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Showing Compound 5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol (FDB021644)

Record Information
Version1.0
Creation date2011-03-17 23:25:28 UTC
Update date2019-11-26 03:20:39 UTC
Primary IDFDB021644
Secondary Accession Numbers
  • FDB013577
Chemical Information
FooDB Name5,6-Dihydro-b,b-carotene-3,3',5,6-tetrol
Description6-epikarpoxanthin is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. 6-epikarpoxanthin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 6-epikarpoxanthin can be found in a number of food items such as italian sweet red pepper, herbs and spices, fruits, and orange bell pepper, which makes 6-epikarpoxanthin a potential biomarker for the consumption of these food products.
CAS Number24204-13-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0011 g/LALOGPS
logP7ALOGPS
logP6.64ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)12.91ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity197.15 m³·mol⁻¹ChemAxon
Polarizability74.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC40H58O4
IUPAC name1-[(1E,3E,5Z,7E,9E,11Z,13Z,15Z,17Z)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,6,6-trimethylcyclohexane-1,2,4-triol
InChI IdentifierInChI=1S/C40H58O4/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40(44)38(8,9)27-35(42)28-39(40,10)43/h11-24,34-35,41-44H,25-28H2,1-10H3/b12-11+,17-13-,18-14-,22-21-,24-23+,29-15-,30-16+,31-19-,32-20+
InChI KeyDJOWTWWHMWQATC-BXBIEBEISA-N
Isomeric SMILESC\C(\C=C/C=C(/C)\C=C/C1=C(C)CC(O)CC1(C)C)=C\C=C\C=C(/C)\C=C/C=C(\C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O
Average Molecular Weight602.8861
Monoisotopic Molecular Weight602.433510344
Classification
Description Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents
Substituents
  • Xanthophyll
  • Cyclohexanol
  • Cyclitol or derivatives
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS6-Epikarpoxanthin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06ri-0000090000-acb4e4149044f4d112d4Spectrum
Predicted GC-MS6-Epikarpoxanthin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4r-3100049000-2fa3c382577a3482f891Spectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TMS_4_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Epikarpoxanthin, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0101392000-48519b85d4347f66921d2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0654970000-045c9bae4cb850eaf1f82016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1695330000-aec5141eb2800222eeaf2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0200049000-1321c73aa9b8e9b284272016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-0200395000-d25c33c39dc8447722df2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-7801690000-5e6108606c87369759962016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0frj-0212392000-c059325956d7022012842021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0113390000-1450f4eeca05cc0493f92021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-0393200000-b9a60c3a508ece8935c92021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0100009000-73255f80d3f79b78afad2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0114396000-41f0f1fe0ee76d6712682021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aps-0434930000-027fb2fd2325729556b32021-09-24View Spectrum
NMRNot Available
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) IDMSM28-R:MSM28-R
EAFUS IDNot Available
Dr. Duke ID5,6-DIHYDROXY-5,6-DIHYDRO-ZEAXANTHIN
BIGG IDNot Available
KNApSAcK IDNot Available
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 IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).