Retinyl acetate

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
3D model (JSmol)
1915439
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.405 Edit this at Wikidata
EC Number
  • 204-844-2
KEGG
UNII
  • 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
  • O=C(OC/C=C(/C=C/C=C(/C=C/C1=C(/CCCC1(C)C)C)C)C)C
Properties
C22H32O2
Molar mass 328.496 g·mol−1
Melting point 57 to 58 °C (135 to 136 °F; 330 to 331 K)[1]
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
Warning
H315, H361, H413
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 [77 °F], 100 kPa).

Retinyl acetate (retinol acetate, vitamin A acetate) is a natural[dubious – discuss] form of vitamin A which is the acetate ester of retinol. It has potential antineoplastic and chemopreventive activities.[2][3]

In the United States, retinyl acetate is classified generally recognized as safe (GRAS) in the amounts used to fortify foods with vitamin A.[4][5]

  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