Record Information
Version1.0
Creation date2011-09-21 00:16:12 UTC
Update date2019-11-26 03:21:04 UTC
Primary IDFDB022576
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRetinal
DescriptionA carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in "dark" reactions to return to the native trans-configuration. [HMDB]. Retinal is found in many foods, some of which are flaxseed, pepper (c. baccatum), climbing bean, and other soy product.
CAS Number116-31-4
Structure
Thumb
Synonyms
SynonymSource
all-trans-RetinaldehydeChEBI
all-trans-RetineneChEBI
all-trans-Vitamin a aldehydeChEBI
RetinaldehydeChEBI
RetineneChEBI
Vitamin a aldehydeChEBI
all-trans-RetinalKegg
Aldehyde, vitamin aHMDB
AxerophthalHMDB
11 cis RetinalHMDB
11-cis-RetinalHMDB
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenalHMDB
all-e-RetinalHMDB
all-epsilon-RetinalHMDB
alpha-RetineneHMDB
e-RetinalHMDB
epsilon-RetinalHMDB
Retinene 1HMDB
trans-RetinalHMDB
trans-Vitamin a aldehydeHMDB
Vitamin a1 aldehydeHMDB
3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-Nonatetraenalhmdb
all-E-Retinalhmdb
All-trans-Retinalhmdb
all-trans-retinenehmdb
all-trans-Vitamin A aldehydehmdb
E-Retinalhmdb
Retinalhmdb
trans-Vitamin A aldehydehmdb
Vitamin A aldehydehmdb
Vitamin A1 aldehydehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0042 g/LALOGPS
logP6.62ALOGPS
logP4.86ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.87 m³·mol⁻¹ChemAxon
Polarizability35.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H28O
IUPAC name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
InChI IdentifierInChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
InChI KeyNCYCYZXNIZJOKI-OVSJKPMPSA-N
Isomeric SMILESC\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O
Average Molecular Weight284.4357
Monoisotopic Molecular Weight284.214015518
Classification
Description Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Retinoid skeleton
  • Diterpenoid
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSRetinal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-2290000000-df9d2aa7545cc60a54f9Spectrum
Predicted GC-MSRetinal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9700000000-c2e22000dfae0765c367Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03g0-0950000000-bccf87de037f98873f41Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-01t9-1910000000-5fe7643c395769c68286Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9700000000-fca532f917595376d653Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0490000000-f543f08fbaf94a2e3f8eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3940000000-74f087cc812b3715e7acSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fri-9830000000-72a5d01c6181340ad986Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-bad35938b77f181c29b9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-1aadad0770df07f98436Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ko-4690000000-f624d342f88456375b9cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00n3-1960000000-43f8c66f164764c37361Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0609-3920000000-dbeab0a82b306761cf6aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-7900000000-d2bb7c1aeeb87d8833d2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-0090000000-2ec2f8f314943441fa15Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0190000000-312cebb17ccd0189ab4dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1590000000-b2551eac481c0c930a4dSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID553582
ChEMBL IDCHEMBL81379
KEGG Compound IDC00376
Pubchem Compound ID638015
Pubchem Substance IDNot Available
ChEBI ID17898
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01358
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34795
KNApSAcK IDNot Available
HET IDRET
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDRetinal
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Retinol dehydrogenase 8RDH8Q9NYR8
Retinol dehydrogenase 11RDH11Q8TC12
Retinol dehydrogenase 10RDH10Q8IZV5
Short-chain dehydrogenase/reductase 3DHRS3O75911
Pathways
NameSMPDB LinkKEGG Link
Retinol MetabolismSMP00074 map00830
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference