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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-08-01 02:14:20 UTC

Update Date

2022-03-07 03:18:00 UTC

HMDB ID

HMDB0094660

Secondary Accession Numbers

HMDB94660

Metabolite Identification

Common Name

Diethyl phthalic acid

Description

Diethyl phthalic acid, also known as diethyl phthalate, 1,2-diethyl phthalic acid or 1,2-benzenedicarboxylic acid diethyl ester, is classified as a member of the benzoic acid esters. Benzoic acid esters are ester derivatives of benzoic acid. Diethyl phthalic acid is considered to be practically insoluble (in water) and basic. This substance is commonly used to make plastics more flexible. Products in which it is found include toothbrushes, automobile parts, tools, toys, and food packaging. Diethyl phthalic acid can be released fairly easily from these products, as it is not part of the chain of chemicals (polymers) that makes up the plastic. Diethyl phthalic acid is also used in cosmetics, insecticides, and aspirin. Phthalate esters can cause reproductive and developmental toxicity. (L1900, A2883) It is a non-carcinogenic (not listed by IARC) potentially toxic compound. (ChemoSummarizer)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0094660
     RDKit          3D
Diethyl phthalic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.7193    1.4217    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450    1.7539    0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5933    0.5808    0.3060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021    0.5348    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    1.5733    0.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6124   -0.6996   -0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4559   -1.7988   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0031   -2.9916   -1.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3180   -3.1948   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606   -2.1427   -1.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392   -0.8914   -0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7011    0.1458   -0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5727    1.2988    0.0912 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0493   -0.2005   -0.5687 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0828    0.7550   -0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0900    1.1795    1.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3094    2.3378    1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0338    1.1495   -0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9234    0.6403    1.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070    2.5115   -0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458    2.1123    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5245   -1.6368   -0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968   -3.8040   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6862   -4.1603   -1.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2293   -2.2947   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500    1.6363   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0526    0.3276   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8105    0.3211    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4380    2.0571    1.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1087    1.4780    1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 11  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 15 26  1  0
 15 27  1  0
 16 28  1  0
 16 29  1  0
 16 30  1  0
M  END


  Mrv1652303202019002D          

 16 16  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    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    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0094660

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1=CC=CC=C1C(=O)OCC

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O4/c1-3-15-11(13)9-7-5-6-8-10(9)12(14)16-4-2/h5-8H,3-4H2,1-2H3

> <INCHI_KEY>
FLKPEMZONWLCSK-UHFFFAOYSA-N

> <FORMULA>
C12H14O4

> <MOLECULAR_WEIGHT>
222.2372

> <EXACT_MASS>
222.089208936

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.15787946647696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2-diethyl benzene-1,2-dicarboxylate

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
2.693815653333333

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.655086586419704

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
59.60580000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diethyl phthalate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0094660
     RDKit          3D
Diethyl phthalic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.7193    1.4217    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450    1.7539    0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5933    0.5808    0.3060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021    0.5348    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    1.5733    0.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6124   -0.6996   -0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4559   -1.7988   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0031   -2.9916   -1.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3180   -3.1948   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606   -2.1427   -1.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392   -0.8914   -0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7011    0.1458   -0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5727    1.2988    0.0912 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0493   -0.2005   -0.5687 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0828    0.7550   -0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0900    1.1795    1.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3094    2.3378    1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0338    1.1495   -0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9234    0.6403    1.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070    2.5115   -0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458    2.1123    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5245   -1.6368   -0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968   -3.8040   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6862   -4.1603   -1.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2293   -2.2947   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500    1.6363   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0526    0.3276   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8105    0.3211    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4380    2.0571    1.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1087    1.4780    1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 11  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 15 26  1  0
 15 27  1  0
 16 28  1  0
 16 29  1  0
 16 30  1  0
M  END

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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0094660
HETATM    1  C1  UNL     1      -4.719   1.422   0.817  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.245   1.754   0.766  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.593   0.581   0.306  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.202   0.535   0.139  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.617   1.573   0.420  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.612  -0.700  -0.335  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.456  -1.799  -0.608  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.003  -2.992  -1.053  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.318  -3.195  -1.265  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.161  -2.143  -1.007  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.739  -0.891  -0.546  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.701   0.146  -0.306  1.00  0.00           C  
HETATM   13  O3  UNL     1       1.573   1.299   0.091  1.00  0.00           O  
HETATM   14  O4  UNL     1       3.049  -0.200  -0.569  1.00  0.00           O  
HETATM   15  C11 UNL     1       4.083   0.755  -0.364  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.090   1.179   1.079  1.00  0.00           C  
HETATM   17  H1  UNL     1      -5.309   2.338   1.091  1.00  0.00           H  
HETATM   18  H2  UNL     1      -5.034   1.150  -0.196  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.923   0.640   1.567  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.107   2.512  -0.053  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.846   2.112   1.725  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.525  -1.637  -0.438  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.697  -3.804  -1.248  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.686  -4.160  -1.626  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.229  -2.295  -1.174  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.850   1.636  -0.992  1.00  0.00           H  
HETATM   27  H11 UNL     1       5.053   0.328  -0.628  1.00  0.00           H  
HETATM   28  H12 UNL     1       3.810   0.321   1.752  1.00  0.00           H  
HETATM   29  H13 UNL     1       3.438   2.057   1.279  1.00  0.00           H  
HETATM   30  H14 UNL     1       5.109   1.478   1.412  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   11
CONECT    7    8   22
CONECT    8    9    9   23
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16   26   27
CONECT   16   28   29   30
END

HMDB0094660
     RDKit          3D
Diethyl phthalic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.7193    1.4217    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450    1.7539    0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5933    0.5808    0.3060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021    0.5348    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    1.5733    0.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6124   -0.6996   -0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4559   -1.7988   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0031   -2.9916   -1.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3180   -3.1948   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606   -2.1427   -1.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392   -0.8914   -0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7011    0.1458   -0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5727    1.2988    0.0912 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0493   -0.2005   -0.5687 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0828    0.7550   -0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0900    1.1795    1.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3094    2.3378    1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0338    1.1495   -0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9234    0.6403    1.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070    2.5115   -0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458    2.1123    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5245   -1.6368   -0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968   -3.8040   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6862   -4.1603   -1.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2293   -2.2947   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500    1.6363   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0526    0.3276   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8105    0.3211    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4380    2.0571    1.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1087    1.4780    1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 11  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 15 26  1  0
 15 27  1  0
 16 28  1  0
 16 29  1  0
 16 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Benzenedicarboxylic acid diethyl ester	ChEBI
1,2-Diethyl phthalate	ChEBI
DEP	ChEBI
Diethyl 1,2-benzenedicarboxylate	ChEBI
Diethyl benzene-1,2-dicarboxylate	ChEBI
Diethyl O-phthalate	ChEBI
Ethyl phthalate	ChEBI
O-Benzenedicarboxylic acid diethyl ester	ChEBI
O-Bis(ethoxycarbonyl)benzene	ChEBI
Phthalic acid diethyl ester	ChEBI
Phthalsaeurediaethylester	ChEBI
1,2-Benzenedicarboxylate diethyl ester	Generator
1,2-Diethyl phthalic acid	Generator
Diethyl 1,2-benzenedicarboxylic acid	Generator
Diethyl benzene-1,2-dicarboxylic acid	Generator
Diethyl O-phthalic acid	Generator
Ethyl phthalic acid	Generator
O-Benzenedicarboxylate diethyl ester	Generator
Phthalate diethyl ester	Generator
Diethyl phthalate	Generator
Diethyl phthalic acid	Generator

Chemical Formula

C₁₂H₁₄O₄

Average Molecular Weight

222.2372

Monoisotopic Molecular Weight

222.089208936

IUPAC Name

1,2-diethyl benzene-1,2-dicarboxylate

Traditional Name

diethyl phthalate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C1=CC=CC=C1C(=O)OCC

InChI Identifier

InChI=1S/C12H14O4/c1-3-15-11(13)9-7-5-6-8-10(9)12(14)16-4-2/h5-8H,3-4H2,1-2H3

InChI Key

FLKPEMZONWLCSK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ethyl ester (CHEBI:34698 )
diester (CHEBI:34698 )
phthalate ester (CHEBI:34698 )
Phthalates (C14175 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.6	ALOGPS
logP	2.69	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	59.61 m³·mol⁻¹	ChemAxon
Polarizability	23.16 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.462	31661259
DarkChem	[M-H]-	149.551	31661259
DeepCCS	[M+H]+	153.273	30932474
DeepCCS	[M-H]-	150.915	30932474
DeepCCS	[M-2H]-	184.797	30932474
DeepCCS	[M+Na]+	160.542	30932474
AllCCS	[M+H]+	149.4	32859911
AllCCS	[M+H-H2O]+	145.5	32859911
AllCCS	[M+NH4]+	152.9	32859911
AllCCS	[M+Na]+	154.0	32859911
AllCCS	[M-H]-	151.6	32859911
AllCCS	[M+Na-2H]-	152.0	32859911
AllCCS	[M+HCOO]-	152.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	7.18 minutes	32390414
Predicted by Siyang on May 30, 2022	16.2318 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.22 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2604.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	505.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	188.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	303.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	334.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	681.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	837.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	77.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1267.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	470.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1634.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	460.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	560.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	419.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	451.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	45.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diethyl phthalic acid	CCOC(=O)C1=CC=CC=C1C(=O)OCC	2416.1	Standard polar	33892256
Diethyl phthalic acid	CCOC(=O)C1=CC=CC=C1C(=O)OCC	1661.6	Standard non polar	33892256
Diethyl phthalic acid	CCOC(=O)C1=CC=CC=C1C(=O)OCC	1630.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Diethyl phthalic acid EI-B (Non-derivatized)	splash10-002b-1900000000-503cf95871c5904aff71	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl phthalic acid CI-B (Non-derivatized)	splash10-004i-0930000000-7086cd5850c044d82e6a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl phthalic acid EI-B (Non-derivatized)	splash10-0002-1900000000-4412971f705146d2fd1f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl phthalic acid EI-B (Non-derivatized)	splash10-004j-0910000000-3da30560fd9393855d42	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl phthalic acid CI-B (Non-derivatized)	splash10-004i-0900000000-417398cedfbfc7e8f2c4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl phthalic acid EI-B (Non-derivatized)	splash10-0002-1900000000-40ef56b72df55d26c8ce	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl phthalic acid EI-B (Non-derivatized)	splash10-002b-1900000000-503cf95871c5904aff71	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl phthalic acid CI-B (Non-derivatized)	splash10-004i-0930000000-7086cd5850c044d82e6a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl phthalic acid EI-B (Non-derivatized)	splash10-0002-1900000000-4412971f705146d2fd1f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl phthalic acid EI-B (Non-derivatized)	splash10-004j-0910000000-3da30560fd9393855d42	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl phthalic acid CI-B (Non-derivatized)	splash10-004i-0900000000-417398cedfbfc7e8f2c4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl phthalic acid EI-B (Non-derivatized)	splash10-0002-1900000000-40ef56b72df55d26c8ce	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethyl phthalic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-4900000000-95f8663192d5c11641bb	2017-09-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethyl phthalic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethyl phthalic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-2900000000-c0f3a0df2bad7bb63a1a	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , negative-QTOF	splash10-00di-7950000000-17006e6795e6cbb4bcf7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , negative-QTOF	splash10-00di-9810000000-2c960e7f0228478b0576	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , negative-QTOF	splash10-00di-9600000000-4bf131a7544bb092312a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , negative-QTOF	splash10-00di-9400000000-2a69601f610fdcd4f477	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , negative-QTOF	splash10-00di-9200000000-19d7f94c7af5b78aca58	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , negative-QTOF	splash10-0100-9100000000-744178d47d141e29f10c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , negative-QTOF	splash10-004i-9000000000-c4fa127cbd14a64144de	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , negative-QTOF	splash10-004i-9000000000-136161f75c32091bf180	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , positive-QTOF	splash10-004j-0900000000-8845fcd110c6da94d554	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-70f0da44ec73bc26362c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-a7761aec74b20d2eb58d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-f41b5fc7349bff165407	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , positive-QTOF	splash10-006t-1900000000-fea3964d97a7809c1bcf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , positive-QTOF	splash10-00xs-4900000000-ac8b2ce4bcb6a6724cf3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , positive-QTOF	splash10-014i-9200000000-4d7079f620d5ad4e4a28	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , positive-QTOF	splash10-014i-9000000000-06f59bdd387a43c56886	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , positive-QTOF	splash10-014i-9000000000-23fb179d6576972a10d3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-adbdc25fa7d0fdb4f868	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethyl phthalic acid 45V, Negative-QTOF	splash10-00di-0900000000-3a6c7d7f9113fed59174	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl phthalic acid 10V, Positive-QTOF	splash10-00di-0590000000-19c4c903328f99b0457d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl phthalic acid 20V, Positive-QTOF	splash10-00ba-0930000000-1634c3a90c28e33287ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl phthalic acid 40V, Positive-QTOF	splash10-0a6r-3900000000-e4a1aeacabe307c97572	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl phthalic acid 10V, Negative-QTOF	splash10-00di-0390000000-6eb1e81609a1c2b23bf8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl phthalic acid 20V, Negative-QTOF	splash10-00di-2960000000-3743338637ef15aafeea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl phthalic acid 40V, Negative-QTOF	splash10-0092-4900000000-9ae1ef130a13535ace14	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24130822	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Autism	24130822	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Pervasive Developmental Disorder Not Otherwise Specified	24130822	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Autism
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]

Associated OMIM IDs

209850 (Autism)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00042472

Chemspider ID

Not Available

KEGG Compound ID

C14175

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diethyl_phthalate

METLIN ID

Not Available

PubChem Compound

6781

PDB ID

Not Available

ChEBI ID

34698

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Guo Y, Wang L, Kannan K: Phthalates and parabens in personal care products from China: concentrations and human exposure. Arch Environ Contam Toxicol. 2014 Jan;66(1):113-9. doi: 10.1007/s00244-013-9937-x. Epub 2013 Jul 24. [PubMed:23880707 ]

Showing metabocard for Diethyl phthalic acid (HMDB0094660)

MOL for HMDB0094660 (Diethyl phthalic acid)

3D MOL for HMDB0094660 (Diethyl phthalic acid)

3D SDF for HMDB0094660 (Diethyl phthalic acid)

3D-SDF for HMDB0094660 (Diethyl phthalic acid)

PDB for HMDB0094660 (Diethyl phthalic acid)

3D PDB for HMDB0094660 (Diethyl phthalic acid)

SMILES for HMDB0094660 (Diethyl phthalic acid)

INCHI for HMDB0094660 (Diethyl phthalic acid)

Structure for HMDB0094660 (Diethyl phthalic acid)

3D Structure for HMDB0094660 (Diethyl phthalic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra