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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

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

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

Source

Exogenous

Exogenous (HMDB: HMDB0034158)

Food

Food (HMDB: HMDB0034158)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0034158)

Biological role

Nutrient (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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Syringol

METLIN ID

Not Available

PubChem Compound

7041

PDB ID

3DM

ChEBI ID

955

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1017771

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2,6-Dimethoxyphenol (HMDB0034158)

MOL for HMDB0034158 (2,6-Dimethoxyphenol)

3D MOL for HMDB0034158 (2,6-Dimethoxyphenol)

3D SDF for HMDB0034158 (2,6-Dimethoxyphenol)

3D-SDF for HMDB0034158 (2,6-Dimethoxyphenol)

PDB for HMDB0034158 (2,6-Dimethoxyphenol)

3D PDB for HMDB0034158 (2,6-Dimethoxyphenol)

SMILES for HMDB0034158 (2,6-Dimethoxyphenol)

INCHI for HMDB0034158 (2,6-Dimethoxyphenol)

Structure for HMDB0034158 (2,6-Dimethoxyphenol)

3D Structure for HMDB0034158 (2,6-Dimethoxyphenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra