Namen und Synonyme
4-Oxoretinoic acid38030-57-84-Ketoretinoic acidall-trans-4-Oxo-retinoic acidRetinoic acid, 4-oxo-(2E,4E,6E,8E)-3,7-DIMETHYL-9-(2,6,6-TRIMETHYL-3-OXO-1-CYCLOHEXENYL)NONA-2,4,6,8-TETRAENOIC ACIDCJN45G18UADTXSID20865895RefChem:100289DTXCID301333643all-trans-4-oxoretinoic acidall-trans 4-Keto Retinoic Acid
Weitere Namen anzeigen
Ro 11-4824Tretinoin Impurity 7Retinoic acid ImpuritiesH
4-Oxo-all-trans-retinoic acid4-Oxotretinoin4-oxo-Retinoic acid4-Oxo-atRARo 12-48244-keto-Retinoic acid4-oxo Isotretinoin(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
Datenbank-Bezeichner
- CAS
38030-57-8- PubChem CID
- 6437063
- DTXSID
DTXSID20865895
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,8
- Polarare Oberfläche (TPSA)
- 54,4 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 23
- Formalladung
- 0
- Komplexität
- 638
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Metabolite of Isotretinoin
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 175 · 175-179 °C
- Siedepunkt
- 509.9 · 509.9±29.0 °C(Predicted)
- Dichte
- 1.07 · 1.070±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Amber Vial, -20°C Freezer, Under Inert Atmosphere
- Löslichkeit
- Chloroform (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 4.73 · 4.73±0.33(Predicted)
- Farbe
- Yellow to Dark Orange
- 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.
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesSkin Irrit. 2 (50%)
Sicherheitsdaten
- wgk
- WGK 3
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Repr. 2
Chemie und Industrie
Pharmakologische Informationen
Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite PathwaysRetinol Metabolism
Anwendungen
VerwendenA metabolite of all-trans-Retinoic Acid, a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR).
Ergänzende Hinweise
DefinitionChEBI: A retinoid that consists of all-trans-retinoic acid bearing an oxo substituent at position 4 on the cyclohexenyl ring.
Zugehörige Reaktionen
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