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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:57:12 UTC

Update Date

2023-02-21 17:23:56 UTC

HMDB ID

HMDB0034158

Secondary Accession Numbers

HMDB34158

Metabolite Identification

Common Name

2,6-Dimethoxyphenol

Description

2,6-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. 2,6-Dimethoxyphenol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 2,6-Dimethoxyphenol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,3-Di-O-methylpyrogallol	ChEBI
1,3-Dimethoxy-2-hydroxybenzene	ChEBI
1,3-Dimethyl pyrogallate	ChEBI
2-Hydroxy-1,3-dimethoxybenzene	ChEBI
Pyrogallol 1,3-dimethyl ether	ChEBI
Syringol	ChEBI
1,3-Dimethyl pyrogallic acid	Generator
2,6-Dimethoxy-phenol	HMDB
2,6-Dimethoxyphenol (syringol)	HMDB
2,6-Dimethoxyphenyl	HMDB
2,6-Dwumetoksyfenol	HMDB
Aldrich	HMDB
Dimethoxyphenol	HMDB
FEMA 3137	HMDB
Pyrogallol dimethylether	HMDB

Chemical Formula

C₈H₁₀O₃

Average Molecular Weight

154.1632

Monoisotopic Molecular Weight

154.062994186

IUPAC Name

2,6-dimethoxyphenol

Traditional Name

2,6-dimethoxyphenol

CAS Registry Number

91-10-1

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 Key

KLIDCXVFHGNTTM-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:955 )
dimethoxybenzene (CHEBI:955 )
a small molecule (CPD-12797 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0034158)
Cytoplasm (HMDB: HMDB0034158)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Exogenous

Food

Food (HMDB: HMDB0034158)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034158)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0034158)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	55 - 56 °C	Not Available
Boiling Point	260.00 to 261.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	17.2 mg/mL at 13 °C	Not Available
LogP	1.15	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	17.3 g/L	ALOGPS
logP	1.29	ALOGPS
logP	1.35	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	9.37	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.97 m³·mol⁻¹	ChemAxon
Polarizability	15.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
DarkChem	[M+H]+	132.957	31661259
DarkChem	[M-H]-	131.625	31661259
DeepCCS	[M+H]+	135.106	30932474
DeepCCS	[M-H]-	132.275	30932474
DeepCCS	[M-2H]-	169.075	30932474
DeepCCS	[M+Na]+	144.192	30932474
AllCCS	[M+H]+	133.0	32859911
AllCCS	[M+H-H2O]+	128.5	32859911
AllCCS	[M+NH4]+	137.2	32859911
AllCCS	[M+Na]+	138.4	32859911
AllCCS	[M-H]-	130.6	32859911
AllCCS	[M+Na-2H]-	132.1	32859911
AllCCS	[M+HCOO]-	133.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethoxyphenol	COC1=CC=CC(OC)=C1O	2168.6	Standard polar	33892256
2,6-Dimethoxyphenol	COC1=CC=CC(OC)=C1O	1294.3	Standard non polar	33892256
2,6-Dimethoxyphenol	COC1=CC=CC(OC)=C1O	1368.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethoxyphenol,1TMS,isomer #1	COC1=CC=CC(OC)=C1O[Si](C)(C)C	1397.5	Semi standard non polar	33892256
2,6-Dimethoxyphenol,1TBDMS,isomer #1	COC1=CC=CC(OC)=C1O[Si](C)(C)C(C)(C)C	1662.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethoxyphenol EI-B (Non-derivatized)	splash10-0udr-8900000000-59569128bf570c85d520	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethoxyphenol EI-B (Non-derivatized)	splash10-0udr-8900000000-59569128bf570c85d520	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethoxyphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-3900000000-4b0c91d5f16ad25f5a7d	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethoxyphenol GC-MS (1 TMS) - 70eV, Positive	splash10-0h9r-9550000000-5310c55f74b926403d46	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethoxyphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethoxyphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxyphenol 10V, Positive-QTOF	splash10-0a4i-0900000000-cc571b20d0faa375e30f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxyphenol 20V, Positive-QTOF	splash10-0a4i-1900000000-3cd67086407b10e28df5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxyphenol 40V, Positive-QTOF	splash10-0ue9-9400000000-9c87ae44ad7b1ce42daa	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxyphenol 10V, Negative-QTOF	splash10-0udi-0900000000-9728418352c4e6881685	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxyphenol 20V, Negative-QTOF	splash10-0udi-2900000000-b0e4064ec22619215a70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxyphenol 40V, Negative-QTOF	splash10-0apr-9500000000-fb84b193c86c084b5110	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxyphenol 10V, Negative-QTOF	splash10-0udi-0900000000-55caab0c9e31716e1c83	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxyphenol 20V, Negative-QTOF	splash10-000i-1900000000-1acccb2bd26affbf87f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxyphenol 40V, Negative-QTOF	splash10-0a4i-9300000000-af88aab0d27bb8b804e6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxyphenol 10V, Positive-QTOF	splash10-0ab9-1900000000-902a7248c65b4d54fb74	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxyphenol 20V, Positive-QTOF	splash10-053r-9700000000-4e3f95dba2c46ca00506	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxyphenol 40V, Positive-QTOF	splash10-0f80-9000000000-022e6dc7cf0a25fb0d03	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details