| Identification | More | [Name]
Retinyl acetate | [CAS]
127-47-9 | [Synonyms]
ALL-TRANS-RETINYL ACETATE
ALL-TRANS VITAMIN A ACETATE
RETINOL ACETATE
RETINOL ACETATE ALL TRANS
RETINOL ACETATE, WATER SOLUBLE
RETINYL ACETATE
TRANS-RETINOL ACETATE
TRANS-RETINYL ACETATE
VITAMIN A ACETATE
VITAMIN A ACETATE 1500
VITAMIN A ACETATE, ALL TRANS
3,7-Dimethyl-9-(2,6,6,-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol acetate
All-trans-retinol acetate
Crystalets
Davitan A 650
Myvak
Myvax
retinyl
trans-Vitamin A acetate
trans-vitaminaacetate | [EINECS(EC#)]
204-844-2 | [Molecular Formula]
C22H32O2 | [MDL Number]
MFCD00019413 | [Molecular Weight]
328.49 | [MOL File]
127-47-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline | [Melting point ]
57-58 °C
| [Boiling point ]
406.22°C (rough estimate) | [density ]
1.0474 (rough estimate) | [refractive index ]
1.547-1.555
| [Fp ]
14℃ | [storage temp. ]
2-8°C
| [solubility ]
absolute ethanol: 25 mg/mL
| [form ]
solid or viscous liquid
| [color ]
Yellow powder | [Odor]
Amine like | [Water Solubility ]
soluble | [Sensitive ]
Light & Air Sensitive & Hygroscopic | [Usage]
Essential micronutrient | [Merck ]
14,10013 | [BRN ]
1915439 | [Specific Activity]
475,000-650,000USP units/g | [Stability:]
Hygroscopic, Light Sensitive | [InChIKey]
QGNJRVVDBSJHIZ-QHLGVNSISA-N | [LogP]
9.4 at 25℃ | [CAS DataBase Reference]
127-47-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Retinol, acetate(127-47-9) | [EPA Substance Registry System]
127-47-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R38:Irritating to the skin.
R63:Possible risk of harm to the unborn child.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN1170 - class 3 - PG 2 - Ethanol | [WGK Germany ]
2
| [RTECS ]
VH6825000
| [F ]
1-8-10 | [TSCA ]
Yes | [HS Code ]
29362100 | [Safety Profile]
Moderately toxic by
ingestion. Experimental teratogenic and
reproductive effects. Questionable
carcinogen with experimental neoplastigenic
data. Mutation data reported. When heated
to decomposition it emits acrid smoke and
irritating fumes. See also VITAMIN A. | [Toxicity]
LD50 (10 day) orally in mice: 4100 mg/kg (Kamm) |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
Crystalline | [Uses]
Essential micronutrient | [Uses]
vitamin precursor | [Definition]
ChEBI: Retinyl acetate is an acetate ester. It is functionally related to an all-trans-retinol. | [Preparation]
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. | [General Description]
Retinyl acetate is suitable(127-47-9) for use in the retention identification of the analyte when using HPLC and GC. Not intended for use as an activity reference standard. It has been thoroughly evaluated to ensure the utmost quality. Neat, unless otherwise noted. Certificate of Composition provided with the purchase.
| [Flammability and Explosibility]
Notclassified | [Biochem/physiol Actions]
Retinyl esters provide pools of vitamin A that are converted into retinol and other retinoids as required. Retinyl acetate is used in a wide range of biological applications. It acts as a chemopreventive agent. Retinyl acetate also has antineoplastic property. | [Purification Methods]
The acetate is separated from retinol by column chromatography, then crystallised from MeOH. [Kofler and Rubin Vitamins and Hormones (NY) 18 315 1960 for purification methods]. Store it in the dark, under N2 or Ar, at 0o. [Beilstein 6 IV 4135.] | [References]
[1] Volker Bühler, Vademecum for Vitamin Formulations, 2001, ISBN 3-8047-1834-5
[2] SUNATDA ARAYACHUKEAT Thapakorn T U Supason P Wanichwecharungruang. Retinyl acetate-loaded nanoparticles: Dermal penetration and release of the retinyl acetate[J]. International Journal of Pharmaceutics, 2011, 404 1: Pages 281-288. DOI:10.1016/j.ijpharm.2010.11.019.
[3] HARRISON E H. Lipases and carboxylesterases: possible roles in the hepatic metabolism of retinol.[J]. Annual review of nutrition, 1998, 18: 259-276. DOI:10.1146/annurev.nutr.18.1.259.
[4] GERSTER H. Vitamin A–functions, dietary requirements and safety in humans.[J]. International Journal for Vitamin and Nutrition Research, 1997, 67 2: 71-90.
[5] https://ods.od.nih.gov/factsheets/VitaminA-HealthProfessional/ |
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