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Showing metabocard for Vanillin (HMDB0012308)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-04-06 16:22:43 UTC
Update Date2023-02-21 17:17:48 UTC
HMDB IDHMDB0012308
Secondary Accession Numbers
  • HMDB12308
Metabolite Identification
Common NameVanillin
DescriptionVanillin, also known as vanillaldehyde or lioxin, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is used by the food industry as well as ethylvanillin. Vanillin exists in all living species, ranging from bacteria to humans. Vanillin is a sweet, chocolate, and creamy tasting compound. Vanillin is found, on average, in the highest concentration within a few different foods, such as corns, ryes, and sherries and in a lower concentration in beers, rums, and oats. Vanillin has also been detected, but not quantified, in several different foods, such as gooseberries, other bread, brazil nuts, shea tree, and ohelo berries. This could make vanillin a potential biomarker for the consumption of these foods. Vanillin is a potentially toxic compound. Synthetic vanillin, instead of natural Vanillin extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. Vanillin is the primary component of the extract of the Vanillin bean. Because of the scarcity and expense of natural Vanillin extract, there has long been interest in the synthetic preparation of its predominant component. Artificial Vanillin flavoring is a solution of pure vanillin, usually of synthetic origin. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol.
Structure
Data?1676999868
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012308 (Vanillin)


  Mrv1652309272007342D          

 11 11  0  0  0  0            999 V2000
 9980.8636 9979.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.1527 9978.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.4383 9979.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.7236 9978.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.7236 9977.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.4381 9977.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.1527 9977.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.0107 9977.3643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.5766 9978.6001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9979.4380 9976.5401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.1508 9976.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  2  1  0  0  0  0
  2  1  1  0  0  0  0
  5  8  1  0  0  0  0
  1  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0012308 (Vanillin)

HMDB0012308
     RDKit          3D
Vanillin
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.2700   -0.9415   -1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9031    0.2379   -0.9871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7213    0.3403   -0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1689   -0.7169   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3592   -0.6118    0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2815   -1.7283    0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368   -1.5760    1.2647 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201    0.6029    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307    1.6543    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4393    1.5374    0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3425    2.6147    0.2447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928   -0.9236   -1.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822   -1.0640   -2.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0312   -1.8666   -1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0340   -1.6652   -0.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310   -2.6473    0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5480    0.6815    1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9740    2.5791    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340    3.4932    0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  3  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
Download

3D SDF for HMDB0012308 (Vanillin)


  Mrv1652309272007342D          

 11 11  0  0  0  0            999 V2000
 9980.8636 9979.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.1527 9978.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.4383 9979.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.7236 9978.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.7236 9977.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.4381 9977.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.1527 9977.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.0107 9977.3643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.5766 9978.6001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9979.4380 9976.5401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.1508 9976.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  2  1  0  0  0  0
  2  1  1  0  0  0  0
  5  8  1  0  0  0  0
  1  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012308

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(C=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3

> <INCHI_KEY>
MWOOGOJBHIARFG-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.81738516647897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-3-methoxybenzaldehyde

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
1.224511573333333

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.807246236597697

> <JCHEM_PKA_STRONGEST_BASIC>
-4.895506955382694

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
41.0861

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vanillin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0012308 (Vanillin)

HMDB0012308
     RDKit          3D
Vanillin
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.2700   -0.9415   -1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9031    0.2379   -0.9871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7213    0.3403   -0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1689   -0.7169   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3592   -0.6118    0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2815   -1.7283    0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368   -1.5760    1.2647 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201    0.6029    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307    1.6543    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4393    1.5374    0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3425    2.6147    0.2447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928   -0.9236   -1.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822   -1.0640   -2.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0312   -1.8666   -1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0340   -1.6652   -0.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310   -2.6473    0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5480    0.6815    1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9740    2.5791    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340    3.4932    0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  3  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
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PDB for HMDB0012308 (Vanillin)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8630.9458627.488   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8629.6188626.722   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8628.2858627.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8626.9518626.721   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8626.9518625.181   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8628.2848624.411   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8629.6188625.181   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8625.6208624.413   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8632.2768626.720   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8628.2848622.875   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8629.6158622.106   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    3    7    1                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    2                                                       
CONECT    8    5                                                            
CONECT    9    1                                                            
CONECT   10    6   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0012308 (Vanillin)

COMPND    HMDB0012308
HETATM    1  C1  UNL     1      -2.270  -0.941  -1.648  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.903   0.238  -0.987  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.721   0.340  -0.282  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.169  -0.717  -0.188  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.359  -0.612   0.523  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.282  -1.728   0.612  1.00  0.00           C  
HETATM    7  O2  UNL     1       3.337  -1.576   1.265  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.620   0.603   1.138  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.731   1.654   1.042  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.439   1.537   0.338  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.342   2.615   0.245  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.393  -0.924  -1.739  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.782  -1.064  -2.641  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.031  -1.867  -1.051  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.034  -1.665  -0.668  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.031  -2.647   0.117  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.548   0.682   1.691  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.974   2.579   1.535  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.134   3.493   0.701  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   15
CONECT    5    6    8    8
CONECT    6    7    7   16
CONECT    8    9   17
CONECT    9   10   10   18
CONECT   10   11
CONECT   11   19
END
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SMILES for HMDB0012308 (Vanillin)

COC1=CC(C=O)=CC=C1O
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INCHI for HMDB0012308 (Vanillin)

InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-Methoxy-4-hydroxybenzaldehydeChEBI
4-Formyl-2-methoxyphenolChEBI
4-Hydroxy-3-methoxy-benzaldehydeChEBI
4-Hydroxy-3-methoxybenzaldehydeChEBI
4-Hydroxy-m-anisaldehydeChEBI
Methylprotocatechuic aldehydeChEBI
p-Hydroxy-m-methoxybenzaldehydeChEBI
p-VanillinChEBI
VanilineChEBI
VanillaldehydeChEBI
Vanillic aldehydeChEBI
5-BromovanillinMeSH
5-ChlorovanillinMeSH
Vanillin, sodium saltMeSH
2-Methoxy-4-formylphenolHMDB
4-Hydroxy 3-methoxybenzaldehydeHMDB
4-Hydroxy-3-methoxy-benzaldehyde-5-chlorovanillinHMDB
4-Hydroxy-3-methoxybenzaldehyde (acd/name 4.0)HMDB
4-Hydroxy-5-methoxybenzaldehydeHMDB
LioxinHMDB
m-Methoxy-p-hydroxybenzaldehydeHMDB
Methyl-protocatechualdehydeHMDB
Methylprotcatechuic aldehydeHMDB
oleo-Resins vanillaHMDB
oleo-Resins vanilla-beanHMDB
Oleoresin vanillaHMDB
PropenylguaetholHMDB
Protocatechualdehyde 3-methyl etherHMDB
trans-2-Ethoxy-5-(1-propenyl)phenolHMDB
VanilinHMDB
VanillaHMDB
Vanilla oleoresinHMDB
Vanillin (3-methoxy-4-hydroxy- benzaldehyde)HMDB
Vanillin (natural)HMDB
Vanillin (NF)HMDB
Vanillin sodium saltHMDB
VanillineHMDB
ZimcoHMDB
4-Hydroxy-3-methoxy-benzyldehydePhytoBank
VanillumPhytoBank
VanillinHMDB
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name4-hydroxy-3-methoxybenzaldehyde
Traditional Namevanillin
CAS Registry Number121-33-5
SMILES
COC1=CC(C=O)=CC=C1O
InChI Identifier
InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
InChI KeyMWOOGOJBHIARFG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Hydroxybenzaldehyde
  • Anisole
  • Benzaldehyde
  • Benzoyl
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Aryl-aldehyde
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organooxygen compound
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point81.5 °CNot Available
Boiling Point285.00 to 286.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility11 mg/mL at 25 °CNot Available
LogP1.21HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg124.30130932474
[M+H]+MetCCS_train_pos129.68530932474
[M-H]-Not Available124.301http://allccs.zhulab.cn/database/detail?ID=AllCCS00000308
[M+H]+Not Available129.601http://allccs.zhulab.cn/database/detail?ID=AllCCS00000308
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.05 g/LALOGPS
logP1.31ALOGPS
logP1.22ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.81ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.09 m³·mol⁻¹ChemAxon
Polarizability14.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.84731661259
DarkChem[M-H]-131.62231661259
DeepCCS[M+H]+131.69830932474
DeepCCS[M-H]-129.20930932474
DeepCCS[M-2H]-165.80630932474
DeepCCS[M+Na]+140.6730932474
AllCCS[M+H]+132.032859911
AllCCS[M+H-H2O]+127.532859911
AllCCS[M+NH4]+136.232859911
AllCCS[M+Na]+137.532859911
AllCCS[M-H]-128.832859911
AllCCS[M+Na-2H]-130.132859911
AllCCS[M+HCOO]-131.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.3.31 minutes32390414
Predicted by Siyang on May 30, 202211.2882 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.14 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1415.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid367.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid124.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid224.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid106.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid443.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid499.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)127.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid949.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid323.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1064.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid297.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid418.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate517.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA344.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water167.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VanillinCOC1=CC(C=O)=CC=C1O2528.8Standard polar33892256
VanillinCOC1=CC(C=O)=CC=C1O1340.4Standard non polar33892256
VanillinCOC1=CC(C=O)=CC=C1O1399.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vanillin,1TMS,isomer #1COC1=CC(C=O)=CC=C1O[Si](C)(C)C1537.6Semi standard non polar33892256
Vanillin,1TBDMS,isomer #1COC1=CC(C=O)=CC=C1O[Si](C)(C)C(C)(C)C1797.0Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.298 +/- 0.902 uMAdult (>18 years old)Male
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified28.258 +/- 24.808 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified4.468 +/- 0.815 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified5.375 +/- 0.91 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified8.309 +/- 3.765 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified4.976 +/- 0.971 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified3.764 +/- 0.869 uMAdult (>18 years old)Male
Normal		 details
BloodDetected and Quantified4.951 +/- 0.92 uMAdult (>18 years old)Male
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.362 +/- 0.053 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleMissing teeth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID724
FooDB IDFDB000838
KNApSAcK IDC00002683
Chemspider ID13860434
KEGG Compound IDC00755
BioCyc IDVANILLIN
BiGG IDNot Available
Wikipedia LinkVanillin
METLIN IDNot Available
PubChem Compound1183
PDB IDV55
ChEBI ID18346
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1011712
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available