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Violaxanthin (FDB014725)

Record Information
Version1.0
Creation date2010-04-08 22:11:26 UTC
Update date2019-11-26 03:10:40 UTC
Primary IDFDB014725
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameViolaxanthin
Description(all-e)-violaxanthin 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 (all-e)-violaxanthin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (all-e)-violaxanthin can be found in a number of food items such as orange bell pepper, green bell pepper, passion fruit, and yellow bell pepper, which makes (all-e)-violaxanthin a potential biomarker for the consumption of these food products.
CAS Number126-29-4
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00057 g/LALOGPS
logP8.33ALOGPS
logP7.26ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)14.84ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.52 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity192.33 m³·mol⁻¹ChemAxon
Polarizability74.98 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC40H56O4
IUPAC name6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
InChI IdentifierInChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+
InChI KeySZCBXWMUOPQSOX-DKLMTRRASA-N
Isomeric SMILESC\C(\C=C\C=C(/C)\C=C\C12OC1(C)CC(O)CC2(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C12OC1(C)CC(O)CC2(C)C
Average Molecular Weight600.8702
Monoisotopic Molecular Weight600.41786028
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
  • Oxepane
  • Cyclic alcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 79.96%; H 9.39%; O 10.65%DFC
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-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0032597000-af64159ae48b8e1fa8992016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ai-0295531000-02d9985c675cc61fb2a62016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xr-3494200000-f5d8d58d659ed07feca72016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-ced1b1342da183c34f3f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0100090000-01c9d49ff3b710660a472016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3700490000-fec974be88afdb5602d92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-ba6a2d7c7dd422ee3fac2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0101290000-0a64d5ce5ee7ec9d7fa02021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052s-0917060000-8099c000bfa6a9628b902021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0011092000-e0d8754827bbad0fb75f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0012090000-21b243d8ae4fd22288b52021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1259320000-31706a73dcec9fb477d22021-10-21View 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) IDJVG51-D:JVG51-D
EAFUS IDNot Available
Dr. Duke IDVIOLAXANTHIN
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
colorant37958 DUKE
ubiquiotDUKE
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).