Record Information
Version1.0
Creation date2011-09-21 00:23:59 UTC
Update date2015-07-21 06:57:29 UTC
Primary IDFDB023058
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFucoxanthin
DescriptionFucoxanthin is a carotenoid, with formula C40H60O6. It is found as an accessory pigment in the chloroplasts of brown algae and most other heterokonts, giving them a brown or olive-green color. Fucoxanthin absorbs light primarily in the blue-green to yellow-green part of the visible spectrum, peaking at around 510-525 nm by various estimates and absorbing significantly in the range of 450 to 540 nm. -- Wikipedia [HMDB]
CAS Number3351-86-8
Structure
Thumb
Synonyms
SynonymSource
3'-Acetate-(7ci)-6',7'-didehydro-5,6-epoxy-4',5,5',6,7,8-hexahydro-3,3',5'-trihydroxy-8-oxo-a-caroteneHMDB
3'-Acetate-(7ci)-6',7'-didehydro-5,6-epoxy-4',5,5',6,7,8-hexahydro-3,3',5'-trihydroxy-8-oxo-alpha-caroteneHMDB
all-trans-FucoxanthinHMDB
3-Hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-3,5,5-trimethylcyclohexyl acetic acidGenerator, HMDB
3'-acetate-(7CI)-6',7'-didehydro-5,6-epoxy-4',5,5',6,7,8-hexahydro-3,3',5'-trihydroxy-8-oxo-a-carotenehmdb
3'-acetate-(7CI)-6',7'-didehydro-5,6-epoxy-4',5,5',6,7,8-hexahydro-3,3',5'-trihydroxy-8-oxo-alpha-carotenehmdb
Fucoxanthinhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00058 g/LALOGPS
logP7.54ALOGPS
logP6.83ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)14.03ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area96.36 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity202.76 m³·mol⁻¹ChemAxon
Polarizability78.29 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC42H58O6
IUPAC name3-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-3,5,5-trimethylcyclohexyl acetate
InChI IdentifierInChI=1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+
InChI KeySJWWTRQNNRNTPU-BWRPRJLXSA-N
Isomeric SMILESCC(=O)OC1CC(C)(C)C(=C=C\C(C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)C(=O)CC23OC2(C)CC(O)CC3(C)C)C(C)(O)C1
Average Molecular Weight658.9063
Monoisotopic Molecular Weight658.423339588
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
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Acryloyl-group
  • Cyclic alcohol
  • Enone
  • Tertiary alcohol
  • Alpha,beta-unsaturated ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
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-MS
TypeDescriptionSplash KeyView
Predicted GC-MSFucoxanthin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-6100569000-dc17b7cf6b9e6d787d62Spectrum
Predicted GC-MSFucoxanthin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFucoxanthin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFucoxanthin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFucoxanthin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFucoxanthin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFucoxanthin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFucoxanthin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFucoxanthin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFucoxanthin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFucoxanthin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFucoxanthin, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFucoxanthin, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFucoxanthin, "Fucoxanthin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0077-0400729000-f2de10007b4a1af17be92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0230911000-4cfe3cce1a708eb557d32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi1-1576900000-18a3b752aa3cd01f622e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4s-1400129000-6d000a9b56e4e44935712017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-4500549000-be7eb19143d533d9bf8d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-9800583000-69a5aa368c41cf1af3a62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0100059000-684d49231a5fa79e76042021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200132000-a85467109d0a3354f0d42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9211301000-56fc91d6b78ccbe676892021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0002159000-92a27db38a66d48237f12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003u-0114895000-30b23f7cacc3883252cb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002s-0528900000-081c56f6cc1ee22150c52021-09-22View Spectrum
NMRNot Available
ChemSpider ID4516336
ChEMBL IDNot Available
KEGG Compound IDC08596
Pubchem Compound ID5364094
Pubchem Substance IDNot Available
ChEBI ID5186
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02741
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
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 IDFucoxanthin
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