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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:53 UTC

Update Date

2023-02-21 17:21:51 UTC

HMDB ID

HMDB0032276

Secondary Accession Numbers

HMDB32276

Metabolite Identification

Common Name

2-Ethyl-3,(5 or 6)-dimethylpyrazine

Description

2-Ethyl-3,(5 or 6)-dimethylpyrazine, also known as 2E3,6DMP, 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 or 6)-dimethylpyrazine is a cocoa, nutty, and potato tasting compound. 2-Ethyl-3,(5 or 6)-dimethylpyrazine has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, robusta coffees (Coffea canephora), herbal tea, and teas (Camellia sinensis). This could make 2-ethyl-3,(5 or 6)-dimethylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Ethyl-3,(5 or 6)-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
2E3,6DMP	MeSH
2-Ethyl-3,6-dimethylpyrazine	MeSH
2-Ethyl-3,5/6-dimethyl-pyrazine	HMDB

Chemical Formula

C₈H₁₂N₂

Average Molecular Weight

136.1943

Monoisotopic Molecular Weight

136.100048394

IUPAC Name

3-ethyl-2,5-dimethylpyrazine

Traditional Name

3-ethyl-2,5-dimethylpyrazine

CAS Registry Number

27043-05-6

SMILES

CCC1=NC(C)=CN=C1C

InChI Identifier

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

InChI Key

WHMWOHBXYIZFPF-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

Cytoplasm (HMDB: HMDB32276)
Extracellular (HMDB: HMDB32276)

Route of exposure

Enteral

Ingestion (HMDB: HMDB32276)

Source

Exogenous

Food

Food (HMDB: HMDB32276)

Tea

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Herb and spice

Herb

Soft-necked garlic (FooDB: FOOD00850)

Endogenous

Plant

Plant (HMDB: HMDB32276)
Coffea (HMDB: HMDB32276)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB32276)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1473 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	21.4 g/L	ALOGPS
logP	1.59	ALOGPS
logP	0.63	ChemAxon
logS	-0.8	ALOGPS
pKa (Strongest Basic)	1.93	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	15.86 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]+	129.554	31661259
DarkChem	[M-H]-	127.192	31661259
DeepCCS	[M+H]+	133.146	30932474
DeepCCS	[M-H]-	130.088	30932474
DeepCCS	[M-2H]-	167.083	30932474
DeepCCS	[M+Na]+	142.199	30932474
AllCCS	[M+H]+	127.9	32859911
AllCCS	[M+H-H2O]+	123.2	32859911
AllCCS	[M+NH4]+	132.3	32859911
AllCCS	[M+Na]+	133.5	32859911
AllCCS	[M-H]-	130.4	32859911
AllCCS	[M+Na-2H]-	132.3	32859911
AllCCS	[M+HCOO]-	134.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Ethyl-3,(5 or 6)-dimethylpyrazine	CCC1=NC(C)=CN=C1C	1430.4	Standard polar	33892256
2-Ethyl-3,(5 or 6)-dimethylpyrazine	CCC1=NC(C)=CN=C1C	1030.4	Standard non polar	33892256
2-Ethyl-3,(5 or 6)-dimethylpyrazine	CCC1=NC(C)=CN=C1C	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 or 6)-dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-5900000000-8972bb1f230d4ce37aa0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethyl-3,(5 or 6)-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 or 6)-dimethylpyrazine 10V, Positive-QTOF	splash10-000i-0900000000-0314177c3c76c33d3a62	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 20V, Positive-QTOF	splash10-000i-2900000000-17c28b506f498cff1d9f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 40V, Positive-QTOF	splash10-00kf-9100000000-53eee1c2cd50606623a0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 10V, Negative-QTOF	splash10-000i-0900000000-ec3a2f6d876ea167479f	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 20V, Negative-QTOF	splash10-000i-1900000000-eb3d7afc9b1afc13d34c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 40V, Negative-QTOF	splash10-0ap0-8900000000-4026d008af47668a5d3d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 10V, Negative-QTOF	splash10-000i-0900000000-560d709635c029cd0cba	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 20V, Negative-QTOF	splash10-000i-6900000000-a822bb86992113f3c90b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 40V, Negative-QTOF	splash10-0f7o-9500000000-43ee0e402d531191a7db	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 10V, Positive-QTOF	splash10-000i-0900000000-ac299646e14f1770c4b5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 20V, Positive-QTOF	splash10-000i-8900000000-14fd5e997abecd36a2f5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 40V, Positive-QTOF	splash10-00l6-9000000000-c858357dc68519b94e38	2021-09-24	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

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

FDB020022

KNApSAcK ID

C00052678

Chemspider ID

24145

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25916

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1426461

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 or 6)-dimethylpyrazine (HMDB0032276)

MOL for HMDB0032276 (2-Ethyl-3,(5 or 6)-dimethylpyrazine)

3D MOL for HMDB0032276 (2-Ethyl-3,(5 or 6)-dimethylpyrazine)

3D SDF for HMDB0032276 (2-Ethyl-3,(5 or 6)-dimethylpyrazine)

3D-SDF for HMDB0032276 (2-Ethyl-3,(5 or 6)-dimethylpyrazine)

PDB for HMDB0032276 (2-Ethyl-3,(5 or 6)-dimethylpyrazine)

3D PDB for HMDB0032276 (2-Ethyl-3,(5 or 6)-dimethylpyrazine)

SMILES for HMDB0032276 (2-Ethyl-3,(5 or 6)-dimethylpyrazine)

INCHI for HMDB0032276 (2-Ethyl-3,(5 or 6)-dimethylpyrazine)

Structure for HMDB0032276 (2-Ethyl-3,(5 or 6)-dimethylpyrazine)

3D Structure for HMDB0032276 (2-Ethyl-3,(5 or 6)-dimethylpyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra