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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:56:42 UTC

Update Date

2022-03-07 02:55:27 UTC

HMDB ID

HMDB0037683

Secondary Accession Numbers

HMDB37683

Metabolite Identification

Common Name

Ethyl vanillin isobutyrate

Description

Ethyl vanillin isobutyrate belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Ethyl vanillin isobutyrate is a sweet, chocolate, and creamy tasting compound. Based on a literature review very few articles have been published on Ethyl vanillin isobutyrate.

Structure

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

HMDB0037683
     RDKit          3D
Ethyl vanillin isobutyrate
 33 33  0  0  0  0  0  0  0  0999 V2000
   -2.3235   -3.0486   -0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178   -1.5663   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2585   -0.9222   -0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2138    0.4182   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3550    1.1584    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3192    2.4955    0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5435    3.2525    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6764    2.7300    0.4562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1035    3.1294    0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    2.4087    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0058    1.0514   -0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2204    0.3764   -0.2343 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986   -0.2207    0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3413   -0.1114    1.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870   -0.9412    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2070    0.0560    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1013   -2.0885   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863   -3.6030   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2992   -3.3135   -0.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4528   -3.2411   -1.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -1.0762   -1.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1052   -1.4408    0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3169    0.6545   -0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5091    4.3124    0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901    4.1886    0.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0181    2.8800    0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5290   -1.2582    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630   -0.4431   -0.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3060    0.9427    0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625    0.4459   -0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1444   -3.0574    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2055   -2.0581   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9841   -2.1107   -0.9657 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
  5  6  1  0
  6  7  1  0
  7  8  2  0
  6  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 11  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 15 27  1  0
 16 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
M  END


  Mrv0541 05061309572D          

 17 17  0  0  0  0            999 V2000
   -2.1434    1.2375    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
    0.7145    3.7125    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
    1.4289    0.8250    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
    0.7145   -1.2375    0.0000 C   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   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  6  5  2  0  0  0  0
  9  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  9  1  0  0  0  0
 14  8  2  0  0  0  0
 15 13  2  0  0  0  0
 16  4  1  0  0  0  0
 16 12  1  0  0  0  0
 17 11  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037683

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC1=C(OC(=O)C(C)C)C=CC(C=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O4/c1-4-16-12-7-10(8-14)5-6-11(12)17-13(15)9(2)3/h5-9H,4H2,1-3H3

> <INCHI_KEY>
BTCQMCOBMIXUCG-UHFFFAOYSA-N

> <FORMULA>
C13H16O4

> <MOLECULAR_WEIGHT>
236.2637

> <EXACT_MASS>
236.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.073011309271966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-ethoxy-4-formylphenyl 2-methylpropanoate

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.7356679493333336

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.919229871131943

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
64.1876

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.56e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-ethoxy-4-formylphenyl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037683
     RDKit          3D
Ethyl vanillin isobutyrate
 33 33  0  0  0  0  0  0  0  0999 V2000
   -2.3235   -3.0486   -0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178   -1.5663   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2585   -0.9222   -0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2138    0.4182   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3550    1.1584    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3192    2.4955    0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5435    3.2525    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6764    2.7300    0.4562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1035    3.1294    0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    2.4087    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0058    1.0514   -0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2204    0.3764   -0.2343 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986   -0.2207    0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3413   -0.1114    1.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870   -0.9412    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2070    0.0560    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1013   -2.0885   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863   -3.6030   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2992   -3.3135   -0.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4528   -3.2411   -1.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -1.0762   -1.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1052   -1.4408    0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3169    0.6545   -0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5091    4.3124    0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901    4.1886    0.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0181    2.8800    0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5290   -1.2582    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630   -0.4431   -0.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3060    0.9427    0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625    0.4459   -0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1444   -3.0574    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2055   -2.0581   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9841   -2.1107   -0.9657 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
  5  6  1  0
  6  7  1  0
  7  8  2  0
  6  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 11  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 15 27  1  0
 16 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   6.930   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   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  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    1   16                                                       
CONECT    5    6   10                                                       
CONECT    6    5   11                                                       
CONECT    7   10   12                                                       
CONECT    8   10   14                                                       
CONECT    9    2    3   13                                                  
CONECT   10    5    7    8                                                  
CONECT   11    6   12   17                                                  
CONECT   12    7   11   16                                                  
CONECT   13    9   15   17                                                  
CONECT   14    8                                                            
CONECT   15   13                                                            
CONECT   16    4   12                                                       
CONECT   17   11   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0037683
HETATM    1  C1  UNL     1      -2.324  -3.049  -0.834  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.518  -1.566  -0.516  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.259  -0.922  -0.424  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.214   0.418  -0.144  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.355   1.158   0.049  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.319   2.496   0.328  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.544   3.252   0.528  1.00  0.00           C  
HETATM    8  O2  UNL     1      -4.676   2.730   0.456  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.104   3.129   0.421  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.042   2.409   0.231  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.006   1.051  -0.052  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.220   0.376  -0.234  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.899  -0.221   0.824  1.00  0.00           C  
HETATM   14  O4  UNL     1       1.341  -0.111   1.963  1.00  0.00           O  
HETATM   15  C11 UNL     1       3.187  -0.941   0.654  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.207   0.056   0.090  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.101  -2.088  -0.298  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.086  -3.603  -0.224  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.299  -3.313  -0.512  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.453  -3.241  -1.912  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.045  -1.076  -1.383  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.105  -1.441   0.431  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.317   0.654  -0.024  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.509   4.312   0.749  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.990   4.189   0.639  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.018   2.880   0.297  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.529  -1.258   1.649  1.00  0.00           H  
HETATM   28  H11 UNL     1       5.163  -0.443  -0.108  1.00  0.00           H  
HETATM   29  H12 UNL     1       4.306   0.943   0.762  1.00  0.00           H  
HETATM   30  H13 UNL     1       3.763   0.446  -0.853  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.144  -3.057   0.274  1.00  0.00           H  
HETATM   32  H15 UNL     1       2.206  -2.058  -0.953  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.984  -2.111  -0.966  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4
CONECT    4    5    5   11
CONECT    5    6   23
CONECT    6    7    9    9
CONECT    7    8    8   24
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   12
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16   17   27
CONECT   16   28   29   30
CONECT   17   31   32   33
END

HMDB0037683
     RDKit          3D
Ethyl vanillin isobutyrate
 33 33  0  0  0  0  0  0  0  0999 V2000
   -2.3235   -3.0486   -0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178   -1.5663   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2585   -0.9222   -0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2138    0.4182   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3550    1.1584    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3192    2.4955    0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5435    3.2525    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6764    2.7300    0.4562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1035    3.1294    0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    2.4087    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0058    1.0514   -0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2204    0.3764   -0.2343 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986   -0.2207    0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3413   -0.1114    1.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870   -0.9412    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2070    0.0560    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1013   -2.0885   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863   -3.6030   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2992   -3.3135   -0.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4528   -3.2411   -1.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -1.0762   -1.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1052   -1.4408    0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3169    0.6545   -0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5091    4.3124    0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901    4.1886    0.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0181    2.8800    0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5290   -1.2582    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630   -0.4431   -0.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3060    0.9427    0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625    0.4459   -0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1444   -3.0574    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2055   -2.0581   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9841   -2.1107   -0.9657 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
  5  6  1  0
  6  7  1  0
  7  8  2  0
  6  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 11  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 15 27  1  0
 16 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Ethoxy-4-formylphenyl isobutyrate	ChEBI
2-Methylpropanoic acid 2-ethoxy-4-formylphenyl ester	ChEBI
4-Isobutanoyloxy-3-ethoxybenzaldehyde	ChEBI
2-Ethoxy-4-formylphenyl isobutyric acid	Generator
2-Methylpropanoate 2-ethoxy-4-formylphenyl ester	Generator
Ethyl vanillin isobutyric acid	Generator
2-Ethoxy-4-formylphenyl 2-methylpropanoate	HMDB
2-Ethoxy-4-formylphenyl 2-methylpropanoic acid	Generator

Chemical Formula

C₁₃H₁₆O₄

Average Molecular Weight

236.2637

Monoisotopic Molecular Weight

236.104859

IUPAC Name

2-ethoxy-4-formylphenyl 2-methylpropanoate

Traditional Name

2-ethoxy-4-formylphenyl 2-methylpropanoate

CAS Registry Number

188417-26-7

SMILES

CCOC1=C(OC(=O)C(C)C)C=CC(C=O)=C1

InChI Identifier

InChI=1S/C13H16O4/c1-4-16-12-7-10(8-14)5-6-11(12)17-13(15)9(2)3/h5-9H,4H2,1-3H3

InChI Key

BTCQMCOBMIXUCG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Phenoxy compound
Benzaldehyde
Benzoyl
Phenol ether
Alkyl aryl ether
Aryl-aldehyde
Monocyclic benzene moiety
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Aldehyde
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037683)
Cell membrane (HMDB: HMDB0037683)

Source

Exogenous

Exogenous (HMDB: HMDB0037683)

Food

Food (HMDB: HMDB0037683)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037683)

Biological role

Nutrient (HMDB: HMDB0037683)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	57.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	295.00 to 296.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	Not Available	Not Available
LogP	1.719 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	2.62	ALOGPS
logP	2.74	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	64.19 m³·mol⁻¹	ChemAxon
Polarizability	25.07 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]+	156.265	31661259
DarkChem	[M-H]-	152.826	31661259
DeepCCS	[M+H]+	158.39	30932474
DeepCCS	[M-H]-	156.032	30932474
DeepCCS	[M-2H]-	188.918	30932474
DeepCCS	[M+Na]+	164.484	30932474
AllCCS	[M+H]+	153.0	32859911
AllCCS	[M+H-H2O]+	149.4	32859911
AllCCS	[M+NH4]+	156.4	32859911
AllCCS	[M+Na]+	157.4	32859911
AllCCS	[M-H]-	156.1	32859911
AllCCS	[M+Na-2H]-	156.5	32859911
AllCCS	[M+HCOO]-	156.9	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.	6.09 minutes	32390414
Predicted by Siyang on May 30, 2022	16.0504 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.06 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2209.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	496.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	176.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	262.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	104.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	629.8 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	780.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	118.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1241.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	484.7 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	1574.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	417.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	429.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	440.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	519.7 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	47.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl vanillin isobutyrate	CCOC1=C(OC(=O)C(C)C)C=CC(C=O)=C1	2643.9	Standard polar	33892256
Ethyl vanillin isobutyrate	CCOC1=C(OC(=O)C(C)C)C=CC(C=O)=C1	1780.2	Standard non polar	33892256
Ethyl vanillin isobutyrate	CCOC1=C(OC(=O)C(C)C)C=CC(C=O)=C1	1739.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl vanillin isobutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9720000000-f588c9c0f098c2a3aec1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl vanillin isobutyrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl vanillin isobutyrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl vanillin isobutyrate 10V, Positive-QTOF	splash10-000i-4590000000-af940bd3520d5b0f27c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl vanillin isobutyrate 20V, Positive-QTOF	splash10-00dl-9530000000-d6e16b6fd561f54ab145	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl vanillin isobutyrate 40V, Positive-QTOF	splash10-00di-9300000000-4030d37b28ce1edee620	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl vanillin isobutyrate 10V, Negative-QTOF	splash10-000i-2190000000-29ae5b031b3648a0dcb4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl vanillin isobutyrate 20V, Negative-QTOF	splash10-000i-7980000000-0854eb06e78aef610b10	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl vanillin isobutyrate 40V, Negative-QTOF	splash10-00kr-9500000000-906c10b2f14dbd1545d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl vanillin isobutyrate 10V, Positive-QTOF	splash10-000i-0290000000-108c7fac3b3430085b7d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl vanillin isobutyrate 20V, Positive-QTOF	splash10-01bi-5960000000-c3b99f82a08581459f94	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl vanillin isobutyrate 40V, Positive-QTOF	splash10-000f-7900000000-9a0d25bdc1f3a3c22581	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl vanillin isobutyrate 10V, Negative-QTOF	splash10-000i-9070000000-1126651e73e268d99c15	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl vanillin isobutyrate 20V, Negative-QTOF	splash10-000i-7920000000-64e31457edf7353e5150	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl vanillin isobutyrate 40V, Negative-QTOF	splash10-0079-9600000000-bc601533b83b6418d94c	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016810

KNApSAcK ID

Not Available

Chemspider ID

586073

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

673160

PDB ID

Not Available

ChEBI ID

143870

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1407661

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Ethyl vanillin isobutyrate (HMDB0037683)

MOL for HMDB0037683 (Ethyl vanillin isobutyrate)

3D MOL for HMDB0037683 (Ethyl vanillin isobutyrate)

3D SDF for HMDB0037683 (Ethyl vanillin isobutyrate)

3D-SDF for HMDB0037683 (Ethyl vanillin isobutyrate)

PDB for HMDB0037683 (Ethyl vanillin isobutyrate)

3D PDB for HMDB0037683 (Ethyl vanillin isobutyrate)

SMILES for HMDB0037683 (Ethyl vanillin isobutyrate)

INCHI for HMDB0037683 (Ethyl vanillin isobutyrate)

Structure for HMDB0037683 (Ethyl vanillin isobutyrate)

3D Structure for HMDB0037683 (Ethyl vanillin isobutyrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra