RETINOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H30O
Molecular Weight	286.4516
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=C/CO)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C

InChI

InChIKey=FPIPGXGPPPQFEQ-OVSJKPMPSA-N

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+

HIDE SMILES / InChI

Molecular Formula	C20H30O
Molecular Weight	286.4516
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	4
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00162https://www.drugs.com/monograph/vitamin-a.html
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Superoxide dismutase 4 Target ID: CHEMBL2354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/30972178	Activator 1447
Lecithin retinol acyltransferase 4 Target ID: O95237 Gene ID: 9227.0 Gene Symbol: LRAT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19920137 \| https://www.ncbi.nlm.nih.gov/pubmed/10819989	Substrate 661
Retinol dehydrogenase 12 4 Target ID: Q96NR8 Gene ID: 145226.0 Gene Symbol: RDH12 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB00162	Substrate 661
11-cis retinol dehydrogenase 5 Target ID: Q92781 Gene ID: 5959.0 Gene Symbol: RDH5 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB00162	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Vitamin A deficiency 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00211341	Preventing	Phase III 665	Unknown Approved Use Unknown
Maternal morbidity 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00211341	Preventing	Phase III 665	Unknown Approved Use Unknown
Maternal mortality 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00211341	Preventing	Phase III 665	Unknown Approved Use Unknown
Vitamin A deficiency 4 Sources: https://www.drugs.com/monograph/vitamin-a.html	Primary	Approved 8583	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 1949
Measles 4 Sources: https://www.drugs.com/monograph/vitamin-a.html	Palliative	Approved 8583	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 1949
Skin photodamage 4 Sources: https://clinicaltrials.gov/ct2/show/NCT01283464	Primary	Phase II 1147	Unknown Approved Use Unknown
Skin aging 5 Sources: https://clinicaltrials.gov/ct2/show/NCT02906566	Primary	Phase IV 63	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Hypervitaminosis A-induced liver fibrosis: stellate cell activation and daily dose consumption.	2006-03	16448456
Retinoic acid regulates sex-specific timing of meiotic initiation in mice.	2006-02-21	16461896
RPE65 is an iron(II)-dependent isomerohydrolase in the retinoid visual cycle.	2006-02-03	16319067
Vitamin A improves Pax3 expression that is decreased in the heart of rats with experimental diaphragmatic hernia.	2006-02	16481245
The acute and chronic toxic effects of vitamin A.	2006-02	16469975
Comparative ligand-binding analysis of ten human lipocalins.	2006-02	16461020
Nonclassical action of retinoic acid on the activation of the cAMP response element-binding protein in normal human bronchial epithelial cells.	2006-02	16280361
Role of retinoic acid receptors alpha1 and gamma in the response of murine limbs to retinol in vitro.	2006-01	16397886
Renal pathology and retinol status in multiple myeloma patients.	2006-01	16374440
Expression of Connexin 43 in the hearts of rat embryos exposed to nitrofen and effects of vitamin A on it.	2006-01	16292552
Vitamin A inhibits pancreatic stellate cell activation: implications for treatment of pancreatic fibrosis.	2006-01	16043492
Effects of nitrofen and vitamins A, C and E on maturation of cultured human H441 pneumocytes.	2006	16490937
The effect of vitamin A on CCl4-induced hepatic injuries in rats: a histochemical, immunohistochemical and ultrastructural study.	2006	16256175
Retinal degeneration associated with RDH12 mutations results from decreased 11-cis retinal synthesis due to disruption of the visual cycle.	2005-12-15	16269441
Vitamin A status in mice affects the histone code of the phosphoenolpyruvate carboxykinase gene in liver.	2005-12	16317119
Retinoid metabolism during development of liver cirrhosis.	2005-11-15	16248980
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.	2005-11-01	16267017
Development of a versatile reporter assay for studies of retinol uptake and metabolism in vivo.	2005-11-01	16150442
Megalin-mediated reuptake of retinol in the kidneys of mice is essential for vitamin A homeostasis.	2005-11	16251603
Expression of nuclear receptor and target genes in liver and intestine of neonatal calves fed colostrum and vitamin A.	2005-11	16230703
Retinol induces permeability transition and cytochrome c release from rat liver mitochondria.	2005-10-30	16202537
Acyl coenzyme A dependent retinol esterification by acyl coenzyme A: diacylglycerol acyltransferase 1.	2005-10-15	16214399
Vitamin A regulation of BMP4 expression in the male germ line.	2005-10-01	16120438
Vitamin A supplementation induces adipose tissue loss through apoptosis in lean but not in obese rats of the WNIN/Ob strain.	2005-10	16216918
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.	2005-10	16194896
Comparison of indices of vitamin A status in children with chronic liver disease.	2005-10	16175620
Transmembrane protein GDE2 induces motor neuron differentiation in vivo.	2005-09-30	16195461
Mutation of key residues of RPE65 abolishes its enzymatic role as isomerohydrolase in the visual cycle.	2005-09-20	16150724
Hypervitaminosis A resulting in DNA aberration in fetal transgenic mice (Muta Mouse).	2005-09-05	16054864
Expression of keratinocyte transglutaminase in cornea of vitamin A-deficient rats.	2005-09	16146918
beta-cryptoxanthin stimulates cell differentiation and mineralization in osteoblastic MC3T3-E1 cells.	2005-08-15	15962303
Fortification of maize meal improved the nutritional status of 1-3-year-old African children.	2005-08	16153327
Effects of prenatal vitamins A, E, and C on the hypoplastic hearts of fetal rats with diaphragmatic hernia.	2005-08	16080930
Phospho-STAT5 accumulation in nuclear fractions from vitamin A-deficient rat liver.	2005-07-04	15963505
Serum and CSF vitamin A concentrations in idiopathic intracranial hypertension.	2005-06-14	15955940
Effect of vitamin A content in cafeteria diet on the expression of nuclear receptors in rat subcutaneous adipose tissue.	2005-06	16180333
Vitamin a deficiency and anaemia in young children living in a malaria endemic district of western Kenya.	2005-06	16175781
Vitamin A deficiency induces prooxidant environment and inflammation in rat aorta.	2005-06	16036340
Inhibitory effects of vitamin A on TCDD-induced cytochrome P-450 1A1 enzyme activity and expression.	2005-05	15728703
Alcohol, vitamin A, and cancer.	2005-04	16054987
Brain tissue fragments in the amniotic fluid of rats with neural tube defect.	2005-04	16028844
What is the safe dose of vitamin A in children with measles?	2005-04	15818308
Retinoid receptor mRNA expression profiles in human bladder cancer specimens.	2005-04	15754000
Extra-hepatic vitamin A concentrations in captive Rhesus (Macaca mulatta) and Marmoset (Callithrix jacchus) monkeys fed excess vitamin A.	2005-03	15929633
Vitamin A supplementation for extremely low birth weight infants: outcome at 18 to 22 months.	2005-03	15713907
Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on vitamin A metabolism in mice.	2005	16292751
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	15959631
Differential effects of vitamin A on fetal lung growth and diaphragmatic formation in nitrofen-induced rat model.	2005	15707848
Age differences in vitamin A intake among Canadian Inuit.	2004-12-30	15622799
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.	2004-11	15531678

Patents

Sample Use Guides

In Vivo Use Guide

Weekly single oral dose 7000 micrograms

Route of Administration: Oral

In Vitro Use Guide

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 `Mon Mar 31 18:12:19 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:19 GMT 2025`
Record UNII	G2SH0XKK91
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-122759

Preferred Name

English

RETINOL

Official Name

English

Retinol [WHO-DD]

Common Name

English

VITAMIN A ALCOHOL

Common Name

English

(2E,4E,6E,8E)-3,7-DIMETHYL-9-(2,6,6-TRIMETHYLCYCLOHEX-1-EN-1-YL)NONA-2,4,6,8-TETRAEN-1-OL

Systematic Name

English

ALL-TRANS-RETINOL

Common Name

English

retinol [INN]

Common Name

English

VITAMIN A [MI]

Common Name

English

RETINOL [HSDB]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QR01AX02