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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:45:44 UTC

Update Date

2023-02-21 17:27:58 UTC

HMDB ID

HMDB0040225

Secondary Accession Numbers

HMDB40225

Metabolite Identification

Common Name

Isoamyl salicylate

Description

Isoamyl salicylate belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. Isoamyl salicylate is a bitter, floral, and herbal tasting compound. Isoamyl salicylate has been detected, but not quantified in, several different foods, such as black tea, teas (Camellia sinensis), alcoholic beverages, fruits, and red tea. This could make isoamyl salicylate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isoamyl salicylate.

Structure

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

HMDB0040225
     RDKit          3D
Isoamyl salicylate
 31 31  0  0  0  0  0  0  0  0999 V2000
   -4.2901   -1.6417   -0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4946   -0.3543   -0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9782    0.4640    0.9616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -0.7085   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1415    0.4959   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2117    0.0395    0.0053 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2541    0.9677    0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9556    2.1780    0.0841 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6307    0.5057    0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786   -0.8769    0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543   -1.3941    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2141   -0.5064    0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9773    0.8379    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6921    1.3582    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5767    2.7080    0.2274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3528   -1.4832    0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8853   -2.4342    0.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3896   -1.9906   -1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6477    0.2151   -1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2790    0.4843    1.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0973    1.5380    0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9756    0.1275    1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8454   -1.4325    0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7953   -1.2497   -1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    1.0332    0.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2285    1.1540   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154   -1.5238    0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3635   -2.4533    0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2328   -0.9058    0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8244    1.5077    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416    3.3405    0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
M  END


  Mrv0541 05061311422D          

 15 15  0  0  0  0            999 V2000
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    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
   -0.7145    2.0625    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
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   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
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  7  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  2  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040225

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCOC(=O)C1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O3/c1-9(2)7-8-15-12(14)10-5-3-4-6-11(10)13/h3-6,9,13H,7-8H2,1-2H3

> <INCHI_KEY>
PMGCQNGBLMMXEW-UHFFFAOYSA-N

> <FORMULA>
C12H16O3

> <MOLECULAR_WEIGHT>
208.2536

> <EXACT_MASS>
208.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.10522292382993

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methylbutyl 2-hydroxybenzoate

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
3.934075569333333

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.719639603218031

> <JCHEM_PKA_STRONGEST_BASIC>
-4.287621094449308

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
58.48640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methylbutyl 2-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040225
     RDKit          3D
Isoamyl salicylate
 31 31  0  0  0  0  0  0  0  0999 V2000
   -4.2901   -1.6417   -0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4946   -0.3543   -0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9782    0.4640    0.9616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -0.7085   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1415    0.4959   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2117    0.0395    0.0053 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2541    0.9677    0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9556    2.1780    0.0841 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6307    0.5057    0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786   -0.8769    0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543   -1.3941    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2141   -0.5064    0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9773    0.8379    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6921    1.3582    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5767    2.7080    0.2274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3528   -1.4832    0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8853   -2.4342    0.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3896   -1.9906   -1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6477    0.2151   -1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2790    0.4843    1.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0973    1.5380    0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9756    0.1275    1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8454   -1.4325    0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7953   -1.2497   -1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    1.0332    0.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2285    1.1540   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154   -1.5238    0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3635   -2.4533    0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2328   -0.9058    0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8244    1.5077    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416    3.3405    0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  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       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   3.080   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      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   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       1.334   0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   11                                                       
CONECT    7    8    9                                                       
CONECT    8    7   15                                                       
CONECT    9    1    2    7                                                  
CONECT   10    5   11   12                                                  
CONECT   11    6   10   13                                                  
CONECT   12   10   14   15                                                  
CONECT   13   11                                                            
CONECT   14   12                                                            
CONECT   15    8   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0040225
HETATM    1  C1  UNL     1      -4.290  -1.642  -0.255  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.495  -0.354  -0.190  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.978   0.464   0.962  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.047  -0.708  -0.124  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.141   0.496  -0.055  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.212   0.039   0.005  1.00  0.00           O  
HETATM    7  C6  UNL     1       1.254   0.968   0.076  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.956   2.178   0.084  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.631   0.506   0.137  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.879  -0.877   0.123  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.154  -1.394   0.178  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.214  -0.506   0.249  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.977   0.838   0.263  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.692   1.358   0.207  1.00  0.00           C  
HETATM   15  O3  UNL     1       3.577   2.708   0.227  1.00  0.00           O  
HETATM   16  H1  UNL     1      -5.353  -1.483   0.084  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.885  -2.434   0.377  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.390  -1.991  -1.316  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.648   0.215  -1.152  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.279   0.484   1.820  1.00  0.00           H  
HETATM   21  H6  UNL     1      -4.097   1.538   0.642  1.00  0.00           H  
HETATM   22  H7  UNL     1      -4.976   0.128   1.319  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.845  -1.432   0.689  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.795  -1.250  -1.072  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.375   1.033   0.882  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.229   1.154  -0.916  1.00  0.00           H  
HETATM   27  H12 UNL     1       2.015  -1.524   0.067  1.00  0.00           H  
HETATM   28  H13 UNL     1       4.363  -2.453   0.169  1.00  0.00           H  
HETATM   29  H14 UNL     1       6.233  -0.906   0.293  1.00  0.00           H  
HETATM   30  H15 UNL     1       5.824   1.508   0.319  1.00  0.00           H  
HETATM   31  H16 UNL     1       2.842   3.340   0.202  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4   19
CONECT    3   20   21   22
CONECT    4    5   23   24
CONECT    5    6   25   26
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   14
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15
CONECT   15   31
END

