Vitamin-A-säure

Retinoic Acid

HCID 444795CAS 302-79-4

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

Retinoic acidtretinoin302-79-4all-trans-Retinoic acidVitamin A acidtrans-Retinoic acidATRAAberelEudynaRenovaDermairolall-trans-Vitamin A acid
Weitere Namen anzeigen
Retinoic(2E,4E,6E,8E)-3,7-DiMethyl-9-(2,6,6-triMethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acidretinic acidretin-aTretinoi
Cordes vasRetin ATretin MAtralinall-trans-TretinoinRetionic acidall-trans-Vitamin A1 acidbeta-Ra

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

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).

Sicherheit und Regulatorisches

Sicherheitsdaten

F
7-8-16-23
wgk
3
tsca
TSCA listed
ridadr
3249
hs_code
29362100
RTECS-Nr.
VH6475000

Chemie und Industrie

Anwendungen · 2 Einträge

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

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
Ergänzende Hinweise · 1 Eintrag

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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