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95140 Sigma-Aldrich

Retinyl acetate

concentrate (~50% (w/w) in peanut oil), ~1500 U/mg

Synonym: Retinol acetate, Vitamin A acetate

  • CAS Number 127-47-9

  • Empirical Formula (Hill Notation) C22H32O2

  • Molecular Weight 328.49

  •  Beilstein/REAXYS Number 1915439

  •  MDL number MFCD00019413

  •  eCl@ss 34058009

  •  PubChem Substance ID 57653653

  •  NACRES NA.79

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Properties

Related Categories Biochemicals and Reagents, Vitamin A, Vitamins More...
Quality Level   200
biological source   synthetic
assay   ~95% (HPLC)
form   liquid
quality   concentrate (~50% (w/w) in peanut oil)
contains   DL-α-tocopherol as stabilizer
color   yellow to very dark yellow
mp   57-58 °C
storage temp.   2-8°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

Description

General description

Vitamin A is also known as retinol. Retinaldehyde, retinoic acid and retinyl esters are the derivatives of retinol. Retinol consists of a 20-carbon molecule. It also contains a cyclohexanyl ring with a side chain of four double bonds and an alcohol end group. Vitamin A is naturally present in the body as retinyl ester and β-carotene. Retinyl acetate, retinyl propionate and retinyl palmitate are analogs of retinol.

Biochem/physiol Actions

Retinyl esters are stored in the liver and get converted to retinol before absorption by the intestine. Retinal plays a role in eye vision as it is a part of rhodopsin. Retinol binds to the retinol binding proteins in the plasma. Retinyl acetate has applications in cosmetology.

Other Notes

isomeric purity: ~95% all-trans- and ~5% 13-cis-isomer

Review: Systematic mode of action of vitamin A

Caution

crystallized product can be liquidified by heating to 65°C

Unit Definition

1 U corresponds to 1 international unit acc. to Ph Eur II, 217 (1983)

Physical form

may partially crystallize

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

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, apopt...
BioFiles 2008, 3.9, 12.
Keywords: Apoptosis, Cancer, Cell proliferation, Cellular processes, Chromatin immunoprecipitation, Condensations, Degradations, Diseases, Gene expression, Hormones, Immunoprecipitation, Ligands, Metabolism, Oxidations, Phosphorylations, Polymerase chain reaction, Sequences, Teratogens, Transcription, Type, Ubiquitinations, Usage, Vitamins

Peer-Reviewed Papers
15

References

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