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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:37 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0003154

Secondary Accession Numbers

HMDB03154

Metabolite Identification

Common Name

Canthaxanthin

Description

Canthaxanthin, also known as Cantaxanthin, Cantaxanthine, or Canthaxanthine is a keto-carotenoid, a pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as terpenoids. Canthaxanin is also classified as a xanthophyll. Xanthophylls are yellow pigments and form one of two major divisions of the carotenoid group; the other division is formed by the carotenes. Both are carotenoids. Xanthophylls and carotenes are similar in structure, but xanthophylls contain oxygen atoms while carotenes are purely hydrocarbons, which do not contain oxygen. Their content of oxygen causes xanthophylls to be more polar (in molecular structure) than carotenes and causes their separation from carotenes in many types of chromatography. (Carotenes are usually more orange in color than xanthophylls. Canthaxanthin is naturally found in bacteria, algae and some fungi. Canthaxanthin is associated with E number E161g and is approved for use as a food coloring agent in different countries, including the United States and the EU. Canthaxanthin is used as poultry feed additive to yield red color in skin and yolks. The European Union permits the use of canthaxanthin in feedstuff at a maximum content of 25 mg/kg of final feedstuff while the United States allows the use of this pigment in broiler chicken and salmonid fish feeds. Canthoxanthin was first isolated in edible chanterelle mushroom (Cantharellus cinnabarinus), from which it derived its name. It has also been found in green algae, bacteria, archea (a halophilic archaeon called Haloferax alexandrines), fungi and bioaccumulates in tissues and egg yolk from wild birds and at low levels in crustaceans and fish such as carp, golden grey mullet, and seabream. Canthaxanthin is not found in wild Atlantic Salmon, but is a minor carotenoid in Pacific Salmon. Canthaxanthin is used in farm-raised trout to give a red/orange color to their flesh similar to wild trout. Canthaxanthin has been used as a food additive for egg yolk, in cosmetics and as a pigmenting agent for human skin applications. It has also been used as a feed additive in fish and crustacean farms. Canthaxanthin is a potent lipid-soluble antioxidant (PMID: 2505240 ). Canthaxanthin increases resistance to lipid peroxidation primarily by enhancing membrane alpha-tocopherol levels and secondarily by providing weak direct antioxidant activity. Canthaxanthin biosynthesis in bacteria and algae proceeds from beta-carotene via the action of an enzyme known as a beta-carotene ketolase, that is able to add a carbonyl group to carbon 4 and 4' of the beta carotene molecule.

Structure

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

Canthaxanthin
  Mrv1652305201900032D          

 42 43  0  0  0  0            999 V2000
    2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1044  -11.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3298  -11.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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  2 20  2  0  0  0  0
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 39 40  1  0  0  0  0
 33 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
M  END

HMDB0003154
     RDKit          3D
Canthaxanthin
 94 95  0  0  0  0  0  0  0  0999 V2000
  -10.9393    3.5142   -1.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2081    0.0168    2.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2514    1.4106    2.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0350    2.1084    3.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
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 40 94  1  0
M  END

Canthaxanthin
  Mrv1652305201900032D          

 42 43  0  0  0  0            999 V2000
    2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2452  -11.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1044  -11.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3298  -11.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  2 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
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 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 33 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003154

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(=O)CCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H52O2/c1-29(17-13-19-31(3)21-23-35-33(5)37(41)25-27-39(35,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-36-34(6)38(42)26-28-40(36,9)10/h11-24H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+

> <INCHI_KEY>
FDSDTBUPSURDBL-DKLMTRRASA-N

> <FORMULA>
C40H52O2

> <MOLECULAR_WEIGHT>
564.854

> <EXACT_MASS>
564.396730914

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
72.15685238575475

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one

> <ALOGPS_LOGP>
8.71

> <JCHEM_LOGP>
9.789514377333333

> <ALOGPS_LOGS>
-6.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.58928982426813

> <JCHEM_PKA_STRONGEST_BASIC>
-4.450363810038525

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
192.9982

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.61e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
canthaxanthin

