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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:49:55 UTC

Update Date

2023-02-21 17:28:09 UTC

HMDB ID

HMDB0040299

Secondary Accession Numbers

HMDB40299

Metabolite Identification

Common Name

2-Ethyl-3,5-dimethylpyrazine

Description

2-Ethyl-3,5-dimethylpyrazine 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. 2-Ethyl-3,5-dimethylpyrazine is a burnt almonds, coffee, and potato tasting compound. 2-Ethyl-3,5-dimethylpyrazine has been detected, but not quantified in, several different foods, such as tortilla chip, green tea, cereals and cereal products, teas (Camellia sinensis), and green vegetables. This could make 2-ethyl-3,5-dimethylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Ethyl-3,5-dimethylpyrazine.

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-3-ethyl-pyrazine	HMDB
2,6-Dimethyl-3-ethylpyrazine	HMDB
2-Ethyl-3,5(6)-dimethyl-pyrazine	HMDB
2-Ethyl-3,5-dimethyl pyrazine	HMDB
2-Ethyl-3,5-dimethyl-pyrazine	HMDB
3,5-Dimethyl-2-ethyl-pyrazine	HMDB
3,5-Dimethyl-2-ethylpyrazine	HMDB
3-Ethyl-2,6-dimethylpyrazine	HMDB
FEMA 3150	HMDB
Pyrazine, 3-ethyl-2,6-dimethyl	HMDB

Chemical Formula

C₈H₁₂N₂

Average Molecular Weight

136.1943

Monoisotopic Molecular Weight

136.100048394

IUPAC Name

2-ethyl-3,5-dimethylpyrazine

Traditional Name

2-ethyl-3,5-dimethylpyrazine

CAS Registry Number

13925-07-0

SMILES

CCC1=NC=C(C)N=C1C

InChI Identifier

InChI=1S/C8H12N2/c1-4-8-7(3)10-6(2)5-9-8/h5H,4H2,1-3H3

InChI Key

JZBCTZLGKSYRSF-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: HMDB0040299)
Cytoplasm (HMDB: HMDB0040299)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040299)

Source

Exogenous

Exogenous (HMDB: HMDB0040299)

Food

Food (HMDB: HMDB0040299)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Tea

Snack

Tortilla chip (FooDB: FOOD00721)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Aquatic origin

Fish

Fishes (FooDB: FOOD00865)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0040299)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040299)

Biological role

Nutrient (HMDB: HMDB0040299)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	180.00 to 182.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1473 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.457 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	21.5 g/L	ALOGPS
logP	1.59	ALOGPS
logP	0.63	ChemAxon
logS	-0.8	ALOGPS
pKa (Strongest Basic)	2.02	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	1	ChemAxon
Refractivity	40.15 m³·mol⁻¹	ChemAxon
Polarizability	15.88 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]+	128.997	31661259
DarkChem	[M-H]-	128.253	31661259
DeepCCS	[M+H]+	133.306	30932474
DeepCCS	[M-H]-	129.478	30932474
DeepCCS	[M-2H]-	166.847	30932474
DeepCCS	[M+Na]+	142.214	30932474
AllCCS	[M+H]+	128.6	32859911
AllCCS	[M+H-H2O]+	124.0	32859911
AllCCS	[M+NH4]+	132.9	32859911
AllCCS	[M+Na]+	134.2	32859911
AllCCS	[M-H]-	131.8	32859911
AllCCS	[M+Na-2H]-	133.7	32859911
AllCCS	[M+HCOO]-	135.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Ethyl-3,5-dimethylpyrazine	CCC1=C(C)N=C(C)C=N1	1429.3	Standard polar	33892256
2-Ethyl-3,5-dimethylpyrazine	CCC1=C(C)N=C(C)C=N1	1033.5	Standard non polar	33892256
2-Ethyl-3,5-dimethylpyrazine	CCC1=C(C)N=C(C)C=N1	1083.9	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-Ethyl-3,5-dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-4900000000-cad80e4e02d7ea7b7e06	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethyl-3,5-dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethyl-3,5-dimethylpyrazine 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-Ethyl-3,5-dimethylpyrazine 10V, Positive-QTOF	splash10-000i-0900000000-e51d3b27b8ac96bfb4d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,5-dimethylpyrazine 20V, Positive-QTOF	splash10-000i-1900000000-9ecf5427f7487618e3d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,5-dimethylpyrazine 40V, Positive-QTOF	splash10-00kf-9100000000-c5ee63807068795e076b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,5-dimethylpyrazine 10V, Negative-QTOF	splash10-000i-0900000000-dd627822ff8e3d137442	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,5-dimethylpyrazine 20V, Negative-QTOF	splash10-000i-1900000000-4c76b26f8a580b4175d9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,5-dimethylpyrazine 40V, Negative-QTOF	splash10-0673-9600000000-78bb12fbad1e38534b52	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,5-dimethylpyrazine 10V, Positive-QTOF	splash10-000i-0900000000-78f8c87482f4ec50ab68	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,5-dimethylpyrazine 20V, Positive-QTOF	splash10-000i-6900000000-1d6b9e60caa3824c002b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,5-dimethylpyrazine 40V, Positive-QTOF	splash10-015c-9000000000-291545cfe146c582d429	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,5-dimethylpyrazine 10V, Negative-QTOF	splash10-000i-0900000000-560d709635c029cd0cba	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,5-dimethylpyrazine 20V, Negative-QTOF	splash10-000i-7900000000-b6eee9068b8be68922d1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,5-dimethylpyrazine 40V, Negative-QTOF	splash10-00kf-9100000000-5adeb727d2c1b4655123	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

FDB020021

KNApSAcK ID

Not Available

Chemspider ID

24536

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

26334

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1008281

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-Ethyl-3,5-dimethylpyrazine (HMDB0040299)

MOL for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

3D MOL for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

3D SDF for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

3D-SDF for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

PDB for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

3D PDB for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

SMILES for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

INCHI for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

Structure for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

3D Structure for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra