3,4-Didehydroretinol (CHEM029118)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:56:37 UTC
Update Date2016-11-09 01:18:49 UTC
Accession NumberCHEM029118
Identification
Common Name3,4-Didehydroretinol
ClassSmall Molecule
DescriptionA retinoid derived from 3,4-desaturation of the beta-ionone ring of all-trans-retinol.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)nona-2,4,6,8-tetraen-1-olChEBI
3,4-Didehydro-all-trans-retinolChEBI
3,4-Didehydro-retinolChEBI
3-DehydoretinolChEBI
all-trans-3-DehydroretinolChEBI
DehydroretinolChEBI
all-trans-3,4-Didehydro retinolHMDB
3,4-DidehydroretinolHMDB
all-trans-3,4-DidehydroretinolHMDB
VA2HMDB
Vitamin a2, (7-cis)-isomerHMDB
3-DehydroretinolHMDB
Vitamin a2ChEBI
Chemical FormulaC20H28O
Average Molecular Mass284.436 g/mol
Monoisotopic Mass284.214 g/mol
CAS Registry Number79-80-1
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)nona-2,4,6,8-tetraen-1-ol
Traditional Namevitamin A 2
SMILESC\C(=C/CO)\C=C\C=C(\C)/C=C/C1=C(C)C=CCC1(C)C
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/h6-13,21H,14-15H2,1-5H3/b9-6+,12-11+,16-8-,17-13+
InChI KeyXWCYDHJOKKGVHC-MKOSUFFBSA-N
Chemical Taxonomy
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
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP5.66ALOGPS
logP4.33ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)16.44ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity99.04 m³·mol⁻¹ChemAxon
Polarizability36.02 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2190000000-3b869065c87d36ed5099Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-8249000000-a550d49727292f80b946Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-1490000000-49ea807dd5aeee7b2838Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-4920000000-96a6d30e24b05021a4d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lei-9820000000-418a688bdad32f088009Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-b56b2d201cdf5f15c840Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0090000000-f93bb9c048e242947532Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-4690000000-10339a6c3a7b2054420eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-219cda37112b6df644daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uei-0190000000-b80f73b4a9625edad010Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0690000000-008f73bd4d70cae5d8acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01bi-0790000000-16543321cc9076d8847cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-1910000000-6a3650fca0f7a58e3cfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tf-4900000000-b2b2774f095b7867f567Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013117
FooDB IDFDB013830
Phenol Explorer IDNot Available
KNApSAcK IDC00044897
BiGG IDNot Available
BioCyc IDCPD-20073
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDehydroretinal
Chemspider ID4940721
ChEBI ID132246
PubChem Compound ID6436043
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12584011
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1768425
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1789986
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19043141
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=2087172
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21895779
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22307745
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22959581
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24330939
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=26549260
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=27059013
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=2856858
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=28701464
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=28776449
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=31548472
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=3367238
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=3390455
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=3654104
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=3874747
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=4067325
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=7371787
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=7720529
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=7803489
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=8032128
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=8352734
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=8592069
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=9080660
28.
29. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
30. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
31. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
32. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
33. The lipid handbook with CD-ROM