{{Short description|Vitamin A chemical compound}}{{chembox| Verifiedfields = changed| verifiedrevid = 464381401| ImageFile=Retinyl palmitate.png| ImageFileL2=Retinyl palmitate spacefill.png| ImageFileR2=Retinyl palmitate2.png| IUPACName=Retinyl hexadecanoate| SystematicName=(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl hexadecanoate| OtherNames=Retinol palmitate|Section1={{Chembox Identifiers

correct|chemspider}}| ChemSpiderID = 10618934

correct|FDA}}| UNII = 1D1K0N0VVC| InChI = 1/C36H58O3/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-34(37)39-35(38)29-31(3)23-20-22-30(2)26-27-33-32(4)24-21-28-36(33,5)6/h20,22-23,26-27,29H,7-19,21,24-25,28H2,1-6H3/b23-20+,27-26+,30-22+,31-29+| InChIKey = SLCSFDSJAUMVCI-UQEJEMEYBQ

correct|chemspider}}| StdInChI = 1S/C36H58O3/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-34(37)39-35(38)29-31(3)23-20-22-30(2)26-27-33-32(4)24-21-28-36(33,5)6/h20,22-23,26-27,29H,7-19,21,24-25,28H2,1-6H3/b23-20+,27-26+,30-22+,31-29+

correct|chemspider}}| StdInChIKey = SLCSFDSJAUMVCI-UQEJEMEYSA-N

correct|CAS}}| CASNo=79-81-2 | ChEBI = 17616

changed|EBI}}| ChEMBL = 1675| PubChem=5280531| KEGG=D00164| SMILES = CC1(C)CCCC(C)=C1C=CC(C)=CC=CC(C)=CC(=O)OC(=O)CCCCCCCCCCCCCCC}}|Section2={{Chembox Properties| Formula=C36H60O2| MolarMass=524.86 g/mol| Appearance=| Density=| MeltingPt=| BoilingPt=

water, ethanol and ethersCRC PRESS

DATE=2014â€“2015

EDITION=95TH

TITLE=CRC HANDBOOK OF CHEMISTRY AND PHYSICS, .

}}|Section3={{Chembox Hazards| NFPA-H = 0| NFPA-F = 1| NFPA-R = 0| MainHazards=| FlashPt=| AutoignitionPt =
}}| Section6 = {{Chembox Pharmacology| Pharmacology_ref = | ATCCode_prefix = | ATCCode_suffix = | ATC_Supplemental = | ATCvet = | Licence_EU = | INN = | INN_EMA = | Licence_US = | Legal_status = | Legal_AU = | Legal_AU_comment = | Legal_CA = | Legal_CA_comment = | Legal_NZ = | Legal_NZ_comment = | Legal_UK = | Legal_UK_comment = | Legal_US = | Legal_US_comment = | Legal_EU = | Legal_EU_comment = | Legal_UN = | Legal_UN_comment = | Pregnancy_category = | Pregnancy_AU = | Pregnancy_AU_comment = | Dependence_liability = | AdminRoutes = | Bioavail = | ProteinBound = | Metabolism = | Metabolites = | OnsetOfAction = | HalfLife = | DurationOfAction = | Excretion =
}}

}}Retinyl palmitate, or vitamin A palmitate, is the ester of retinol (vitamin A) and palmitic acid, with formula C36H60O2. It is the most abundant form of vitamin A storage in animals.JOURNAL, O’Byrne, SM, Blaner, WS, Retinol and retinyl esters: biochemistry and physiology., Journal of Lipid Research, July 2013, 54, 7, 1731â€“43, 10.1194/jlr.R037648, free, 23625372, 3679378, An alternate spelling, retinol palmitate, which violates the -yl organic chemical naming convention for esters, is also frequently seen.In 2021, vitamin A was the 298th most commonly prescribed medication in the United States, with more than 500,000 prescriptions.WEB, The Top 300 of 2021,clincalc.com/DrugStats/Top300Drugs.aspx, ClinCalc, 14 January 2024, 15 January 2024,web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx, live, WEB, Vitamin A - Drug Usage Statistics, ClinCalc,clincalc.com/DrugStats/Drugs/VitaminA, 14 January 2024,

Biology

Animals use long-chain esters of vitamin A, most abundantly the palmitate form, as a form of vitamin A storage. The storage reaction is catalyzed by LRAT, and the inverse is catalyzed by REH. The esters are also intermediates in the visual cycle: RPE65 isomerizes the retinyl part to 11-cis-retinal.

Uses

Vitamin A palmitate is a common vitamin supplement, available in both oral and injectable forms for treatment of vitamin A deficiency, under the brand names Aquasol A, Palmitate A and many others. It is a constituent of intra ocular treatment for dry eyes at a concentration of 138 Î¼g/g (VitA-Pos) by Ursapharm. It is a pre-formed version of vitamin A; therefore, the intake should not exceed the Recommended Dietary Allowance (RDA). Overdosing preformed Vitamin A forms such as retinyl palmitate leads to adverse physiological reactions (hypervitaminosis A).Vitamin A, Linus Pauling InstituteRetinyl palmitate is used as an antioxidant and a source of vitamin A added to low fat milk and other dairy products to replace the vitamin content lost through the removal of milk fat. Palmitate is attached to the alcohol form of vitamin A, retinol, in order to make vitamin A stable in milk.{{Citation needed|date=July 2007}}Retinyl palmitate is also a constituent of some topically applied skin care products. After its absorption into the skin, retinyl palmitate is converted to retinol, and ultimately to retinoic acid (the active form of vitamin A present in Retin-A), though neither its skin absorptionJOURNAL

, E. A. Duell, S. Kang & J. J. Voorhees
, Unoccluded retinol penetrates human skin in vivo more effectively than unoccluded retinyl palmitate or retinoic acid
, The Journal of Investigative Dermatology
, 109
, 3
, 301â€“305
, 1997
, 9284094, 10.1111/1523-1747.ep12335788
, free
, nor its conversionJOURNAL, Boehnlein, James, Sakr, Adel, Lichtin, J. Leon, Bronaugh, Robert L., Pharmaceutical Research, Characterization of Esterase and Alcohol Dehydrogenase Activity in Skin. Metabolism of Retinyl Palmitate to Retinol (Vitamin A) During Percutaneous Absorption, 11, 8, 1994, 1155â€“1159, 0724-8741, 10.1023/A:1018941016563, 7971717, 25458156, is very effective.

Carcinogenicity controversy

New York Senator Chuck Schumer has called attention to the fact that high doses of topical retinyl palmitate were shown to accelerate cancer in lab animals,NEWS,www.nydailynews.com/lifestyle/health/2010/06/14/2010-06-14_chuck_cool_on_sunscreen.html, Possible link between ingredient in sunscreen and skin cancer: Schumer, New York Daily News, June 14, 2010, fueling the sunscreen controversy in the popular press.JOURNAL, 20692724, 2010, Wang, SQ, Dusza, SW, Lim, HW, Safety of retinyl palmitate in sunscreens: a critical analysis., 63, 5, 903â€“6, 10.1016/j.jaad.2010.07.015, Journal of the American Academy of Dermatology, One toxicological analysis determined that “there is no convincing evidence to support the notion that [retinyl palmitate] in sunscreens is carcinogenic.” A technical report issued thereafter by the National Toxicology Program concluded that diisopropyl adipate increased incidence of skin tumors in mice, and the addition of either retinoic acid or retinyl palmitate both exacerbated the rate and frequency of tumors.National Toxicology Program. (2012). NTP technical report on the photocarcinogenesis study of retinoic acid and retinyl palmitate [CAS Nos. 302-79-4 (All-trans-retinoic acid)

and 79-81-2 (All-trans-retinyl palmitate)] in SKH-1 mice (Simulated solar light and topical application study). Available atntp.niehs.nih.gov/ntp/htdocs/LT_rpts/TR568_508.pdf. Accessed September 19, 2013.

Teratogenicity

World Health Organization recommendation on Maternal Supplementation 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 [preformed] vitamin A (3000 Î¼g RE) at any time during pregnancy.“{{citation |url=http://whqlibdoc.who.int/hq/1998/WHO_NUT_98.4_eng.pdf |title=Safe vitamin A dosage during pregnancy and lactation |publisher=World Health Organization (WHO) |year=1998}}. Preformed Vitamin A refers to retinyl palmitate and retinyl acetate.

References

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retinyl palmitate

Biology

Uses

Carcinogenicity controversy

Teratogenicity

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References