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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:56:10 UTC
Update Date2018-05-19 23:37:36 UTC
HMDB IDHMDB0061865
Secondary Accession Numbers
  • HMDB61865
Metabolite Identification
Common NameDocosane
Description, also known as CH3-[CH2]20-CH3 or dokosan, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, is considered to be a hydrocarbon lipid molecule. exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. has been primarily detected in saliva. is also a parent compound for other transformation products, including but not limited to, docosan-1-ol, 1,2-docosanediol, and docosanedioic acid. is an alkane and waxy tasting compound that can be found in a number of food items such as sunflower, papaya, linden, and allspice. This makes a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
CH3-[CH2]20-CH3ChEBI
DokosanChEBI
N-DocosaneChEBI
Chemical FormulaC22H46
Average Molecular Weight310.6006
Monoisotopic Molecular Weight310.359951472
IUPAC Namedocosane
Traditional Namedocosane
CAS Registry Number629-97-0
SMILES
CCCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C22H46/c1-3-5-7-9-11-13-15-17-19-21-22-20-18-16-14-12-10-8-6-4-2/h3-22H2,1-2H3
InChI KeyHOWGUJZVBDQJKV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acyclic alkanes. These are acyclic hydrocarbons consisting only of n carbon atoms and m hydrogen atoms where m=2*n + 2.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassAlkanes
Sub ClassAcyclic alkanes
Direct ParentAcyclic alkanes
Alternative ParentsNot Available
Substituents
  • Acyclic alkane
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.4e-06 g/LALOGPS
logP10.16ALOGPS
logP10.24ChemAxon
logS-7.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity103.02 m³·mol⁻¹ChemAxon
Polarizability46.26 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00dr-9200000000-ab9d7f8bb8ea819c4519View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0abc-9100000000-aedb20bd247f19684b98View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-ff50dcb9226e5bfc0225View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-3329000000-6fea29f2d799a1ec5db7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000g-7950000000-12e3b6a943950437f0ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-2a269fde28ea3cc859a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-6769000000-652d6a4a0f0970754ae3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9460000000-39be7901ea5389caef9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-87ef9136157e06fb668fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0009000000-09825fdfa45cfa0949cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-6792000000-476f2fcebfc73b003b3fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4l-9100000000-5e09407960ebf7a97cdfView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)BothNormal details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004725
KNApSAcK IDNot Available
Chemspider ID11899
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHigher alkanes
METLIN IDNot Available
PubChem Compound12405
PDB IDTWT
ChEBI ID46050
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Elovson J, Vagelos PR: Structure of the major species of chlorosulfolipid from Ochromonas danica. 2,2,11,13,15,16-hexachloro-N-docosane 1,14-disulfate. Biochemistry. 1970 Aug 4;9(16):3110-26. [PubMed:4321366 ]
  2. Elovson J: Biosynthesis of chlorosulfolipids in Ochromonas danica. Assembly of the docosane-1,14-diol structure in vivo. Biochemistry. 1974 Aug 13;13(17):3483-7. [PubMed:4844176 ]
  3. Sokolov GP, Turovskii IV, Lukevits E: [The synthesis of phosphates of long-chain omega-hydroxyalkyl esters of 11-deoxyprostaglandin E1]. Bioorg Khim. 2002 Jan-Feb;28(1):69-71. [PubMed:11875977 ]
  4. Sheikh S: Calculation the surface tension of heptane, eicosane, docosane, tetracosane, and their asymmetric mixtures. J Colloid Interface Sci. 2005 Sep 1;289(1):218-22. [PubMed:16009230 ]
  5. Hearn JD, Smith GD: Ozonolysis of mixed oleic acid/n-docosane particles: the roles of phase, morphology, and metastable states. J Phys Chem A. 2007 Nov 1;111(43):11059-65. Epub 2007 Oct 5. [PubMed:17918818 ]
  6. Zhu G, Liang B, Negishi E: Efficient and selective synthesis of (S,R,R,S,R,S)-4,6,8,10,16,18-hexamethyl-docosane via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction). Org Lett. 2008 Mar 20;10(6):1099-101. doi: 10.1021/ol703056u. Epub 2008 Feb 15. [PubMed:18275210 ]
  7. Fu D, Su Y, Xie B, Zhu H, Liu G, Wang D: Phase change materials of n-alkane-containing microcapsules: observation of coexistence of ordered and rotator phases. Phys Chem Chem Phys. 2011 Feb 14;13(6):2021-6. doi: 10.1039/c0cp01173h. Epub 2011 Jan 11. [PubMed:21225038 ]
  8. Choi JH, Subhan MA, Ng SW: {3,14-Dimethyl-2,6,13,17-tetra-aza-tricyclo-[16.4.0.0]docosane-kappaN,N',N'',N''' )bis-(nitrato-kappaO)copper(II). Acta Crystallogr Sect E Struct Rep Online. 2012 Feb 1;68(Pt 2):m190. doi: 10.1107/S1600536812001845. Epub 2012 Jan 21. [PubMed:22346860 ]
  9. Moon D, Subhan MA, Choi JH: 3,14-Diethyl-2,13-di-aza-6,17-diazonia-tri-cyclo-[16.4.0.0(7,12)]docosane dichloride tetra-hydrate from synchrotron radiation. Acta Crystallogr Sect E Struct Rep Online. 2013 Oct 9;69(Pt 11):o1620. doi: 10.1107/S1600536813027232. eCollection 2013 Oct 9. [PubMed:24454070 ]
  10. Wikipedia [Link]