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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:53:01 UTC

Update Date

2023-02-21 17:22:53 UTC

HMDB ID

HMDB0032972

Secondary Accession Numbers

HMDB32972

Metabolite Identification

Common Name

2,6-Dimethylpyridine

Description

2,6-Dimethylpyridine, also known as alpha,alpha'-lutidine or 2,6-lutidine, belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group. 2,6-Dimethylpyridine has been detected, but not quantified in, several different foods, such as black tea, green tea, herbal tea, red tea, and teas (Camellia sinensis). This could make 2,6-dimethylpyridine 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-Dimethylpyridine.

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-Lutidine	ChEBI
alpha,Alpha'-dimethylpyridine	ChEBI
alpha,Alpha'-lutidine	ChEBI
lut	ChEBI
Lutidine	ChEBI
a,Alpha'-dimethylpyridine	Generator
Α,alpha'-dimethylpyridine	Generator
a,Alpha'-lutidine	Generator
Α,alpha'-lutidine	Generator
2,6-Dimethyl-pyridine	HMDB
2,6-Dimethypyridine	HMDB
2,6-Lutidene	HMDB
2,6-Lutidine, 8ci	HMDB
alpha,Alpha'-lutidin	HMDB
FEMA 3540	HMDB
HSDB 79	HMDB

Chemical Formula

C₇H₉N

Average Molecular Weight

107.1531

Monoisotopic Molecular Weight

107.073499293

IUPAC Name

2,6-dimethylpyridine

Traditional Name

lutidine

CAS Registry Number

108-48-5

SMILES

CC1=CC=CC(C)=N1

InChI Identifier

InChI=1S/C7H9N/c1-6-4-3-5-7(2)8-6/h3-5H,1-2H3

InChI Key

OISVCGZHLKNMSJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Methylpyridines

Direct Parent

Methylpyridines

Alternative Parents

Substituents

Methylpyridine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

methylpyridines (CHEBI:32548 )

Ontology

Feces (PMID: 17314143)

Cellular substructure

Extracellular (HMDB: HMDB0032972)
Cytoplasm (HMDB: HMDB0032972)

Source

Exogenous

Exogenous (HMDB: HMDB0032972)

Food

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Tea

Herb and spice

Herb

Peppermint (FooDB: FOOD00113)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-6 °C	Not Available
Boiling Point	143.00 to 145.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	300 mg/mL at 34 °C	Not Available
LogP	1.68	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	88.3 g/L	ALOGPS
logP	1.6	ALOGPS
logP	1.02	ChemAxon
logS	-0.08	ALOGPS
pKa (Strongest Basic)	6.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.89 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.08 m³·mol⁻¹	ChemAxon
Polarizability	12.54 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]+	121.194	31661259
DarkChem	[M-H]-	118.615	31661259
DeepCCS	[M+H]+	124.155	30932474
DeepCCS	[M-H]-	121.17	30932474
DeepCCS	[M-2H]-	157.753	30932474
DeepCCS	[M+Na]+	132.726	30932474
AllCCS	[M+H]+	116.8	32859911
AllCCS	[M+H-H2O]+	111.7	32859911
AllCCS	[M+NH4]+	121.6	32859911
AllCCS	[M+Na]+	123.0	32859911
AllCCS	[M-H]-	120.3	32859911
AllCCS	[M+Na-2H]-	122.8	32859911
AllCCS	[M+HCOO]-	125.5	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.	2.88 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4406 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.88 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	39.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1413.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	392.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	136.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	238.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	75.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	304.7 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	284.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	124.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	807.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	165.6 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	897.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	247.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	270.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	467.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	394.9 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	233.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethylpyridine	CC1=CC=CC(C)=N1	1258.4	Standard polar	33892256
2,6-Dimethylpyridine	CC1=CC=CC(C)=N1	875.8	Standard non polar	33892256
2,6-Dimethylpyridine	CC1=CC=CC(C)=N1	886.7	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-Dimethylpyridine EI-B (Non-derivatized)	splash10-0a4i-9700000000-abf9246bc54aec804ce8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethylpyridine EI-B (Non-derivatized)	splash10-0a4i-9700000000-21f6cd85259c97e309c8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethylpyridine EI-B (Non-derivatized)	splash10-0a4i-9700000000-abf9246bc54aec804ce8	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethylpyridine EI-B (Non-derivatized)	splash10-0a4i-9700000000-21f6cd85259c97e309c8	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethylpyridine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-ab9bc60c370aee33febf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethylpyridine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine ESI-ITFT , positive-QTOF	splash10-0a4i-0900000000-20d8f41814b827b590d5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine ESI-ITFT , positive-QTOF	splash10-0006-9400000000-8773930bbd2ae1280514	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine ESI-ITFT , positive-QTOF	splash10-0006-9000000000-4bd146c289dc841a5488	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine ESI-ITFT , positive-QTOF	splash10-0a4i-0900000000-20d8f41814b827b590d5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine ESI-ITFT , positive-QTOF	splash10-0a4i-0900000000-20d8f41814b827b590d5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine ESI-ITFT , positive-QTOF	splash10-0a4i-0900000000-352c0f01108810c08db1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine ESI-ITFT , positive-QTOF	splash10-0a4i-0900000000-593d3d6c2ddc13af9d1d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine ESI-ITFT , positive-QTOF	splash10-0a4i-0900000000-0020b1ca2a77aa01ca31	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine ESI-ITFT , positive-QTOF	splash10-0a4i-1900000000-1d77120610f63cb4b65a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine ESI-ITFT , positive-QTOF	splash10-0a4i-3900000000-697e916148151a1e0912	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine ESI-ITFT , positive-QTOF	splash10-0a4i-7900000000-3e920c032c5b181fa5cf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine ESI-ITFT , positive-QTOF	splash10-0aou-9600000000-28cd303c8ddcd4a931e6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine APCI-ITFT , positive-QTOF	splash10-0a4i-0900000000-20d8f41814b827b590d5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine APCI-ITFT , positive-QTOF	splash10-0a4i-0900000000-deaa134af46653d96fed	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine APCI-ITFT , positive-QTOF	splash10-0a4i-0900000000-deaa134af46653d96fed	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine APCI-ITFT , positive-QTOF	splash10-0a4i-0900000000-f46a1b64d808d3e937c1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine APCI-ITFT , positive-QTOF	splash10-0a4i-0900000000-b8cad215383971cfdc7d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine APCI-ITFT , positive-QTOF	splash10-0a4i-0900000000-a97869f23833751a9501	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dimethylpyridine APCI-ITFT , positive-QTOF	splash10-0a4i-1900000000-6d6cdfa62412038cc7b3	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyridine 10V, Positive-QTOF	splash10-0a4i-0900000000-b5b465bf457cee49a007	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyridine 20V, Positive-QTOF	splash10-0a4i-1900000000-a0df8401e93f9e0e66cd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyridine 40V, Positive-QTOF	splash10-066r-9200000000-40a876b97fbbdb6de51b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyridine 10V, Negative-QTOF	splash10-0a4i-0900000000-ce4d324bcf8475cc2ea5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyridine 20V, Negative-QTOF	splash10-0a4i-0900000000-962e010c36f1f6323591	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyridine 40V, Negative-QTOF	splash10-0a4i-9500000000-7472da01c93f92718072	2016-08-03	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details

Associated Disorders and Diseases

Disease References

Ulcerative colitis
Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004392

KNApSAcK ID

Not Available

Chemspider ID

13842613

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,6-Lutidine

METLIN ID

Not Available

PubChem Compound

7937

PDB ID

Not Available

ChEBI ID

32548

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1005491

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-Dimethylpyridine (HMDB0032972)

MOL for HMDB0032972 (2,6-Dimethylpyridine)

3D MOL for HMDB0032972 (2,6-Dimethylpyridine)

3D SDF for HMDB0032972 (2,6-Dimethylpyridine)

3D-SDF for HMDB0032972 (2,6-Dimethylpyridine)

PDB for HMDB0032972 (2,6-Dimethylpyridine)

3D PDB for HMDB0032972 (2,6-Dimethylpyridine)

SMILES for HMDB0032972 (2,6-Dimethylpyridine)

INCHI for HMDB0032972 (2,6-Dimethylpyridine)

Structure for HMDB0032972 (2,6-Dimethylpyridine)

3D Structure for HMDB0032972 (2,6-Dimethylpyridine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra