Capsanthin (CHEM030259)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:46:27 UTC
Update Date2016-11-09 01:19:02 UTC
Accession NumberCHEM030259
Identification
Common NameCapsanthin
ClassSmall Molecule
DescriptionCapsanthin is found in green vegetables. Capsanthin is a constituent of paprika (Capsicum annuum) and asparagus (Asparagus officinalis). Potential nutriceutical.Paprika oleoresin (also known as paprika extract) is an oil soluble extract from the fruits of Capsicum Annum Linn or Capsicum Frutescens(Indian red chillies), and is primarily used as a colouring and/or flavouring in food products. It is composed of capsaicin, the main flavouring compound giving pungency in higher concentrations, and capsanthin and capsorubin, the main colouring compounds (among other carotenoids)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3R,3's,5'r)-3,3'-Dihydroxy-beta,kappa-caroten-6'-oneHMDB
3,3'-Dihydroxy-b,K-caroten-6'-oneHMDB
3,3'-Dihydroxy-beta,kappa-caroten-6'oneHMDB
3,3'Dihydroxy-beta,kappa-caroten-6'oneHMDB
Capsanthin/capsorubinHMDB
Paprika extractHMDB
Chemical FormulaC40H56O3
Average Molecular Mass584.871 g/mol
Monoisotopic Mass584.423 g/mol
CAS Registry Number465-42-9
IUPAC Name(2E,4Z,6E,8E,10E,12E,14E,16Z,18E)-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)-19-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
Traditional Name(2E,4Z,6E,8E,10E,12E,14E,16Z,18E)-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)-19-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
SMILESC/C(/C=C/C=C(/C)\C=C\C(=O)C1(C)CC(O)CC1(C)C)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CC(O)CC1(C)C
InChI IdentifierInChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-23-36-33(5)25-34(41)26-38(36,6)7)15-11-12-16-30(2)18-14-20-32(4)22-24-37(43)40(10)28-35(42)27-39(40,8)9/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19-,32-20-
InChI KeyVYIRVAXUEZSDNC-QGLVDCRNSA-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
  • Cyclopentanol
  • Alpha,beta-unsaturated ketone
  • Enone
  • Cyclic alcohol
  • Acryloyl-group
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00068 g/LALOGPS
logP8.2ALOGPS
logP8.51ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)15.21ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity194.96 m³·mol⁻¹ChemAxon
Polarizability73.9 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-1000390000-9168df6e83b6f3559682Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-2100219000-d6685bf191ff1d9cf61dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Capsanthin,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0110290000-8efbbb300dc99ca54e94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-0635960000-c46df5f79c0b8400f6ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07dk-0946620000-b7f05289e89d51313099Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0100090000-cccefbb02a471fcf8ba5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-0200390000-14a64216d2c88e3204abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uy0-0600590000-34c915ac447d608bc04aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0012090000-38f2d4ce91fe1eceb204Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3003290000-32dc16dd3f2a023f4f61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004s-0349310000-3f91fe727242c79d0ec5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002u-0002490000-143e5096de33d87d6b7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014s-0013940000-6a388220c76ac3f2e22eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-0434900000-7855f730399ae0a5dd54Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0036590
FooDB IDFDB015502
Phenol Explorer IDNot Available
KNApSAcK IDC00003763
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPaprika oleoresin
Chemspider ID8048820
ChEBI ID3375
PubChem Compound ID9873131
Kegg Compound IDC08584
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Zhang X, Zhao WE, Hu L, Zhao L, Huang J: Carotenoids inhibit proliferation and regulate expression of peroxisome proliferators-activated receptor gamma (PPARgamma) in K562 cancer cells. Arch Biochem Biophys. 2011 Aug 1;512(1):96-106. doi: 10.1016/j.abb.2011.05.004. Epub 2011 May 18.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
7. The lipid handbook with CD-ROM