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Retinyl acetate

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Retinyl acetate
Names
IUPAC name (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate
Other names Retinol acetate; Vitamin A acetate; Vitamin A1 acetate; Acetylretinol; all-trans-Retinol acetate; all-trans-Retinyl acetate; all-trans-Vitamin A acetate;
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1915439
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.405 Edit this at Wikidata
EC Number
  • 204-844-2
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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+Key: QGNJRVVDBSJHIZ-QHLGVNSISA-N
  • InChI=1/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+Key: QGNJRVVDBSJHIZ-QHLGVNSIBE
SMILES
  • O=C(OC/C=C(/C=C/C=C(/C=C/C1=C(/CCCC1(C)C)C)C)C)C
Properties
Chemical formula C22H32O2
Molar mass 328.496 g·mol
Melting point 57 to 58 °C (135 to 136 °F; 330 to 331 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS08: Health hazard
Signal word Warning
Hazard statements H315, H361, H413
Precautionary statements P201, P202, P264, P273, P280, P281, P302+P352, P308+P313, P321, P332+P313, P362, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Retinyl acetate (retinol acetate, vitamin A acetate) is a natural form of vitamin A which is the acetate ester of retinol. It has potential antineoplastic and chemopreventive activities.

In the United States, retinyl acetate is classified generally recognized as safe (GRAS) in the amounts used to fortify foods with vitamin A.

Toxicology

See also: Hypervitaminosis A

World Health Organization "Recommendations for preformed vitamin A supplements for mothers during pregnancy" states that "health benefits are expected for the mother and her developing fetus with little risk of detriment to either, from a daily supplement not exceeding 10,000 IU vitamin A (3000mcg RE) at any time during pregnancy." Preformed Vitamin A refers to retinol and retinyl esters, such as retinyl palmitate and retinyl acetate.

References

  1. Retinyl acetate from Sigma-Aldrich
  2. Moon, Richard C.; Grubbs, Clinton J.; Sporn, Michael B.; Goodman, Dawn G. (1977). "Retinyl acetate inhibits mammary carcinogenesis induced by N-methyl-N-nitrosourea". Nature. 267 (5612): 620–1. Bibcode:1977Natur.267..620M. doi:10.1038/267620a0. PMID 876383. S2CID 4211886.
  3. Retinyl acetate, National Cancer Institute Drug Dictionary
  4. Select Committee on GRAS Substances (SCOGS) Opinion: Vitamin A, United States Food and Drug Administration
  5. 21 CFR 184.1930
  6. World Health Organization Nutrition Unit (1998). Safe vitamin A dosage during pregnancy and lactation. World Health Organization. hdl:10665/63838.
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