beta-Cryptoxanthin (CHEM027984)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:08:16 UTC
Update Date2016-11-09 01:18:34 UTC
Accession NumberCHEM027984
Identification
Common Namebeta-Cryptoxanthin
ClassSmall Molecule
DescriptionIsolated from papaya (Carica papaya) and many other higher plants, also from fish eggs [DFC]. beta-Cryptoxanthin is found in many foods, some of which are smelt, soy yogurt, common carp, and rose hip.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
b-CryptoxanthinGenerator
Β-cryptoxanthinGenerator
3-Hydroxy-b-caroteneHMDB
b,b-Caroten-3-olHMDB
b-KrypoxanthinHMDB
CaricaxanthinHMDB
CryptoxanthinHMDB
CryptoxantholHMDB
NeocryptoxanthinHMDB
Chemical FormulaC40H56O
Average Molecular Mass552.872 g/mol
Monoisotopic Mass552.433 g/mol
CAS Registry Number472-70-8
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
Traditional 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
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
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
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
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Solubility0.0005 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1000190000-56ac432f8bd5a3e11667Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0bt9-4100039000-889b04a7bfe4d06209e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0423290000-bf7a8e40a11eff7bfe3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0649100000-9c3f50cab7f2d02e22fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002k-0569000000-8a2e2a50f957c26b3ab1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-d34ae69e503c3f381911Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000090000-2fe3377fd40bc851dfc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0546190000-d1d53215d44121d13684Spectrum
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 IDHMDB0033844
FooDB IDFDB012019
Phenol Explorer IDNot Available
KNApSAcK IDC00000920
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4904571
ChEBI IDNot Available
PubChem Compound ID6384256
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Wingerath T, Stahl W, Sies H: beta-Cryptoxanthin selectively increases in human chylomicrons upon ingestion of tangerine concentrate rich in beta-cryptoxanthin esters. Arch Biochem Biophys. 1995 Dec 20;324(2):385-90.
2. Irwig MS, El-Sohemy A, Baylin A, Rifai N, Campos H: Frequent intake of tropical fruits that are rich in beta-cryptoxanthin is associated with higher plasma beta-cryptoxanthin concentrations in Costa Rican adolescents. J Nutr. 2002 Oct;132(10):3161-7.
3. Pattison DJ, Symmons DP, Lunt M, Welch A, Bingham SA, Day NE, Silman AJ: Dietary beta-cryptoxanthin and inflammatory polyarthritis: results from a population-based prospective study. Am J Clin Nutr. 2005 Aug;82(2):451-5.
4. Yuan JM, Ross RK, Chu XD, Gao YT, Yu MC: Prediagnostic levels of serum beta-cryptoxanthin and retinol predict smoking-related lung cancer risk in Shanghai, China. Cancer Epidemiol Biomarkers Prev. 2001 Jul;10(7):767-73.
5. Child JA: Haematology reporting. Nurs Times. 1975 Jul 3;71(27):1045-8.
6. Ruano-Ravina A, Barros-Dios JM, Figueiras A, Branas-Tato P: Correspondence re Yuan JM et al., Prediagnostic levels of serum beta-cryptoxanthin and retinol predict smoking-related lung cancer risk in Shanghai, China. 2001;10:767-73. Neuhoser ML et al., Fruits and vegetables are associated with lower lung cancer risk only in the placebo arm of the beta-carotene and retinol efficacy trial (CARET). 2002;12:350-8. Satia-Abouta J et al., Associations of micronutrients with colon cancer risk in African Americans and whites: results from the North Carolina Colon Cancer Study. 2003;12:747-54. Cancer Epidemiol Biomarkers Prev. 2004 Apr;13(4):679-80; author reply 680.
7. Lian F, Hu KQ, Russell RM, Wang XD: Beta-cryptoxanthin suppresses the growth of immortalized human bronchial epithelial cells and non-small-cell lung cancer cells and up-regulates retinoic acid receptor beta expression. Int J Cancer. 2006 Nov 1;119(9):2084-9.
8. Uchiyama S, Sumida T, Yamaguchi M: Oral administration of beta-cryptoxanthin induces anabolic effects on bone components in the femoral tissues of rats in vivo. Biol Pharm Bull. 2004 Feb;27(2):232-5.
9. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
10. 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.
11. 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.
12. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
13. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
14. The lipid handbook with CD-ROM