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Details

Stereochemistry ACHIRAL
Molecular Formula C22H32O2
Molecular Weight 328.4891
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of VITAMIN A ACETATE

SMILES

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

InChI

InChIKey=QGNJRVVDBSJHIZ-QHLGVNSISA-N
InChI=1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3/b10-7+,13-12+,17-9+,18-14+

HIDE SMILES / InChI

Molecular Formula C22H32O2
Molecular Weight 328.4891
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 4
Optical Activity NONE

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
[Review of acute hydrocephalus caused by administration of vitamin A in massive doses in nursing infants; based on 100 cases].
1957 Feb
[Renal tubular failure after treatment with high dose of vitamin A (author's transl)].
1976 Feb 6
Effect of avitaminosis A and hypervitaminosis A on urinary bladder carcinogenicity of N-(4-(5-Nitro-2-furyl)-2-thiazolyl)formamide.
1976 Jul
Vitamin neurotoxicity.
1992 Spring
The anemia of vitamin A deficiency: epidemiology and pathogenesis.
2002 Apr
[Treatment of acne with consequences -- pseudotumor cerebri due to hypervitaminosis A].
2002 Jan 9
PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation.
2003 Feb
Vitamin A deficiency and relational memory deficit in adult mice: relationships with changes in brain retinoid signalling.
2003 Oct 17
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
Carotenoids and their metabolites are naturally occurring activators of gene expression via the pregnane X receptor.
2004 Dec
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
Hypercalcaemia from non-prescription vitamin A.
2004 Nov
Age differences in vitamin A intake among Canadian Inuit.
2004 Nov-Dec
Ocular side effects from herbal medicines and nutritional supplements.
2004 Oct
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
Alcohol, vitamin A, and cancer.
2005 Apr
What is the safe dose of vitamin A in children with measles?
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
Phospho-STAT5 accumulation in nuclear fractions from vitamin A-deficient rat liver.
2005 Jul 4
Effect of vitamin A content in cafeteria diet on the expression of nuclear receptors in rat subcutaneous adipose tissue.
2005 Jun
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
Megalin-mediated reuptake of retinol in the kidneys of mice is essential for vitamin A homeostasis.
2005 Nov
Development of a versatile reporter assay for studies of retinol uptake and metabolism in vivo.
2005 Nov 1
Retinoid metabolism during development of liver cirrhosis.
2005 Nov 15
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
Acyl coenzyme A dependent retinol esterification by acyl coenzyme A: diacylglycerol acyltransferase 1.
2005 Oct 15
Retinol induces permeability transition and cytochrome c release from rat liver mitochondria.
2005 Oct 30
Expression of keratinocyte transglutaminase in cornea of vitamin A-deficient rats.
2005 Sep
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
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
Retinoic acid regulates sex-specific timing of meiotic initiation in mice.
2006 Feb 21
Role of retinoic acid receptors alpha1 and gamma in the response of murine limbs to retinol in vitro.
2006 Jan
Vitamin A inhibits pancreatic stellate cell activation: implications for treatment of pancreatic fibrosis.
2006 Jan
Hypervitaminosis A-induced liver fibrosis: stellate cell activation and daily dose consumption.
2006 Mar
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:03:47 UTC 2021
Edited
by admin
on Sat Jun 26 05:03:47 UTC 2021
Record UNII
3LE3D9D6OY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VITAMIN A ACETATE
MI   VANDF  
Common Name English
RO-1-5275
Code English
VITAMIN A (AS ACETATE & BETA CAROTENE) [VANDF]
Common Name English
NSC-122760
Code English
VITAMIN A ACETATE [VANDF]
Common Name English
RETINYL ACETATE [INCI]
Common Name English
ORISTAR RA
Brand Name English
VITAMIN A ACETATE [MI]
Common Name English
RETINYL ACETATE [USP-RS]
Common Name English
NSC-122045
Code English
RETINYL ACETATE
INCI   USP-RS  
INCI  
Official Name English
ALL-(E)-RETINOL ACETATE [WHO-IP]
Common Name English
VITAMIN A (AS ACETATE) [VANDF]
Common Name English
VITAMIN A ACETATE 1.5 M.I.U./G
Brand Name English
RETINOL ACETATE [JAN]
Common Name English
RETINOL ACETATE [WHO-DD]
Common Name English
RETINOL ACETATE
WHO-DD  
Common Name English
Classification Tree Code System Code
DSLD 3238 (Number of products:173)
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
DSLD 2650 (Number of products:125)
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
NCI_THESAURUS C804
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
Code System Code Type Description
PUBCHEM
638034
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY
CAS
127-47-9
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY
ChEMBL
CHEMBL986
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY
DRUG BANK
DBSALT001720
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
VITAMIN A ACETATE
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 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 shouldbe 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 as the content of vitamin A in International Units (IU) per gram, whether any stabilizing agents are added and their quantities, as well as 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.
FDA UNII
3LE3D9D6OY
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY
MERCK INDEX
M11481
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C1216
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY
RXCUI
35400
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
2372
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY
WIKIPEDIA
RETINYL ACETATE
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-844-2
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY
MESH
C009166
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY
EPA CompTox
127-47-9
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY
USP_CATALOG
1716002
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY USP-RS
EVMPD
SUB04224MIG
Created by admin on Sat Jun 26 05:03:47 UTC 2021 , Edited by admin on Sat Jun 26 05:03:47 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY