Hmdb loader

Showing metabocard for p-Xylene (HMDB0059924)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-03-20 21:10:29 UTC
Update Date2019-07-31 22:49:29 UTC
HMDB IDHMDB0059924
Secondary Accession Numbers
  • HMDB59924
Metabolite Identification
Common Namep-Xylene
Descriptionp-Xylene, also known as p-methyltoluene or para-xylene, belongs to the class of organic compounds known as p-xylenes. These are aromatic compounds that contain a p-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 4-positions. p-Xylene is possibly neutral. Outside of the human body, p-Xylene is found, on average, in the highest concentration within black walnuts. p-Xylene has also been detected, but not quantified in, several different foods, such as parsley, green bell peppers, pepper (c. frutescens), cauliflowers, and yellow bell peppers. This could make p-xylene a potential biomarker for the consumption of these foods. The p stands for para, identifying the location of the methyl groups as across from one another. p-Xylene is a potentially toxic compound. For skin contact, the skin should be washed with soap and water. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur.
Structure
Data?1563865991
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0059924 (p-Xylene)


  Mrv1652303202019012D          

  8  8  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
M  END
Download

3D MOL for HMDB0059924 (p-Xylene)

HMDB0059924
     RDKit          3D
p-Xylene
 18 18  0  0  0  0  0  0  0  0999 V2000
    2.8899    0.2041   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4091    0.0970   -0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989   -0.6187   -0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759   -0.7264   -0.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140   -0.1117    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8959   -0.2056    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7019    0.6055    0.9769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6721    0.7102    0.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3739   -0.4816    0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2340    1.2457    0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838    0.0176   -1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2620   -1.1136   -1.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2301   -1.2957   -1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1806   -1.2678    0.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3554    0.2016   -0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658    0.3681    0.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3063    1.0839    1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020    1.2873    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
M  END
Download

3D SDF for HMDB0059924 (p-Xylene)


  Mrv1652303202019012D          

  8  8  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059924

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H10/c1-7-3-5-8(2)6-4-7/h3-6H,1-2H3

> <INCHI_KEY>
URLKBWYHVLBVBO-UHFFFAOYSA-N

> <FORMULA>
C8H10

> <MOLECULAR_WEIGHT>
106.165

> <EXACT_MASS>
106.07825032

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.119484394427246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,4-xylene

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
3.000088594666667

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
36.1404

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
para-xylene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0059924 (p-Xylene)

HMDB0059924
     RDKit          3D
p-Xylene
 18 18  0  0  0  0  0  0  0  0999 V2000
    2.8899    0.2041   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4091    0.0970   -0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989   -0.6187   -0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759   -0.7264   -0.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140   -0.1117    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8959   -0.2056    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7019    0.6055    0.9769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6721    0.7102    0.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3739   -0.4816    0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2340    1.2457    0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838    0.0176   -1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2620   -1.1136   -1.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2301   -1.2957   -1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1806   -1.2678    0.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3554    0.2016   -0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658    0.3681    0.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3063    1.0839    1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2020    1.2873    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
M  END
Download

PDB for HMDB0059924 (p-Xylene)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    2                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
Download

3D PDB for HMDB0059924 (p-Xylene)

COMPND    HMDB0059924
HETATM    1  C1  UNL     1       2.890   0.204  -0.087  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.409   0.097  -0.043  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.699  -0.619  -0.986  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.676  -0.726  -0.957  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.414  -0.112   0.033  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.896  -0.206   0.096  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.702   0.606   0.977  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.672   0.710   0.944  1.00  0.00           C  
HETATM    9  H1  UNL     1       3.374  -0.482   0.640  1.00  0.00           H  
HETATM   10  H2  UNL     1       3.234   1.246   0.171  1.00  0.00           H  
HETATM   11  H3  UNL     1       3.284   0.018  -1.105  1.00  0.00           H  
HETATM   12  H4  UNL     1       1.262  -1.114  -1.778  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.230  -1.296  -1.708  1.00  0.00           H  
HETATM   14  H6  UNL     1      -3.181  -1.268   0.253  1.00  0.00           H  
HETATM   15  H7  UNL     1      -3.355   0.202  -0.852  1.00  0.00           H  
HETATM   16  H8  UNL     1      -3.266   0.368   0.942  1.00  0.00           H  
HETATM   17  H9  UNL     1      -1.306   1.084   1.751  1.00  0.00           H  
HETATM   18  H10 UNL     1       1.202   1.287   1.710  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    8
CONECT    3    4   12
CONECT    4    5    5   13
CONECT    5    6    7
CONECT    6   14   15   16
CONECT    7    8    8   17
CONECT    8   18
END
Download

SMILES for HMDB0059924 (p-Xylene)

CC1=CC=C(C)C=C1
Download

INCHI for HMDB0059924 (p-Xylene)

InChI=1S/C8H10/c1-7-3-5-8(2)6-4-7/h3-6H,1-2H3
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
1,4-DimethylbenzeneChEBI
1,4-DimethylbenzolChEBI
4-MethyltolueneChEBI
4-XyleneChEBI
p-DimethylbenzeneChEBI
p-MethyltolueneChEBI
p-XylolChEBI
PARA-xyleneChEBI
1,4-XyleneHMDB
ParaxyleneHMDB
Chemical FormulaC8H10
Average Molecular Weight106.165
Monoisotopic Molecular Weight106.07825032
IUPAC Name1,4-xylene
Traditional Namepara-xylene
CAS Registry NumberNot Available
SMILES
CC1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C8H10/c1-7-3-5-8(2)6-4-7/h3-6H,1-2H3
InChI KeyURLKBWYHVLBVBO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-xylenes. These are aromatic compounds that contain a p-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 4-positions.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassXylenes
Direct Parentp-Xylenes
Alternative Parents
Substituents
  • P-xylene
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological location
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 Solubility0.2 g/LALOGPS
logP3.15ALOGPS
logP3ChemAxon
logS-2.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.14 m³·mol⁻¹ChemAxon
Polarizability13.12 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]+121.93531661259
DarkChem[M-H]-119.21231661259
DeepCCS[M+H]+126.61630932474
DeepCCS[M-H]-123.17330932474
DeepCCS[M-2H]-160.09330932474
DeepCCS[M+Na]+135.24930932474
AllCCS[M+H]+114.832859911
AllCCS[M+H-H2O]+109.632859911
AllCCS[M+NH4]+119.632859911
AllCCS[M+Na]+120.932859911
AllCCS[M-H]-117.732859911
AllCCS[M+Na-2H]-120.132859911
AllCCS[M+HCOO]-122.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.47 minutes32390414
Predicted by Siyang on May 30, 202215.8473 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.96 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1873.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid606.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid240.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid422.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid304.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid660.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid688.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)361.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1361.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid562.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1429.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid456.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid433.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate567.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA378.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water59.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-XyleneCC1=CC=C(C)C=C11196.5Standard polar33892256
p-XyleneCC1=CC=C(C)C=C1862.8Standard non polar33892256
p-XyleneCC1=CC=C(C)C=C1853.5Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not SpecifiedAsthma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
Associated Disorders and Diseases
Disease References
Asthma
  1. Dallinga JW, Robroeks CM, van Berkel JJ, Moonen EJ, Godschalk RW, Jobsis Q, Dompeling E, Wouters EF, van Schooten FJ: Volatile organic compounds in exhaled breath as a diagnostic tool for asthma in children. Clin Exp Allergy. 2010 Jan;40(1):68-76. doi: 10.1111/j.1365-2222.2009.03343.x. Epub 2009 Sep 28. [PubMed:19793086 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005820
KNApSAcK IDNot Available
Chemspider ID7521
KEGG Compound IDC06756
BioCyc IDCPD-1422
BiGG IDNot Available
Wikipedia LinkP-Xylene
METLIN IDNot Available
PubChem Compound7809
PDB IDNot Available
ChEBI ID27417
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. 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 ]
  2. Grunder S, Valente C, Whalley AC, Sampath S, Portmann J, Botros YY, Stoddart JF: Molecular gauge blocks for building on the nanoscale. Chemistry. 2012 Dec 3;18(49):15632-49. doi: 10.1002/chem.201201985. Epub 2012 Oct 22. [PubMed:23090871 ]
  3. Latrache H, El GA, Karroua M, Hakkou A, Ait MH, El BA, Bourlioux P: Relations between hydrophobicity tested by three methods and surface chemical composition of Escherichia coli. New Microbiol. 2002 Jan;25(1):75-82. [PubMed:11837394 ]
  4. Lyons TW, Guironnet D, Findlater M, Brookhart M: Synthesis of p-xylene from ethylene. J Am Chem Soc. 2012 Sep 26;134(38):15708-11. Epub 2012 Sep 13. [PubMed:22934909 ]
  5. Grunder S, Stoddart JF: Giving substance to the Losanitsch series. Chem Commun (Camb). 2012 Mar 28;48(26):3158-60. doi: 10.1039/c2cc17734j. Epub 2012 Feb 16. [PubMed:22343755 ]
  6. Svecova V, Topinka J, Solansky I, Sram RJ: Personal exposure to volatile organic compounds in the Czech Republic. J Expo Sci Environ Epidemiol. 2012 Sep;22(5):455-60. doi: 10.1038/jes.2012.30. Epub 2012 Jun 6. [PubMed:22669500 ]
  7. Kirimura K, Nakagawa H, Tsuji K, Matsuda K, Kurane R, Usami S: Selective and continuous degradation of carbazole contained in petroleum oil by resting cells of Sphingomonas sp. CDH-7. Biosci Biotechnol Biochem. 1999 Sep;63(9):1563-8. [PubMed:10540744 ]