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Retinyl palmitate, or vitamin A palmitate, is the ester of retinol (vitamin A) and palmitic acid, with formula C₃₆H₆₀O₂.

An alternate spelling, retinol palmitate, which violates the -yl organic chemical naming convention for esters, is also frequently seen.

Uses

Retinyl palmitate is a synthetic alternate for retinyl acetate in vitamin A supplements, and is available in oily or dry forms. It 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 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 (hypervitaminosis A).^[1]

Retinyl 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]}

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).

Carcinogenicity controversy

The Environmental Working Group (EWG) and New York Senator Chuck Schumer have called attention to the fact that high doses of topical retinyl palmitate were shown to accelerate cancer in lab animals,^[2] fueling the sunscreen controversy in the popular press.^[3] Although concerns about other sunscreen ingredients remain undisputed,^{[citation needed]} one toxicological analysis determined that "there is no convincing evidence to support the notion that [retinyl palmitate] in sunscreens is carcinogenic."^[4] 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.^[5]

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 µg RE) at any time during pregnancy."^[6] Preformed Vitamin A refers to retinyl palmitate and retinyl acetate.

References

^ Vitamin A, Linus Pauling Institute
^ "Possible link between ingredient in sunscreen and skin cancer: Schumer". New York Daily News. June 14, 2010.
^ Wang, SQ; Dusza, SW; Lim, HW (2010). "Safety of retinyl palmitate in sunscreens: a critical analysis.". Journal of the American Academy of Dermatology 63 (5): 903–6. doi:10.1016/j.jaad.2010.07.015. PMID 20692724.
^ Wang, SQ; Dusza, SW; Lim, HW (2010). "Safety of retinyl palmitate in sunscreens: a critical analysis.". Journal of the American Academy of Dermatology 63 (5): 903–6. doi:10.1016/j.jaad.2010.07.015. PMID 20692724.
^ 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 at http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/TR568_508.pdf. Accessed September 19, 2013.
^ Safe vitamin A dosage during pregnancy and lactation (PDF), WHO, 1998

UpToDate Contents

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1. ビタミンAの概要 overview of vitamin a
2. 光による老化 photoaging
3. 疾患予防におけるビタミン補給 vitamin supplementation in disease prevention
4. シェーグレン症候群におけるドライアイの治療 treatment of dry eyes in sjogrens syndrome
5. 毛孔性紅色粃糠疹 pityriasis rubra pilaris

English Journal

Synthesis of retinyl palmitate catalyzed by Candida sp.99-125 lipase immobilized on fiber-like SBA-15 mesoporous material.

Kai Z, Jianqiang W, Yan-hua W, Hui L, Ping-fang H, Ping W.SourceCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing, 210009, China.
Journal of nanoscience and nanotechnology.J Nanosci Nanotechnol.2011 Sep;11(9):7593-602.
Candida sp.99-125 lipase was suitable for transesterification of fats and oils to produce fatty acid methyl ester. The adsorption of Candida sp.99-125 lipase onto the fiber-like SBA-15 mesoporous material has been studied. The unaltered structural order of the fiber-like SBA-15 before and after the
PMID 22097463

Xeroderma pigmentosum family support group: Helping families and promoting clinical initiatives.

Milota M, Jones DL, Cleaver J, Jamall IS.SourceXP Family Support Group, Sacramento, CA 95826, USA.
DNA repair.DNA Repair (Amst).2011 Jul 15;10(7):792-7. Epub 2011 May 13.
The past two decades of research into Xeroderma pigmentosum (XP), an autosomal recessive disease, has been marked by significant progress in understanding the molecular basis of this rare disease. More importantly, especially from the perspective of the affected families, is that this knowledge has
PMID 21570926

Structural characterization and in vivo evaluation of retinyl palmitate in non-ionic lamellar liquid crystalline system.

Chorilli M, Prestes PS, Rigon RB, Leonardi GR, Chiavacci LA, Sarmento VH, Oliveira AG, Scarpa MV.SourceDepartamento de Fármacos e Medicamentos, Faculdade de Ciências Farmacêuticas - UNESP, Rodovia Araraquara-Jaú, Km 01, 14.801-902, Araraquara, SP, Brazil.
Colloids and surfaces. B, Biointerfaces.Colloids Surf B Biointerfaces.2011 Jul 1;85(2):182-8. Epub 2011 Mar 1.
Carrier systems for lipophilic drugs, such as the liquid crystalline systems (LCS) have been extensively studied to improve effect and selectivity. Retinyl palmitate (RP) is widely used in pharmaceutical and cosmetics products to improve the skin elasticity. The aim of this study was the development
PMID 21411295

Japanese Journal

The Effects of Vitamin A Compounds on Hyaluronic Acid Released from Cultured Rabbit Corneal Epithelial Cells and Keratocytes

TOSHIDA Hiroshi,TABUCHI Nobuhito,KOIKE Daisuke,KOIDE Misao,SUGIYAMA Keikichi,NAKAYASU Kiyoo,KANAI Atsushi,MURAKAMI Akira
Journal of Nutritional Science and Vitaminology 58(4), 223-229, 2012
… The medium was then replaced with medium containing 0.1, 1, 10, or 100 μM retinoic acid or retinol palmitate (VApal) and incubated for another 48 h. …
NAID 130002103012

母子牛血漿におけるビタミン A と βカロテン量,ならびにレチノール輸送タンパク質量の動態解析

吉田豊,原ひろみ,半澤惠,渡邉誠喜
東京農業大学農学集報 56(3), 227-235, 2011-12-09
黒毛和種牛とホルスタイン種牛の母子21頭を用いて,分挽前後の母牛と出生直後の子牛(新生子牛)の血漿に含まれるレチノール(ROH),レチニールパルミテート(RPAL),βカロテン(β-c),ならびにROH輸送担体であるROH結合タンパク質(RBP4)とトランスサイレチン(TTR)量の動態を時系列で観察し,母子牛におけるこれらの生理的動態と各種成分との関連を明らかにした。母牛の血漿ROHとβ-c量は, …
NAID 110008721748

パルミチン酸レチノール内服が著効した小児毛孔性紅色粃糠疹の1例

西元順子,瀬戸山充,青木洋子
西日本皮膚科 = The Nishinihon journal of dermatology 72(4), 349-352, 2010-08-01
NAID 10026636860

Related Pictures

★リンクテーブル★

リンク元	「レチノール」「retinol acetate」「パルミチン酸レチノール」
関連記事	「palmitate」

「レチノール」

Retinyl palmitate
Names
	IUPAC name [(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl] hexadecanoate
	Other names Retinol palmitate
Identifiers
CAS Registry Number	79-81-2
ChemSpider	10618934
	InChI InChI=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+ ; Key: SLCSFDSJAUMVCI-UQEJEMEYSA-N ; 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+; Key: SLCSFDSJAUMVCI-UQEJEMEYBQ ;
Jmol-3D images	Image
PubChem	5280531
	SMILES CC1(C)CCCC(\C)=C1\C=C\C(\C)=C\C=C\C(\C)=C\C(=O)OC(=O)CCCCCCCCCCCCCCC ;
UNII	1D1K0N0VVC
Properties
Chemical formula	C36H60O2
Molar mass	524.86 g/mol
Hazards
NFPA 704	1 0 0
	Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references