Record Information
Version1.0
Creation date2010-04-08 22:11:53 UTC
Update date2019-11-26 03:11:42 UTC
Primary IDFDB015502
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCapsanthin
DescriptionConstituent 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). Capsanthin is found in many foods, some of which are italian sweet red pepper, red bell pepper, herbs and spices, and pepper (c. annuum).
CAS Number465-42-9
Structure
Thumb
Synonyms
SynonymSource
(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
(3R,3'S,5'R)-3,3'-Dihydroxy-beta,kappa-caroten-6'-onebiospider
3,3'-Dihydroxy-b,k-caroten-6'-onedb_source
beta,kappa-Caroten-6'one, 3,3'dihydroxy-biospider
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC40H56O3
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
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
Isomeric 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
Average Molecular Weight584.8708
Monoisotopic Molecular Weight584.422945658
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
  • 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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 82.14%; H 9.65%; O 8.21%DFC
Melting PointMp 175-176°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]643.8 +36 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-1000390000-9168df6e83b6f3559682JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-2100219000-d6685bf191ff1d9cf61dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0110290000-8efbbb300dc99ca54e94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-0635960000-c46df5f79c0b8400f6ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07dk-0946620000-b7f05289e89d51313099JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0100090000-cccefbb02a471fcf8ba5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-0200390000-14a64216d2c88e3204abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uy0-0600590000-34c915ac447d608bc04aJSpectraViewer
ChemSpider ID8048820
ChEMBL IDNot Available
KEGG Compound IDC08584
Pubchem Compound ID9873131
Pubchem Substance IDNot Available
ChEBI ID3375
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36590
CRC / DFC (Dictionary of Food Compounds) IDKCW33-J:KCW33-J
EAFUS IDNot Available
Dr. Duke IDCAPSANTHIN
BIGG IDNot Available
KNApSAcK IDC00003763
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCapsanthin
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
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
colorant37958 DUKE
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.