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Retinol information


Retinol
Retinol
Clinical data
AHFS/Drugs.comMonograph
License data
  • US DailyMed: Retinol
Routes of
administration
By mouth, intramuscular[1]
Drug classvitamin
ATC code
  • A11CA01 (WHO) D10AD02 (WHO), R01AX02 (WHO), S01XA02 (WHO)
Legal status
Legal status
  • US: OTC
Identifiers
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-ol
CAS Number
  • 68-26-8
  • mixture: 11103-57-4
PubChem CID
  • 445354
IUPHAR/BPS
  • 4053
DrugBank
  • DB00162
ChemSpider
  • 393012
UNII
  • G2SH0XKK91
  • mixture: 81G40H8B0T
KEGG
  • D00069
ChEBI
  • CHEBI:17336
ChEMBL
  • ChEMBL986
PDB ligand
  • RTL (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID3023556 Edit this at Wikidata
ECHA InfoCard100.000.621 Edit this at Wikidata
Chemical and physical data
FormulaC20H30O
Molar mass286.459 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point62–64 °C (144–147 °F)
Boiling point137–138 °C (279–280 °F) (10−6 mm Hg)
SMILES
  • OC/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)/CCCC1(C)C
InChI
  • InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
  • Key:FPIPGXGPPPQFEQ-OVSJKPMPSA-N

Retinol, also called vitamin A1, is a fat-soluble vitamin in the vitamin A family that is found in food and used as a dietary supplement.[2] Retinol or other forms of vitamin A are needed for vision, cellular development, maintenance of skin and mucous membranes, immune function and reproductive development.[2] Dietary sources include fish, dairy products, and meat.[2] As a supplement it is used to treat and prevent vitamin A deficiency, especially that which results in xerophthalmia.[1] It is taken by mouth or by injection into a muscle.[1] As an ingredient in skin-care products, it is used to reduce wrinkles and other effects of skin aging.[3]

Retinol at normal doses is well tolerated.[1] High doses may cause enlargement of the liver, dry skin, and hypervitaminosis A.[1][4] High doses during pregnancy may harm the fetus.[1] The body converts retinol to retinal and retinoic acid, through which it acts.[2]

Retinol was discovered in 1909, isolated in 1931, and first made in 1947.[5][6] It is on the World Health Organization's List of Essential Medicines.[7] Retinol is available as a generic medication and over the counter.[1] In 2021, vitamin A was the 298th most commonly prescribed medication in the United States, with more than 500,000 prescriptions.[8][9]

  1. ^ a b c d e f g "Vitamin A". The American Society of Health-System Pharmacists. Archived from the original on 30 December 2016. Retrieved 8 December 2016.
  2. ^ a b c d "Office of Dietary Supplements - Vitamin A". ods.od.nih.gov. 31 August 2016. Archived from the original on 12 December 2016. Retrieved 30 December 2016.
  3. ^ Kong R, Cui Y, Fisher GJ, Wang X, Chen Y, Schneider LM, et al. (March 2016). "A comparative study of the effects of retinol and retinoic acid on histological, molecular, and clinical properties of human skin". Journal of Cosmetic Dermatology. 15 (1): 49–57. doi:10.1111/jocd.12193. PMID 26578346. S2CID 13391046.
  4. ^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 701. ISBN 9780857111562.
  5. ^ Squires VR (2011). The Role of Food, Agriculture, Forestry and Fisheries in Human Nutrition. Vol. IV. EOLSS Publications. p. 121. ISBN 9781848261952. Archived from the original on 5 November 2017.
  6. ^ Ullmann's Food and Feed, 3 Volume Set. John Wiley & Sons. 2016. p. Chapter 2. ISBN 9783527695522. Archived from the original on 5 November 2017.
  7. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  8. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  9. ^ "Vitamin A - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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Retinol

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Retinol, also called vitamin A1, is a fat-soluble vitamin in the vitamin A family that is found in food and used as a dietary supplement. Retinol or other...

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Vitamin A

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encompasses a group of chemically related organic compounds that includes retinol, retinal (also known as retinaldehyde), retinoic acid, and several provitamin...

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Retinol dehydrogenase

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In enzymology, a retinol dehydrogenase (RDH) (EC 1.1.1.105) is an enzyme that catalyzes the chemical reaction retinol + NAD+ ⇌ {\displaystyle \rightleftharpoons...

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Retinyl palmitate

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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...

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Hypervitaminosis A

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toxic effects of ingesting too much preformed vitamin A (retinyl esters, retinol, and retinal). Symptoms arise as a result of altered bone metabolism and...

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Retinol binding protein 4

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Retinol binding protein 4, also known as RBP4, is a transporter protein for retinol (vitamin A alcohol). RBP4 has a molecular weight of approximately...

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Retinyl acetate

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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...

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Cod liver oil

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tablespoon (13.6 grams or 14.8 mL) of cod liver oil contains 4,080 μg of retinol (vitamin A) and 34 μg (1360 IU) of vitamin D. The Dietary Reference Intake...

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Retinoid

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intestinal lumen to yield free retinol and the corresponding fatty acid (i.e. palmitate or stearate). After hydrolysis, retinol is taken up by the enterocytes...

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Retinol isomerase

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\rightleftharpoons } 11-cis-retinol Hence, this enzyme has one substrate, all-trans-retinol, and one product, 11-cis-retinol. These enzymes are alternatively...

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Lecithin retinol acyltransferase

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Lecithin retinol acyltransferase is an enzyme that in humans is encoded by the LRAT gene. Lecithin retinol acyltransferase is a microsomal enzyme that...

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Visual cycle

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all-trans-retinol + NADP+; all-trans-retinol dehydrogenases; all-trans-retinol + fatty acid → all-trans-retinyl ester + H2O; lecithin retinol acyltransferases...

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Retinoic acid

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for all-trans-retinoic acid) is a metabolite of vitamin A1 (all-trans-retinol) that mediates the functions of vitamin A1 required for growth and development...

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Bakuchiol

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Despite having no structural resemblance to retinol, Bakuchiol was found to have retinol functionality through retinol-like regulation of gene expression. In...

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Retinal

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all-trans-retinol + NADP+; all-trans-retinol dehydrogenases; all-trans-retinol + fatty acid → all-trans-retinyl ester + H2O; lecithin retinol acyltransferases...

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Carotenosis

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certain disease states, the metabolism and conversion of carotenoids to retinol is slowed, which can lead to decreased clearance and increased plasma levels...

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Carotene

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convert a trace of β-carotene to retinol, although the amount is totally insufficient for meeting their daily retinol needs. Carotenes are polyunsaturated...

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Provitamin

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activity of retinol (vitamin A); the body uses an enzyme to convert β-carotene to retinol. In other contexts, both β-carotene and retinol are simply considered...

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Diterpene

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Diterpenes form the basis for biologically important compounds such as retinol, retinal, and phytol. They are known to be antimicrobial and anti-inflammatory...

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Vitamin A deficiency

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seen in VAD; suppressed synthesis of retinol binding protein (RBP) due to protein deficiency leads to reduced retinol uptake. Excess alcohol consumption...

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RBP7

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Retinol binding protein 7 is a protein that in humans is encoded by the RBP7 gene. The protein encoded by this gene is a member of the cellular retinol-binding...

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RPE65

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the conversion of all-trans-retinyl esters to 11-cis-retinol during phototransduction. 11-cis-retinol is then used in visual pigment regeneration in photoreceptor...

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