You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusDetected and Quantified
Creation Date2006-05-22 14:17:45 UTC
Update Date2020-10-09 21:02:36 UTC
Secondary Accession Numbers
  • HMDB02268
Metabolite Identification
Common NameAlpha-Cryptoxanthin
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.
Chemical FormulaC40H56O
Average Molecular Weight552.872
Monoisotopic Molecular Weight552.433116414
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
CAS Registry Number24480-38-4
InChI Identifier
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
  • Xanthophyll
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.00051 g/LALOGPS
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
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Breast Milk
Tissue LocationsNot Available
Normal Concentrations
BloodDetected and Quantified0.465 +/- 0.351 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.140 (0.078-0.240) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.14 +/- 0.018 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.30 +/- 0.20 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.29 +/- 0.20 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0832 +/- 0.0307 uMAdult (>18 years old)FemaleNormal details
Breast MilkDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015827
KNApSAcK IDC00003770
Chemspider IDNot Available
KEGG Compound IDC15981
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23724629
PDB IDNot Available
ChEBI ID10223
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000388
Synthesis ReferenceKhachik, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:17266370 ]
  2. 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. [PubMed:23237648 ]
  3. 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. [PubMed:22550343 ]
  4. 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. [PubMed:19813226 ]
  5. 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. [PubMed:17298702 ]