Record Information
Version1.0
Creation date2010-04-08 22:05:06 UTC
Update date2019-11-26 02:56:39 UTC
Primary IDFDB001761
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameApo-15-zeaxanthinal
DescriptionApo-15-zeaxanthinal, also known as (-)-(R)-all-trans-3-hydroxyretinal, is a member of the class of compounds known as retinoids. Retinoids are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Thus, apo-15-zeaxanthinal is considered to be an isoprenoid lipid molecule. Apo-15-zeaxanthinal is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Apo-15-zeaxanthinal can be found in a number of food items such as red bell pepper, pepper (c. annuum), green bell pepper, and italian sweet red pepper, which makes apo-15-zeaxanthinal a potential biomarker for the consumption of these food products.
CAS Number60046-53-9
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP5.41ALOGPS
logP3.47ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)18.91ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.53 m³·mol⁻¹ChemAxon
Polarizability36.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H28O2
IUPAC name(2E,4E,6E,8E)-9-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenal
InChI IdentifierInChI=1S/C20H28O2/c1-15(7-6-8-16(2)11-12-21)9-10-19-17(3)13-18(22)14-20(19,4)5/h6-12,18,22H,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-11+/t18-/m1/s1
InChI KeyQPRQNCDEPWLQRO-ZCEAMUHZSA-N
Isomeric SMILESO=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C
Average Molecular Weight300.4351
Monoisotopic Molecular Weight300.20893014
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
  • Secondary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)Not Available2022-08-06View Spectrum
Predicted GC-MSApo-15-zeaxanthinal, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-6f1827d978a7af571b952016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-0090000000-e33093f76e973f2c51bd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kuu-3490000000-85fce3c6e95e75c84f702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dj-0090000000-278c0fa598d6deffd1362021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0l6r-0190000000-a8fd41c4171a15d025a42021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1490000000-15f17b7d3f91fa89d45e2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0393000000-a90c31e618611c8a66082016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-1960000000-66b51a6069e97fbeae7c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-8920000000-69fe9abac7ad7fc3a7f32016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0k9x-0972000000-18ea9dd309fbc0744cda2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-1790000000-f00fcf0aee0791e1c7962021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-7900000000-09aeb4970c071dd9fee02021-10-21View Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00022188
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Green bell pepperExpected but not quantifiedNot AvailableKNAPSACK
Italian sweet red pepperExpected but not quantifiedNot AvailableKNAPSACK
Orange bell pepperExpected but not quantifiedNot AvailableKNAPSACK
PepperExpected but not quantifiedNot AvailableKNAPSACK
Red bell pepperExpected but not quantifiedNot AvailableKNAPSACK
Yellow bell pepperExpected but not quantifiedNot AvailableKNAPSACK
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.