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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:32:01 UTC

Update Date

2023-02-21 17:19:01 UTC

HMDB ID

HMDB0029680

Secondary Accession Numbers

HMDB29680

Metabolite Identification

Common Name

2,6-Dimethoxy-4-methylphenol

Description

2,6-Dimethoxy-4-methylphenol 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-Dimethoxy-4-methylphenol is a caramel, eugenol, and medicinal tasting compound. 2,6-Dimethoxy-4-methylphenol has been detected, but not quantified in, fishes. This could make 2,6-dimethoxy-4-methylphenol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2,6-Dimethoxy-4-methylphenol.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.926   0.385   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.539  -0.386   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.693   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.080  -0.386   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.468  -2.697   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.926  -2.697   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.539  -1.926   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.693  -2.697   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.080  -1.926   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.468  -2.697   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.693   1.926   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.539   2.697   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    9                                                       
CONECT    5    6                                                            
CONECT    6    5    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    4    8   10                                                  
CONECT   10    9                                                            
CONECT   11    3   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,6-Dimethoxy-4-methyl-phenol	HMDB
2,6-Dimethoxy-4-methylphenol, 9ci	HMDB
2,6-Dimethoxy-P-cresol	HMDB
4-Methyl-2,6-dimethoxyphenol	HMDB
4-Methyl-2,6-dimethoxyphenol (4-methylsyringol)	HMDB
4-Methylsyringol	HMDB
FEMA 3704	HMDB
Phenol, 4-methyl-2,6-dimethoxy	HMDB
Syringol, 4-methyl	HMDB

Chemical Formula

C₉H₁₂O₃

Average Molecular Weight

168.1898

Monoisotopic Molecular Weight

168.07864425

IUPAC Name

2,6-dimethoxy-4-methylphenol

Traditional Name

2,6-dimethoxy-4-methylphenol

CAS Registry Number

6638-05-7

SMILES

COC1=CC(C)=CC(OC)=C1O

InChI Identifier

InChI=1S/C9H12O3/c1-6-4-7(11-2)9(10)8(5-6)12-3/h4-5,10H,1-3H3

InChI Key

ZFBNNSOJNZBLLS-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

Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Anisole
Phenoxy compound
P-cresol
Phenol ether
Methoxybenzene
Alkyl aryl ether
Toluene
Monocyclic benzene moiety
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Extracellular (HMDB: HMDB0029680)
Cytoplasm (HMDB: HMDB0029680)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029680)

Source

Endogenous

Endogenous (HMDB: HMDB0029680)

Animal

Animal (HMDB: HMDB0029680)

Exogenous

Food

Food (HMDB: HMDB0029680)

Aquatic origin

Fish

Fishes (FooDB: FOOD00865)

Exogenous (HMDB: HMDB0029680)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0029680)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	36 °C	Not Available
Boiling Point	145.00 to 146.00 °C. @ 14.00 mm Hg	The Good Scents Company Information System
Water Solubility	2173 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.859 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.22 g/L	ALOGPS
logP	1.71	ALOGPS
logP	1.87	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.75	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	46.01 m³·mol⁻¹	ChemAxon
Polarizability	17.74 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	138.622	31661259
DarkChem	[M-H]-	136.993	31661259
DeepCCS	[M+H]+	139.03	30932474
DeepCCS	[M-H]-	135.822	30932474
DeepCCS	[M-2H]-	172.746	30932474
DeepCCS	[M+Na]+	148.043	30932474
AllCCS	[M+H]+	135.2	32859911
AllCCS	[M+H-H2O]+	130.8	32859911
AllCCS	[M+NH4]+	139.3	32859911
AllCCS	[M+Na]+	140.5	32859911
AllCCS	[M-H]-	134.5	32859911
AllCCS	[M+Na-2H]-	135.7	32859911
AllCCS	[M+HCOO]-	137.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	3.43 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5926 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.91 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1572.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	354.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	146.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	207.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	114.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	500.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	477.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	114.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1040.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	366.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1087.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	315.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	360.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	433.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	308.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	55.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethoxy-4-methylphenol	COC1=CC(C)=CC(OC)=C1O	2355.7	Standard polar	33892256
2,6-Dimethoxy-4-methylphenol	COC1=CC(C)=CC(OC)=C1O	1407.8	Standard non polar	33892256
2,6-Dimethoxy-4-methylphenol	COC1=CC(C)=CC(OC)=C1O	1463.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethoxy-4-methylphenol,1TMS,isomer #1	COC1=CC(C)=CC(OC)=C1O[Si](C)(C)C	1467.7	Semi standard non polar	33892256
2,6-Dimethoxy-4-methylphenol,1TBDMS,isomer #1	COC1=CC(C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	1733.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethoxy-4-methylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0900000000-615983e715e733ef9a09	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethoxy-4-methylphenol GC-MS (1 TMS) - 70eV, Positive	splash10-00vi-8690000000-62e44c19e923dcdcc887	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethoxy-4-methylphenol 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-Dimethoxy-4-methylphenol 10V, Positive-QTOF	splash10-014i-0900000000-48d7cabf4d2223396f9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-4-methylphenol 20V, Positive-QTOF	splash10-014i-0900000000-b8c6df2224b707a42d73	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-4-methylphenol 40V, Positive-QTOF	splash10-0v5j-7900000000-79ec71a33f4c8674e872	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-4-methylphenol 10V, Negative-QTOF	splash10-014i-0900000000-34952f92c621652e974a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-4-methylphenol 20V, Negative-QTOF	splash10-014i-0900000000-fd0beb8f093205bceb9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-4-methylphenol 40V, Negative-QTOF	splash10-0kms-8900000000-5bd38eb0c635a05efa03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-4-methylphenol 10V, Positive-QTOF	splash10-014r-0900000000-618d7bcd950b31cde17f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-4-methylphenol 20V, Positive-QTOF	splash10-014i-2900000000-20ce7507ea621c013331	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-4-methylphenol 40V, Positive-QTOF	splash10-014j-9100000000-5751515e944c8c0954c5	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-4-methylphenol 10V, Negative-QTOF	splash10-014i-0900000000-6dc4bdec95461e1d7366	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-4-methylphenol 20V, Negative-QTOF	splash10-000i-1900000000-c7159e96abadad4b5a1a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-4-methylphenol 40V, Negative-QTOF	splash10-014i-6900000000-ad2ee6b29ab5ce06841f	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB000865

KNApSAcK ID

Not Available

Chemspider ID

210530

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

240925

PDB ID

Not Available

ChEBI ID

446746

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1037511

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-Dimethoxy-4-methylphenol (HMDB0029680)

MOL for HMDB0029680 (2,6-Dimethoxy-4-methylphenol)

3D MOL for HMDB0029680 (2,6-Dimethoxy-4-methylphenol)

3D SDF for HMDB0029680 (2,6-Dimethoxy-4-methylphenol)

3D-SDF for HMDB0029680 (2,6-Dimethoxy-4-methylphenol)

PDB for HMDB0029680 (2,6-Dimethoxy-4-methylphenol)

3D PDB for HMDB0029680 (2,6-Dimethoxy-4-methylphenol)

SMILES for HMDB0029680 (2,6-Dimethoxy-4-methylphenol)

INCHI for HMDB0029680 (2,6-Dimethoxy-4-methylphenol)

Structure for HMDB0029680 (2,6-Dimethoxy-4-methylphenol)

3D Structure for HMDB0029680 (2,6-Dimethoxy-4-methylphenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra