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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:08 UTC

Update Date

2023-02-21 17:21:40 UTC

HMDB ID

HMDB0032150

Secondary Accession Numbers

HMDB32150

Metabolite Identification

Common Name

2,6-Dimethylphenol

Description

2,6-Dimethylphenol, also known as 2,6-xylenol, belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively. 2,6-Dimethylphenol is a sweet, coffee, and medicinal tasting compound. 2,6-Dimethylphenol has been detected, but not quantified in, several different foods, such as alcoholic beverages, arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 2,6-dimethylphenol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2,6-Dimethylphenol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,6-Xylenol	MeSH
26-Dimethyl phenol	ChEMBL, HMDB
26-Dimethyl-phenol	ChEMBL, HMDB
26-Dimethylphenol	ChEMBL, HMDB
1,3,2-Xylenol	HMDB
1,3-Dimethyl-2-hydroxybenzene	HMDB
1-Hydroxy-2, 6-dimethylbenzene	HMDB
1-Hydroxy-2,6-dimethylbenzene	HMDB
2,6-Dimethyl-phenol	HMDB
2,6-Xylenol, 8ci	HMDB
2-Hydroxy-1,3-dimethylbenzene	HMDB
2-Hydroxy-m-xylene	HMDB
FEMA 3249	HMDB
m-2-Xylenol	HMDB

Chemical Formula

C₈H₁₀O

Average Molecular Weight

122.1644

Monoisotopic Molecular Weight

122.073164942

IUPAC Name

2,6-dimethylphenol

Traditional Name

2,6-dimethylphenol

CAS Registry Number

576-26-1

SMILES

CC1=CC=CC(C)=C1O

InChI Identifier

InChI=1S/C8H10O/c1-6-4-3-5-7(2)8(6)9/h3-5,9H,1-2H3

InChI Key

NXXYKOUNUYWIHA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

M-xylene
Xylene
O-cresol
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032150)

Source

Endogenous

Endogenous (HMDB: HMDB0032150)

Plant

Coffea (HMDB: HMDB0032150)

Exogenous

Food

Food (HMDB: HMDB0032150)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Environmental

Sludge (HMDB: HMDB0032150)

Exogenous (HMDB: HMDB0032150)

