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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 18:37:02 UTC
Update Date2018-05-20 19:10:40 UTC
HMDB IDHMDB0033844
Secondary Accession Numbers
  • HMDB33844
Metabolite Identification
Common Namebeta-Cryptoxanthin
Descriptionbeta-Cryptoxanthin is found in abalone. beta-Cryptoxanthin is isolated from papaya (Carica papaya) and many other higher plants, also from fish eggs. Cryptoxanthin is a natural carotenoid pigment. It has been isolated from a variety of sources including the petals and flowers of plants in the genus Physalis, orange rind, papaya, egg yolk, butter, apples, and bovine blood serum. In a pure form, cryptoxanthin is a red crystalline solid with a metallic luster. It is freely soluble in chloroform, benzene, pyridine and carbon disulfide. In the human body, cryptoxanthin is converted to vitamin A (retinol) and is therefore considered a provitamin A. As with other carotenoids, cryptoxanthin is an antioxidant and may help prevent free radical damage to cells and DNA, as well as stimulate the repair of oxidative damage to DNA. Structurally, cryptoxanthin is closely related to beta-carotene, with only the addition of a hydroxyl group. It is a member of the class of carotenoids known as xanthophylls. beta-Cryptoxanthin is a major source of vitamin A, often second only to beta-carotene, and is present in fruits such as oranges, tangerines, and papayas. (PMID: 8554331 ); Frequent intake of tropical fruits that are rich in beta-cryptoxanthin is associated with higher plasma beta-cryptoxanthin concentrations in Costa Rican adolescents. Papaya intake was the best food predictor of plasma beta-cryptoxanthin concentrations. Subjects that frequently (> or =3 times/day) consumed tropical fruits with at least 50 micro g/100 g beta-cryptoxanthin (papaya, tangerine, orange and watermelon) had twofold the plasma beta-cryptoxanthin concentrations of those with intakes of <4 times/week. In sum, the diet-plasma carotenoid and tocopherol correlations were generally low in Costa Rican adolescents. (PMID: 12368412 ); Modest increase in beta-cryptoxanthin intake, equivalent to one glass of freshly squeezed orange juice per day, is associated with a reduced risk of developing inflammatory disorders such as rheumatoid arthritis. (PMID: 16087992 ); Higher prediagnostic serum levels of total carotenoids and beta-cryptoxanthin were associated with lower smoking-related lung cancer risk in middle-aged and older men in Shanghai, China. (PMID: 11440962 ); The study by Yuan et al. (PMID 1144092 , above) reports a 35 to 40% protective effect among smokers due to the intake of carotenoids, beta-cryptoxanthin, and retinol. beta-Cryptoxanthin is a correct interpretation yields an effect size of 54 to 66%, an important difference. detected during the process of reviewing articles published in Cancer Epidemiology Biomarkers & Prevention, it has come to the author's attention that the interpretation of relative risk (RR) and odds ratio (OR) as an estimated measure of hypothetical protective effects is wrong in some of them. (PMID: 15066939 ); Consistent with inhibition of the lung cancer cell growth, beta-cryptoxanthin induced the mRNA levels of retinoic acid receptor beta (RARbeta) in BEAS-2B cells, although this effect was less pronounced in A549 cells. Furthermore, beta-cryptoxanthin transactivated RAR-mediated transcription activity of the retinoic acid response element. These findings suggest a mechanism of anti-proliferative action of beta-cryptoxanthin and indicate that beta-cryptoxanthin may be a promising chemopreventive agent against lung cancer. (PMID: 16841329
Structure
Thumb
Synonyms
ValueSource
3-Hydroxy-b-caroteneHMDB
b,b-Caroten-3-olHMDB
b-KrypoxanthinHMDB
CaricaxanthinHMDB
CryptoxanthinHMDB
CryptoxantholHMDB
NeocryptoxanthinHMDB
Chemical FormulaC40H56O
Average Molecular Weight552.872
Monoisotopic Molecular Weight552.433116414
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
CAS Registry Number472-70-8
SMILES
C\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 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/h11-14,16-21,23-26,36,41H,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
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
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point172 - 173 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1000190000-56ac432f8bd5a3e11667View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0bt9-4100039000-889b04a7bfe4d06209e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0423290000-bf7a8e40a11eff7bfe3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0649100000-9c3f50cab7f2d02e22fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002k-0569000000-8a2e2a50f957c26b3ab1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-d34ae69e503c3f381911View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000090000-2fe3377fd40bc851dfc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0546190000-d1d53215d44121d13684View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Breast Milk
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.16 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.18 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.094 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.181 +/- 0.00500 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.150 +/- 0.0800 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.180 +/- 0.120 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.136 +/- 0.150 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.160 +/- 0.110 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.270 +/- 0.170 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.107 +/- 0.130 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.180 +/- 0.100 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.200 +/- 0.120 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.130 +/- 0.180 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.327 +/- 0.175 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.620 +/- 0.330 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.700 +/- 0.310 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.09 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.09 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified170 +/- 50 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.313 +/- 0.172 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.147 +/- 0.102 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.14 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.16 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.091 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.196 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.245 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.289 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.209 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.23 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.283 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.14 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.141 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.422 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0400 +/- 0.0300 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.130 +/- 0.190 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.150 +/- 0.0850 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.170 +/- 0.112 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.250 +/- 0.350 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.324 +/- 0.174 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.169 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.177 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.18 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.215 uMChildren (1-13 years old)FemaleNormal details
BloodDetected and Quantified0.27 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.34 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.190 +/- 0.160 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.194 +/- 0.121 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.225 +/- 0.167 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.275 +/- 0.295 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.295 +/- 0.279 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.374 +/- 0.190 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.465 +/- 0.351 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified221.751 +/- 113.408 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.152 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.16 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.17 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.174 uMChildren (1-13 years old)MaleNormal details
BloodDetected and Quantified0.23 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.116 +/- 0.0778 uMAdult (>18 years old)MaleNormal details
BloodDetected but not Quantified Adult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.125 +/- 0.0742 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.148 +/- 0.101 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.150 +/- 0.160 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.167 +/- 0.132 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.181 +/- 0.202 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.203 +/- 0.165 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.259 +/- 0.123 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified130 +/- 90 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified240 +/- 160 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified240.381 +/- 118.291 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.220 +/- 0.210 uMChildren (1 - 13 years old)Not SpecifiedNormal details
Breast MilkDetected but not Quantified Adult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.103 +/- 0.110 uMAdult (>18 years old)Not Specified
Obese
details
BloodDetected and Quantified0.135 +/- 0.160 uMAdult (>18 years old)Not Specified
Overweight
details
BloodDetected and Quantified0.420 +/- 0.330 uMAdult (>18 years old)BothType I diabetes details
BloodDetected and Quantified0.100 +/- 0.0500 uMChildren (1 - 13 years old)Not SpecifiedObese details
BloodDetected and Quantified0.180 +/- 0.110 uMChildren (1 - 13 years old)Not SpecifiedOverweight details
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 1
  1. Granado-Lorencio F, Olmedilla-Alonso B, Blanco-Navarro I, Botella-Romero F, Simal-Anton A: Assessment of carotenoid status and the relation to glycaemic control in type I diabetics: a follow-up study. Eur J Clin Nutr. 2006 Aug;60(8):1000-8. Epub 2006 Feb 1. [PubMed:16452910 ]
Obesity
  1. Vioque J, Weinbrenner T, Asensio L, Castello A, Young IS, Fletcher A: Plasma concentrations of carotenoids and vitamin C are better correlated with dietary intake in normal weight than overweight and obese elderly subjects. Br J Nutr. 2007 May;97(5):977-86. [PubMed:17408529 ]
  2. Burrows TL, Warren JM, Colyvas K, Garg ML, Collins CE: Validation of overweight children's fruit and vegetable intake using plasma carotenoids. Obesity (Silver Spring). 2009 Jan;17(1):162-8. doi: 10.1038/oby.2008.495. Epub 2008 Nov 6. [PubMed:18997681 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012019
KNApSAcK IDC00000920
Chemspider ID4904571
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6384256
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:8554331 ]
  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. [PubMed:12368412 ]
  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. [PubMed:16087992 ]
  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. [PubMed:11440962 ]
  5. Child JA: Haematology reporting. Nurs Times. 1975 Jul 3;71(27):1045-8. [PubMed:1144092 ]
  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. [PubMed:15066939 ]
  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. [PubMed:16841329 ]
  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. [PubMed:14758041 ]
  9. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  13. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  14. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.