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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-03-07 21:31:26 UTC
Update Date2022-03-07 03:17:36 UTC
HMDB IDHMDB0059823
Secondary Accession Numbers
  • HMDB59823
Metabolite Identification
Common NamePrehnitene
DescriptionPrehnitene, also known as prehnitol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Prehnitene is possibly neutral. These are compounds containing a benzene ring which bears a methane group.
Structure
Data?1563865979
Synonyms
ValueSource
PrehnitolChEBI
Chemical FormulaC10H14
Average Molecular Weight134.2182
Monoisotopic Molecular Weight134.109550448
IUPAC Name1,2,3,4-tetramethylbenzene
Traditional Name1,2,3,4-tetramethylbenzene
CAS Registry NumberNot Available
SMILES
[H]C1=C([H])C(=C(C(=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C10H14/c1-7-5-6-8(2)10(4)9(7)3/h5-6H,1-4H3
InChI KeyUOHMMEJUHBCKEE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot 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 Solubility0.031 g/LALOGPS
logP4.07ALOGPS
logP4.03ChemAxon
logS-3.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.22 m³·mol⁻¹ChemAxon
Polarizability17.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.10731661259
DarkChem[M-H]-127.08131661259
DeepCCS[M+H]+148.70930932474
DeepCCS[M-H]-146.71930932474
DeepCCS[M-2H]-180.05430932474
DeepCCS[M+Na]+154.80230932474
AllCCS[M+H]+124.832859911
AllCCS[M+H-H2O]+120.432859911
AllCCS[M+NH4]+128.932859911
AllCCS[M+Na]+130.132859911
AllCCS[M-H]-124.332859911
AllCCS[M+Na-2H]-125.932859911
AllCCS[M+HCOO]-127.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Prehnitene[H]C1=C([H])C(=C(C(=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]1808.5Standard polar33892256
Prehnitene[H]C1=C([H])C(=C(C(=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]1193.0Standard non polar33892256
Prehnitene[H]C1=C([H])C(=C(C(=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]1334.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Prehnitene EI-B (Non-derivatized)splash10-014i-4900000000-28da1a5b7cbbccda1f382017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Prehnitene CI-B (Non-derivatized)splash10-000i-0900000000-72f3f4dc86cbc594259e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Prehnitene EI-B (Non-derivatized)splash10-014i-4900000000-28da1a5b7cbbccda1f382018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Prehnitene CI-B (Non-derivatized)splash10-000i-0900000000-72f3f4dc86cbc594259e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prehnitene GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-3900000000-74a8e03648e32bae639e2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prehnitene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prehnitene 10V, Positive-QTOFsplash10-000i-0900000000-4611abcb869468b1fa702016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prehnitene 20V, Positive-QTOFsplash10-000i-0900000000-06a4fe1a9da3ac5427c42016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prehnitene 40V, Positive-QTOFsplash10-0v00-9300000000-f3cb280395f8494e693c2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prehnitene 10V, Negative-QTOFsplash10-001i-0900000000-05d9aa7c63c8c1b8b31e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prehnitene 20V, Negative-QTOFsplash10-001i-0900000000-19fdd4802bab4898a43f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prehnitene 40V, Negative-QTOFsplash10-00lr-2900000000-974e18eb3001abf2957e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prehnitene 10V, Positive-QTOFsplash10-0019-5900000000-10777b22ab7f07472f402021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prehnitene 20V, Positive-QTOFsplash10-001i-9500000000-07776fd135790c8873202021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prehnitene 40V, Positive-QTOFsplash10-004i-9100000000-98b28b6b012c48e625142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prehnitene 10V, Negative-QTOFsplash10-001i-0900000000-f5fa2e4eafb73a2ce5ef2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prehnitene 20V, Negative-QTOFsplash10-001i-0900000000-f5fa2e4eafb73a2ce5ef2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prehnitene 40V, Negative-QTOFsplash10-001i-2900000000-4ca7c509cbbe24c884882021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetramethylbenzenes
METLIN IDNot Available
PubChem Compound10263
PDB IDNot Available
ChEBI ID38997
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
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  2. Baker MV, Bosnich MJ, Brown DH, Byrne LT, Hesler VJ, Skelton BW, White AH, Williams CC: Azolium-linked cyclophanes: a comprehensive examination of conformations by 1H NMR spectroscopy and structural studies. J Org Chem. 2004 Oct 29;69(22):7640-52. [PubMed:15497992 ]
  3. Sousa JP, Brancalion AP, Souza AB, Turatti IC, Ambrosio SR, Furtado NA, Lopes NP, Bastos JK: Validation of a gas chromatographic method to quantify sesquiterpenes in copaiba oils. J Pharm Biomed Anal. 2011 Mar 25;54(4):653-9. doi: 10.1016/j.jpba.2010.10.006. Epub 2010 Oct 16. [PubMed:21095089 ]
  4. Zhu D, Kwon S, Pignatello JJ: Adsorption of single-ring organic compounds to wood charcoals prepared under different thermochemical conditions. Environ Sci Technol. 2005 Jun 1;39(11):3990-8. [PubMed:15984774 ]
  5. Lynch DW, Perone VB, Schuler RL, Ushry WB, Lewis TR: Acute toxicity of tetramethylbenzenes: durene, isodurene and prehnitene. Drug Chem Toxicol. 1978;1(3):219-30. [PubMed:755669 ]
  6. Zhang Q, He L, Liu JM, Wang W, Zhang J, Su CY: Pd2L2 metallacycles as molecular containers for small molecules. Dalton Trans. 2010 Dec 14;39(46):11171-9. doi: 10.1039/c0dt00406e. Epub 2010 Oct 21. [PubMed:20967343 ]
  7. Hwang DH, Park MJ, Eom JH, Shim HK, Lee S, Yang NG, Lian D, Suh MC, Chin BD: Synthesis of a new polymeric host material for efficient organic electro-phosphorescent devices. J Nanosci Nanotechnol. 2008 Sep;8(9):4649-52. [PubMed:19049077 ]
  8. Zou RQ, Bu XH, Zhang RH: Novel eclipsed 2D cadmium(II) coordination polymers with open-channel structure constructed from terephthalate and 3-(2-pyridyl)pyrazole: crystal structures, emission properties, and inclusion of guest molecules. Inorg Chem. 2004 Aug 23;43(17):5382-6. [PubMed:15310217 ]
  9. Kralj P, Zupan M, Stavber S: Remarkable effect of water on functionalization of the phenyl ring in methyl-substituted benzene derivatives with F-TEDA-BF4. J Org Chem. 2006 May 12;71(10):3880-8. [PubMed:16674064 ]
  10. Bellows D, Gingras E, Aly SM, Abd-El-Aziz AS, Leclerc M, Harvey PD: Organometallic and conjugated organic polymers held together by strong electrostatic interactions to form luminescent hybrid materials. Inorg Chem. 2008 Dec 15;47(24):11720-33. doi: 10.1021/ic801461j. [PubMed:19007160 ]
  11. Pawlukojc A, Natkaniec I, Bator G, Sobczyk L, Grech E, Nowicka-Scheibe J: Low frequency internal modes of 1,2,4,5-tetramethylbenzene, tetramethylpyrazine and tetramethyl-1,4-benzoquinone INS, Raman, infrared and theoretical DFT studies. Spectrochim Acta A Mol Biomol Spectrosc. 2006 Mar 1;63(3):766-73. Epub 2005 Aug 10. [PubMed:16098791 ]
  12. Berube JF, Gagnon K, Fortin D, Decken A, Harvey PD: Solution and solid-state properties of luminescent M-M bond-containing coordination/organometallic polymers using the RNC-M2(dppm)2-CNR building blocks (M = Pd, Pt; R = Aryl, Alkyl). Inorg Chem. 2006 Apr 3;45(7):2812-23. [PubMed:16562938 ]
  13. Schneider CJ, Moubaraki B, Cashion JD, Turner DR, Leita BA, Batten SR, Murray KS: Spin crossover in di-, tri- and tetranuclear, mixed-ligand tris(pyrazolyl)methane iron(II) complexes. Dalton Trans. 2011 Jul 14;40(26):6939-51. doi: 10.1039/c0dt01725f. Epub 2011 Jun 6. [PubMed:21643603 ]
  14. Jalowiecki P, Janasik B: Physiologically-based toxicokinetic modeling of durene (1,2,3,5-tetramethylbenzene) and isodurene (1,2,4,5-tetramethylbenzene) in humans. Int J Occup Med Environ Health. 2007;20(2):155-65. [PubMed:17638682 ]
  15. Muranaka A, Shibahara M, Watanabe M, Matsumoto T, Shinmyozu T, Kobayashi N: Optical resolution, absolute configuration, and chiroptical properties of three-layered [3.3]paracyclophane. J Org Chem. 2008 Nov 21;73(22):9125-8. doi: 10.1021/jo801441h. Epub 2008 Oct 21. [PubMed:18937416 ]
  16. Torrisi A, Mellot-Draznieks C, Bell RG: Impact of ligands on CO2 adsorption in metal-organic frameworks: first principles study of the interaction of CO2 with functionalized benzenes. I. Inductive effects on the aromatic ring. J Chem Phys. 2009 May 21;130(19):194703. doi: 10.1063/1.3120909. [PubMed:19466851 ]
  17. Nelsen SF, Konradsson AE, Weaver MN, Stephenson RM, Lockard JV, Zink JI, Zhao Y: Comparisons of measured rate constants with spectroscopically determined electron-transfer parameters. J Phys Chem B. 2007 Jun 21;111(24):6776-81. Epub 2007 Mar 24. [PubMed:17388559 ]
  18. Mohapatra H, Umapathy S: Influence of solvent on photoinduced electron-transfer reaction: time-resolved resonance Raman study. J Phys Chem A. 2009 Jun 25;113(25):6904-9. doi: 10.1021/jp903973q. [PubMed:19473021 ]