U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C36H60O2
Molecular Weight 524.8617
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of VITAMIN A PALMITATE

SMILES

CCCCCCCCCCCCCCCC(=O)OC/C(/[H])=C(\C)/C(/[H])=C(\[H])/C(/[H])=C(\C)/C(/[H])=C(\[H])/C1=C(C)CCCC1(C)C

InChI

InChIKey=VYGQUTWHTHXGQB-FFHKNEKCSA-N
InChI=1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22+,32-28+

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8801161

Retonol, also known as Vitamin A1, is a vitamin found in food and used as a dietary supplement. It is used to treat and prevent vitamin A deficiency. It is also used to prevent further issues in those who have measles. Retinol is used as a metabolic precursor of retinoic acid to treat skin-related conditions, such as cellulite, skin aging, photodamage.

CNS Activity

Curator's Comment:: Evidence indicates that retinol is transported by retinol binding protein across the blood–brain barrier and blood–CSF barrier to the CNS

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O95237
Gene ID: 9227.0
Gene Symbol: LRAT
Target Organism: Homo sapiens (Human)
Target ID: Q96NR8
Gene ID: 145226.0
Gene Symbol: RDH12
Target Organism: Homo sapiens (Human)
Target ID: Q92781
Gene ID: 5959.0
Gene Symbol: RDH5
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
AQUASOL A

Approved Use

Used to treat and prevent symptoms of vitamin A deficiency such as xerophthalmia and night blindness. Used as a dietary supplement to prevent vitamin A deficiency in patients with GI diseases (e.g., malabsorption syndromes) and those with abnormal storage and transport of vitamin A (e.g., abetalipoproteinemia, protein deficiency, diabetes mellitus, hyperthyroidism, fever, liver disease, cystic fibrosis with hepatic involvement).

Launch Date

-6.5093763E11
Palliative
AQUASOL A

Approved Use

Children with severe measles have been found to have low serum concentrations of vitamin A; WHO and AAP recommend that vitamin A supplements be given to all children with acute measles, regardless of their country of residence.

Launch Date

-6.5093763E11
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Bilateral transverse sinus obstruction in benign intracranial hypertension due to hypervitaminosis A.
1978 Aug
Retinol-induced mdr1 and mdr3 modulation in cultured rat Sertoli cells is attenuated by free radical scavengers.
2004
Vitamin A prevents high fat diet-induced ACF development and modifies the pattern of expression of peroxisome proliferator and retinoic acid receptor m-RNA.
2004
Dietary vitamin A intakes of Filipino elders with adequate or low liver vitamin A concentrations as assessed by the deuterated-retinol-dilution method: implications for dietary requirements.
2004 Apr
Modulation of resistin expression by retinoic acid and vitamin A status.
2004 Apr
Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1.
2004 Aug
Carotenoids and their metabolites are naturally occurring activators of gene expression via the pregnane X receptor.
2004 Dec
Capillary leak syndrome induced by acitretin.
2004 Jan
Inverse gene expression patterns for macrophage activating hepatotoxicants and peroxisome proliferators in rat liver.
2004 Jun 1
A palmitoylation switch mechanism in the regulation of the visual cycle.
2004 Jun 11
Safety and efficacy of dose-intensive oral vitamin A in subjects with sun-damaged skin.
2004 Mar 15
Use of the deuterated-retinol-dilution technique to monitor the vitamin A status of Nicaraguan schoolchildren 1 y after initiation of the Nicaraguan national program of sugar fortification with vitamin A.
2004 Nov
Hypercalcaemia from non-prescription vitamin A.
2004 Nov
Ocular side effects from herbal medicines and nutritional supplements.
2004 Oct
Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on vitamin A metabolism in mice.
2005
Protein and m-RNA expression of farnesyl-transferases, RhoA and RhoB in rat liver hepatocytes: action of perillyl alcohol and vitamin A in vivo.
2005
Differential effects of vitamin A on fetal lung growth and diaphragmatic formation in nitrofen-induced rat model.
2005
Alcohol, vitamin A, and cancer.
2005 Apr
Brain tissue fragments in the amniotic fluid of rats with neural tube defect.
2005 Apr
What is the safe dose of vitamin A in children with measles?
2005 Apr
Retinoid receptor mRNA expression profiles in human bladder cancer specimens.
2005 Apr
Fortification of maize meal improved the nutritional status of 1-3-year-old African children.
2005 Aug
Effects of prenatal vitamins A, E, and C on the hypoplastic hearts of fetal rats with diaphragmatic hernia.
2005 Aug
beta-cryptoxanthin stimulates cell differentiation and mineralization in osteoblastic MC3T3-E1 cells.
2005 Aug 15
Vitamin A status in mice affects the histone code of the phosphoenolpyruvate carboxykinase gene in liver.
2005 Dec
Vitamin a deficiency and anaemia in young children living in a malaria endemic district of western Kenya.
2005 Jun
Vitamin A deficiency induces prooxidant environment and inflammation in rat aorta.
2005 Jun
Serum and CSF vitamin A concentrations in idiopathic intracranial hypertension.
2005 Jun 14
Extra-hepatic vitamin A concentrations in captive Rhesus (Macaca mulatta) and Marmoset (Callithrix jacchus) monkeys fed excess vitamin A.
2005 Mar
Retinol inhibits the growth of all-trans-retinoic acid-sensitive and all-trans-retinoic acid-resistant colon cancer cells through a retinoic acid receptor-independent mechanism.
2005 Nov 1
Regulation of a highly specific retinoic acid-4-hydroxylase (CYP26A1) enzyme and all-trans-retinoic acid metabolism in human intestinal, liver, endothelial, and acute promyelocytic leukemia cells.
2005 Oct
Comparison of indices of vitamin A status in children with chronic liver disease.
2005 Oct
Vitamin A regulation of BMP4 expression in the male germ line.
2005 Oct 1
Expression of keratinocyte transglutaminase in cornea of vitamin A-deficient rats.
2005 Sep
Mutation of key residues of RPE65 abolishes its enzymatic role as isomerohydrolase in the visual cycle.
2005 Sep 20
Transmembrane protein GDE2 induces motor neuron differentiation in vivo.
2005 Sep 30
Hypervitaminosis A resulting in DNA aberration in fetal transgenic mice (Muta Mouse).
2005 Sep 5
Effects of nitrofen and vitamins A, C and E on maturation of cultured human H441 pneumocytes.
2006
The effect of vitamin A on CCl4-induced hepatic injuries in rats: a histochemical, immunohistochemical and ultrastructural study.
2006
Vitamin A improves Pax3 expression that is decreased in the heart of rats with experimental diaphragmatic hernia.
2006 Feb
The acute and chronic toxic effects of vitamin A.
2006 Feb
Comparative ligand-binding analysis of ten human lipocalins.
2006 Feb
Nonclassical action of retinoic acid on the activation of the cAMP response element-binding protein in normal human bronchial epithelial cells.
2006 Feb
Retinoic acid regulates sex-specific timing of meiotic initiation in mice.
2006 Feb 21
RPE65 is an iron(II)-dependent isomerohydrolase in the retinoid visual cycle.
2006 Feb 3
Role of retinoic acid receptors alpha1 and gamma in the response of murine limbs to retinol in vitro.
2006 Jan
Renal pathology and retinol status in multiple myeloma patients.
2006 Jan
Expression of Connexin 43 in the hearts of rat embryos exposed to nitrofen and effects of vitamin A on it.
2006 Jan
Vitamin A inhibits pancreatic stellate cell activation: implications for treatment of pancreatic fibrosis.
2006 Jan
Retinol palmitate protects against myocardial ischemia/reperfusion injury via reducing oxidative stress and inhibiting apoptosis.
2019
Patents

Sample Use Guides

Weekly single oral dose 7000 micrograms
Route of Administration: Oral
The role of vitamin A (2.72 μM/7 ml culture), a naturally occurring antioxidant upon arsenic-induced genotoxicity; with respect to chromosomal aberrations (structural and numerical) and micronuclei. Whole blood cultures set for 72 h were exposed to test chemicals for a period of 24 h ahead of harvesting. Arsenic concentrations tested in the present study are 0.36, 0.72 and 1.4 μM/7 ml culture. Mitomycin C (MMC), the direct acting mutagen was used as positive control.
Name Type Language
VITAMIN A PALMITATE
MI   ORANGE BOOK   VANDF  
Common Name English
RETINOL, HEXADECANOATE
Common Name English
RETINOL PALMITATE [JAN]
Common Name English
NSC-758478
Code English
VITAMIN A (AS PALMITATE & BETA CAROTENE) [VANDF]
Common Name English
RETINOL PALMITATE
WHO-DD  
Common Name English
ALL-(E)-RETINOL PALMITATE [WHO-IP]
Common Name English
RETINOL, PALMITATE, ALL-TRANS
Common Name English
RETINYL PALMITATE [VANDF]
Common Name English
VITAMIN A PALMITATE [MI]
Common Name English
RETINOL PALMITATE [WHO-DD]
Common Name English
VITAMIN A PALMITATE [ORANGE BOOK]
Common Name English
RETINYL PALMITATE
INCI   USP-RS   VANDF  
INCI  
Official Name English
RETINYL PALMITATE [USP-RS]
Common Name English
VITAMIN A PALMITATE [VANDF]
Common Name English
VITAMIN A PALMITATE (SOLUBILIZED) [VANDF]
Common Name English
RETINYL PALMITATE [INCI]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 525116
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
NCI_THESAURUS C804
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
FDA ORPHAN DRUG 295109
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
FDA ORPHAN DRUG 805420
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
LOINC 38496-6
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
FDA ORPHAN DRUG 583417
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
FDA ORPHAN DRUG 483315
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
DSLD 2624 (Number of products:460)
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
DSLD 2782 (Number of products:618)
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
Code System Code Type Description
WIKIPEDIA
RETINYL PALMITATE
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY
FDA UNII
1D1K0N0VVC
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY
DRUG BANK
DBSALT000855
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY
ChEMBL
CHEMBL1675
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY
PUBCHEM
5280531
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY
ChEMBL
CHEMBL986
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY
NCI_THESAURUS
C1217
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY
RXCUI
35406
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY RxNorm
CAS
79-81-2
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY
MERCK INDEX
M11481
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1602502
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY USP-RS
WHO INTERNATIONAL PHARMACOPEIA
VITAMIN A PALMITATE
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY Description: A yellow to brownish yellow, oily liquid. Solubility: Practically insoluble in water; soluble or partly soluble in dehydrated ethanol R; miscible with organic solvents. Category: Vitamin. Storage: The oily form of Retinol concentrate should be kept in a well-closed and well-filled container, protected from light. Once the container has been opened its contents should be used as soon as possible; any part of the contents not used at once should be protected by an atmosphere of inert gas. Labelling: The designation on the container should state the name of the retinol ester or esters, and their quantities expressed asthe content of vitamin A in International Units (IU) per gram, whether any stabilizing agents are added and their quantities, as wellas the method of restoring the solution if partial crystallization has occurred.Additional information: Even in the absence of light the oily form of Retinol concentrate is gradually degraded on exposure to ahumid atmosphere, the decomposition being faster at higher temperatures. Partial crystallization may occur in concentrated solutions and upon refrigeration.
EPA CompTox
79-81-2
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY
DRUG CENTRAL
4197
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-228-5
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY
MESH
C014794
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY
EVMPD
SUB04225MIG
Created by admin on Fri Jun 25 21:30:40 UTC 2021 , Edited by admin on Fri Jun 25 21:30:40 UTC 2021
PRIMARY