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Record Information
Version4.0
Creation Date2006-05-22 14:17:45 UTC
Update Date2017-09-27 08:24:14 UTC
HMDB IDHMDB0002268
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.
Structure
Thumb
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 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
SMILES
C\C(\C=C\C=C(/C)\C=C\C1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C
InChI Identifier
InChI=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/h11-14,16-21,23-26,28,36,38,41H,15,22,27,29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-,38?/m0/s1
InChI KeyORAKUVXRZWMARG-DWADUKLPSA-N
Chemical Taxonomy
DescriptionThis compound 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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Breast Milk
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 Quantified Adult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0832 +/- 0.0307 uMAdult (>18 years old)FemaleNormal details
Breast MilkDetected but not Quantified Adult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB015827
KNApSAcK IDC00003770
Chemspider IDNot Available
KEGG Compound IDC15981
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCryptoxanthin
METLIN IDNot Available
PubChem Compound23724629
PDB IDNot Available
ChEBI ID10223
References
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 ]