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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:32 UTC
Update Date2020-04-21 15:25:29 UTC
HMDB IDHMDB0003101
Secondary Accession Numbers
  • HMDB03101
Metabolite Identification
Common NameViolaxanthin
DescriptionViolaxanthin 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. Xanthophylls arise by oxygenation of the carotene backbone. Thus, violaxanthin is considered to be an isoprenoid lipid molecule. Violaxanthin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Violaxanthin is an orange-coloured pigment that is found in brown algae and various plants (e.g. pansies). It is biosynthesized from the epoxidation of zeaxanthin. Violaxanthin is a food additive that is only approved for use in Australia and New Zealand (INS: 161e) (PMID: 29890662 ).
Structure
Data?1587482729
Synonyms
ValueSource
(3S,3's,5R,5'r,6S,6's)-5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene-3,3'-diolChEBI
(3S,5R,6S,3's,5'r,6's)-5,6,5',6'-DIEPOXY-5,6,5',6'-tetrahydro-BETA,BETA-carotene-3,3'-diolChEBI
e 161EChEBI
all-trans-ViolaxanthinKegg
(3S,3's,5R,5'r,6S,6's)-5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-b,b-carotene-3,3'-diolGenerator
(3S,3's,5R,5'r,6S,6's)-5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-β,β-carotene-3,3'-diolGenerator
(3S,5R,6S,3's,5'r,6's)-5,6,5',6'-DIEPOXY-5,6,5',6'-tetrahydro-b,b-carotene-3,3'-diolGenerator
(3S,5R,6S,3's,5'r,6's)-5,6,5',6'-DIEPOXY-5,6,5',6'-tetrahydro-β,β-carotene-3,3'-diolGenerator
Zeaxanthin diepoxideMeSH
5,6:5',6'-Diepoxy-5,5',6,6'- tetrahydro-beta-carotene-3,3'-diolMeSH
(3S,3’S,5R,5’R,6S,6’S)-5,6:5’,6’-Diepoxy-5,5’,6,6’-tetrahydro-β,β-carotene-3,3’-diolHMDB
ViolaxanthinHMDB
all-E-ViolaxanthinHMDB
trans-ViolaxanthinHMDB
5,6:5′,6′-Diepoxy-5,5′,6,6′-tetrahydro-beta-carotene-3,3′-diolHMDB
5,6:5′,6′-Diepoxy-5,5′,6,6′-tetrahydro-β-carotene-3,3′-diolHMDB
Chemical FormulaC40H56O4
Average Molecular Weight600.884
Monoisotopic Molecular Weight600.417860283
IUPAC Name(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-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
Traditional Nameviolaxanthin
CAS Registry Number126-29-4
SMILES
C\C(\C=C\C=C(/C)\C=C\[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C
InChI Identifier
InChI=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+/t33-,34-,37+,38+,39-,40-/m0/s1
InChI KeySZCBXWMUOPQSOX-WVJDLNGLSA-N
Chemical Taxonomy
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 Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point208 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot 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 Area62.22 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity192.33 m³·mol⁻¹ChemAxon
Polarizability74.54 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0032597000-af64159ae48b8e1fa899Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ai-0295531000-02d9985c675cc61fb2a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xr-3494200000-f5d8d58d659ed07feca7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-ced1b1342da183c34f3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0100090000-01c9d49ff3b710660a47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3700490000-fec974be88afdb5602d9Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03460
Phenol Explorer Compound IDNot Available
FooDB IDFDB015879
KNApSAcK IDC00003787
Chemspider ID395237
KEGG Compound IDC08614
BioCyc IDCPD1F-133
BiGG IDNot Available
Wikipedia LinkViolaxanthin
METLIN IDNot Available
PubChem Compound448438
PDB IDNot Available
ChEBI ID35288
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceAcemoglu, Murat; Uebelhart, Peter; Rey, Max; Eugster, Conrad Hans. , Zurich, Zurich, Switz. Syntheses of enantiomerically pure violaxanthins and related compounds. Helvetica Chimica Acta (1988), 71(5), 931-56.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wehner A, Grasses T, Jahns P: De-epoxidation of violaxanthin in the minor antenna proteins of photosystem II, LHCB4, LHCB5, and LHCB6. J Biol Chem. 2006 Aug 4;281(31):21924-33. Epub 2006 Jun 5. [PubMed:16754673 ]
  2. Czeczuga-Semeniuk E, Wolczynski S: Identification of carotenoids in ovarian tissue in women. Oncol Rep. 2005 Nov;14(5):1385-92. [PubMed:16211314 ]
  3. Latowski D, Kruk J, Burda K, Skrzynecka-Jaskier M, Kostecka-Gugala A, Strzalka K: Kinetics of violaxanthin de-epoxidation by violaxanthin de-epoxidase, a xanthophyll cycle enzyme, is regulated by membrane fluidity in model lipid bilayers. Eur J Biochem. 2002 Sep;269(18):4656-65. [PubMed:12230579 ]
  4. Torregrosa-Crespo J, Montero Z, Fuentes JL, Reig Garcia-Galbis M, Garbayo I, Vilchez C, Martinez-Espinosa RM: Exploring the Valuable Carotenoids for the Large-Scale Production by Marine Microorganisms. Mar Drugs. 2018 Jun 8;16(6). pii: md16060203. doi: 10.3390/md16060203. [PubMed:29890662 ]