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0003154
     RDKit          3D
Canthaxanthin
 94 95  0  0  0  0  0  0  0  0999 V2000
  -10.9393    3.5142   -1.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9772    2.8692    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9391    2.1220    0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7825    1.9608   -0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7651    1.2117   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1858    1.5182   -2.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7317    0.0099   -0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 78  1  0
 34 79  1  0
 34 80  1  0
 34 81  1  0
 35 82  1  0
 35 83  1  0
 35 84  1  0
 37 85  1  0
 37 86  1  0
 37 87  1  0
 38 88  1  0
 38 89  1  0
 38 90  1  0
 39 91  1  0
 39 92  1  0
 40 93  1  0
 40 94  1  0
M  END

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Canthaxanthin                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001 -20.790   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334 -20.790   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000 -21.560   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334 -20.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334 -19.250   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667 -21.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667 -26.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335 -26.180   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.335 -27.720   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -6.668 -25.410   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668 -23.870   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.058 -21.740   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.612 -21.740   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336 -20.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669 -23.100   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.003 -20.790   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.337 -21.560   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.671 -20.790   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.004 -21.560   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.004 -23.100   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.338 -20.790   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.338 -19.250   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.672 -16.940   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      20.005 -16.170   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      20.005 -14.630   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      21.339 -18.480   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      20.005 -19.250   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      20.728 -20.610   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.282 -20.610   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    2   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   40                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   33   41   42                                             
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

COMPND    HMDB0003154
HETATM    1  C1  UNL     1     -10.939   3.514  -1.231  1.00  0.00           C  
HETATM    2  C2  UNL     1     -10.977   2.869   0.105  1.00  0.00           C  
HETATM    3  C3  UNL     1      -9.939   2.122   0.517  1.00  0.00           C  
HETATM    4  C4  UNL     1      -8.783   1.961  -0.351  1.00  0.00           C  
HETATM    5  C5  UNL     1      -7.765   1.212  -0.059  1.00  0.00           C  
HETATM    6  C6  UNL     1      -6.538   0.957  -0.791  1.00  0.00           C  
HETATM    7  C7  UNL     1      -6.186   1.518  -2.069  1.00  0.00           C  
HETATM    8  C8  UNL     1      -5.732   0.010  -0.270  1.00  0.00           C  
HETATM    9  C9  UNL     1      -4.455  -0.370  -0.809  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.869  -1.400  -0.327  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.562  -1.829  -0.711  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.759  -0.651  -1.348  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.829  -2.941  -0.524  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.525  -2.828  -1.073  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.475  -3.804  -1.155  1.00  0.00           C  
HETATM   16  C16 UNL     1       1.632  -3.416  -1.639  1.00  0.00           C  
HETATM   17  C17 UNL     1       2.866  -3.411  -2.071  1.00  0.00           C  
HETATM   18  C18 UNL     1       2.822  -5.256  -1.800  1.00  0.00           C  
HETATM   19  C19 UNL     1       4.094  -3.439  -2.538  1.00  0.00           C  
HETATM   20  C20 UNL     1       4.851  -2.595  -1.546  1.00  0.00           C  
HETATM   21  C21 UNL     1       6.211  -2.343  -1.704  1.00  0.00           C  
HETATM   22  C22 UNL     1       6.869  -1.667  -0.717  1.00  0.00           C  
HETATM   23  C23 UNL     1       5.887  -1.343   0.447  1.00  0.00           C  
HETATM   24  C24 UNL     1       8.077  -0.921  -0.769  1.00  0.00           C  
HETATM   25  C25 UNL     1       8.582  -0.501   0.304  1.00  0.00           C  
HETATM   26  C26 UNL     1       9.763   0.331   0.608  1.00  0.00           C  
HETATM   27  C27 UNL     1      10.058   0.581   1.900  1.00  0.00           C  
HETATM   28  C28 UNL     1       9.208   0.017   2.995  1.00  0.00           C  
HETATM   29  C29 UNL     1      11.251   1.411   2.126  1.00  0.00           C  
HETATM   30  O1  UNL     1      11.035   2.108   3.293  1.00  0.00           O  
HETATM   31  C30 UNL     1      12.349   1.458   1.309  1.00  0.00           C  
HETATM   32  C31 UNL     1      11.795   1.675  -0.124  1.00  0.00           C  
HETATM   33  C32 UNL     1      10.576   0.894  -0.473  1.00  0.00           C  
HETATM   34  C33 UNL     1       9.671   1.924  -1.246  1.00  0.00           C  
HETATM   35  C34 UNL     1      10.958  -0.088  -1.549  1.00  0.00           C  
HETATM   36  C35 UNL     1     -10.185   1.559   1.871  1.00  0.00           C  
HETATM   37  C36 UNL     1      -9.212   0.659   2.520  1.00  0.00           C  
HETATM   38  C37 UNL     1     -11.444   0.639   1.773  1.00  0.00           C  
HETATM   39  C38 UNL     1     -10.524   2.756   2.759  1.00  0.00           C  
HETATM   40  C39 UNL     1     -12.003   3.020   2.426  1.00  0.00           C  
HETATM   41  C40 UNL     1     -12.145   3.097   0.957  1.00  0.00           C  
HETATM   42  O2  UNL     1     -13.269   3.356   0.446  1.00  0.00           O  
HETATM   43  H1  UNL     1     -11.830   4.129  -1.374  1.00  0.00           H  
HETATM   44  H2  UNL     1     -10.902   2.607  -1.980  1.00  0.00           H  
HETATM   45  H3  UNL     1      -9.993   4.094  -1.336  1.00  0.00           H  
HETATM   46  H4  UNL     1      -8.717   2.486  -1.309  1.00  0.00           H  
HETATM   47  H5  UNL     1      -7.767   0.806   0.993  1.00  0.00           H  
HETATM   48  H6  UNL     1      -6.413   0.601  -2.780  1.00  0.00           H  
HETATM   49  H7  UNL     1      -5.131   1.845  -2.184  1.00  0.00           H  
HETATM   50  H8  UNL     1      -6.821   2.344  -2.477  1.00  0.00           H  
HETATM   51  H9  UNL     1      -6.107  -0.507   0.611  1.00  0.00           H  
HETATM   52  H10 UNL     1      -3.971   0.179  -1.647  1.00  0.00           H  
HETATM   53  H11 UNL     1      -4.378  -2.042   0.441  1.00  0.00           H  
HETATM   54  H12 UNL     1      -0.852  -0.502  -0.702  1.00  0.00           H  
HETATM   55  H13 UNL     1      -1.595  -0.939  -2.372  1.00  0.00           H  
HETATM   56  H14 UNL     1      -2.312   0.300  -1.192  1.00  0.00           H  
HETATM   57  H15 UNL     1      -2.326  -3.727   0.001  1.00  0.00           H  
HETATM   58  H16 UNL     1      -0.146  -1.895  -1.507  1.00  0.00           H  
HETATM   59  H17 UNL     1       0.080  -4.746  -0.789  1.00  0.00           H  
HETATM   60  H18 UNL     1       1.626  -2.095  -1.644  1.00  0.00           H  
HETATM   61  H19 UNL     1       1.805  -5.391  -2.103  1.00  0.00           H  
HETATM   62  H20 UNL     1       3.134  -5.145  -0.807  1.00  0.00           H  
HETATM   63  H21 UNL     1       3.510  -5.400  -2.620  1.00  0.00           H  
HETATM   64  H22 UNL     1       4.798  -3.660  -3.263  1.00  0.00           H  
HETATM   65  H23 UNL     1       4.145  -2.278  -0.825  1.00  0.00           H  
HETATM   66  H24 UNL     1       6.831  -2.646  -2.512  1.00  0.00           H  
HETATM   67  H25 UNL     1       6.328  -0.663   1.154  1.00  0.00           H  
HETATM   68  H26 UNL     1       5.609  -2.293   0.920  1.00  0.00           H  
HETATM   69  H27 UNL     1       4.993  -0.839  -0.046  1.00  0.00           H  
HETATM   70  H28 UNL     1       8.551  -0.743  -1.721  1.00  0.00           H  
HETATM   71  H29 UNL     1       8.045  -0.826   1.221  1.00  0.00           H  
HETATM   72  H30 UNL     1       9.046  -1.084   2.723  1.00  0.00           H  
HETATM   73  H31 UNL     1       9.789  -0.026   3.958  1.00  0.00           H  
HETATM   74  H32 UNL     1       8.285   0.542   3.179  1.00  0.00           H  
HETATM   75  H33 UNL     1      13.171   2.157   1.467  1.00  0.00           H  
HETATM   76  H34 UNL     1      12.776   0.376   1.205  1.00  0.00           H  
HETATM   77  H35 UNL     1      11.552   2.753  -0.129  1.00  0.00           H  
HETATM   78  H36 UNL     1      12.666   1.503  -0.791  1.00  0.00           H  
HETATM   79  H37 UNL     1      10.329   2.712  -1.650  1.00  0.00           H  
HETATM   80  H38 UNL     1       9.220   1.444  -2.082  1.00  0.00           H  
HETATM   81  H39 UNL     1       9.020   2.437  -0.501  1.00  0.00           H  
HETATM   82  H40 UNL     1      10.760  -1.134  -1.313  1.00  0.00           H  
HETATM   83  H41 UNL     1      12.085  -0.076  -1.685  1.00  0.00           H  
HETATM   84  H42 UNL     1      10.535   0.168  -2.533  1.00  0.00           H  
HETATM   85  H43 UNL     1      -8.413   1.010   3.147  1.00  0.00           H  
HETATM   86  H44 UNL     1      -9.069  -0.267   1.894  1.00  0.00           H  
HETATM   87  H45 UNL     1      -9.899   0.114   3.358  1.00  0.00           H  
HETATM   88  H46 UNL     1     -11.124  -0.314   1.285  1.00  0.00           H  
HETATM   89  H47 UNL     1     -11.622   0.281   2.887  1.00  0.00           H  
HETATM   90  H48 UNL     1     -12.333   1.040   1.421  1.00  0.00           H  
HETATM   91  H49 UNL     1      -9.984   3.623   2.360  1.00  0.00           H  
HETATM   92  H50 UNL     1     -10.461   2.553   3.842  1.00  0.00           H  
HETATM   93  H51 UNL     1     -12.649   2.279   2.939  1.00  0.00           H  
HETATM   94  H52 UNL     1     -12.264   4.008   2.868  1.00  0.00           H  
CONECT    1    2   43   44   45
CONECT    2    3    3   41
CONECT    3    4   36
CONECT    4    5    5   46
CONECT    5    6   47
CONECT    6    7    8    8
CONECT    7   48   49   50
CONECT    8    9   51
CONECT    9   10   10   52
CONECT   10   11   53
CONECT   11   12   13   13
CONECT   12   54   55   56
CONECT   13   14   57
CONECT   14   15   15   58
CONECT   15   16   59
CONECT   16   17   17   60
CONECT   17   18   19
CONECT   18   61   62   63
CONECT   19   20   20   64
CONECT   20   21   65
CONECT   21   22   22   66
CONECT   22   23   24
CONECT   23   67   68   69
CONECT   24   25   25   70
CONECT   25   26   71
CONECT   26   27   27   33
CONECT   27   28   29
CONECT   28   72   73   74
CONECT   29   30   30   31
CONECT   31   32   75   76
CONECT   32   33   77   78
CONECT   33   34   35
CONECT   34   79   80   81
CONECT   35   82   83   84
CONECT   36   37   38   39
CONECT   37   85   86   87
CONECT   38   88   89   90
CONECT   39   40   91   92
CONECT   40   41   93   94
CONECT   41   42   42
END

