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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:09:00 UTC

Update Date

2022-03-07 02:55:55 UTC

HMDB ID

HMDB0038804

Secondary Accession Numbers

HMDB38804

Metabolite Identification

Common Name

3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid

Description

3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid, also known as trolox C, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. Based on a literature review a significant number of articles have been published on 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid.

Structure

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

HMDB0038804
     RDKit          3D
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.6286    1.6279    0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053    0.7870    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662    1.3121    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0681    2.7370    0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0701    0.4708    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1856   -0.8647   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4132   -1.3349   -0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6020   -2.7197   -0.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5333   -0.5304   -0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8172   -1.0155   -0.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0516   -1.6359   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195   -0.7326   -0.7935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903    0.3421    0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9847   -0.3958    1.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3200    1.3284   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9540    2.5225   -0.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064    1.0163   -0.7070 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.9534    0.5874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3790    1.2256   -0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0225    1.5106    1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3793    2.6974   -0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6568    2.9405    1.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3969    3.4264   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120    2.9464    0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4281   -3.1452   -0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253   -2.7092   -1.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7718   -3.3946   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9075   -1.9733   -0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0690   -2.5820   -0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3991   -1.7788    0.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0206   -1.2883   -1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244   -0.2311   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8194    0.2149    1.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3775   -1.3809    1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2359   -0.5142    2.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7120    0.1678   -1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 13 18  1  0
  9  2  1  0
 18  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 17 36  1  0
M  END


  Mrv0541 05061310402D          

 18 19  0  0  0  0            999 V2000
    5.0013    1.2375    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165    0.6817    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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3343   -0.0935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862    1.3137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  7  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 14  4  1  0  0  0  0
 14  6  1  0  0  0  0
 14 13  1  0  0  0  0
 15 11  1  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038804

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(O)C(C)=C2CCC(C)(OC2=C1C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O4/c1-7-8(2)12-10(9(3)11(7)15)5-6-14(4,18-12)13(16)17/h15H,5-6H2,1-4H3,(H,16,17)

> <INCHI_KEY>
GLEVLJDDWXEYCO-UHFFFAOYSA-N

> <FORMULA>
C14H18O4

> <MOLECULAR_WEIGHT>
250.2903

> <EXACT_MASS>
250.120509064

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.937731874970144

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
3.65943605

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.683424566841119

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.765815991743847

> <JCHEM_PKA_STRONGEST_BASIC>
-4.911183415952698

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
68.07950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trolox

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038804
     RDKit          3D
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.6286    1.6279    0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053    0.7870    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662    1.3121    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0681    2.7370    0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0701    0.4708    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1856   -0.8647   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4132   -1.3349   -0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6020   -2.7197   -0.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5333   -0.5304   -0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8172   -1.0155   -0.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0516   -1.6359   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195   -0.7326   -0.7935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903    0.3421    0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9847   -0.3958    1.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3200    1.3284   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9540    2.5225   -0.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064    1.0163   -0.7070 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.9534    0.5874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3790    1.2256   -0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0225    1.5106    1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3793    2.6974   -0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6568    2.9405    1.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3969    3.4264   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120    2.9464    0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4281   -3.1452   -0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253   -2.7092   -1.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7718   -3.3946   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9075   -1.9733   -0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0690   -2.5820   -0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3991   -1.7788    0.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0206   -1.2883   -1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244   -0.2311   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8194    0.2149    1.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3775   -1.3809    1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2359   -0.5142    2.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7120    0.1678   -1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 13 18  1  0
  9  2  1  0
 18  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 17 36  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       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.141   2.987   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.151   1.273   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.624  -0.175   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.161   2.452   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4   14                                                            
CONECT    5    6   10                                                       
CONECT    6    5   14                                                       
CONECT    7    1    8   11                                                  
CONECT    8    2    7   12                                                  
CONECT    9    3   10   11                                                  
CONECT   10    5    9   12                                                  
CONECT   11    7    9   15                                                  
CONECT   12    8   10   18                                                  
CONECT   13   14   16   17                                                  
CONECT   14    4    6   13   18                                             
CONECT   15   11                                                            
CONECT   16   13                                                            
CONECT   17   13                                                            
CONECT   18   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0038804
HETATM    1  C1  UNL     1      -3.629   1.628   0.098  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.405   0.787   0.036  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.166   1.312   0.357  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.068   2.737   0.768  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.070   0.471   0.276  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.186  -0.865  -0.113  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.413  -1.335  -0.417  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.602  -2.720  -0.828  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.533  -0.530  -0.350  1.00  0.00           C  
HETATM   10  O1  UNL     1      -3.817  -1.015  -0.666  1.00  0.00           O  
HETATM   11  C10 UNL     1       1.052  -1.636  -0.155  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.119  -0.733  -0.793  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.390   0.342   0.270  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.985  -0.396   1.459  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.320   1.328  -0.294  1.00  0.00           C  
HETATM   16  O2  UNL     1       2.954   2.522  -0.418  1.00  0.00           O  
HETATM   17  O3  UNL     1       4.606   1.016  -0.707  1.00  0.00           O  
HETATM   18  O4  UNL     1       1.184   0.953   0.587  1.00  0.00           O  
HETATM   19  H1  UNL     1      -4.379   1.226  -0.592  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.022   1.511   1.147  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.379   2.697  -0.090  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.657   2.940   1.692  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.397   3.426  -0.031  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.012   2.946   0.975  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.428  -3.145  -0.184  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.025  -2.709  -1.866  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.772  -3.395  -0.817  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.907  -1.973  -0.947  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.069  -2.582  -0.646  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.399  -1.779   0.899  1.00  0.00           H  
HETATM   31  H13 UNL     1       3.021  -1.288  -1.054  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.624  -0.231  -1.650  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.819   0.215   1.857  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.377  -1.381   1.204  1.00  0.00           H  
HETATM   35  H17 UNL     1       2.236  -0.514   2.264  1.00  0.00           H  
HETATM   36  H18 UNL     1       4.712   0.168  -1.272  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    9
CONECT    3    4    5
CONECT    4   22   23   24
CONECT    5    6    6   18
CONECT    6    7   11
CONECT    7    8    9    9
CONECT    8   25   26   27
CONECT    9   10
CONECT   10   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   15   18
CONECT   14   33   34   35
CONECT   15   16   16   17
CONECT   17   36
END

HMDB0038804
     RDKit          3D
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.6286    1.6279    0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053    0.7870    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662    1.3121    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0681    2.7370    0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0701    0.4708    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1856   -0.8647   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4132   -1.3349   -0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6020   -2.7197   -0.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5333   -0.5304   -0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8172   -1.0155   -0.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0516   -1.6359   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195   -0.7326   -0.7935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903    0.3421    0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9847   -0.3958    1.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3200    1.3284   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9540    2.5225   -0.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064    1.0163   -0.7070 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.9534    0.5874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3790    1.2256   -0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0225    1.5106    1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3793    2.6974   -0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6568    2.9405    1.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3969    3.4264   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120    2.9464    0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4281   -3.1452   -0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253   -2.7092   -1.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7718   -3.3946   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9075   -1.9733   -0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0690   -2.5820   -0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3991   -1.7788    0.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0206   -1.2883   -1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244   -0.2311   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8194    0.2149    1.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3775   -1.3809    1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2359   -0.5142    2.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7120    0.1678   -1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 13 18  1  0
  9  2  1  0
 18  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 17 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid	ChEBI
Trolox C	ChEBI
6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylate	Generator
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylate	Generator
Trolox	HMDB
Trolox(TM)	HMDB
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid	ChEBI
6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxylic acid	MeSH
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2- carboxylic acid	MeSH
(+--)-Trolox	MeSH

Chemical Formula

C₁₄H₁₈O₄

Average Molecular Weight

250.2903

Monoisotopic Molecular Weight

250.120509064

IUPAC Name

6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

Traditional Name

trolox

CAS Registry Number

56305-04-5

SMILES

CC1=C(O)C(C)=C2CCC(C)(OC2=C1C)C(O)=O

InChI Identifier

InChI=1S/C14H18O4/c1-7-8(2)12-10(9(3)11(7)15)5-6-14(4,18-12)13(16)17/h15H,5-6H2,1-4H3,(H,16,17)

InChI Key

GLEVLJDDWXEYCO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Alkyl aryl ether
Benzenoid
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:82625 )
phenols (CHEBI:82625 )
chromanol (CHEBI:82625 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038804)

Cellular substructure

Membrane (HMDB: HMDB0038804)

Source

Exogenous

Food

Food (HMDB: HMDB0038804)

Not Available

Nutrient (HMDB: HMDB0038804)

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
Water Solubility	0.38 g/L	ALOGPS
logP	2.75	ALOGPS
logP	3.66	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.08 m³·mol⁻¹	ChemAxon
Polarizability	26.94 Å³	ChemAxon
Number of Rings	2	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]+	157.641	31661259
DarkChem	[M-H]-	154.285	31661259
DeepCCS	[M+H]+	159.816	30932474
DeepCCS	[M-H]-	157.458	30932474
DeepCCS	[M-2H]-	190.345	30932474
DeepCCS	[M+Na]+	165.91	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	151.8	32859911
AllCCS	[M+NH4]+	159.1	32859911
AllCCS	[M+Na]+	160.1	32859911
AllCCS	[M-H]-	161.6	32859911
AllCCS	[M+Na-2H]-	161.6	32859911
AllCCS	[M+HCOO]-	161.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid	CC1=C(O)C(C)=C2CCC(C)(OC2=C1C)C(O)=O	3384.7	Standard polar	33892256
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid	CC1=C(O)C(C)=C2CCC(C)(OC2=C1C)C(O)=O	2018.2	Standard non polar	33892256
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid	CC1=C(O)C(C)=C2CCC(C)(OC2=C1C)C(O)=O	2174.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid,1TMS,isomer #1	CC1=C(C)C2=C(CCC(C)(C(=O)O)O2)C(C)=C1O[Si](C)(C)C	2098.3	Semi standard non polar	33892256
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid,1TMS,isomer #2	CC1=C(C)C2=C(CCC(C)(C(=O)O[Si](C)(C)C)O2)C(C)=C1O	2013.7	Semi standard non polar	33892256
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid,2TMS,isomer #1	CC1=C(C)C2=C(CCC(C)(C(=O)O[Si](C)(C)C)O2)C(C)=C1O[Si](C)(C)C	2127.5	Semi standard non polar	33892256
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid,1TBDMS,isomer #1	CC1=C(C)C2=C(CCC(C)(C(=O)O)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	2338.3	Semi standard non polar	33892256
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid,1TBDMS,isomer #2	CC1=C(C)C2=C(CCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O	2268.8	Semi standard non polar	33892256
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid,2TBDMS,isomer #1	CC1=C(C)C2=C(CCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	2577.6	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 - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0nml-1790000000-34dbaaa9d2d537ea683c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-9125000000-c355b1eafb56448742b0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid LC-ESI-qTof , Positive-QTOF	splash10-066r-1910000000-d3110bbdbf84bfc4a51a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid , positive-QTOF	splash10-066r-1910000000-d3110bbdbf84bfc4a51a	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 10V, Positive-QTOF	splash10-0uxr-0970000000-6d332fcae90355a38722	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 20V, Positive-QTOF	splash10-0o7i-1950000000-e9a6dccef7c156db25eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 40V, Positive-QTOF	splash10-08fr-1900000000-dbf2f9ed4cf23ec2fa22	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 10V, Negative-QTOF	splash10-0002-0090000000-8d9e92e3b8dbc69e9384	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 20V, Negative-QTOF	splash10-0a4j-0290000000-27b5e1cc9a996f954b5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 40V, Negative-QTOF	splash10-03di-1900000000-68b68f1c88d2469ed89a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 10V, Negative-QTOF	splash10-0002-0090000000-18320cb565cfb33802ea	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 20V, Negative-QTOF	splash10-0a4i-0190000000-8e5dd5c019e57ddfbe1e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 40V, Negative-QTOF	splash10-03di-2900000000-c87b3764a772e98228f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 10V, Positive-QTOF	splash10-0udi-0190000000-2e81bd608e8c504411e7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 20V, Positive-QTOF	splash10-0rki-1940000000-9838ee98efbe94a73dfd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid 40V, Positive-QTOF	splash10-0002-9800000000-023a301f5823935c0e1d	2021-09-22	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

FDB018229

KNApSAcK ID

Not Available

Chemspider ID

37117

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trolox

METLIN ID

Not Available

PubChem Compound

40634

PDB ID

Not Available

ChEBI ID

82625

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

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

Showing metabocard for 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid (HMDB0038804)

MOL for HMDB0038804 (3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid)

3D MOL for HMDB0038804 (3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid)

3D SDF for HMDB0038804 (3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid)

3D-SDF for HMDB0038804 (3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid)

PDB for HMDB0038804 (3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid)

3D PDB for HMDB0038804 (3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid)

SMILES for HMDB0038804 (3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid)

INCHI for HMDB0038804 (3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid)

Structure for HMDB0038804 (3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid)

3D Structure for HMDB0038804 (3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra