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Showing NP-Card for 4-Methylbenzyl alcohol (NP0002770)

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Record Information
Version1.0
Created at2020-11-23 19:39:59 UTC
Updated at2021-08-19 23:59:21 UTC
NP-MRD IDNP0002770
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Methylbenzyl alcohol
Provided ByBMRBBMRB logo
Description4-Methylbenzyl alcohol, also known as alpha-hydroxy-p-xylene or 4-tolylcarbinol, belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure. 4-Methylbenzyl alcohol exists in all living organisms, ranging from bacteria to humans. 4-Methylbenzyl alcohol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 4-Methylbenzyl alcohol is found in Vitis vinifera. It was first documented in 1992 (PMID: 1518957). Based on a literature review a significant number of articles have been published on 4-Methylbenzyl alcohol (PMID: 17984079) (PMID: 22033096) (PMID: 33675814) (PMID: 32361489) (PMID: 31334728) (PMID: 31265274).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002770 (4-Methylbenzyl alcohol)


     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
    3.2731   -0.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7768   -0.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9380   -1.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2159    0.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123    0.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2086    0.3626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3772    1.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1191    1.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686   -1.6565    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3777    1.3362    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7695   -0.2647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5957   -2.6474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3970   -2.4383    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8169   -1.2383    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6077    1.7544    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0474   -0.8810    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348    2.7453    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9579    2.5361    0.0000 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
  6  7  1  0
  5  8  1  0
  8  9  2  0
  9  2  1  0
  1 10  1  1
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  6
  6 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
M  END
Download

3D MOL for NP0002770 (4-Methylbenzyl alcohol)

NP0002770
     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -3.0724   -0.1269    0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5824   -0.1153    0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8301    0.7646    0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5485    0.7813    0.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420   -0.0955   -0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7368   -0.1008   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2851    0.8624    0.6842 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4878   -0.9734   -0.8265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8917   -0.9934   -0.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4070    0.5259    0.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5316    0.2521   -0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4673   -1.1564    0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3683    1.4656    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226    1.4839    1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1055    0.1057   -1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1554   -1.0761    0.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292    1.7462    0.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0228   -1.6670   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850   -1.6827   -1.3719 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
  6  7  1  0
  5  8  1  0
  8  9  2  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
M  END
Download

3D SDF for NP0002770 (4-Methylbenzyl alcohol)


     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
    3.2731   -0.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7768   -0.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9380   -1.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2159    0.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123    0.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2086    0.3626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3772    1.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1191    1.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686   -1.6565    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3777    1.3362    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7695   -0.2647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5957   -2.6474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3970   -2.4383    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8169   -1.2383    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6077    1.7544    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0474   -0.8810    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348    2.7453    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9579    2.5361    0.0000 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
  6  7  1  0
  5  8  1  0
  8  9  2  0
  9  2  1  0
  1 10  1  1
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  6
  6 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
M  END
> <DATABASE_ID>
NP0002770

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O/c1-7-2-4-8(6-9)5-3-7/h2-5,9H,6H2,1H3

> <INCHI_KEY>
KMTDMTZBNYGUNX-UHFFFAOYSA-N

> <FORMULA>
C8H10O

> <MOLECULAR_WEIGHT>
122.167

> <EXACT_MASS>
122.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.057707504919842

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4-methylphenyl)methanol

> <ALOGPS_LOGP>
1.54

> <JCHEM_LOGP>
1.7193174379999998

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.059817231466234

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7726359429566694

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
37.9151

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methylbenzyl alcohol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002770 (4-Methylbenzyl alcohol)

NP0002770
     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -3.0724   -0.1269    0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5824   -0.1153    0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8301    0.7646    0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5485    0.7813    0.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420   -0.0955   -0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7368   -0.1008   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2851    0.8624    0.6842 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4878   -0.9734   -0.8265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8917   -0.9934   -0.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4070    0.5259    0.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5316    0.2521   -0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4673   -1.1564    0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3683    1.4656    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226    1.4839    1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1055    0.1057   -1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1554   -1.0761    0.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292    1.7462    0.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0228   -1.6670   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850   -1.6827   -1.3719 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
  6  7  1  0
  5  8  1  0
  8  9  2  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
M  END
Download

PDB for NP0002770 (4-Methylbenzyl alcohol)

HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUL-19         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    4    7                                                       
CONECT    3    5    7                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    8    9                                                       
CONECT    7    1    2    3                                                  
CONECT    8    4    5    6                                                  
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0002770 (4-Methylbenzyl alcohol)

COMPND    NP0002770
HETATM    1  C1  UNL     1      -3.072  -0.127   0.079  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.582  -0.115   0.025  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.830   0.765   0.774  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.549   0.781   0.730  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.242  -0.095  -0.079  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.737  -0.101  -0.148  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.285   0.862   0.684  1.00  0.00           O  
HETATM    8  C7  UNL     1       0.488  -0.973  -0.826  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.892  -0.993  -0.785  1.00  0.00           C  
HETATM   10  H1  UNL     1      -3.407   0.526   0.900  1.00  0.00           H  
HETATM   11  H2  UNL     1      -3.532   0.252  -0.853  1.00  0.00           H  
HETATM   12  H3  UNL     1      -3.467  -1.156   0.237  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.368   1.466   1.420  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.123   1.484   1.330  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.106   0.106  -1.173  1.00  0.00           H  
HETATM   16  H7  UNL     1       3.155  -1.076   0.159  1.00  0.00           H  
HETATM   17  H8  UNL     1       2.929   1.746   0.364  1.00  0.00           H  
HETATM   18  H9  UNL     1       1.023  -1.667  -1.466  1.00  0.00           H  
HETATM   19  H10 UNL     1      -1.485  -1.683  -1.372  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    9
CONECT    3    4   13
CONECT    4    5    5   14
CONECT    5    6    8
CONECT    6    7   15   16
CONECT    7   17
CONECT    8    9    9   18
CONECT    9   19
END
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SMILES for NP0002770 (4-Methylbenzyl alcohol)

CC1=CC=C(CO)C=C1
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INCHI for NP0002770 (4-Methylbenzyl alcohol)

InChI=1S/C8H10O/c1-7-2-4-8(6-9)5-3-7/h2-5,9H,6H2,1H3
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View in JSmol
Synonyms
ValueSource
4-(Hydroxymethyl)tolueneChEBI
4-TolylcarbinolChEBI
alpha-Hydroxy-p-xyleneChEBI
p-Methylbenzyl alcoholChEBI
p-Tolyl alcoholChEBI
p-TolylcarbinolChEBI
a-Hydroxy-p-xyleneGenerator
Α-hydroxy-p-xyleneGenerator
1-Hydroxymethyl-4-methylbenzeneHMDB
4-Methylbenzenemethanol, 9ciHMDB
p-TolylmethanolHMDB
Para-methylbenzyl alcoholMeSH
Chemical FormulaC8H10O
Average Mass122.1670 Da
Monoisotopic Mass122.07316 Da
IUPAC Name(4-methylphenyl)methanol
Traditional Name4-methylbenzyl alcohol
CAS Registry NumberNot Available
SMILES
CC1=CC=C(CO)C=C1
InChI Identifier
InChI=1S/C8H10O/c1-7-2-4-8(6-9)5-3-7/h2-5,9H,6H2,1H3
InChI KeyKMTDMTZBNYGUNX-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyl alcohols
Direct ParentBenzyl alcohols
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point61.00 to 62.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point217.00 to 218.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility7710 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP1.580The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP1.54ALOGPS
logP1.72ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)15.06ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.92 m³·mol⁻¹ChemAxon
Polarizability14.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041609
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021764
KNApSAcK IDNot Available
Chemspider ID11021
KEGG Compound IDC06757
BioCyc ID4-METHYLBENZYL-ALCOHOL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11505
PDB IDNot Available
ChEBI ID1895
Good Scents IDrw1051051
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Day BJ, Carlson GP: Effect of p-xylene metabolites, p-methylbenzyl alcohol and 2,5-dimethylphenol, on rat hepatic and pulmonary microsomal metabolism. Res Commun Chem Pathol Pharmacol. 1992 Apr;76(1):117-20. [PubMed:1518957 ]
  3. Scognamiglio J, Jones L, Letizia CS, Api AM: Fragrance material review on p-tolyl alcohol. Food Chem Toxicol. 2012 Sep;50 Suppl 2:S108-12. doi: 10.1016/j.fct.2011.10.006. Epub 2011 Oct 19. [PubMed:22033096 ]
  4. Plapp BV, Subramanian R: Alternative binding modes in abortive NADH-alcohol complexes of horse liver alcohol dehydrogenase. Arch Biochem Biophys. 2021 Apr 15;701:108825. doi: 10.1016/j.abb.2021.108825. Epub 2021 Mar 3. [PubMed:33675814 ]
  5. Duan W, Du S, Meng F, Peng X, Peng L, Lin Y, Wang G, Wu J: The pathways by which the marine diatom Thalassiosira sp. OUC2 biodegrades p-xylene, combined with a mechanistic analysis at the proteomic level. Ecotoxicol Environ Saf. 2020 Jul 15;198:110687. doi: 10.1016/j.ecoenv.2020.110687. Epub 2020 Apr 30. [PubMed:32361489 ]
  6. Sutradhar M, Roy Barman T, Alegria ECBA, Guedes da Silva MFC, Liu CM, Kou HZ, Pombeiro AJL: Cu(ii) complexes of N-rich aroylhydrazone: magnetism and catalytic activity towards microwave-assisted oxidation of xylenes. Dalton Trans. 2019 Sep 14;48(34):12839-12849. doi: 10.1039/c9dt02196e. Epub 2019 Jul 23. [PubMed:31334728 ]
  7. Yang W, Godin R, Kasap H, Moss B, Dong Y, Hillman SAJ, Steier L, Reisner E, Durrant JR: Electron Accumulation Induces Efficiency Bottleneck for Hydrogen Production in Carbon Nitride Photocatalysts. J Am Chem Soc. 2019 Jul 17;141(28):11219-11229. doi: 10.1021/jacs.9b04556. Epub 2019 Jul 2. [PubMed:31265274 ]
  8. Li F, Duan W, Du S, Meng F, Peng X, Peng L, Lin Y, Wu J, Wang G: Toxicological Assessment of Intermediates in Natural Attenuation of p-Xylene to Marine Microalgae. Bull Environ Contam Toxicol. 2019 Sep;103(3):441-446. doi: 10.1007/s00128-019-02646-6. Epub 2019 Jun 14. [PubMed:31201469 ]
  9. Duan W, Meng F, Peng X, Lin Y, Wang G, Wu J: Kinetic analysis and degradation mechanism for natural attenuation of xylenes under simulated marine conditions. Ecotoxicol Environ Saf. 2019 Jan 30;168:443-449. doi: 10.1016/j.ecoenv.2018.10.103. Epub 2018 Nov 5. [PubMed:30408745 ]