StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Verbindung

Retinylacetat

Retinol, acetate

HCID 638034
Neue NotizNeue ReaktionAnfrage stellen
Druckvorschau
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
127-47-9
Standard-SMILES
CC(=O)OC/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C
InChIKey
QGNJRVVDBSJHIZ-QHLGVNSISA-N
Summenformel
C22H32O2
Durchschnittliche Molmasse
328,5 g/mol
Monoisotopische Masse
328,24023026

Überblick

Retinyl acetate is an acetate ester. It is functionally related to an all-trans-retinol.

Namen und Bezeichner

Bevorzugter Name
Retinol, acetate
IUPAC
[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] acetate
Lokaler Name
Retinylacetat
Englischer Name
Retinyl acetate
Summenformel
C22H32O2
Molmasse
328.49

Namen und Synonyme

RETINYL ACETATEVitamin A acetateRetinol acetate127-47-9Retinol, acetateVitamin A1 acetateall-trans-Retinol acetateCrystaletsVitamin A alcohol acetateDavitan A 650all-trans-Vitamin A acetateRetinol, acetate, all-trans-
Weitere Namen anzeigen
retinylVITAMIN A ACETATALL-TRANS-RETINYL ACETATERetinylacetatRETINOL ACETATE ALL TRANSMyvakMyvax
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetateall-trans-RetinylacetateAcetic acid, retinyl ester[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] acetateDTXSID60212403LE3D9D6OYVitamin A, acetateVitamin A acetate (tritiated)

Datenbank-Bezeichner

CAS
127-47-9、64536-04-5
PubChem CID

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6,3
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
7
Schwere Atome
24
Formalladung
0
Komplexität
595

Experimentelle und physikochemische Eigenschaften

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]
CosmeticsSkin conditioning
SpringerMaterials PropertiesChemical diffusion
Food AdditivesNUTRIENT SUPPLEMENT -> FDA Substance added to food

Physikochemische Eigenschaften

Schmelzpunkt
57 · 57-58 °C
Siedepunkt
406.22 °C · 406.22°C (rough estimate)
Dichte
1.0474 · 1.0474 (rough estimate)
Brechungsindex
1.547 · 1.547-1.555
Flammpunkt
14 ℃ · 14℃
storage temp.
2 · 2-8°C
Löslichkeit
25 mg/mL · absolute ethanol: 25 mg/mL
Aggregatzustand
solid or viscous liquid

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 · 5 Einträge

This chemical does not meet GHS hazard criteria for 0.3% (1 of 374) of reports.

Danger

H315 (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.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Retinol, acetate

Regulation (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 CategoriesSkin Irrit. 2 (83.4%)

Toxikologische Informationen

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

F
1-8-10
wgk
2
tsca
TSCA listed
ridadr
UN1170 - class 3 - PG 2 - Ethanol
hs_code
29362100
RTECS-Nr.
VH6825000

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 2 Einträge

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.

Verwendung und Herstellung

Household ProductsInformation on 4 consumer products that contain Retinyl acetate in the following categories is provided:
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing InformationRetinol, acetate: ACTIVE
Anwendungen · 2 Einträge

BeschreibungRetinyl 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.

VerwendenRetinyl 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

Zugehörige Reaktionen

6
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 230739
HRID 230739als Eduktuspto-grants-2009_07
Reaktionsgleichung von HRID 651541
HRID 651541als Eduktuspto-grants-2001_08
Reaktionsgleichung von HRID 987357
HRID 987357als Eduktuspto-grants-2003_10
Reaktionsgleichung von HRID 987358
HRID 987358als Eduktuspto-grants-2003_10
Reaktionsgleichung von HRID 1722492
HRID 1722492als Produktuspto-grants-1989_08
Reaktionsgleichung von HRID 2165979
HRID 2165979als Produktuspto-grants-1990_07

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Weitere Aktionen
Neue NotizNeue ReaktionAnfrage stellen
638034
DTXSID
DTXSID6021240
ChEMBL
CHEMBL486193
ChEBI
CHEBI:32095
UNII
3LE3D9D6OY
EC Number
204-844-2
Nikkaji
J34.628D
Farbe
Yellow powder
Geruch (Odor)
Amine like
Biologische Quelle
synthetic (organic)
Wasserlöslichkeit
soluble
Merck
14 · 14,10013
BRN
1915439 · 1915439
Specific Activity
475 · 475,000-650,000USP units/g
Stabilität
Hygroscopic, Light Sensitive
Major Application
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
9.4 at · 9.4 at 25℃
CAS Datenbank
127 · 127-47-9(CAS DataBase Reference)
NIST chemische Informationen
Retinol, acetate(127-47-9)
EPA chemische Informationen
Retinol acetate (127-47-9)
risk_code
38-63-36/37/38-53-61-11
Toxizität
LD50 (10 day) orally in mice: 4100 mg/kg (Kamm)
hazard_code
Xn,Xi,T,F
safety_code
36/37-45-37/39-26-53-16
Speicherklasse
3 - Flammable liquids
Hazard Classifications
Eye Irrit. 2Flam. Liq. 2
Darstellung · 1 Eintrag

synthetischeA 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.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

9-cis-Retinalβ,β-Carotin