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R3250

Sigma-Aldrich

Retinyl acetate

synthetic, matrix dispersion, 475,000-650,000 USP units/g

Synonym(s):

Retinol acetate, Vitamin A acetate

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About This Item

Empirical Formula (Hill Notation):
C22H32O2
CAS Number:
127-47-9
Molecular Weight:
328.49
Beilstein:
1915439
EC Number:
204-844-2
MDL number:
MFCD00019413
UNSPSC Code:
12352205
eCl@ss:
34058009
PubChem Substance ID:
57654589
NACRES:
NA.79

biological source

synthetic

form

matrix dispersion

specific activity

475,000-650,000 USP units/g

color

yellow

mp

57-58 °C

storage temp.

−20°C

SMILES string

CC1=C(/C=C/C(C)=C/C=C/C(C)=C/COC(C)=O)C(C)(C)CCC1

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+

InChI key

QGNJRVVDBSJHIZ-QHLGVNSISA-N

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General description

Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A. The retinoids exist as many geometric isomers due to the unsaturated bonds in the aliphatic chain. Retinoids also exist as retinyl esters such as retinyl propionate, retinyl acetate and retinyl palmitate.

Application

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

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.

Physical form

Dispersion in cornstarch-gelatin matrix. Oil dispersible

Analysis Note

Activity based on HPLC comparison to USP standard.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360D,H413

Hazard Classifications

Aquatic Chronic 4 - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Effect of combined selenium and retinyl acetate treatment on mammary carcinogenesis
Thompson HJ, et al.
Cancer Research, 41(4), 1413-1416 (1981)
Cancer chemopreventive activity mediated by deguelin, a naturally occurring rotenoid
Udeani GO, et al.
Cancer Research, 57(16), 3424-3428 (1997)
Therapeutic Use of Medicinal Plants and their Extracts:Phytochemistry and Bioactive Compounds (2018)
A survey of vitamin A and D contents of fortified fluid milk in Ontario
Faulkner H, et al.
Journal of Dairy Science, 83(6), 1210-1216 (2000)
Laure A N Villeneuve et al.
The British journal of nutrition, 95(4), 677-687 (2006-03-31)
The effect of the feeding period on larval development was investigated in European sea bass larvae by considering the expression level of some genes involved in morphogenesis. Larvae were fed a control diet except during three different periods (period A:
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Articles

Retinoic Acid and Gene Expression

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.

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