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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:56:10 UTC
Update Date2022-03-07 03:17:48 UTC
HMDB IDHMDB0061865
Secondary Accession Numbers
  • HMDB61865
Metabolite Identification
Common NameDocosane
DescriptionDocosane, 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. Docosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, docosane is considered to be a hydrocarbon lipid molecule. Docosane is an alkane and waxy tasting compound. Docosane is found, on average, in the highest concentration within lemon balms. Docosane has also been detected, but not quantified, in several different foods, such as allspices, lindens, papaya, and sunflowers. This could make docosane a potential biomarker for the consumption of these foods. A straight-chain alkane with 22 carbon atoms.
Structure
Data?1563866240
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
Description 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.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassSaturated hydrocarbons
Sub ClassAlkanes
Direct ParentAlkanes
Alternative ParentsNot Available
Substituents
  • Acyclic alkane
  • Alkane
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
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 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+184.80731661259
DarkChem[M-H]-185.68331661259
DeepCCS[M+H]+180.8530932474
DeepCCS[M-H]-177.9830932474
DeepCCS[M-2H]-213.6930932474
DeepCCS[M+Na]+189.50430932474
AllCCS[M+H]+200.632859911
AllCCS[M+H-H2O]+198.032859911
AllCCS[M+NH4]+203.132859911
AllCCS[M+Na]+203.832859911
AllCCS[M-H]-189.132859911
AllCCS[M+Na-2H]-191.032859911
AllCCS[M+HCOO]-193.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DocosaneCCCCCCCCCCCCCCCCCCCCCC2210.0Standard polar33892256
DocosaneCCCCCCCCCCCCCCCCCCCCCC2204.7Standard non polar33892256
DocosaneCCCCCCCCCCCCCCCCCCCCCC2204.0Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB004725
KNApSAcK IDC00035592
Chemspider ID11899
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHigher alkanes
METLIN IDNot Available
PubChem Compound12405
PDB IDTWT
ChEBI ID46050
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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]