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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:01 UTC

Update Date

2023-02-21 17:22:53 UTC

HMDB ID

HMDB0032971

Secondary Accession Numbers

HMDB32971

Metabolite Identification

Common Name

2,3-Dimethylpyrazine

Description

2,3-Dimethylpyrazine, also known as fema 3271, 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. Some alkylpyrazines are naturally occurring highly aromatic substances which often have a very low odor threshold and contribute to the taste and aroma of various foods including coffee and wines. 2,3-Dimethylpyrazine is an almond, butter, and caramel tasting compound. 2,3-Dimethylpyrazine has been detected, but not quantified, in several different foods, such as asparagus, fruits, red bell peppers, orange bell peppers, and green bell peppers. This could make 2,3-dimethylpyrazine a potential biomarker for the consumption of these foods. 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. 2,3-Dimethylpyrazine 2,3-Dimethylpyrazine is a component of the aroma of roasted sesame seeds. Alkylpyrazines are also formed during the cooking of some foods via Maillard reactions. Alkylpyrazines are chemical compounds based on pyrazine with different substitution patterns.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3-DMP Pyrazine	MeSH
23-Dimethyl-pyrazine	ChEMBL, HMDB
2,3-Dimethyl-1,4-diazine	HMDB
2,3-Dimethyl-pyrazine	HMDB
FEMA 3271	HMDB

Chemical Formula

C₆H₈N₂

Average Molecular Weight

108.1411

Monoisotopic Molecular Weight

108.068748266

IUPAC Name

2,3-dimethylpyrazine

Traditional Name

pyrazine, 2,3-dimethyl-

CAS Registry Number

5910-89-4

SMILES

CC1=C(C)N=CC=N1

InChI Identifier

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

InChI Key

OXQOBQJCDNLAPO-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

Cellular substructure

Extracellular (HMDB: HMDB0032971)
Cytoplasm (HMDB: HMDB0032971)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032971)

Source

Exogenous

Exogenous (HMDB: HMDB0032971)

Food

Food (HMDB: HMDB0032971)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Root vegetable

Kohlrabi (FooDB: FOOD00033)

Fruit vegetable

Tuber

Potato (FooDB: FOOD00175)

Brassica

Brassicas (FooDB: FOOD00857)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Pulse

Bean

Mung bean (FooDB: FOOD00200)

Soy

Soy bean (FooDB: FOOD00085)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Tea

Snack

Tortilla chip (FooDB: FOOD00721)

Dish

Tex-mex cuisine

Taco (FooDB: FOOD00708)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Nut

Nuts (FooDB: FOOD00869)

Fruit

Fruits (FooDB: FOOD00871)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Endogenous

Plant

Plant (HMDB: HMDB0032971)
Poaceae (HMDB: HMDB0032971)

Animal

Animal (HMDB: HMDB0032971)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032971)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	155.00 to 157.00 °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	180 g/L	ALOGPS
logP	0.63	ALOGPS
logP	-0.2	ChemAxon
logS	0.22	ALOGPS
pKa (Strongest Basic)	1.62	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	11.75 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]+	119.833	31661259
DarkChem	[M-H]-	116.658	31661259
DeepCCS	[M+H]+	125.188	30932474
DeepCCS	[M-H]-	122.229	30932474
DeepCCS	[M-2H]-	158.773	30932474
DeepCCS	[M+Na]+	133.751	30932474
AllCCS	[M+H]+	121.0	32859911
AllCCS	[M+H-H2O]+	116.0	32859911
AllCCS	[M+NH4]+	125.6	32859911
AllCCS	[M+Na]+	127.0	32859911
AllCCS	[M-H]-	121.1	32859911
AllCCS	[M+Na-2H]-	123.7	32859911
AllCCS	[M+HCOO]-	126.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dimethylpyrazine	CC1=C(C)N=CC=N1	1342.0	Standard polar	33892256
2,3-Dimethylpyrazine	CC1=C(C)N=CC=N1	884.7	Standard non polar	33892256
2,3-Dimethylpyrazine	CC1=C(C)N=CC=N1	914.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,3-Dimethylpyrazine EI-B (Non-derivatized)	splash10-066u-9300000000-a8e384b21f05e8366901	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,3-Dimethylpyrazine EI-B (Non-derivatized)	splash10-066u-9300000000-a8e384b21f05e8366901	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9800000000-84b80cbd4522b6d41120	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-066u-9200000000-81c62da205b82b71c5f4	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 - 2,3-Dimethylpyrazine 10V, Positive-QTOF	splash10-0a4i-0900000000-be85de85cd4c9c268d1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 20V, Positive-QTOF	splash10-0a4i-1900000000-e32b9221fcb3b6f14e7f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 40V, Positive-QTOF	splash10-0ldl-9000000000-c45c1029e88c6f7f1abe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 10V, Negative-QTOF	splash10-0a4i-0900000000-8bc06f3195c254237e31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 20V, Negative-QTOF	splash10-0a4i-0900000000-c7cbca7309a958b109e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 40V, Negative-QTOF	splash10-0pb9-9400000000-bbf99b74f59a4b21d37c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 10V, Negative-QTOF	splash10-0a4i-0900000000-1d4d8b4513a018558199	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 20V, Negative-QTOF	splash10-0a4i-1900000000-5e56bb9f78bc0c56fa72	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 40V, Negative-QTOF	splash10-0006-9000000000-12edac38431654aaa839	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 10V, Positive-QTOF	splash10-0a4i-0900000000-f6048b98ce921f15f893	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 20V, Positive-QTOF	splash10-0a4i-9700000000-36854acac26b155e72da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 40V, Positive-QTOF	splash10-0udi-9000000000-5dfe58276533b985a7b6	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+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

FDB010958

KNApSAcK ID

C00052588

Chemspider ID

20843

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alkylpyrazine

METLIN ID

Not Available

PubChem Compound

22201

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1008121

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 2,3-Dimethylpyrazine (HMDB0032971)

MOL for HMDB0032971 (2,3-Dimethylpyrazine)

3D MOL for HMDB0032971 (2,3-Dimethylpyrazine)

3D SDF for HMDB0032971 (2,3-Dimethylpyrazine)

3D-SDF for HMDB0032971 (2,3-Dimethylpyrazine)

PDB for HMDB0032971 (2,3-Dimethylpyrazine)

3D PDB for HMDB0032971 (2,3-Dimethylpyrazine)

SMILES for HMDB0032971 (2,3-Dimethylpyrazine)

INCHI for HMDB0032971 (2,3-Dimethylpyrazine)

Structure for HMDB0032971 (2,3-Dimethylpyrazine)

3D Structure for HMDB0032971 (2,3-Dimethylpyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra