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R4632

Sigma-Aldrich

Retinyl acetate

synthetic, crystalline solid or supercooled liquid

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:
57654592
NACRES:
NA.79

biological source

synthetic

Assay

≥90% (HPLC)

form

crystalline solid or supercooled liquid

potency

2,600,000-2,940,000 I.U. per g

color

light yellow to dark yellow

mp

57-58 °C
~58 °C (lit.)

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

Vitamin A usually occurs in food as retinyl esters, which are the pre-formed sources of vitamin A. Retinyl acetate exists as yellow crystals and is insoluble in water. It is soluble in ethanol and oils.

Application

Retinyl acetate has been used:
  • to study its effects on cochlear development in mice
  • as a component of an internal standard to quantify antioxidants in yolk
  • as an internal standard to determine serum retinol concentration

Biochem/physiol Actions

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. Retinyl esters provide pools of vitamin A that are converted into retinol and other retinoids as needed. Retinyl acetate is used in a wide range of biological applications.

Physical form

Packaged as a melt and may exist as a crystalline solid or a supercooled viscous liquid

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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Assessment of the relative dose-response test based on serum retinol-binding protein instead of serum retinol in determining low hepatic vitamin A stores
Fujita M, et al.
American Journal of Clinical Nutrition (2009)
Capillary electrophoresis Food Additives
Frazier RA
Encyclopedia of Separation Science (2007)
Effects of retinoid treatment on cochlear development, connexin expression and hearing thresholds in mice
Kim Yy, et al.
Journal of Otolaryngology - Head & Neck Surgery = Le Journal D'Oto-rhino-laryngologie et de Chirurgie Cervico-Faciale (2018)
Buhler Volker
Vademecum for Vitamin Formulations (2001)
The common marmoset in captivity and biomedical research
Marini RP
Common Fragrance and Flavor Materials (2018)
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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.

Protocols

Determination of Vitamin A and E Using HPLC with UV Detection Following the Chinese National Standard (GB) Method

Following GB method for Vitamin A and Vitamin E as it is written with a 250 x 4.6 mm Ascentis® Express C30 column gives baseline resolution between the critical pair (gamma-, and beta-tocopherol; peaks 3 and 4).

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