| Revision as of 12:47, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 428432941 of page Retinyl_palmitate for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 19:37, 15 August 2024 edit MarkEPhD (talk | contribs)29 editsm Minor correction - retinyl palmitate is not a chemical antioxidant in food fortificationTag: Visual edit |
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{{Short description|Vitamin A chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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| verifiedrevid = 402585648 |
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| verifiedrevid = 464381401 |
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|ImageFile=Retinyl palmitate.png |
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| ImageFile=Retinyl palmitate.png |
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|ImageSize=200px |
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|ImageFileL2=Retinyl palmitate spacefill.png |
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| ImageFileL2=Retinyl palmitate spacefill.png |
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|ImageFileR2=Retinyl palmitate2.png |
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| ImageFileR2=Retinyl palmitate2.png |
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| IUPACName=Retinyl hexadecanoate |
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|IUPACName= hexadecanoate |
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| SystematicName=(2''E'',4''E'',6''E'',8''E'')-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl hexadecanoate |
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|OtherNames=Retinol palmitate |
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| OtherNames=Retinol palmitate |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10618934 |
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| ChemSpiderID = 10618934 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=79-81-2 |
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| CASNo=79-81-2 |
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| ChEBI = 17616 |
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| PubChem=5280531 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| SMILES = CC1(C)CCCC(\C)=C1\C=C\C(\C)=C\C=C\C(\C)=C\C(=O)OC(=O)CCCCCCCCCCCCCCC |
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| ChEMBL = 1675 |
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| PubChem=5280531 |
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| KEGG=D00164 |
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| SMILES = CC1(C)CCCC(\C)=C1\C=C\C(\C)=C\C=C\C(\C)=C\C(=O)OC(=O)CCCCCCCCCCCCCCC |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>36</sub>H<sub>60</sub>O<sub>2</sub> |
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| Formula=C<sub>36</sub>H<sub>60</sub>O<sub>2</sub> |
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| MolarMass=524.86 g/mol |
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| MolarMass=524.86 g/mol |
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| Solubility=In ], ] and ]<ref>{{cite book|publisher=CRC Press|author1=William M. Haynes|date=2014–2015|isbn=978-1-4822-08672|edition=95th|page=622|title=]}}.</ref> |
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| Solubility= |
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}} |
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}} |
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|Section3={{Chembox Hazards |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| Section6 = {{Chembox Pharmacology |
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'''Retinyl palmitate''', or '''vitamin A palmitate,''' is the ] of ] (]) and ], with formula C<sub>36</sub>H<sub>60</sub>O<sub>2</sub>. It is the most abundant form of vitamin A storage in animals.<ref name=pmid23625372>{{cite journal |last1=O'Byrne |first1=SM |last2=Blaner |first2=WS |title=Retinol and retinyl esters: biochemistry and physiology. |journal=Journal of Lipid Research |date=July 2013 |volume=54 |issue=7 |pages=1731–43 |doi=10.1194/jlr.R037648 |doi-access=free |pmid=23625372 |pmc=3679378}}</ref> |
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An alternate spelling, '''retinol palmitate''', which violates the '''-yl''' organic chemical naming convention for ]s, is also frequently seen. |
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In 2021, vitamin A was the 298th most commonly prescribed medication in the United States, with more than 500,000 prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Vitamin A - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/VitaminA | access-date = 14 January 2024}}</ref> |
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== Biology == |
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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 ], and the inverse is catalyzed by ].<ref name=pmid23625372/> The esters are also intermediates in the ]: ] isomerizes the retinyl part to 11-cis-retinal.<ref name=pmid23625372/> |
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==Uses== |
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Vitamin A palmitate is a common ], available in both oral and ] forms for treatment of ], 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 μg/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 (]).<ref>, Linus Pauling Institute</ref> |
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Retinyl palmitate is used as a source of ] added to low fat ] 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, ], in order to make vitamin A stable in milk.{{Citation needed|date=July 2007}} |
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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 ] (the active form of vitamin A present in Retin-A), though neither its skin absorption<ref>{{Cite journal |
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| author = E. A. Duell, S. Kang & J. J. Voorhees |
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| title = Unoccluded retinol penetrates human skin in vivo more effectively than unoccluded retinyl palmitate or retinoic acid |
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| journal = ] |
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| volume = 109 |
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| issue = 3 |
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| pages = 301–305 |
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| year = 1997 |
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| pmid = 9284094 |
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| doi = 10.1111/1523-1747.ep12335788 |
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| doi-access = free |
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}}</ref> nor its conversion<ref name="BoehnleinSakr1994">{{cite journal|last1=Boehnlein|first1=James|last2=Sakr|first2=Adel|last3=Lichtin|first3=J. Leon|last4=Bronaugh|first4=Robert L.|journal=Pharmaceutical Research|title=Characterization of Esterase and Alcohol Dehydrogenase Activity in Skin. Metabolism of Retinyl Palmitate to Retinol (Vitamin A) During Percutaneous Absorption|volume=11|issue=8|year=1994|pages=1155–1159|issn=0724-8741|doi=10.1023/A:1018941016563|pmid=7971717|s2cid=25458156}}</ref> is very effective. |
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==Carcinogenicity controversy== |
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New York Senator ] has called attention to the fact that high doses of topical retinyl palmitate were shown to accelerate cancer in lab animals,<ref>{{cite news | url = http://www.nydailynews.com/lifestyle/health/2010/06/14/2010-06-14_chuck_cool_on_sunscreen.html | title = Possible link between ingredient in sunscreen and skin cancer: Schumer | newspaper = ] | date = June 14, 2010}}</ref> fueling the sunscreen controversy in the popular press.<ref name="auto">{{cite journal | pmid = 20692724 | year = 2010 | last1 = Wang | first1 = SQ | last2 = Dusza | first2 = SW | last3 = Lim | first3 = HW | title = Safety of retinyl palmitate in sunscreens: a critical analysis. | volume = 63 | issue = 5 | pages = 903–6 | doi = 10.1016/j.jaad.2010.07.015 | journal = Journal of the American Academy of Dermatology}}</ref> One toxicological analysis determined that "there is no convincing evidence to support the notion that in sunscreens is carcinogenic."<ref name="auto"/> A technical report issued thereafter by the ] concluded that diisopropyl adipate increased incidence of skin tumors in mice, and the addition of either ] or retinyl palmitate both exacerbated the rate and frequency of tumors.<ref>]. (2012). NTP technical report on the photocarcinogenesis study of retinoic acid and retinyl palmitate [CAS Nos. 302-79-4 (All-trans-retinoic acid) |
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and 79-81-2 (All-trans-retinyl palmitate)] in SKH-1 mice (Simulated solar light and topical application study). Available at http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/TR568_508.pdf. Accessed September 19, 2013.</ref> |
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==Teratogenicity== |
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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 vitamin A (3000 μg ]) at any time during pregnancy."<ref>{{citation |url=http://whqlibdoc.who.int/hq/1998/WHO_NUT_98.4_eng.pdf |title=Safe vitamin A dosage during pregnancy and lactation |publisher=] (WHO) |year=1998}}.</ref> Preformed Vitamin A refers to retinyl palmitate and retinyl acetate. |
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==See also== |
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* ] |
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* ] |
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* ] |
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==References== |
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{{Reflist}} |
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{{Retinoid receptor modulators}} |
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