Process

Not Available

Role

Environmental role

Air pollutant (HMDB: HMDB0032150)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032150)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	49 °C	Not Available
Boiling Point	201.00 to 203.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	6.05 mg/mL at 25 °C	Not Available
LogP	2.36	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.18 g/L	ALOGPS
logP	2.32	ALOGPS
logP	2.7	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.73	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	38.12 m³·mol⁻¹	ChemAxon
Polarizability	13.89 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]+	125.881	31661259
DarkChem	[M-H]-	121.288	31661259
DeepCCS	[M+H]+	130.273	30932474
DeepCCS	[M-H]-	128.046	30932474
DeepCCS	[M-2H]-	164.175	30932474
DeepCCS	[M+Na]+	139.007	30932474
AllCCS	[M+H]+	121.7	32859911
AllCCS	[M+H-H2O]+	116.8	32859911
AllCCS	[M+NH4]+	126.2	32859911
AllCCS	[M+Na]+	127.5	32859911
AllCCS	[M-H]-	120.3	32859911
AllCCS	[M+Na-2H]-	122.3	32859911
AllCCS	[M+HCOO]-	124.7	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.	3.52 minutes	32390414
Predicted by Siyang on May 30, 2022	13.7204 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.11 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1550.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	483.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	198.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	326.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	298.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	616.5 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	618.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	163.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1173.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	457.4 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	1276.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	391.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	418.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	498.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	287.4 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	77.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethylphenol	CC1=CC=CC(C)=C1O	1937.4	Standard polar	33892256
2,6-Dimethylphenol	CC1=CC=CC(C)=C1O	1051.4	Standard non polar	33892256
2,6-Dimethylphenol	CC1=CC=CC(C)=C1O	1126.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethylphenol,1TMS,isomer #1	CC1=CC=CC(C)=C1O[Si](C)(C)C	1230.7	Semi standard non polar	33892256
2,6-Dimethylphenol,1TBDMS,isomer #1	CC1=CC=CC(C)=C1O[Si](C)(C)C(C)(C)C	1488.9	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-Dimethylphenol EI-B (Non-derivatized)	splash10-05i0-8900000000-6952903111c603d9229d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethylphenol EI-B (Non-derivatized)	splash10-00di-9800000000-18a8beede2ffebb7acf4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethylphenol EI-B (Non-derivatized)	splash10-05fr-7900000000-25623d364ea2e2daec20	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethylphenol EI-B (Non-derivatized)	splash10-05i0-8900000000-8a1b0af5939a912cc32f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethylphenol EI-B (Non-derivatized)	splash10-05i0-8900000000-6952903111c603d9229d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethylphenol EI-B (Non-derivatized)	splash10-00di-9800000000-18a8beede2ffebb7acf4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethylphenol EI-B (Non-derivatized)	splash10-05fr-7900000000-25623d364ea2e2daec20	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethylphenol EI-B (Non-derivatized)	splash10-05i0-8900000000-8a1b0af5939a912cc32f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-3900000000-9b5f6494ca218c03206e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethylphenol GC-MS (1 TMS) - 70eV, Positive	splash10-00fu-8900000000-8f9c7b7a59d4fb237f02	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethylphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05i0-9700000000-f5b0e950983b55b33fa2	2014-09-20	Not Available	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-Dimethylphenol 10V, Positive-QTOF	splash10-00di-0900000000-656a3c18896c3e420d9d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylphenol 20V, Positive-QTOF	splash10-00di-2900000000-6789ab1fffe1496b1752	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylphenol 40V, Positive-QTOF	splash10-0gbc-9100000000-b183d531d75f7ddf1106	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylphenol 10V, Negative-QTOF	splash10-00di-0900000000-67a3ee9ce567d04f8006	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylphenol 20V, Negative-QTOF	splash10-00di-0900000000-c0586196c5ab3ff267e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylphenol 40V, Negative-QTOF	splash10-00di-9700000000-9ce80634a7f8a53d9884	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylphenol 10V, Positive-QTOF	splash10-00di-0900000000-13e3a8efc7bb649866e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylphenol 20V, Positive-QTOF	splash10-00kf-9200000000-ae0483aa3e2cedd8acac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylphenol 40V, Positive-QTOF	splash10-00or-9100000000-5a5a1da18bb71a4b3b17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylphenol 10V, Negative-QTOF	splash10-00di-0900000000-99acd0a74fdc923b2838	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylphenol 20V, Negative-QTOF	splash10-00di-4900000000-c72d08db24c5083cb768	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylphenol 40V, Negative-QTOF	splash10-02t9-9300000000-b29e0573447f367550d1	2021-09-22	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

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB008878

KNApSAcK ID

C00052613

Chemspider ID

13839174

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11335

PDB ID

2MY

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035711

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

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-Dimethylphenol (HMDB0032150)

MOL for HMDB0032150 (2,6-Dimethylphenol)

3D MOL for HMDB0032150 (2,6-Dimethylphenol)

3D SDF for HMDB0032150 (2,6-Dimethylphenol)

3D-SDF for HMDB0032150 (2,6-Dimethylphenol)

PDB for HMDB0032150 (2,6-Dimethylphenol)

3D PDB for HMDB0032150 (2,6-Dimethylphenol)

SMILES for HMDB0032150 (2,6-Dimethylphenol)

INCHI for HMDB0032150 (2,6-Dimethylphenol)

Structure for HMDB0032150 (2,6-Dimethylphenol)

3D Structure for HMDB0032150 (2,6-Dimethylphenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra