Retinylacetat
VITAMIN A ACETATE · RETINOL ACETATE · retinyl · VITAMIN A ACETAT · ALL-TRANS-RETINYL ACETATE · Crystalets · Retinylacetat · RETINOL ACETATE ALL TRANS
Identifikatoren & physikalische Daten
| CAS No. | 127-47-9 |
|---|---|
| Summenformel | C22H32O2 |
| Durchschnittliche Molmasse | 328,5 g/mol |
| Monoisotopische Masse | 328,24023026 g/mol |
| SMILES | CC(=O)OC/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C |
| InChIKey | QGNJRVVDBSJHIZ-QHLGVNSISA-N |
| PubChem CID | 638034 |
| ChEMBL | CHEMBL486193 |
| ChEBI | CHEBI:32095 |
| EC No. | 204-844-2 |
| DTXSID | DTXSID6021240 |
| Lokaler Name | Retinylacetat |
Chemische & physikalische Eigenschaften
| XLogP | 6,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 24 |
| Formalladung | 0 |
| Komplexität | 595 |
| Lipide | Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109] |
| Kosmetika | Skin conditioning |
| SpringerMaterials Properties | Chemical diffusion |
| Lebensmittelzusatzstoffe | NUTRIENT SUPPLEMENT -> FDA Substance added to food |
| Schmelzpunkt | 57-58 °C |
| Siedepunkt | 406.22°C (rough estimate) |
| Dichte | 1.0474 (rough estimate) |
| Brechungsindex | 1.547-1.555 |
| Flammpunkt | 14℃ |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | absolute ethanol: 25 mg/mLsoluble |
| Aggregatzustand | solid or viscous liquid |
| Farbe | Yellow powder |
| Geruch | Amine like |
| Biologische Quelle | synthetic (organic) |
| Merck | 14,10013 |
| BRN | 1915439 |
| Specific Activity | 475,000-650,000USP units/g |
| Stabilität | Hygroscopic, Light Sensitive |
| Hauptanwendungen | clinical testing |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING - MISCELLANEOUS |
| InChI | 1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3/b10-7+,13-12+,17-9+,18-14+ |
| InChIKey | QGNJRVVDBSJHIZ-QHLGVNSISA-N |
| SMILES | O(C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(CCCC1(C)C)C)C(=O)C |
| LogP (Verteilungskoeffizient) | 9.4 at 25℃ |
| CAS Datenbank | 127-47-9(CAS DataBase Reference) |
| NIST chemische Informationen | Retinol, acetate(127-47-9) |
| EPA chemische Informationen | Retinol acetate (127-47-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.3% (1 of 374) of reports.DangerH315 (83.4%): Causes skin irritation [Warning Skin corrosion/irritation]P203, P264, P273, P280, P302+P352, P318, P321, P332+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 374 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Retinol, acetateRegulation (EC) No 1831/2003 (amended)REACH registered substance: Retinyl acetate (EC: 204-844-2)Retinol acetate: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (83.4%) |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| F | 1-8-10 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN1170 - class 3 - PG 2 - Ethanol |
| Zollcode | 29362100 |
| RTECS-Nr. | VH6825000 |
| R-Sätze (R) | 38-63-36/37/38-53-61-11 |
| Toxizität | LD50 (10 day) orally in mice: 4100 mg/kg (Kamm) |
| Gefahrensymbole | Xn,Xi,T,F |
| Sicherheitshinweise (S) | 36/37-45-37/39-26-53-16 |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrenklasse | Eye Irrit. 2Flam. Liq. 2 |
Anwendungen & Verwendung
Beschreibung
Retinyl acetate (retinol acetate, vitamin A acetate,127-47-9) is a natural form of vitamin A. It is the acetate ester of retinol. It consists of yellow crystals which are greasy or sticky. It has a mild, characteristic odor. It has potential antineoplastic and chemo-preventive activities. It can be used to fortify food with vitamin A. As vitamin A acetate can induce cell differentiation and inhibit cell proliferation, it is used in skin-conditioning agent.
Verwenden
Retinyl acetate has been used: a control diet to study its effect at different developmental periods in fish larvae to study its inhibitory effects on Mycobacterium aviumsubspeciesparatuberculosis(MAP) strains as an internal standard in high performance liquid chromatography (HPLC) to quantify vitamin A in fortified milk
Herstellung & Synthese
synthetische
A method for preparing retinyl acetate the following steps:Under alkaline conditions, 3-methyl-4-oxo-2-butene-1-yl acetate (referred to as C5 aldehyde ester) and tetraethyl methylene diphosphate undergo a condensation reaction to form an intermediate C6 phosphate (chemical name: 5-(diethyl phosphate)-3-methyl-2,4-hexadiene-1-acetate).Under alkaline conditions, the C6 phosphate undergoes a transposition reaction. C14 aldehyde (chemical name: 2-methyl-4-(2,6,6-trimethyl-1-cyclohexene-1-yl)-3-butene-1-aldehyde) is then added to undergo a Wittig-Horner condensation reaction, yielding retinyl acetate.