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Showing NP-Card for 2,6-Dimethoxyphenol (NP0001477)

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Record Information
Version2.0
Created at2012-09-11 18:57:12 UTC
Updated at2024-09-15 13:58:58 UTC
NP-MRD IDNP0001477
Natural Product DOIhttps://doi.org/10.57994/2715
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,6-Dimethoxyphenol
Description2,6-Dimethoxyphenol, also known as syringol, 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. 2,6-Dimethoxyphenol is a bacon, balsamic, and medicine tasting compound.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0001477 (2,6-Dimethoxyphenol)


  Mrv1652305261923562D          

 11 11  0  0  0  0            999 V2000
    1.4289    2.4750    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
    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    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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  1  1  0  0  0  0
 10  6  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  1  0  0  0  0
M  END
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3D MOL for NP0001477 (2,6-Dimethoxyphenol)

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3D SDF for NP0001477 (2,6-Dimethoxyphenol)

  Mrv1652305261923562D          

 11 11  0  0  0  0            999 V2000
    1.4289    2.4750    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
    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    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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  1  1  0  0  0  0
 10  6  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001477

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3

> <INCHI_KEY>
KLIDCXVFHGNTTM-UHFFFAOYSA-N

> <FORMULA>
C8H10O3

> <MOLECULAR_WEIGHT>
154.1632

> <EXACT_MASS>
154.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.576107679097149

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6-dimethoxyphenol

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
1.3543379629999999

> <ALOGPS_LOGS>
-0.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.372544155372394

> <JCHEM_PKA_STRONGEST_BASIC>
-4.60129971541918

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
40.9653

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dimethoxyphenol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0001477 (2,6-Dimethoxyphenol)
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PDB for NP0001477 (2,6-Dimethoxyphenol)
HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   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      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334   3.850   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   10                                                            
CONECT    2   11                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8   10                                                  
CONECT    7    5    8   11                                                  
CONECT    8    6    7    9                                                  
CONECT    9    8                                                            
CONECT   10    1    6                                                       
CONECT   11    2    7                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0001477 (2,6-Dimethoxyphenol)
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SMILES for NP0001477 (2,6-Dimethoxyphenol)
COC1=CC=CC(OC)=C1O
Download
INCHI for NP0001477 (2,6-Dimethoxyphenol)
InChI=1S/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3
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View in JSmol
Synonyms
ValueSource
1,3-Di-O-methylpyrogallolChEBI
1,3-Dimethoxy-2-hydroxybenzeneChEBI
1,3-Dimethyl pyrogallateChEBI
2-Hydroxy-1,3-dimethoxybenzeneChEBI
Pyrogallol 1,3-dimethyl etherChEBI
SyringolChEBI
1,3-Dimethyl pyrogallic acidGenerator
2,6-Dimethoxy-phenolHMDB
2,6-Dimethoxyphenol (syringol)HMDB
2,6-DimethoxyphenylHMDB
2,6-DwumetoksyfenolHMDB
AldrichHMDB
DimethoxyphenolHMDB
FEMA 3137HMDB
Pyrogallol dimethyletherHMDB
Chemical FormulaC8H10O3
Average Mass154.1632 Da
Monoisotopic Mass154.06299 Da
IUPAC Name2,6-dimethoxyphenol
Traditional Name2,6-dimethoxyphenol
CAS Registry Number91-10-1
SMILES
COC1=CC=CC(OC)=C1O
InChI Identifier
InChI=1S/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3
InChI KeyKLIDCXVFHGNTTM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
FAILED_TO_DETECT NMR[13C, 13C] NMR Spectrum (2D, 201 MHz, CDCl3, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CDCl3, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CDCl3, simulated)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
Species
Species of Origin
Species NameSourceReference
Acanthopanax giraldiiPlant
Allium spp.Plant
Bistorta manshuriensis
Gymnadenia conopsea
Gymnadenia conopsea R.BR.Plant
Mucuna birdwoodianaPlant
Panax Japonicus
var.Allium spp.-
Vitis vinifera
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
  • M-dimethoxybenzene
    • 

  • Dimethoxybenzene
    • 

  • Methoxyphenol
    • 

  • Phenoxy compound
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Anisole
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Monocyclic benzene moiety
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point55 - 56 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility17.2 mg/mL at 13 °CNot Available
LogP1.15Not Available
Predicted Properties
PropertyValueSource
Water Solubility17.3 g/LALOGPS
logP1.29ALOGPS
logP1.35ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)9.37ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.97 m³·mol⁻¹ChemAxon
Polarizability15.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034158  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012443  
KNApSAcK IDC00002646  
Chemspider ID6774  
KEGG Compound IDC10787  
BioCyc IDCPD-12797  
BiGG IDNot Available
Wikipedia LinkSyringol  
METLIN IDNot Available
PubChem Compound7041  
PDB ID3DM  
ChEBI ID955  
Good Scents IDNot Available
References
General References
  1. Kjallstrand J, Petersson G: Phenolic antioxidants in wood smoke. Sci Total Environ. 2001 Sep 28;277(1-3):69-75. doi: 10.1016/s0048-9697(00)00863-9. [PubMed:11589408  ] 
  2. Klamrassamee T, Laosiripojana N, Cronin D, Moghaddam L, Zhang Z, Doherty WO: Effects of mesostructured silica catalysts on the depolymerization of organosolv lignin fractionated from woody eucalyptus. Bioresour Technol. 2015 Mar;180:222-9. doi: 10.1016/j.biortech.2014.12.098. Epub  2015 Jan 6. [PubMed:25614246  ] 
  3.  (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .