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Details

Stereochemistry ACHIRAL
Molecular Formula C22H32O2
Molecular Weight 328.4883
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of VITAMIN A ACETATE

SMILES

CC(=O)OC\C=C(C)\C=C\C=C(C)\C=C\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 328.4883
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
Bilateral transverse sinus obstruction in benign intracranial hypertension due to hypervitaminosis A.
1978 Aug
Vitamin A abuse: development of cirrhosis despite cessation of vitamin A. A six-year clinical and histopathologic follow-up.
1992 Dec
Vitamin neurotoxicity.
1992 Spring
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
Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1.
2004 Aug
Vitamin A regulates proliferation and apoptosis of human T- and B-cells.
2004 Dec
Carotenoids and their metabolites are naturally occurring activators of gene expression via the pregnane X receptor.
2004 Dec
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
Hypercalcaemia from non-prescription vitamin A.
2004 Nov
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
Brain tissue fragments in the amniotic fluid of rats with neural tube defect.
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
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
Retinal degeneration associated with RDH12 mutations results from decreased 11-cis retinal synthesis due to disruption of the visual cycle.
2005 Dec 15
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
Vitamin A supplementation for extremely low birth weight infants: outcome at 18 to 22 months.
2005 Mar
Inhibitory effects of vitamin A on TCDD-induced cytochrome P-450 1A1 enzyme activity and expression.
2005 May
Megalin-mediated reuptake of retinol in the kidneys of mice is essential for vitamin A homeostasis.
2005 Nov
Expression of nuclear receptor and target genes in liver and intestine of neonatal calves fed colostrum and vitamin A.
2005 Nov
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
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
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
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
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
Hypervitaminosis A-induced liver fibrosis: stellate cell activation and daily dose consumption.
2006 Mar
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 Fri Dec 15 15:06:55 UTC 2023
Edited
by admin
on Fri Dec 15 15:06:55 UTC 2023
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
Retinol acetate [WHO-DD]
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
Classification Tree Code System Code
DSLD 3238 (Number of products:173)
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
DSLD 2650 (Number of products:125)
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
NCI_THESAURUS C804
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
Code System Code Type Description
PUBCHEM
638034
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
CAS
127-47-9
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
SMS_ID
100000090581
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
NSC
122760
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
ChEMBL
CHEMBL986
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
DRUG BANK
DBSALT001720
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
RS_ITEM_NUM
1716002
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
VITAMIN A ACETATE
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
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 Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
MERCK INDEX
m11481
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C1216
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
CHEBI
32095
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
RXCUI
35400
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY RxNorm
DRUG CENTRAL
2372
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
WIKIPEDIA
RETINYL ACETATE
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
NSC
122045
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-844-2
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
MESH
C009166
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
EPA CompTox
DTXSID6021240
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
DAILYMED
3LE3D9D6OY
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
EVMPD
SUB04224MIG
Created by admin on Fri Dec 15 15:06:55 UTC 2023 , Edited by admin on Fri Dec 15 15:06:55 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY