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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:45 UTC
Update Date2022-03-07 02:49:14 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
Data?1582752240
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
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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+246.21131661259
DarkChem[M-H]-249.95731661259
DeepCCS[M+H]+260.22230932474
DeepCCS[M-H]-258.39730932474
DeepCCS[M-2H]-291.64130932474
DeepCCS[M+Na]+265.82830932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Alpha-Cryptoxanthin,1TMS,isomer #1CC1=C[C@H](O[Si](C)(C)C)CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C4622.5Semi standard non polar33892256
Alpha-Cryptoxanthin,1TMS,isomer #1CC1=C[C@H](O[Si](C)(C)C)CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C4596.3Standard non polar33892256
Alpha-Cryptoxanthin,1TMS,isomer #1CC1=C[C@H](O[Si](C)(C)C)CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C4348.9Standard polar33892256
Alpha-Cryptoxanthin,1TBDMS,isomer #1CC1=C[C@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C4804.8Semi standard non polar33892256
Alpha-Cryptoxanthin,1TBDMS,isomer #1CC1=C[C@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C4829.9Standard non polar33892256
Alpha-Cryptoxanthin,1TBDMS,isomer #1CC1=C[C@H](O[Si](C)(C)C(C)(C)C)CC(C)(C)C1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C4446.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Alpha-Cryptoxanthin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2100190000-9d58bb486a79a7b0d65b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alpha-Cryptoxanthin GC-MS (1 TMS) - 70eV, Positivesplash10-0bt9-7010029000-faf43dffc0b286002b4a2017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 10V, Positive-QTOFsplash10-0f79-0513190000-a823a0279255ebaaeef12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 20V, Positive-QTOFsplash10-000t-0937200000-73617d89dc5cfe4b81502017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 40V, Positive-QTOFsplash10-002k-1649210000-d61b6ac72098bbabce1f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 10V, Negative-QTOFsplash10-0udi-0000090000-9648cd92e47a068874732017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 20V, Negative-QTOFsplash10-0udi-0000090000-741c92b14aa8e655218b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 40V, Negative-QTOFsplash10-000i-0523390000-30cf545a0a3c2e6d481a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 10V, Negative-QTOFsplash10-0udi-0201090000-89b12c6670e6ff645b952021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 20V, Negative-QTOFsplash10-0udr-0655190000-34b4cc9611aa9015ae392021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 40V, Negative-QTOFsplash10-0avs-0619000000-d6873bb91373d82692a72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 10V, Positive-QTOFsplash10-0m02-0439550000-2f94eab30c482944b04f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 20V, Positive-QTOFsplash10-0079-0539610000-771f480490febb3af8352021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alpha-Cryptoxanthin 40V, Positive-QTOFsplash10-01q1-0329100000-12b336b001d2105232542021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Breast Milk
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 ID30791985
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
Good Scents IDNot Available
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 ]