Back to Compounds

(all-E)-Violaxanthin (FDB015879)

Record Information
Version1.0
Creation date2010-04-08 22:12:06 UTC
Update date2019-11-26 03:12:22 UTC
Primary IDFDB015879
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(all-E)-Violaxanthin
Description3 (violaxanthin, zeaxanthin and antheraxanthin) participate in series of photo-induced interconversions known as ''violaxanthin cycle''; Xanthophyll; a carotene epoxide that is precursor to capsanthin; cleavage of 9-cis-epoxycarotenoids (violaxanthin) to xanthoxin, catalyzed by 9-cis-epoxycarotenoid dioxygenase, is the key regulatory step of abscisic acid biosynthesis; one of 3 xanthophylls involved in evolution of plastids of green plants (oxygen evolution). (all-E)-Violaxanthin is found in many foods, some of which are orange bell pepper, passion fruit, pepper (c. annuum), and italian sweet red pepper.
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 - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 79.96%; H 9.39%; O 10.65%DFC
Melting PointMp 208°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +38 (CHCl3)DFC
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 IDC08614
Pubchem Compound ID53477762
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03101
CRC / DFC (Dictionary of Food Compounds) IDJVG51-D:KKH11-I
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00003787
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 / 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.