Retinyl acetate Chemical Properties

Melting point:

57-58 °C

Boiling point:

406.22°C (rough estimate)

Density 

1.0474 (rough estimate)

refractive index 

1.547-1.555

Flash point:

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

Merck 

14,10013

BRN 

1915439

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

Retinol acetate (127-47-9)

Safety Information

Hazard Codes 

Xn,Xi,T,F

Risk Statements 

38-63-36/37/38-53-61-11

Safety Statements 

36/37-45-37/39-26-53-16

RIDADR 

UN1170 - class 3 - PG 2 - Ethanol

WGK Germany 

2

RTECS 

VH6825000

F 

1-8-10

TSCA 

Yes

HS Code 

29362100

Toxicity

LD50 (10 day) orally in mice: 4100 mg/kg (Kamm)

MSDS

• Language:English Provider:all-trans Vitamin A acetate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Retinyl acetate Usage And Synthesis

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

Retinyl acetate is a yellow, prism-shaped crystal and a lipid-soluble compound, with better chemical stability than vitamin A. In clinical practice, either vitamin A acetate or its palmitate form is typically dissolved in vegetable oil for administration, where it is hydrolyzed by enzymes in the body to release active vitamin A. The form of vitamin A listed in the Chinese Pharmacopoeia refers to the active vitamin A compound.

Uses

Essential micronutrient

Uses

vitamin precursor

Uses

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 avium?subspecies?paratuberculosis?(MAP) strains
• as an internal standard in high performance liquid chromatography (HPLC) to quantify vitamin A in fortified milk

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.

Definition

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

General Description

Retinyl acetate is suitable 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

Not classified

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.

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.

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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