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beta-Cryptoxanthin (FDB012019)

Record Information
Version1.0
Creation date2010-04-08 22:09:57 UTC
Update date2019-11-26 03:05:58 UTC
Primary IDFDB012019
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namebeta-Cryptoxanthin
Descriptionbeta-Cryptoxanthin, also known as 3-hydroxy-b-carotene or b,b-caroten-3-ol, 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. beta-Cryptoxanthin is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number472-70-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0005 g/LALOGPS
logP9.08ALOGPS
logP9.74ChemAxon
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
Refractivity193.28 m³·mol⁻¹ChemAxon
Polarizability72.71 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,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-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/h11-14,16-21,23-26,36,41H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+
InChI KeyDMASLKHVQRHNES-QQGJMDNJSA-N
Isomeric SMILESC\C(\C=C\C=C(/C)\C=C\C1=C(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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 86.90%; H 10.21%; O 2.89%DFC
Melting PointMp 172-173° (169°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data480 () (no solvent reported)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSbeta-Cryptoxanthin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1000190000-56ac432f8bd5a3e11667Spectrum
Predicted GC-MSbeta-Cryptoxanthin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0bt9-4100039000-889b04a7bfe4d06209e4Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0423290000-bf7a8e40a11eff7bfe3c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0649100000-9c3f50cab7f2d02e22fd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002k-0569000000-8a2e2a50f957c26b3ab12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-d34ae69e503c3f3819112016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000090000-2fe3377fd40bc851dfc42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0546190000-d1d53215d44121d136842016-08-03View Spectrum
NMRNot Available
ChemSpider ID4904571
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6384256
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33844
CRC / DFC (Dictionary of Food Compounds) IDHCP52-Y:HCP52-Y
EAFUS IDNot Available
Dr. Duke IDNEOCRYPTOXANTHIN|CRYTOXANTHIN|KRYPTOXANTHIN|CRYPTOXANTHIN|BETA-CRYPTOXANTHIN
BIGG IDNot Available
KNApSAcK IDC00000920
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCryptoxanthin
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
anti mutagenicDUKE
colorant37958 DUKE
vitamin-A activityDUKE
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.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— 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.