HMDB0003154
     RDKit          3D
Canthaxanthin
 94 95  0  0  0  0  0  0  0  0999 V2000
  -10.9393    3.5142   -1.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9772    2.8692    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9391    2.1220    0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7825    1.9608   -0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7651    1.2117   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5382    0.9569   -0.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1858    1.5182   -2.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7317    0.0099   -0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4554   -0.3704   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8685   -1.3996   -0.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5619   -1.8287   -0.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7594   -0.6511   -1.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8295   -2.9407   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5246   -2.8279   -1.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4746   -3.8039   -1.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6315   -3.4164   -1.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8665   -3.4111   -2.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8224   -5.2558   -1.7996 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0943   -3.4391   -2.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511   -2.5947   -1.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2109   -2.3433   -1.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8694   -1.6674   -0.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8874   -1.3428    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0770   -0.9213   -0.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5823   -0.5014    0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7629    0.3313    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0583    0.5809    1.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2081    0.0168    2.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2514    1.4106    2.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0350    2.1084    3.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3487    1.4585    1.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7946    1.6752   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5763    0.8943   -0.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6711    1.9242   -1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9580   -0.0884   -1.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1847    1.5587    1.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2119    0.6588    2.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4439    0.6388    1.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5245    2.7560    2.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0032    3.0197    2.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1446    3.0972    0.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2693    3.3565    0.4465 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8304    4.1288   -1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9019    2.6072   -1.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9931    4.0940   -1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7166    2.4863   -1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7672    0.8059    0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4128    0.6007   -2.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1308    1.8448   -2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8207    2.3444   -2.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1073   -0.5066    0.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9708    0.1788   -1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3779   -2.0418    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525   -0.5021   -0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5946   -0.9391   -2.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116    0.2996   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263   -3.7267    0.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458   -1.8954   -1.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0795   -4.7460   -0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6256   -2.0950   -1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8048   -5.3906   -2.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1338   -5.1454   -0.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5101   -5.4001   -2.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7979   -3.6597   -3.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1450   -2.2782   -0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8308   -2.6460   -2.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3279   -0.6635    1.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091   -2.2930    0.9196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9935   -0.8394   -0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5510   -0.7428   -1.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0446   -0.8257    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0456   -1.0839    2.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7893   -0.0260    3.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2853    0.5419    3.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1711    2.1570    1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7756    0.3758    1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5518    2.7526   -0.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6663    1.5027   -0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3291    2.7125   -1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2195    1.4445   -2.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0202    2.4372   -0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7598   -1.1338   -1.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0854   -0.0759   -1.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5347    0.1681   -2.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4132    1.0104    3.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0692   -0.2670    1.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8985    0.1144    3.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1241   -0.3137    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6225    0.2809    2.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3330    1.0404    1.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9836    3.6233    2.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4606    2.5527    3.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6491    2.2792    2.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2641    4.0085    2.8676 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
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 15 16  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,4'-Dioxo-beta-carotene	ChEBI
all-trans-beta-Carotene-4,4'-dione	ChEBI
Carophyll red	ChEBI
e 161g	ChEBI
FOOD Orange 8	ChEBI
Orobronze	ChEBI
4,4'-Dioxo-b-carotene	Generator
4,4'-Dioxo-β-carotene	Generator
all-trans-b-Carotene-4,4'-dione	Generator
all-trans-Β-carotene-4,4'-dione	Generator
4,4'-Diketo-b-carotene	HMDB
4,4'-Diketo-beta-carotene	HMDB
all-trans,beta-Carotene-4,4'-dione	HMDB
beta,beta-Carotene-4,4'-dione	HMDB
Cantaxanthin	HMDB
Cantaxanthine	HMDB
Canthaxanthine	HMDB
L-Orange 7	HMDB
Roxanthin red 10	HMDB

Chemical Formula

C₄₀H₅₂O₂

Average Molecular Weight

564.854

Monoisotopic Molecular Weight

564.396730914

IUPAC Name

2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-2-en-1-one

Traditional Name

canthaxanthin

CAS Registry Number

514-78-3

SMILES

C\C(\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(=O)CCC1(C)C

InChI Identifier

InChI=1S/C40H52O2/c1-29(17-13-19-31(3)21-23-35-33(5)37(41)25-27-39(35,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-36-34(6)38(42)26-28-40(36,9)10/h11-24H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+

InChI Key

FDSDTBUPSURDBL-DKLMTRRASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

carotenone (CHEBI:3362 )
C40 isoprenoids (tetraterpenes) (C08583 )
Carotenoids (C08583 )
C40 isoprenoids (tetraterpenes) (LMPR01070264 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8895059)

Tissue

Epithelium

Epidermis (HMDB: HMDB0003154)

Cellular substructure

Membrane (HMDB: HMDB0003154)
Extracellular (HMDB: HMDB0003154)

Source

Exogenous

Exogenous (HMDB: HMDB0003154)

Fishes (FooDB: FOOD00865)

Crustacean

Crustaceans (FooDB: FOOD00862)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	717.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2.5e-10 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	9.526 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00046 g/L	ALOGPS
logP	8.71	ALOGPS
logP	9.79	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	19.59	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	193 m³·mol⁻¹	ChemAxon
Polarizability	72.16 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	258.278	30932474
DeepCCS	[M-H]-	256.453	30932474
DeepCCS	[M-2H]-	289.695	30932474
DeepCCS	[M+Na]+	263.884	30932474
AllCCS	[M+H]+	252.0	32859911
AllCCS	[M+H-H2O]+	250.2	32859911
AllCCS	[M+NH4]+	253.6	32859911
AllCCS	[M+Na]+	254.1	32859911
AllCCS	[M-H]-	225.1	32859911
AllCCS	[M+Na-2H]-	228.3	32859911
AllCCS	[M+HCOO]-	232.0	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.	5.95 minutes	32390414
Predicted by Siyang on May 30, 2022	44.6727 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.93 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	5781.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	1351.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	505.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	821.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	605.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1780.1 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	1349.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	133.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	3848.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1306.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2457.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1492.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	939.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	571.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	1173.6 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	10.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Canthaxanthin	C\C(\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(=O)CCC1(C)C	5761.4	Standard polar	33892256
Canthaxanthin	C\C(\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(=O)CCC1(C)C	4918.2	Standard non polar	33892256
Canthaxanthin	C\C(\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(=O)CCC1(C)C	4913.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Canthaxanthin,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)=CCC2(C)C)C(C)(C)CCC1=O	4783.5	Semi standard non polar	33892256
Canthaxanthin,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)=CCC2(C)C)C(C)(C)CCC1=O	4448.4	Standard non polar	33892256
Canthaxanthin,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)=CCC2(C)C)C(C)(C)CCC1=O	4555.3	Standard polar	33892256
Canthaxanthin,2TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)=CCC2(C)C)C(C)(C)CC=C1O[Si](C)(C)C	4646.8	Semi standard non polar	33892256
Canthaxanthin,2TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)=CCC2(C)C)C(C)(C)CC=C1O[Si](C)(C)C	4280.2	Standard non polar	33892256
Canthaxanthin,2TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C)=CCC2(C)C)C(C)(C)CC=C1O[Si](C)(C)C	4526.0	Standard polar	33892256
Canthaxanthin,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C)C(C)(C)CCC1=O	5005.6	Semi standard non polar	33892256
Canthaxanthin,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C)C(C)(C)CCC1=O	4641.7	Standard non polar	33892256
Canthaxanthin,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C)C(C)(C)CCC1=O	4645.6	Standard polar	33892256
Canthaxanthin,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	5082.5	Semi standard non polar	33892256
Canthaxanthin,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	4641.4	Standard non polar	33892256
Canthaxanthin,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC2(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	4668.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Canthaxanthin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1213290000-9719da4262f629366440	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canthaxanthin FAB-EBEB (JMS-HX/HX 110A, JEOL) , Positive-QTOF	splash10-016u-2920000000-bf9cf6df0a7dd95006af	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canthaxanthin EI-EBEB (JMS-HX/HX 110A, JEOL) , Positive-QTOF	splash10-03xr-1951160000-000e09c523a6561e2707	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canthaxanthin Linear Ion Trap , positive-QTOF	splash10-0ika-0296420000-b19acaaf1afb00cf9fc1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canthaxanthin Linear Ion Trap , positive-QTOF	splash10-0002-0001910000-a35bcbebdd90994a2f3d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canthaxanthin Linear Ion Trap , positive-QTOF	splash10-01pc-0025970000-423e791499171562736f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canthaxanthin 40V, Positive-QTOF	splash10-001i-0920000000-639f9f3228c4c2396f90	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canthaxanthin 20V, Positive-QTOF	splash10-0ue9-0892000000-742de39d976dca6ca15d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canthaxanthin 10V, Positive-QTOF	splash10-0gb9-0492060000-fef850b3839e24097342	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canthaxanthin 10V, Positive-QTOF	splash10-014i-0322390000-eee87729039394ef2242	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canthaxanthin 20V, Positive-QTOF	splash10-03dj-0596730000-20a001319fad4fff32bf	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canthaxanthin 40V, Positive-QTOF	splash10-0hft-1598720000-1c73c717692c05971680	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canthaxanthin 10V, Negative-QTOF	splash10-03di-0000090000-3323cd427776bc321533	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canthaxanthin 20V, Negative-QTOF	splash10-03di-0000090000-3a19aa461bcf5ed2f3a5	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canthaxanthin 40V, Negative-QTOF	splash10-0002-1454390000-1441e3b85e17841ccd5b	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canthaxanthin 10V, Positive-QTOF	splash10-07bs-0372890000-a2aa999a4582f599bbd7	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canthaxanthin 20V, Positive-QTOF	splash10-000b-0465940000-6e2f92273172d86d6e7d	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canthaxanthin 40V, Positive-QTOF	splash10-0fvs-0124900000-ddb1b9f3fe5c49bcb826	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canthaxanthin 10V, Negative-QTOF	splash10-03di-0001090000-3588cb304de167acfcd7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canthaxanthin 20V, Negative-QTOF	splash10-08fr-0215290000-5a34259c64d9108eece6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canthaxanthin 40V, Negative-QTOF	splash10-0002-0229020000-8b0c64a50d1fea3655ef	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Epidermis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.07 +/- 0.06 uM	Adult (>18 years old)	Both	Normal	8895059	details
Blood	Detected and Quantified	0.00900 +/- 0.0150 uM	Adult (>18 years old)	Female	Normal	15054421	details
Blood	Detected and Quantified	0.0100 +/- 0.0130 uM	Adult (>18 years old)	Male	Normal	15054421	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Canthaxanthin

METLIN ID

3597

PubChem Compound

5281227

PDB ID

Not Available

ChEBI ID

3362

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1365301

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Paetau I, Chen H, Goh NM, White WS: Interactions in the postprandial appearance of beta-carotene and canthaxanthin in plasma triacylglycerol-rich lipoproteins in humans. Am J Clin Nutr. 1997 Nov;66(5):1133-43. [PubMed:9356530 ]
Meyer JC, Grundmann HP, Seeger B, Schnyder UW: Plasma concentrations of beta-carotene and canthaxanthin during and after stopping intake of a combined preparation. Dermatologica. 1985;171(2):76-81. [PubMed:3930305 ]
Rollman O, Vahlquist A: Psoriasis and vitamin A. Plasma transport and skin content of retinol, dehydroretinol and carotenoids in adult patients versus healthy controls. Arch Dermatol Res. 1985;278(1):17-24. [PubMed:4096526 ]
Bluhm R, Branch R, Johnston P, Stein R: Aplastic anemia associated with canthaxanthin ingested for 'tanning' purposes. JAMA. 1990 Sep 5;264(9):1141-2. [PubMed:2117075 ]
Mayne ST, Parker RS: Antioxidant activity of dietary canthaxanthin. Nutr Cancer. 1989;12(3):225-36. doi: 10.1080/01635588909514022. [PubMed:2505240 ]

Showing metabocard for Canthaxanthin (HMDB0003154)

MOL for HMDB0003154 (Canthaxanthin)

3D MOL for HMDB0003154 (Canthaxanthin)

3D SDF for HMDB0003154 (Canthaxanthin)

3D-SDF for HMDB0003154 (Canthaxanthin)

PDB for HMDB0003154 (Canthaxanthin)

3D PDB for HMDB0003154 (Canthaxanthin)

SMILES for HMDB0003154 (Canthaxanthin)

INCHI for HMDB0003154 (Canthaxanthin)

Structure for HMDB0003154 (Canthaxanthin)

3D Structure for HMDB0003154 (Canthaxanthin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra