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alpha-Cryptoxanthin (FDB015827)

Record Information
Version1.0
Creation date2010-04-08 22:12:04 UTC
Update date2019-11-26 03:12:17 UTC
Primary IDFDB015827
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-Cryptoxanthin
Descriptionalpha-Cryptoxanthin, also known as α-cryptoxanthin, 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. alpha-Cryptoxanthin is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number24480-38-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00054 g/LALOGPS
logP9.19ALOGPS
logP9.78ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.91ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity193.55 m³·mol⁻¹ChemAxon
Polarizability71.52 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC40H56O
IUPAC name3,5,5-trimethyl-4-[(1E,3Z,5E,7E,9Z,11E,13Z,15Z,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-2-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-3-en-1-ol
InChI IdentifierInChI=1S/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-26,36-37,41H,15,27-29H2,1-10H3/b12-11-,18-13-,19-14+,25-23+,26-24+,30-16+,31-17+,32-20-,33-21-
InChI KeyNBZANZVJRKXVBH-QYIWYULDSA-N
Isomeric SMILESC\C(\C=C/C=C(/C)\C=C\C1C(C)=CCCC1(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 Weight552.872
Monoisotopic Molecular Weight552.433116414
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
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 86.90%; H 10.21%; O 2.89%DFC
Melting PointMp 175-176° (157.5-158.5°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -508.3 (c, 0.36 in Me2CO)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, Positivesplash10-0f79-0423290000-7f59c262ef004e78ee7a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0649100000-104f8d87c85f4fe4e1872016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002k-0569200000-81dbadb0b33e8edc45362016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-f1fb94bebc1ea7fc8a942016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000090000-70345a8f9e69fa5f01842016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0835290000-91db63b94bbcdf2139142016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC15981
Pubchem Compound ID23724629
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02268
CRC / DFC (Dictionary of Food Compounds) IDKJR65-S:KJR65-S
EAFUS IDNot Available
Dr. Duke IDZEINOXANTHIN|3-HYDROXY-ALPHA-CAROTENE|ALPHA-CRYPTOXANTHIN|HYDROXY-ALPHA-CAROTENE
BIGG IDNot Available
KNApSAcK IDC00003770
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 / Bioactivities
DescriptorIDDefinitionReference
colorant37958 DUKE
vitamin-A activityDUKE
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.
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.