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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 20:11:58 UTC

Update Date

2023-02-21 17:24:44 UTC

HMDB ID

HMDB0035248

Secondary Accession Numbers

HMDB35248

Metabolite Identification

Common Name

2,6-Dimethylpyrazine

Description

2,6-Dimethylpyrazine, also known as fema 3273 or 2,5-DMP, belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. Alkylpyrazines are chemical compounds based on pyrazine with different substitution patterns. 2,6-Dimethylpyrazine is a cocoa, roastbeef, and roastednut tasting compound. 2,6-Dimethylpyrazine has been detected, but not quantified, in tea. This could make 2,6-dimethylpyrazine a potential biomarker for the consumption of these foods. Alkylpyrazines are also formed during the cooking of some foods via Maillard reactions. It occurs naturally in asparagus, black or green tea, crispbread, malt, raw shrimp, soya, squid, Swiss cheeses, and wheat bread. It occurs naturally in baked potato, black or green tea, crispbread, French fries, malt, peated malt, raw asparagus, roasted barley, roasted filberts or pecans, squid, wheat bread, wild rice (Zizania aquatica), and wort.

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-Dimethyl-1,4-diazine	HMDB
2,6-Dimethyl-pyrazine	HMDB
2,6-Dimethylparadiazine	HMDB
2,6-Dimethylpiazine	HMDB
3,5-Dimethylpyrazine	HMDB
FEMA 3273	HMDB
2,5-Dimethylpyrazine	HMDB
2,5-DMP	HMDB

Chemical Formula

C₆H₈N₂

Average Molecular Weight

108.1411

Monoisotopic Molecular Weight

108.068748266

IUPAC Name

2,6-dimethylpyrazine

Traditional Name

pyrazine, 2,6-dimethyl-

CAS Registry Number

108-50-9

SMILES

CC1=CN=CC(C)=N1

InChI Identifier

InChI=1S/C6H8N2/c1-5-3-7-4-6(2)8-5/h3-4H,1-2H3

InChI Key

HJFZAYHYIWGLNL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazines

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Feces (HMDB: HMDB0035248)

Cellular substructure

Cytoplasm (HMDB: HMDB0035248)
Extracellular (HMDB: HMDB0035248)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035248)

Source

Exogenous

Exogenous (HMDB: HMDB0035248)

Food

Food (HMDB: HMDB0035248)

Tea

Endogenous

Plant

Plant (HMDB: HMDB0035248)
Poaceae (HMDB: HMDB0035248)

Animal

Animal (HMDB: HMDB0035248)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035248)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	47 - 48 °C	Not Available
Boiling Point	154.00 to 155.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	38160 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.54	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	183 g/L	ALOGPS
logP	0.63	ALOGPS
logP	-0.2	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Basic)	2.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.78 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.93 m³·mol⁻¹	ChemAxon
Polarizability	11.87 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]+	120.585	31661259
DarkChem	[M-H]-	118.463	31661259
DeepCCS	[M+H]+	123.941	30932474
DeepCCS	[M-H]-	120.943	30932474
DeepCCS	[M-2H]-	157.54	30932474
DeepCCS	[M+Na]+	132.516	30932474
AllCCS	[M+H]+	121.4	32859911
AllCCS	[M+H-H2O]+	116.5	32859911
AllCCS	[M+NH4]+	126.0	32859911
AllCCS	[M+Na]+	127.4	32859911
AllCCS	[M-H]-	121.4	32859911
AllCCS	[M+Na-2H]-	124.1	32859911
AllCCS	[M+HCOO]-	127.1	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.	1.94 minutes	32390414
Predicted by Siyang on May 30, 2022	8.2057 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.18 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	91.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	446.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	315.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	97.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	209.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	59.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	275.4 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	258.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	355.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	607.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	34.2 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	749.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	232.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	509.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	469.9 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	272.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethylpyrazine	CC1=CN=CC(C)=N1	1309.0	Standard polar	33892256
2,6-Dimethylpyrazine	CC1=CN=CC(C)=N1	873.3	Standard non polar	33892256
2,6-Dimethylpyrazine	CC1=CN=CC(C)=N1	905.9	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-Dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9800000000-b2ca42d940665139e5ca	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9300000000-395e4386e978089b15fc	2015-03-01	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-Dimethylpyrazine 10V, Positive-QTOF	splash10-0a4i-0900000000-9c7893ac24151b7d1d78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyrazine 20V, Positive-QTOF	splash10-0a4i-0900000000-28b9cea57c6481c96a64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyrazine 40V, Positive-QTOF	splash10-00kf-9000000000-0c9410f133dc565bffe5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyrazine 10V, Negative-QTOF	splash10-0a4i-0900000000-009c433da111c3f58a6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyrazine 20V, Negative-QTOF	splash10-0a4i-0900000000-f3af7ee5a27a31ac6253	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyrazine 40V, Negative-QTOF	splash10-0a4i-9600000000-854ff4a5310c6d449e6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyrazine 10V, Negative-QTOF	splash10-0a4i-0900000000-1d4d8b4513a018558199	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyrazine 20V, Negative-QTOF	splash10-0a4l-5900000000-ccf491cc922a64bef413	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyrazine 40V, Negative-QTOF	splash10-0uxu-9100000000-9d303006af154773726b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyrazine 10V, Positive-QTOF	splash10-0a4i-0900000000-0f7e6606314edbd6492a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyrazine 20V, Positive-QTOF	splash10-0a4i-9700000000-a50e54ec018925c4f608	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylpyrazine 40V, Positive-QTOF	splash10-0006-9000000000-06aa400f310cd86471cb	2021-09-22	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]+)	2023-02-04	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	Newborn (0-30 days old)	Both	Normal	21386183	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

FDB004391

KNApSAcK ID

C00052612

Chemspider ID

7650

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alkylpyrazine

METLIN ID

Not Available

PubChem Compound

7938

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1008151

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-Dimethylpyrazine (HMDB0035248)

MOL for HMDB0035248 (2,6-Dimethylpyrazine)

3D MOL for HMDB0035248 (2,6-Dimethylpyrazine)

3D SDF for HMDB0035248 (2,6-Dimethylpyrazine)

3D-SDF for HMDB0035248 (2,6-Dimethylpyrazine)

PDB for HMDB0035248 (2,6-Dimethylpyrazine)

3D PDB for HMDB0035248 (2,6-Dimethylpyrazine)

SMILES for HMDB0035248 (2,6-Dimethylpyrazine)

INCHI for HMDB0035248 (2,6-Dimethylpyrazine)

Structure for HMDB0035248 (2,6-Dimethylpyrazine)

3D Structure for HMDB0035248 (2,6-Dimethylpyrazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra