alpha-Cryptoxanthin (CHEM030524)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:57:25 UTC
Update Date2016-11-09 01:19:05 UTC
Accession NumberCHEM030524
Identification
Common Namealpha-Cryptoxanthin
ClassSmall Molecule
DescriptionAlpha-cryptoxanthin is a naturally occurring carotenoid pigment with provitamin A activity whose structure is very similar to that of beta-carotene (HMDB00561). These dietary hydroxycarotenoids have been identified in human serum, milk, and ocular tissues. Industrial production of optically active (3R,6′R)-alpha-cryptoxanthin has not yet been achieved. Little is known about the potential physiological role of alpha-cryptoxanthin.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3'r,6'r)-beta,epsilon-Caroten-3'-olKegg
(3'r,6'r)-b,epsilon-Caroten-3'-olGenerator
(3'r,6'r)-Β,epsilon-caroten-3'-olGenerator
a-CryptoxanthinGenerator
Α-cryptoxanthinGenerator
(3'r,6'r)-Β,ε-caroten-3'-olHMDB
(3R)-beta,beta-Carotene-3-olHMDB
beta-Caroten-3-olHMDB
C15981HMDB
CaricaxanthinHMDB
CryptoxanthinHMDB
CryptoxanthineHMDB
Chemical FormulaC40H56O
Average Molecular Mass552.872 g/mol
Monoisotopic Mass552.433 g/mol
CAS Registry Number24480-38-4
IUPAC Name(1R)-3,5,5-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-2-en-1-ol
Traditional Nameα-cryptoxanthin
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
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
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 Descriptors
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 Solubility0.00051 g/LALOGPS
logP9.1ALOGPS
logP9.94ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.22ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity193.39 m³·mol⁻¹ChemAxon
Polarizability72.46 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-2100190000-9d58bb486a79a7b0d65bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0bt9-7010029000-faf43dffc0b286002b4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0513190000-a823a0279255ebaaeef1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0937200000-73617d89dc5cfe4b8150Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002k-1649210000-d61b6ac72098bbabce1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-9648cd92e47a06887473Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000090000-741c92b14aa8e655218bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0523390000-30cf545a0a3c2e6d481aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0201090000-89b12c6670e6ff645b95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0655190000-34b4cc9611aa9015ae39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avs-0619000000-d6873bb91373d82692a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0m02-0439550000-2f94eab30c482944b04fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0539610000-771f480490febb3af835Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q1-0329100000-12b336b001d210523254Spectrum
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 IDHMDB0002268
FooDB IDFDB015827
Phenol Explorer IDNot Available
KNApSAcK IDC00003770
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30791985
ChEBI ID10223
PubChem Compound ID23724629
Kegg Compound IDC15981
YMDB IDNot Available
ECMDB IDM2MDB005302
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Khachik, Frederick; Liu, Yufa; Showalter, Holly. Process for the preparation of alpha- and beta-cryptoxanthin from lutein and/or lutein esters by catalytic hydrogenation. U.S. Pat. Appl. Publ. (2006), 17 pp. Khachik F, Chang AN, Gana A, Mazzola E. Partial synthesis of (3R,6'R)-alpha-cryptoxanthin and (3R)-beta-cryptoxanthin from (3R,3'R,6'R)-lutein. J Nat Prod. 2007 Feb;70(2):220-6. Epub 2007 Feb 1.
2. Khachik F, Chang AN, Gana A, Mazzola E: Partial synthesis of (3R,6'R)-alpha-cryptoxanthin and (3R)-beta-cryptoxanthin from (3R,3'R,6'R)-lutein. J Nat Prod. 2007 Feb;70(2):220-6. Epub 2007 Feb 1.
3. Song BJ, Jouni ZE, Ferruzzi MG: Assessment of phytochemical content in human milk during different stages of lactation. Nutrition. 2013 Jan;29(1):195-202. doi: 10.1016/j.nut.2012.07.015.
4. Ollberding NJ, Maskarinec G, Conroy SM, Morimoto Y, Franke AA, Cooney RV, Wilkens LR, Le Marchand L, Goodman MT, Hernandez BY, Henderson BE, Kolonel LN: Prediagnostic circulating carotenoid levels and the risk of non-Hodgkin lymphoma: the Multiethnic Cohort. Blood. 2012 Jun 14;119(24):5817-23. doi: 10.1182/blood-2012-02-413609. Epub 2012 May 1.
5. de Azevedo-Meleiro CH, Rodriguez-Amaya DB: Qualitative and quantitative differences in the carotenoid composition of yellow and red peppers determined by HPLC-DAD-MS. J Sep Sci. 2009 Nov;32(21):3652-8. doi: 10.1002/jssc.200900311.
6. Breithaupt DE, Yahia EM, Velazquez FJ: Comparison of the absorption efficiency of alpha- and beta-cryptoxanthin in female Wistar rats. Br J Nutr. 2007 Feb;97(2):329-36.