Common NameAll-trans-retinol
DescriptionVitamin A (retinol) is a yellow fat-soluble, antioxidant vitamin important in vision and bone growth. It belongs to the family of chemical compounds known as retinoids. Retinol is ingested in a precursor form; animal sources (milk and eggs) contain retinyl esters, whereas plants (carrots, spinach) contain pro-vitamin A carotenoids. Hydrolysis of retinyl esters results in retinol while pro-vitamin A carotenoids can be cleaved to produce retinal. Retinal, also known as retinaldehyde, can be reversibly reduced to produce retinol or it can be irreversibly oxidized to produce retinoic acid. Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of carotenoids found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.
Structure
Molecular FormulaC20H30O
Average Mass286.45160
Monoisotopic Mass286.22967
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
Traditional NameVitamin a
CAS Registry Number68-26-8
SMILESCC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO)C(C)(C)CCC1
InChI IdentifierInChI=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+
InChI KeyFPIPGXGPPPQFEQ-OVSJKPMPSA-N
CHEBI IDCHEBI:17336
HMDB IDHMDB0000305
Pathways
NameSMPDB/PathBank
Retinol Metabolism
Vitamin A Deficiency
StateNot Available
Water Solubility7.58e-03 g/l
logP6.38
logS-4.58
pKa (Strongest Acidic)16.44
pKa (Strongest Basic)-2.17
Hydrogen Acceptor Count1
Hydrogen Donor Count1
Polar Surface Area20.23 Ų
Rotatable Bond Count5
Physiological Charge0
Formal Charge0
Refractivity97.92 m³·mol⁻¹
Polarizability36.56

We require the use of cookies for essential features like storing your previously submitted BASys2 queries. Rejecting the usage of cookies will result in certain features being disabled. By clicking ACCEPT or continuing to use the website you are agreeing to our use of cookies.

ACCEPT