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Showing NP-Card for o-vanillin (NP0211495)

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Record Information
Version2.0
Created at2022-09-05 09:48:01 UTC
Updated at2022-09-05 09:48:01 UTC
NP-MRD IDNP0211495
Secondary Accession NumbersNone
Natural Product Identification
Common Nameo-vanillin
DescriptionOrtho-vanillin, also known as 6-formylguaiacol, 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. Ortho-vanillin is an extremely weak basic (essentially neutral) compound (based on its pKa). Ortho-Vanillin, a compound of the formula C8H8O3, is distinctly different from its more prevalent isomer, vanillin. By 1910, methods for its purification had been developed by Francis Noelting, who similarly demonstrated its versatility as a general synthetic precursor for a diverse array of compounds, such as the coumarins. It is a weak inhibitor of tyrosinase, and displays both antimutagenic and comutagenic properties in Escherichia coli. However, its net effect makes it a “potent comutagen.”Ortho-Vanillin possesses moderate antifungal and antibacterial properties. Its functional groups include aldehyde, ether and phenol. Today, most ortho-vanillin is used in the study of mutagenesis and as a synthetic precursor for pharmaceuticals, for example, benafentrine and an antiandrogen compound called Pentomone. Ortho-Vanillin (2-Hydroxy-3-methoxybenzaldehyde) is an organic solid present in the extracts and essential oils of many plants. o-vanillin is found in Hyssopus officinalis, Panax ginseng and Strychnos cathayensis. o-vanillin was first documented in 1947 (PMID: 20292487). Present in a variety of food products, it is not specifically sought after, and is therefore a less-commonly produced and encountered food additive.Ortho-Vanillin was first isolated, in 1876, by renowned German chemist Ferdinand Tiemann (PMID: 22904806) (PMID: 23625436) (PMID: 2671704).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0211495 (o-vanillin)


  Mrv1652310091719352D          

 11 11  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  1  1  0  0  0  0
 11  7  1  0  0  0  0
M  END
Download

3D MOL for NP0211495 (o-vanillin)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -3.0513    0.6501   -0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7055    1.0805   -0.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6524    0.2137    0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -1.1290    0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3158   -1.9161    0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -1.4222    0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7582   -0.0733    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1053    0.4800    0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3230    1.6987   -0.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6309    0.7213   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8527    2.0795   -0.2800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7285    1.4392   -0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3824    0.4914    1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1445   -0.2768   -0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8171   -1.5442    0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2110   -2.9778    0.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4761   -2.0769    0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9618   -0.1535    0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0570    2.7155   -0.3965 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  7 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
  5 16  1  0
  6 17  1  0
  8 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0211495 (o-vanillin)


  Mrv1652310091719352D          

 11 11  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  1  1  0  0  0  0
 11  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211495

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
JJVNINGBHGBWJH-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.149

> <EXACT_MASS>
152.047344118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.746440815367011

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-3-methoxybenzaldehyde

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
1.874511573333333

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.93550394325374

> <JCHEM_PKA_STRONGEST_BASIC>
-4.895543733707597

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
41.0861

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-vanillin

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0211495 (o-vanillin)

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PDB for NP0211495 (o-vanillin)
HEADER    PROTEIN                                 09-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-OCT-17         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   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
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    6    9                                                       
CONECT    6    3    5    8                                                  
CONECT    7    4    8   11                                                  
CONECT    8    6    7   10                                                  
CONECT    9    5                                                            
CONECT   10    8                                                            
CONECT   11    1    7                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0211495 (o-vanillin)
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SMILES for NP0211495 (o-vanillin)
COC1=CC=CC(C=O)=C1O
Download
INCHI for NP0211495 (o-vanillin)
InChI=1S/C8H8O3/c1-11-7-4-2-3-6(5-9)8(7)10/h2-5,10H,1H3
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View in JSmol
Synonyms
ValueSource
2-Hydroxy-m-anisaldehydeChEBI
2-VanillinChEBI
3-MethoxysalicylaldehydeChEBI
6-Formyl-2-methoxyphenolChEBI
6-FormylguaiacolChEBI
Oxy-2 methoxy-3 benzaldehydeChEBI
2-Hydroxy-3-methoxybenzaldehydeMeSH
O-VanilinMeSH
O-VanillinMeSH
Chemical FormulaC8H8O3
Average Mass152.1490 Da
Monoisotopic Mass152.04734 Da
IUPAC Name2-hydroxy-3-methoxybenzaldehyde
Traditional NameO-vanillin
CAS Registry NumberNot Available
SMILES
COC1=CC=CC(C=O)=C1O
InChI Identifier
InChI=1S/C8H8O3/c1-11-7-4-2-3-6(5-9)8(7)10/h2-5,10H,1H3
InChI KeyJJVNINGBHGBWJH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Hyssopus officinalis L.LOTUS Database
Panax ginsengLOTUS Database
Strychnos cathayensisLOTUS Database
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
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Benzaldehyde
    • 

  • Methoxybenzene
    • 

  • Benzoyl
    • 

  • Phenol ether
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Aryl-aldehyde
    • 

  • Monocyclic benzene moiety
    • 

  • Vinylogous acid
    • 

  • Ether
    • 

  • Aldehyde
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.31ALOGPS
logP1.87ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)8.94ChemAxon
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
Polarizability14.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0171094  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOrtho-Vanillin  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID78339  
Good Scents IDNot Available
References
General References
  1. HORNING EC, HORNING MG: Coumarins from 2-hydroxy-3-methoxybenzaldehyde. J Am Chem Soc. 1947 Apr;69(4):968. doi: 10.1021/ja01196a506. [PubMed:20292487  ] 
  2. Shin D, Muller P: 2-Hy-droxy-3-meth-oxy-benzaldehyde (o-vanillin) revisited. Acta Crystallogr Sect E Struct Rep Online. 2012 Aug 1;68(Pt 8):o2336-7. doi:  10.1107/S1600536812029571. Epub 2012 Jul 4. [PubMed:22904806  ] 
  3. Esmaeili A: Biological activities and chemical composition of the stems and roots of Helichrysum oligocephalum DC grown in Iran. Pak J Pharm Sci. 2013 May;26(3):599-604. [PubMed:23625436  ] 
  4. Watanabe K, Ohta T, Shirasu Y: Enhancement and inhibition of mutation by o-vanillin in Escherichia coli. Mutat Res. 1989 Sep;218(2):105-9. doi: 10.1016/0921-8777(89)90016-5. [PubMed:2671704  ] 
  5. LOTUS database [Link]