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Showing NP-Card for o-Tolualdehyde (NP0002791)

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Record Information
Version2.0
Created at2020-11-23 19:40:32 UTC
Updated at2021-08-19 23:59:23 UTC
NP-MRD IDNP0002791
Secondary Accession NumbersNone
Natural Product Identification
Common Nameo-Tolualdehyde
Provided ByBMRBBMRB logo
Description2-Methylbenzaldehyde, also known as O-toluic aldehyde or 2-formyltoluene, belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-). 2-Methylbenzaldehyde exists in all living organisms, ranging from bacteria to humans. 2-Methylbenzaldehyde is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. o-Tolualdehyde is found in Cichorium endivia and Gossypium hirsutum. o-Tolualdehyde was first documented in 2010 (PMID: 20016999). Based on a literature review very few articles have been published on 2-Methylbenzaldehyde (PMID: 24312872) (PMID: 28747743) (PMID: 25434408) (PMID: 31347360) (PMID: 27193865) (PMID: 28809218).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002791 (o-Tolualdehyde)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    1.8860   -1.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -0.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6783   -1.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810   -1.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3219    0.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601    1.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2425    0.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    1.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633    3.3181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4177    0.2792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3544   -2.5261    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2886   -1.6551    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375   -3.0212    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427   -1.9579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7245    1.0031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010    2.9009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8069    1.3059    0.0000 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  2  0
  7  8  1  0
  8  9  2  0
  7  2  1  0
  1 10  1  1
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
M  END
Download

3D MOL for NP0002791 (o-Tolualdehyde)

NP0002791
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -1.6738   -1.2019    0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3490   -0.5620    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7901   -1.3302   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181   -0.7404   -0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152    0.6354   -0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018    1.3993   -0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539    0.8051    0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4165    1.6349    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5406    1.1441    0.4967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5337   -2.3287    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4228   -0.9221   -0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164   -1.0092    1.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6351   -2.4026   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8953   -1.3724   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    1.0588   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0900    2.4737   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3388    2.7183    0.3630 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  2  0
  7  8  1  0
  8  9  2  0
  7  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
M  END
Download

3D SDF for NP0002791 (o-Tolualdehyde)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    1.8860   -1.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -0.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6783   -1.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0810   -1.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3219    0.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1601    1.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2425    0.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    1.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633    3.3181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4177    0.2792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3544   -2.5261    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2886   -1.6551    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375   -3.0212    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427   -1.9579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7245    1.0031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010    2.9009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8069    1.3059    0.0000 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  2  0
  7  8  1  0
  8  9  2  0
  7  2  1  0
  1 10  1  1
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
M  END
> <DATABASE_ID>
NP0002791

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC=CC=C1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O/c1-7-4-2-3-5-8(7)6-9/h2-6H,1H3

> <INCHI_KEY>
BTFQKIATRPGRBS-UHFFFAOYSA-N

> <FORMULA>
C8H8O

> <MOLECULAR_WEIGHT>
120.1485

> <EXACT_MASS>
120.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
13.02461965328535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylbenzaldehyde

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
2.19916955

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.118545287314168

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
37.68320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methylbenzaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002791 (o-Tolualdehyde)

NP0002791
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -1.6738   -1.2019    0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3490   -0.5620    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7901   -1.3302   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181   -0.7404   -0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152    0.6354   -0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018    1.3993   -0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539    0.8051    0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4165    1.6349    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5406    1.1441    0.4967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5337   -2.3287    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4228   -0.9221   -0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164   -1.0092    1.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6351   -2.4026   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8953   -1.3724   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    1.0588   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0900    2.4737   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3388    2.7183    0.3630 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  2  0
  7  8  1  0
  8  9  2  0
  7  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
M  END
Download

PDB for NP0002791 (o-Tolualdehyde)

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      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    8                                                       
CONECT    6    8    9                                                       
CONECT    7    1    4    8                                                  
CONECT    8    5    6    7                                                  
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0002791 (o-Tolualdehyde)

COMPND    NP0002791
HETATM    1  C1  UNL     1      -1.674  -1.202   0.230  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.349  -0.562   0.029  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.790  -1.330  -0.208  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.018  -0.740  -0.394  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.115   0.635  -0.344  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.002   1.399  -0.111  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.254   0.805   0.080  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.416   1.635   0.324  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.541   1.144   0.497  1.00  0.00           O  
HETATM   10  H1  UNL     1      -1.534  -2.329   0.224  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.423  -0.922  -0.537  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.116  -1.009   1.228  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.635  -2.403  -0.233  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.895  -1.372  -0.578  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.100   1.059  -0.495  1.00  0.00           H  
HETATM   16  H7  UNL     1       1.090   2.474  -0.074  1.00  0.00           H  
HETATM   17  H8  UNL     1      -1.339   2.718   0.363  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    7
CONECT    3    4   13
CONECT    4    5    5   14
CONECT    5    6   15
CONECT    6    7    7   16
CONECT    7    8
CONECT    8    9    9   17
END
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SMILES for NP0002791 (o-Tolualdehyde)

CC1=CC=CC=C1C=O
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INCHI for NP0002791 (o-Tolualdehyde)

InChI=1S/C8H8O/c1-7-4-2-3-5-8(7)6-9/h2-6H,1H3
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View in JSmol
Synonyms
ValueSource
2-FormyltolueneChEBI
2-TolualdehydeChEBI
O-MethylbenazldehydeChEBI
O-Toluic aldehydeChEBI
O-ToluylaldehydeChEBI
O-TolylaldehydeChEBI
O-TolualdehydeKegg
2-Methyl-benzaldehydeHMDB
O-MethylbenzaldehydeHMDB
O-Tolualdehyde (8ci)HMDB
Toluic aldehydeHMDB
2-MethylbenzaldehydeChEBI
Chemical FormulaC8H8O
Average Mass120.1485 Da
Monoisotopic Mass120.05751 Da
IUPAC Name2-methylbenzaldehyde
Traditional Name2-methylbenzaldehyde
CAS Registry NumberNot Available
SMILES
CC1=CC=CC=C1C=O
InChI Identifier
InChI=1S/C8H8O/c1-7-4-2-3-5-8(7)6-9/h2-6H,1H3
InChI KeyBTFQKIATRPGRBS-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium sativumFooDB
Carum carviFooDB
Cichorium endiviaLOTUS Database
Cinnamomum aromaticumFooDB
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Gossypium hirsutumLOTUS Database
Prunus aviumFooDB
    • Bernalte, M. J., Hernandez, M. T., Vidal-Aragon, M. C. & Sabio, E. (1999) Physical, chemical, fla...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoyl derivatives
Direct ParentBenzoyl derivatives
Alternative Parents
Substituents
  • Benzoyl
  • Benzaldehyde
  • Aryl-aldehyde
  • Toluene
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point200.00 to 201.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1178 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.260The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP1.91ALOGPS
logP2.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.68 m³·mol⁻¹ChemAxon
Polarizability13.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029636
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000806
KNApSAcK IDNot Available
Chemspider ID21106524
KEGG Compound IDC07214
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Methylbenzaldehyde
METLIN IDNot Available
PubChem Compound10722
PDB IDNot Available
ChEBI ID27434
Good Scents IDrw1055241
References
General References
  1. Huang J, Feng Y, Fu J, Sheng G: A method of detecting carbonyl compounds in tree leaves in China. Environ Sci Pollut Res Int. 2010 Jun;17(5):1129-36. doi: 10.1007/s11356-009-0277-3. Epub 2009 Dec 17. [PubMed:20016999 ]
  2. Hamedeyazdan S, Asnaashari S, Fathiazad F: Characterization of Non-Terpenoids in Marrubium crassidens Boiss. Essential Oil. Adv Pharm Bull. 2013;3(2):429-32. doi: 10.5681/apb.2013.069. Epub 2013 Aug 20. [PubMed:24312872 ]
  3. Park JH, Lee NH, Yang YC, Lee HS: Food Protective Effects of 3-Methylbenzaldehyde Derived from Myosotis arvensis and Its Analogues against Tyrophagus putrescentiae. Sci Rep. 2017 Jul 26;7(1):6608. doi: 10.1038/s41598-017-07001-5. [PubMed:28747743 ]
  4. Yang JY, Kim MG, Park JH, Hong ST, Lee HS: Evaluation of benzaldehyde derivatives from Morinda officinalis as anti-mite agents with dual function as acaricide and mite indicator. Sci Rep. 2014 Dec 1;4:7149. doi: 10.1038/srep07149. [PubMed:25434408 ]
  5. Wang B, Wang XH, Huang W, Zhou J, Zhu HP, Peng C, Han B: Protecting Group-Directed Diastereodivergent Synthesis of Chiral Tetrahydronaphthalene-Fused Spirooxindoles via Bifunctional Tertiary Amine Catalysis. J Org Chem. 2019 Aug 16;84(16):10349-10361. doi: 10.1021/acs.joc.9b01501. Epub 2019 Aug 7. [PubMed:31347360 ]
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