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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 of RETINOL

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
Curator's Comment: description was created based on several sources, including: https://en.wikipedia.org/wiki/Vitamin_A

Vitamin A is important for growth and development as well as maintenance of the immune system and good vision. Vitamin A is needed by the retina of the eye in the form of retinal, which combines with the protein opsin to form rhodopsin. Together Vitamin A and Rhodopsin form the light-absorbing molecule necessary for both low-light (scotopic vision) and color vision. Vitamin A also functions in a very different role as retinoic acid (an irreversibly oxidized form of retinol) which is an important hormone-like growth factor for epithelial and other cells. In foods of animal origin, the major form of vitamin A is an ester, primarily retinyl palmitate, which is converted to retinol (chemically an alcohol) in the small intestine. The retinol form functions as a storage form of the vitamin, and can be converted to and from its visually active aldehyde form, retinal. Vitamin A is effective for the treatment of Vitamin A deficiency. Vitamin A refers to a group of fat-soluble substances that are structurally related to and possess the biological activity of the parent substance of the group called all-trans retinol or retinol. Vitamin A plays vital roles in vision, epithelial differentiation, growth, reproduction, pattern formation during embryogenesis, bone development, hematopoiesis and brain development. It is also important for the maintenance of a proper functioning immune system. The precise mechanism of action of vitamin A differs based on the biological use case, and some mechanisms are better known than others. To facilitate vision Vitamin A (all-trans retinol) is converted in the retina to the 11-cis-isomer of retinaldehyde or 11-cis-retinal. 11-cis-retinal functions in the retina contributing to the transduction of light into the neural signals necessary for vision. While attached to opsin in rhodopsin 11-cis-retinal is isomerized to all-trans-retinal by light which triggers the nerve impulse to the brain allowing for the perception of light. All-trans-retinal is then released from opsin and reduced to all-trans-retinol. All-trans-retinol is isomerized to 11-cis-retinol in the absence of light and then oxidized to 11-cis-retinal. 11-cis-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to re-synthesize 11-cis retinal rapidly. During epithelial differentiation the role of Vitamin A (as in other physiological processes) involves the binding of Vitamin A to two families of nuclear retinoid receptors (retinoic acid receptors, RARs; and retinoid-X receptors, RXRs). These receptors function as ligand-activated transcription factors that modulate gene transcription. When there is not enough Vitamin A to bind these receptors, natural cell differentiation and growth are interrupted.

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
Vitamin A induced benign intracranial hypertension.
1976 Feb
Effect of avitaminosis A and hypervitaminosis A on urinary bladder carcinogenicity of N-(4-(5-Nitro-2-furyl)-2-thiazolyl)formamide.
1976 Jul
McCollum Award Lecture, 1992: vitamin A absorption, transport, cellular uptake, and storage.
1992 Oct
Vitamin A induced stellate cell hyperplasia and fibrosis in renal failure.
2000 Jan
Hepatic hyper-vitaminosis A: importance of retinyl ester level determination.
2000 Mar
Low serum retinol levels are associated with hepatocellular carcinoma in patients with chronic liver disease.
2000 Oct
[Hypercalcemia due to chronic vitamin A use by an elderly patient with renal insufficiency].
2001 Jan 13
Influence of vitamin A status on the regulation of uridine (5'-)diphosphate-glucuronosyltransferase (UGT) 1A1 and UGT1A6 expression by L-triiodothyronine.
2001 Mar
Restoring effects of vitamin A on surfactant synthesis in nitrofen-induced congenital diaphragmatic hernia in rats.
2001 Sep 15
[Treatment of acne with consequences -- pseudotumor cerebri due to hypervitaminosis A].
2002 Jan 9
Impact of 'Mad Cow Disease' publicity on trends in meat and total vitamin A consumption in Geneva between 1993 and 2000.
2003 Jan
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
Inverse gene expression patterns for macrophage activating hepatotoxicants and peroxisome proliferators in rat liver.
2004 Jun 1
Hypercalcaemia from non-prescription vitamin A.
2004 Nov
Age differences in vitamin A intake among Canadian Inuit.
2004 Nov-Dec
Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on vitamin A metabolism in mice.
2005
Alcohol, vitamin A, and cancer.
2005 Apr
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
Vitamin A deficiency induces prooxidant environment and inflammation in rat aorta.
2005 Jun
Vitamin A supplementation for extremely low birth weight infants: outcome at 18 to 22 months.
2005 Mar
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
Vitamin A supplementation induces adipose tissue loss through apoptosis in lean but not in obese rats of the WNIN/Ob strain.
2005 Oct
Acyl coenzyme A dependent retinol esterification by acyl coenzyme A: diacylglycerol acyltransferase 1.
2005 Oct 15
Mutation of key residues of RPE65 abolishes its enzymatic role as isomerohydrolase in the visual cycle.
2005 Sep 20
Hypervitaminosis A resulting in DNA aberration in fetal transgenic mice (Muta Mouse).
2005 Sep 5
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
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
Hypervitaminosis A-induced liver fibrosis: stellate cell activation and daily dose consumption.
2006 Mar
Patents

Sample Use Guides

Retinol should be administered orally or by intramuscular injection. For skin conditions retinol is applied topically.
Route of Administration: Other
Kinetic analyses of retinol esterification by lecithin retinol acyltransferase (LRAT) were carried out by measuring the rates of 3H-all-trans-retinyl ester formation under conditions where 3H-all-trans-retinol was varied at saturating lecithin concentrations. LRAT catalyzes esterification of retinol with Km of 0.94 uM.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:22:03 UTC 2023
Edited
by admin
on Wed Jul 05 23:22:03 UTC 2023
Record UNII
G2SH0XKK91
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RETINOL
HSDB   INCI   INN   WHO-DD  
INN   INCI  
Official Name English
NSC-122759
Code 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
RETINOL [INCI]
Common Name English
Classification Tree Code System Code
WHO-VATC QR01AX02
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
LOINC 20947-8
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
LOINC 14905-4
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
WHO-VATC QS01XA02
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
NCI_THESAURUS C68299
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
NCI_THESAURUS C938
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
WHO-VATC QD10AD02
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 27
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
LOINC 20948-6
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
DSLD 3441 (Number of products:6)
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
WHO-ATC S01XA02
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
WHO-ATC A11CA01
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
EU-Orphan Drug EU/3/17/1895
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
LOINC 20946-0
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
LOINC 87673-0
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
LOINC 2923-1
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
WHO-ATC D10AD02
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
WHO-ATC R01AX02
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
WHO-VATC QA11CA01
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
LOINC 2922-3
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
Code System Code Type Description
DRUG CENTRAL
2831
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID3023556
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
CHEBI
45479
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
CAS
68-26-8
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
RXCUI
1367187
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY RxNorm
PUBCHEM
445354
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
DRUG BANK
DB00162
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
HSDB
815
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
ChEMBL
CHEMBL986
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
CHEBI
50211
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
INN
2243
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
WIKIPEDIA
RETINOL
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
FDA UNII
G2SH0XKK91
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
CHEBI
17336
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-683-7
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
EVMPD
SUB16102MIG
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
NCI_THESAURUS
C68302
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
DAILYMED
G2SH0XKK91
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
NSC
122759
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY
MERCK INDEX
M11481
Created by admin on Wed Jul 05 23:22:03 UTC 2023 , Edited by admin on Wed Jul 05 23:22:03 UTC 2023
PRIMARY Merck Index
Related Record Type Details
ACTIVE MOIETY