HMDB0040225
     RDKit          3D
Isoamyl salicylate
 31 31  0  0  0  0  0  0  0  0999 V2000
   -4.2901   -1.6417   -0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4946   -0.3543   -0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9782    0.4640    0.9616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -0.7085   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1415    0.4959   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2117    0.0395    0.0053 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2541    0.9677    0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9556    2.1780    0.0841 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6307    0.5057    0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786   -0.8769    0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543   -1.3941    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2141   -0.5064    0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9773    0.8379    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6921    1.3582    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5767    2.7080    0.2274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3528   -1.4832    0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8853   -2.4342    0.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3896   -1.9906   -1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6477    0.2151   -1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2790    0.4843    1.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0973    1.5380    0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9756    0.1275    1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8454   -1.4325    0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7953   -1.2497   -1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    1.0332    0.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2285    1.1540   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154   -1.5238    0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3635   -2.4533    0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2328   -0.9058    0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8244    1.5077    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416    3.3405    0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isoamyl salicylic acid	Generator
2-Hydroxybenzoic acid, 3-methylbutyl ester	HMDB
3-Methylbutyl O-hydroxybenzoate	HMDB
3-Methylbutyl salicylate	HMDB
Benzoic acid, 2-hydroxy-, 3-methylbutyl ester	HMDB
Benzoic acid, O-hydroxy, 3-methylbutyl ester	HMDB
Isoamyl O-hydroxybenzoate	HMDB
Isopentyl O-hydroxybenzoate	HMDB
Isopentyl salicylate	HMDB
Isopentyl-2-hydroxyphenyl methanoate	HMDB
Orchidee	HMDB
Salicylic acid, isopentyl ester	HMDB
Sanfoin	HMDB
Trefle	HMDB
Trefol	HMDB
Tressane	HMDB
3-Methylbutyl 2-hydroxybenzoic acid	Generator
Isoamyl salicylate	MeSH

Chemical Formula

C₁₂H₁₆O₃

Average Molecular Weight

208.2536

Monoisotopic Molecular Weight

208.109944378

IUPAC Name

3-methylbutyl 2-hydroxybenzoate

Traditional Name

3-methylbutyl 2-hydroxybenzoate

CAS Registry Number

87-20-7

SMILES

CC(C)CCOC(=O)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C12H16O3/c1-9(2)7-8-15-12(14)10-5-3-4-6-11(10)13/h3-6,9,13H,7-8H2,1-2H3

InChI Key

PMGCQNGBLMMXEW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

o-Hydroxybenzoic acid esters

Alternative Parents

Substituents

O-hydroxybenzoic acid ester
Salicylic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Bitter

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040225)
Cell membrane (HMDB: HMDB0040225)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040225)

Source

Exogenous

Exogenous (HMDB: HMDB0040225)

Food

Food (HMDB: HMDB0040225)

Tea

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0040225)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040225)

Biological role

Nutrient (HMDB: HMDB0040225)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	277.00 to 278.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.14 mg/mL at 25 °C	Not Available
LogP	4.370	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	3.44	ALOGPS
logP	3.93	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.72	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.49 m³·mol⁻¹	ChemAxon
Polarizability	23.11 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]+	148.019	31661259
DarkChem	[M-H]-	143.696	31661259
DeepCCS	[M+H]+	147.903	30932474
DeepCCS	[M-H]-	145.342	30932474
DeepCCS	[M-2H]-	181.301	30932474
DeepCCS	[M+Na]+	156.712	30932474
AllCCS	[M+H]+	146.9	32859911
AllCCS	[M+H-H2O]+	143.0	32859911
AllCCS	[M+NH4]+	150.5	32859911
AllCCS	[M+Na]+	151.5	32859911
AllCCS	[M-H]-	150.0	32859911
AllCCS	[M+Na-2H]-	150.6	32859911
AllCCS	[M+HCOO]-	151.5	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.	7.71 minutes	32390414
Predicted by Siyang on May 30, 2022	16.4962 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.05 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	23.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2538.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	506.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	205.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	308.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	414.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	768.1 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	832.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1326.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	510.7 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	1552.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	461.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	550.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	444.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	348.4 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	29.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoamyl salicylate	CC(C)CCOC(=O)C1=CC=CC=C1O	2167.8	Standard polar	33892256
Isoamyl salicylate	CC(C)CCOC(=O)C1=CC=CC=C1O	1541.1	Standard non polar	33892256
Isoamyl salicylate	CC(C)CCOC(=O)C1=CC=CC=C1O	1598.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoamyl salicylate,1TMS,isomer #1	CC(C)CCOC(=O)C1=CC=CC=C1O[Si](C)(C)C	1701.8	Semi standard non polar	33892256
Isoamyl salicylate,1TBDMS,isomer #1	CC(C)CCOC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C	1926.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isoamyl salicylate EI-B (Non-derivatized)	splash10-00dl-9800000000-e932949ffff596a0e7a8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isoamyl salicylate EI-B (Non-derivatized)	splash10-00dl-9600000000-5a35db6cf062e262bd0f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isoamyl salicylate EI-B (Non-derivatized)	splash10-00di-9700000000-e62a29f19910b38602dc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isoamyl salicylate EI-B (Non-derivatized)	splash10-00dl-9800000000-e932949ffff596a0e7a8	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isoamyl salicylate EI-B (Non-derivatized)	splash10-00dl-9600000000-5a35db6cf062e262bd0f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isoamyl salicylate EI-B (Non-derivatized)	splash10-00di-9700000000-e62a29f19910b38602dc	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoamyl salicylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-8900000000-221dcc93cd4e631a6b26	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoamyl salicylate GC-MS (1 TMS) - 70eV, Positive	splash10-0006-7910000000-ca285106374821c7dff0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoamyl salicylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoamyl salicylate 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 - Isoamyl salicylate 10V, Positive-QTOF	splash10-0ab9-5490000000-1a44be2d7c5cbd1859f4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl salicylate 20V, Positive-QTOF	splash10-00di-9410000000-7a0e217d95aa026bd9c3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl salicylate 40V, Positive-QTOF	splash10-0kml-9100000000-7898e32ef213461a0f5a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl salicylate 10V, Negative-QTOF	splash10-0a4i-4390000000-48cde09d2017c6869000	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl salicylate 20V, Negative-QTOF	splash10-052o-9820000000-4948a94706f178549d11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl salicylate 40V, Negative-QTOF	splash10-0006-9100000000-48773c923f8afdbfa8cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl salicylate 10V, Negative-QTOF	splash10-052f-9070000000-c97178794593493ca4ca	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl salicylate 20V, Negative-QTOF	splash10-0006-9110000000-b5a678739c9679b6c0f3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl salicylate 40V, Negative-QTOF	splash10-0006-9000000000-c24304b5660720a960ed	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl salicylate 10V, Positive-QTOF	splash10-00fr-0920000000-972274e34fe69d12098e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl salicylate 20V, Positive-QTOF	splash10-00di-4900000000-bf7823578da1a19f182d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamyl salicylate 40V, Positive-QTOF	splash10-0a4i-9300000000-35f8c7a337f718d6149d	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX 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

FDB019939

KNApSAcK ID

Not Available

Chemspider ID

6612

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6874

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1006772

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 Isoamyl salicylate (HMDB0040225)

MOL for HMDB0040225 (Isoamyl salicylate)

3D MOL for HMDB0040225 (Isoamyl salicylate)

3D SDF for HMDB0040225 (Isoamyl salicylate)

3D-SDF for HMDB0040225 (Isoamyl salicylate)

PDB for HMDB0040225 (Isoamyl salicylate)

3D PDB for HMDB0040225 (Isoamyl salicylate)

SMILES for HMDB0040225 (Isoamyl salicylate)

INCHI for HMDB0040225 (Isoamyl salicylate)

Structure for HMDB0040225 (Isoamyl salicylate)

3D Structure for HMDB0040225 (Isoamyl salicylate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra