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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:58:02 UTC

Update Date

2022-03-07 02:56:35 UTC

HMDB ID

HMDB0040424

Secondary Accession Numbers

HMDB40424

Metabolite Identification

Common Name

Ethyl 2-benzylacetoacetate

Description

Ethyl 2-benzylacetoacetate belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom. Ethyl 2-benzylacetoacetate is a balsam, fruity, and jasmine tasting compound. Based on a literature review very few articles have been published on Ethyl 2-benzylacetoacetate.

Structure

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

HMDB0040424
     RDKit          3D
Ethyl 2-benzylacetoacetate
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.8410   -1.6797   -0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6571   -1.9894    0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9659   -0.7777    0.9583 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4175   -0.0077   -0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5165   -0.3682   -1.2380 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7054    1.2524    0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881    1.0235    1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4984    0.1217    0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464    0.5844   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4902   -0.3015   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867   -1.6453   -0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437   -2.1244    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4136   -1.2389    0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3510    2.0098   -0.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3386    3.3218   -0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.5692   -2.0588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497   -0.6732   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8497   -2.4051   -1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7978   -1.7101    0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0047   -2.7500    0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0547   -2.3205    1.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217    1.8751    0.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1124    0.6303    2.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8968    2.0217    1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178    1.6478   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3021    0.0926   -1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1482   -2.2940   -0.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643   -3.1886    0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6201   -1.6560    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    3.4760   -1.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205    3.4102   -0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4676    4.0939   -0.7963 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  1  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
  6 14  1  0
 14 15  1  0
 14 16  2  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
M  END


  Mrv0541 05061311502D          

 16 16  0  0  0  0            999 V2000
    3.1599    2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099    5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8724    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349    2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    5.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 10  2  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  2  0  0  0  0
 15 13  2  0  0  0  0
 16  3  1  0  0  0  0
 16 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040424

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O3/c1-3-16-13(15)12(10(2)14)9-11-7-5-4-6-8-11/h4-8,12H,3,9H2,1-2H3

> <INCHI_KEY>
XDWQYMXQMNUWID-UHFFFAOYSA-N

> <FORMULA>
C13H16O3

> <MOLECULAR_WEIGHT>
220.2643

> <EXACT_MASS>
220.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.59419074275887

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 2-benzyl-3-oxobutanoate

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
2.622569181

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.605577672239995

> <JCHEM_PKA_STRONGEST_BASIC>
-7.010968684509268

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
61.32710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 2-benzyl-3-oxobutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040424
     RDKit          3D
Ethyl 2-benzylacetoacetate
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.8410   -1.6797   -0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6571   -1.9894    0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9659   -0.7777    0.9583 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4175   -0.0077   -0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5165   -0.3682   -1.2380 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7054    1.2524    0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881    1.0235    1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4984    0.1217    0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464    0.5844   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4902   -0.3015   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867   -1.6453   -0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437   -2.1244    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4136   -1.2389    0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3510    2.0098   -0.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3386    3.3218   -0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.5692   -2.0588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497   -0.6732   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8497   -2.4051   -1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7978   -1.7101    0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0047   -2.7500    0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0547   -2.3205    1.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217    1.8751    0.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1124    0.6303    2.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8968    2.0217    1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178    1.6478   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3021    0.0926   -1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1482   -2.2940   -0.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643   -3.1886    0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6201   -1.6560    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    3.4760   -1.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205    3.4102   -0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4676    4.0939   -0.7963 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  1  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
  6 14  1  0
 14 15  1  0
 14 16  2  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  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       5.898   5.596   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.828   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.908   9.597   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.138  10.931   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.138   8.264   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.598  10.931   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.598   8.264   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.288   9.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.288   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.828   9.597   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.518   8.264   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.978   8.264   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.518   5.596   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.208   9.597   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.208   6.930   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   10                                                            
CONECT    3    1   16                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   11                                                       
CONECT    8    6   11                                                       
CONECT    9   11   12                                                       
CONECT   10    2   12   14                                                  
CONECT   11    7    8    9                                                  
CONECT   12    9   10   13                                                  
CONECT   13   12   15   16                                                  
CONECT   14   10                                                            
CONECT   15   13                                                            
CONECT   16    3   13                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0040424
HETATM    1  C1  UNL     1       3.841  -1.680  -0.162  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.657  -1.989   0.723  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.966  -0.778   0.958  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.417  -0.008  -0.044  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.516  -0.368  -1.238  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.705   1.252   0.271  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.488   1.023   1.170  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.498   0.122   0.596  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.546   0.584  -0.162  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.490  -0.302  -0.696  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.387  -1.645  -0.474  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.344  -2.124   0.282  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.414  -1.239   0.807  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.351   2.010  -0.954  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.339   3.322  -0.899  1.00  0.00           C  
HETATM   16  O3  UNL     1       0.620   1.569  -2.059  1.00  0.00           O  
HETATM   17  H1  UNL     1       3.750  -0.673  -0.618  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.850  -2.405  -1.015  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.798  -1.710   0.402  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.005  -2.750   0.256  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.055  -2.320   1.716  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.422   1.875   0.881  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.112   0.630   2.163  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.897   2.022   1.433  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.618   1.648  -0.328  1.00  0.00           H  
HETATM   26  H10 UNL     1      -4.302   0.093  -1.287  1.00  0.00           H  
HETATM   27  H11 UNL     1      -4.148  -2.294  -0.913  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.264  -3.189   0.456  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.620  -1.656   1.388  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.933   3.476  -1.823  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.021   3.410  -0.035  1.00  0.00           H  
HETATM   32  H16 UNL     1       0.468   4.094  -0.796  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   14   22
CONECT    7    8   23   24
CONECT    8    9    9   13
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   12   27
CONECT   12   13   13   28
CONECT   13   29
CONECT   14   15   16   16
CONECT   15   30   31   32
END

HMDB0040424
     RDKit          3D
Ethyl 2-benzylacetoacetate
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.8410   -1.6797   -0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6571   -1.9894    0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9659   -0.7777    0.9583 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4175   -0.0077   -0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5165   -0.3682   -1.2380 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7054    1.2524    0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881    1.0235    1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4984    0.1217    0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464    0.5844   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4902   -0.3015   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867   -1.6453   -0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437   -2.1244    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4136   -1.2389    0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3510    2.0098   -0.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3386    3.3218   -0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.5692   -2.0588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497   -0.6732   -0.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8497   -2.4051   -1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7978   -1.7101    0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0047   -2.7500    0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0547   -2.3205    1.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217    1.8751    0.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1124    0.6303    2.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8968    2.0217    1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178    1.6478   -0.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3021    0.0926   -1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1482   -2.2940   -0.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643   -3.1886    0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6201   -1.6560    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    3.4760   -1.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205    3.4102   -0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4676    4.0939   -0.7963 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  1  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
  6 14  1  0
 14 15  1  0
 14 16  2  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethyl 2-benzylacetoacetic acid	Generator
2-Benzylacetoacetic acid ethyl ester	HMDB
Benzenepropanoic acid, alpha-acetyl-, ethyl ester	HMDB
Ethyl 2-acetyl-3-phenylpropionate	HMDB
Ethyl 2-benzyl-3-oxobutanoate	HMDB
Ethyl alpha-acetylhydrocinnamate	HMDB
Ethyl alpha-benzylacetoacetate	HMDB
Ethyl benzylacetoacetate	HMDB
Ethyl-a-benzylacetoacetate	HMDB
FEMA 2416	HMDB
Hydrocinnamic acid, alpha-acetyl-, ethyl ester	HMDB
Ethyl 2-benzyl-3-oxobutanoic acid	Generator

Chemical Formula

C₁₃H₁₆O₃

Average Molecular Weight

220.2643

Monoisotopic Molecular Weight

220.109944378

IUPAC Name

ethyl 2-benzyl-3-oxobutanoate

Traditional Name

ethyl 2-benzyl-3-oxobutanoate

CAS Registry Number

620-79-1

SMILES

CCOC(=O)C(CC1=CC=CC=C1)C(C)=O

InChI Identifier

InChI=1S/C13H16O3/c1-3-16-13(15)12(10(2)14)9-11-7-5-4-6-8-11/h4-8,12H,3,9H2,1-2H3

InChI Key

XDWQYMXQMNUWID-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Beta-keto acids and derivatives

Direct Parent

Beta-keto acids and derivatives

Alternative Parents

Substituents

Beta-keto acid
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
1,3-dicarbonyl compound
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cell membrane (HMDB: HMDB0040424)

Cellular substructure

Membrane (HMDB: HMDB0040424)

Source

Exogenous

Food

Food (HMDB: HMDB0040424)

Not Available

Nutrient (HMDB: HMDB0040424)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0040424)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	276.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	241.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.52	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.15	ALOGPS
logP	2.62	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	61.33 m³·mol⁻¹	ChemAxon
Polarizability	23.59 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]+	151.558	31661259
DarkChem	[M-H]-	151.615	31661259
DeepCCS	[M+H]+	149.295	30932474
DeepCCS	[M-H]-	146.937	30932474
DeepCCS	[M-2H]-	181.319	30932474
DeepCCS	[M+Na]+	157.239	30932474
AllCCS	[M+H]+	149.8	32859911
AllCCS	[M+H-H2O]+	145.9	32859911
AllCCS	[M+NH4]+	153.4	32859911
AllCCS	[M+Na]+	154.5	32859911
AllCCS	[M-H]-	153.3	32859911
AllCCS	[M+Na-2H]-	153.8	32859911
AllCCS	[M+HCOO]-	154.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 2-benzylacetoacetate	CCOC(=O)C(CC1=CC=CC=C1)C(C)=O	2422.0	Standard polar	33892256
Ethyl 2-benzylacetoacetate	CCOC(=O)C(CC1=CC=CC=C1)C(C)=O	1505.6	Standard non polar	33892256
Ethyl 2-benzylacetoacetate	CCOC(=O)C(CC1=CC=CC=C1)C(C)=O	1585.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 2-benzylacetoacetate,1TMS,isomer #1	CCOC(=O)C(CC1=CC=CC=C1)=C(C)O[Si](C)(C)C	1753.5	Semi standard non polar	33892256
Ethyl 2-benzylacetoacetate,1TMS,isomer #1	CCOC(=O)C(CC1=CC=CC=C1)=C(C)O[Si](C)(C)C	1698.5	Standard non polar	33892256
Ethyl 2-benzylacetoacetate,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(CC1=CC=CC=C1)C(=O)OCC	1642.5	Semi standard non polar	33892256
Ethyl 2-benzylacetoacetate,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(CC1=CC=CC=C1)C(=O)OCC	1681.9	Standard non polar	33892256
Ethyl 2-benzylacetoacetate,1TBDMS,isomer #1	CCOC(=O)C(CC1=CC=CC=C1)=C(C)O[Si](C)(C)C(C)(C)C	1980.1	Semi standard non polar	33892256
Ethyl 2-benzylacetoacetate,1TBDMS,isomer #1	CCOC(=O)C(CC1=CC=CC=C1)=C(C)O[Si](C)(C)C(C)(C)C	1894.9	Standard non polar	33892256
Ethyl 2-benzylacetoacetate,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(CC1=CC=CC=C1)C(=O)OCC	1869.8	Semi standard non polar	33892256
Ethyl 2-benzylacetoacetate,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(CC1=CC=CC=C1)C(=O)OCC	1889.4	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 2-benzylacetoacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9400000000-32a3b4ce69ea00325764	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 2-benzylacetoacetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 2-benzylacetoacetate 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 2-benzylacetoacetate 10V, Negative-QTOF	splash10-014i-1890000000-ccf3b735f61c0a1f9b0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-benzylacetoacetate 20V, Negative-QTOF	splash10-0059-2900000000-c494d37f1accdcd02286	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-benzylacetoacetate 40V, Negative-QTOF	splash10-0002-4900000000-d15bc2bee83f69dfe61f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-benzylacetoacetate 10V, Negative-QTOF	splash10-014i-0890000000-f6180a4db2eec236976f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-benzylacetoacetate 20V, Negative-QTOF	splash10-0006-4910000000-a2a9dfa4a9409a2e160f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-benzylacetoacetate 40V, Negative-QTOF	splash10-0f6x-4900000000-278223498bc5dbc058af	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-benzylacetoacetate 10V, Positive-QTOF	splash10-00di-1690000000-65c9235205af36f80ed1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-benzylacetoacetate 20V, Positive-QTOF	splash10-002f-5930000000-02ef713b8f2c11cb5577	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-benzylacetoacetate 40V, Positive-QTOF	splash10-003u-4900000000-66930d9f224828983eee	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-benzylacetoacetate 10V, Positive-QTOF	splash10-006y-4920000000-c6431ae7e7042093bd0c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-benzylacetoacetate 20V, Positive-QTOF	splash10-000x-5900000000-c77d65840e230eebb446	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 2-benzylacetoacetate 40V, Positive-QTOF	splash10-004i-3900000000-b5ebe3fb1b871d0c91f2	2021-09-25	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

FDB020157

KNApSAcK ID

Not Available

Chemspider ID

216124

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

246929

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1022241

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 2-benzylacetoacetate (HMDB0040424)

MOL for HMDB0040424 (Ethyl 2-benzylacetoacetate)

3D MOL for HMDB0040424 (Ethyl 2-benzylacetoacetate)

3D SDF for HMDB0040424 (Ethyl 2-benzylacetoacetate)

3D-SDF for HMDB0040424 (Ethyl 2-benzylacetoacetate)

PDB for HMDB0040424 (Ethyl 2-benzylacetoacetate)

3D PDB for HMDB0040424 (Ethyl 2-benzylacetoacetate)

SMILES for HMDB0040424 (Ethyl 2-benzylacetoacetate)

INCHI for HMDB0040424 (Ethyl 2-benzylacetoacetate)

Structure for HMDB0040424 (Ethyl 2-benzylacetoacetate)

3D Structure for HMDB0040424 (Ethyl 2-benzylacetoacetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra