SUCROSE (CED0000420)

Record Information
Version1.0
Creation Date2016-05-19 02:27:46 UTC
Update Date2026-05-14 17:46:13 UTC
Accession NumberCHEM007586
Identification
Common NameSUCROSE
ClassSmall Molecule
Description
Sucrose is an organic oxygen compound with the chemical formula C12H22O11 and an average molecular weight of 342.30 g/mol. SUCROSE belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. In industrial applications, the compound serves as a humectant, softener, conditioner, fragrance, and flavouring and nutrient. It is also utilized as a processing aid not otherwise specified and is used in the production of polyurethane plastics. Sucrose is found in or released from 39 recorded sources, including building and construction materials such as roofs and ceilings. It is present in household cleaning and consumer products, including bleaching agents, perfumes within soaps and detergents, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices. Additionally, it is found in food, food processing and cookware sources, such as food preservation, molasses and treatment of molasses, food contact materials, agglomerated sugar products, and fermentation processes for beer. It is also associated with electrical and electronic equipment, including antennas, amplifiers, adjustable resistors, contacts, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for the compound include oral, touch, and inhalation. At the molecular level, sucrose interacts with 14 recorded protein targets. These include amylosucrase (ams), actin alpha skeletal muscle (ACTA1), lysozyme C (LYZ), and it acts as an inhibitor of Beta-lactamase (ampC), along with 10 other proteins.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
1-alpha-D-Glucopyranosyl-2-beta-D-fructofuranosideChEBI
beta-D-Fruf-(21)-alpha-D-GLCPChEBI
Cane sugarChEBI
SacarosaChEBI
SaccharoseChEBI
SacharoseChEBI
Table sugarChEBI
White sugarChEBI
White soft sugarKegg
Sugar, compressibleKegg
Sugar, confectioner'sKegg
Sugar spheresKegg
Sucrose, purifiedKegg
1-a-D-Glucopyranosyl-2-b-D-fructofuranosideGenerator
1-Α-D-glucopyranosyl-2-β-D-fructofuranosideGenerator
b-D-Fruf-(21)-a-D-GLCPGenerator
Β-D-fruf-(21)-α-D-GLCPGenerator
(+)-SucroseHMDB
b -D-Fructofuranosyl a-D-glucopyranosideHMDB
D-(+)-SaccharoseHMDB
D-(+)-SucroseHMDB
D-SucroseHMDB
SaccharumHMDB
SugarHMDB
Chemical FormulaC12H22O11
Average Molecular Mass342.297 g/mol
Monoisotopic Mass342.116 g/mol
CAS Registry Number57-50-1
IUPAC Name(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Namesucrose
SMILESOC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1
InChI KeyCZMRCDWAGMRECN-UGDNZRGBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • C-glycosyl compound
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility824 g/LALOGPS
logP-2.6ALOGPS
logP-4.5ChemAxon
logS0.38ALOGPS
pKa (Strongest Acidic)11.84ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity68.77 m³·mol⁻¹ChemAxon
Polarizability31.04 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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GC-MSGC-MS Spectrumsplash10-0gba-0930000000-594ae5d59d217235e6c7Not AvailableView Spectrum
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LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-1ba130720abffe5e93d0Not AvailableView Spectrum
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LC-MS/MSLC-MS/MS Spectrumsplash10-0040-0591000000-7087bb9a939bd10f818aNot AvailableView Spectrum
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Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-9633000000-4209813458884c7aec8eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-7900000000-3b2f87c483af7aa103ceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000x-0709000000-09b3d35b7d6a4dc357bfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001s-3920000000-c84d50bd01956b1b810cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006w-9410000000-e8dd5d98ff469d52dd33Not AvailableView Spectrum
MSMS Spectrumsplash10-05dm-9100000000-ff1c60103a4253a94cf7Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, H2O, experimental)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
13244.0Log mg/kg[7400:24000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
490Personal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
495CeilingsBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
512ContactsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
541Agglomerated Sugar ProductsFood, food processing & cookwareNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
568Tobacco Product Moisture ControlHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureLectinB4EH87Burkholderia cenocepacia (strain ATCC BAA-245 / DSM 16553 / LMG 16656/ NCTC 13227 / J2315 / CF5610) (Burkholderia cepacia (strain J2315))Predicted (SEA)0.389246
Click to view 3D structureType 1 fimbrin D-mannose specific adhesinP08191Escherichia coli K-12Predicted (SEA)0.622794
Click to view 3D structurePA-I galactophilic lectinQ05097Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)Predicted (SEA)0.934191
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)199.839
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)163.717
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)303.301
Click to view 3D structureEndo-beta-N-acetylglucosaminidaseQ9ZB22Arthrobacter protophormiaePredicted (SEA)1.01204
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)449.112
Click to view 3D structureN-acetyllactosaminide alpha-1,3-galactosyltransferaseP50127Sus scrofaPredicted (SEA)3.97031
Solute carrier family 28 member 3 structureClick to view 3D structureSolute carrier family 28 member 3Q9HAS3HumansPredicted (SEA)18.606
Gap junction beta-2 protein structureClick to view 3D structureGap junction beta-2 proteinP29033HumansPredicted (SEA)1.16774
CD44 antigen structureClick to view 3D structureCD44 antigenP16070HumansPredicted (SEA)2.17978
Click to view 3D structureCD44 antigenP15379Mus musculusPredicted (SEA)2.17978
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)752.724
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)228.254
Click to view 3D structureOligo-1,6-glucosidase IMA1P53051Saccharomyces cerevisiae S288cPredicted (SEA)12.6116
Click to view 3D structureTaste receptor type 2 member 16Q9NYV7HumansPredicted (SEA)1.79053
Click to view 3D structureCytidine deaminaseP56389Mus musculusPredicted (SEA)12.923
Click to view 3D structurePeptidoglycan-N-acetylglucosamine deacetylaseQ8DP63Streptococcus pneumoniae (strain ATCC BAA-255 / R6)Predicted (SEA)4.04816
Galectin-3 structureClick to view 3D structureGalectin-3P17931HumansPredicted (SEA)13.3122
Cytidine deaminase structureClick to view 3D structureCytidine deaminaseP32320HumansPredicted (SEA)12.923
Click to view 3D structureBeta-1,4-galactosyltransferase 1P08037Bos taurusPredicted (SEA)7.62922
Click to view 3D structureLysosomal alpha-glucosidaseQ6P7A9Rattus norvegicusPredicted (SEA)4.98235
Click to view 3D structureAdenosine kinaseA5U4N0Mycobacterium tuberculosis (strain ATCC 25177 / H37Ra)Predicted (SEA)32.3853
Adenosine receptor A1 structureClick to view 3D structureAdenosine receptor A1P30542HumansPredicted (SEA)580.911
Concentrations
Not Available
External Links
DrugBank IDDB02772
HMDB IDHMDB0000258
FooDB IDFDB003715
Phenol Explorer IDNot Available
KNApSAcK IDC00001151
BiGG IDNot Available
BioCyc IDSUCROSE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSucrose
Chemspider IDNot Available
ChEBI ID17992
PubChem Compound ID5988
Kegg Compound IDC00089
YMDB IDYMDB00906
ECMDB IDECMDB00258
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Fitremann, Juliette; Queneau, Yves; Maitre, Jean-Paul; Bouchu, Alain. Co-melting of solid sucrose and multivalent cation soaps for solvent-free synthesis of sucrose esters. Tetrahedron Letters (2007), 48(23), 4111-4114.
2. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en
3. Fitremann, Juliette; Queneau, Yves; Maitre, Jean-Paul; Bouchu, Alain. Co-melting of solid sucrose and multivalent cation soaps for solvent-free synthesis of sucrose esters. Tetrahedron Letters (2007), 48(23), 4111-4114.
4. Rogers AJ, Greenwald MH, Deguzman MA, Kelley ME, Simon HK: A randomized, controlled trial of sucrose analgesia in infants younger than 90 days of age who require bladder catheterization in the pediatric emergency department. Acad Emerg Med. 2006 Jun;13(6):617-22. Epub 2006 Apr 24.
5. Nakano S, Kato T, Nakamura S, Kameyama M: Acetylcholinesterase activity in cerebrospinal fluid of patients with Alzheimer's disease and senile dementia. J Neurol Sci. 1986 Sep;75(2):213-23.
6. Ponec M, Wauben-Penris PJ, Burger A, Kempenaar J, Bodde HE: Nitroglycerin and sucrose permeability as quality markers for reconstructed human epidermis. Skin Pharmacol. 1990;3(2):126-35.
7. Rodrigues Silva C, Dutra de Oliveira JE, de Souza RA, Silva HC: Effect of a rice bran fiber diet on serum glucose levels of diabetic patients in Brazil. Arch Latinoam Nutr. 2005 Mar;55(1):23-7.
8. Nakamura J, Koh N, Sakakibara F, Hamada Y, Wakao T, Sasaki H, Mori K, Nakashima E, Naruse K, Hotta N: Diabetic neuropathy in sucrose-fed Otsuka Long-Evans Tokushima fatty rats: effect of an aldose reductase inhibitor, TAT. Life Sci. 1997;60(21):1847-57.
9. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38.
10. Calderilla-Fajardo SB, Cazares-Delgadillo J, Villalobos-Garcia R, Quintanar-Guerrero D, Ganem-Quintanar A, Robles R: Influence of sucrose esters on the in vivo percutaneous penetration of octyl methoxycinnamate formulated in nanocapsules, nanoemulsion, and emulsion. Drug Dev Ind Pharm. 2006 Jan;32(1):107-13.
11. Poschalko A, Rohr T, Gruber H, Bianco A, Guichard G, Briand JP, Weber V, Falkenhagen D: SUBPOL: a novel SUcrose-Based Polymer support for solid-phase peptide synthesis and affinity chromatography applications. J Am Chem Soc. 2003 Nov 5;125(44):13415-26.
12. Hamer I, Jadot M: Endolysosomal transport of newly-synthesized cathepsin D in a sucrose model of lysosomal storage. Exp Cell Res. 2005 Oct 1;309(2):284-95.
13. Chambers ST, Kunin CM: Isolation of glycine betaine and proline betaine from human urine. Assessment of their role as osmoprotective agents for bacteria and the kidney. J Clin Invest. 1987 Mar;79(3):731-7.
14. Wilson M, Patel H, Kpendema H, Noar JH, Hunt NP, Mordan NJ: Corrosion of the intra-oral magnets by multi-species biofilms in the presence and absence of sucrose. Biomaterials. 1997 Jan;18(1):53-7.
15. Giofre MR, Meduri G, Pallio S, Calandra S, Magnano A, Niceforo D, Cinquegrani M, di Leo V, Mazzon E, Sturniolo GC, Longo G, Fries W: Gastric permeability to sucrose is increased in portal hypertensive gastropathy. Eur J Gastroenterol Hepatol. 2000 May;12(5):529-33.
16. Chanarat P, Chiewsilp P: A simple method for the elimination of platelets from the lymphocyte-platelet mixture by sucrose. Am J Clin Pathol. 1975 Feb;63(2):237-9.
17. Skogsdal Y, Eriksson M, Schollin J: Analgesia in newborns given oral glucose. Acta Paediatr. 1997 Feb;86(2):217-20.
18. Cohen J, Malter H, Wright G, Kort H, Massey J, Mitchell D: Partial zona dissection of human oocytes when failure of zona pellucida penetration is anticipated. Hum Reprod. 1989 May;4(4):435-42.
19. Ayala-Bravo HA, Quintanar-Guerrero D, Naik A, Kalia YN, Cornejo-Bravo JM, Ganem-Quintanar A: Effects of sucrose oleate and sucrose laureate on in vivo human stratum corneum permeability. Pharm Res. 2003 Aug;20(8):1267-73.
20. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
21. Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5.
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=11021636
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=11093712
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=11111003
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=12065720
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=12706980
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=13508893
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=15291457
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=15660210
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=15792978
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=15845855
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=16228482
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=16304615
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=16313996
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=16525719
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=16660545
37. https://www.ncbi.nlm.nih.gov/pubmed/?term=16663947
38. https://www.ncbi.nlm.nih.gov/pubmed/?term=16665852
39. https://www.ncbi.nlm.nih.gov/pubmed/?term=17233733
40. https://www.ncbi.nlm.nih.gov/pubmed/?term=17439666
41. https://www.ncbi.nlm.nih.gov/pubmed/?term=17597061
42. https://www.ncbi.nlm.nih.gov/pubmed/?term=18625236
43. https://www.ncbi.nlm.nih.gov/pubmed/?term=19199566
44. https://www.ncbi.nlm.nih.gov/pubmed/?term=19726178
45. https://www.ncbi.nlm.nih.gov/pubmed/?term=21703290
46. https://www.ncbi.nlm.nih.gov/pubmed/?term=21972845
47. https://www.ncbi.nlm.nih.gov/pubmed/?term=22085755
48. https://www.ncbi.nlm.nih.gov/pubmed/?term=22311778
49. https://www.ncbi.nlm.nih.gov/pubmed/?term=22404833
50. https://www.ncbi.nlm.nih.gov/pubmed/?term=22751876