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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:33:02 UTC

Update Date

2023-02-21 17:27:21 UTC

HMDB ID

HMDB0039998

Secondary Accession Numbers

HMDB39998

Metabolite Identification

Common Name

2-Acetyl-3,6-dimethylpyrazine

Description

2-Acetyl-3,6-dimethylpyrazine belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. 2-Acetyl-3,6-dimethylpyrazine is a hazelnut, popcorn, and roasted tasting compound. 2-Acetyl-3,6-dimethylpyrazine has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 2-acetyl-3,6-dimethylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Acetyl-3,6-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
1-(3,6-Dimethyl-2-pyrazinyl)-ethanone	HMDB
1-(3,6-Dimethylpyrazinyl)-ethanone	HMDB
1-(3,6-Dimethylpyrazinyl)ethan-1-one	HMDB
1-(3,6-Dimethylpyrazinyl)ethanone, 9ci	HMDB
Pyrazine, 2-acetyl-3,6-dimethyl	HMDB

Chemical Formula

C₈H₁₀N₂O

Average Molecular Weight

150.1778

Monoisotopic Molecular Weight

150.079312952

IUPAC Name

1-(3,6-dimethylpyrazin-2-yl)ethan-1-one

Traditional Name

1-(3,6-dimethylpyrazin-2-yl)ethanone

CAS Registry Number

54300-09-3

SMILES

CC(=O)C1=C(C)N=CC(C)=N1

InChI Identifier

InChI=1S/C8H10N2O/c1-5-4-9-6(2)8(10-5)7(3)11/h4H,1-3H3

InChI Key

JFUVDGXTDCVGHA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Pyrazine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0039998)
Cytoplasm (HMDB: HMDB0039998)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039998)

Source

Exogenous

Food

Food (HMDB: HMDB0039998)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0039998)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039998)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	238.00 to 239.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	18550 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.080	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	18 g/L	ALOGPS
logP	0.81	ALOGPS
logP	-0.26	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	14.67	ChemAxon
pKa (Strongest Basic)	0.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	42.85 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40.96 m³·mol⁻¹	ChemAxon
Polarizability	16 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.831	31661259
DarkChem	[M-H]-	130.847	31661259
DeepCCS	[M+H]+	135.603	30932474
DeepCCS	[M-H]-	131.885	30932474
DeepCCS	[M-2H]-	169.395	30932474
DeepCCS	[M+Na]+	144.933	30932474
AllCCS	[M+H]+	131.4	32859911
AllCCS	[M+H-H2O]+	126.9	32859911
AllCCS	[M+NH4]+	135.6	32859911
AllCCS	[M+Na]+	136.8	32859911
AllCCS	[M-H]-	131.5	32859911
AllCCS	[M+Na-2H]-	133.0	32859911
AllCCS	[M+HCOO]-	134.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Acetyl-3,6-dimethylpyrazine	CC(=O)C1=C(C)N=CC(C)=N1	1567.6	Standard polar	33892256
2-Acetyl-3,6-dimethylpyrazine	CC(=O)C1=C(C)N=CC(C)=N1	1148.2	Standard non polar	33892256
2-Acetyl-3,6-dimethylpyrazine	CC(=O)C1=C(C)N=CC(C)=N1	1172.1	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-Acetyl-3,6-dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-6900000000-f6ecede38b746020c64c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Acetyl-3,6-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-Acetyl-3,6-dimethylpyrazine 10V, Negative-QTOF	splash10-0002-0900000000-4ba657d933028e27f469	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,6-dimethylpyrazine 20V, Negative-QTOF	splash10-052b-0900000000-a89b419408dc989dd26c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,6-dimethylpyrazine 40V, Negative-QTOF	splash10-0a4i-5900000000-5141cd7bfd9ff622bd02	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,6-dimethylpyrazine 10V, Negative-QTOF	splash10-0002-0900000000-17f73e472e7588abf61b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,6-dimethylpyrazine 20V, Negative-QTOF	splash10-0a4j-2900000000-3ed88aa110e52816c668	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,6-dimethylpyrazine 40V, Negative-QTOF	splash10-0pc0-7900000000-39f7255f982995faf6cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,6-dimethylpyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-3527cd5b0f62e3660216	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,6-dimethylpyrazine 20V, Positive-QTOF	splash10-0ue9-0900000000-4ef04c71b86717f0dca9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,6-dimethylpyrazine 40V, Positive-QTOF	splash10-014i-9600000000-704db3679a8fce037889	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,6-dimethylpyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-af2586a68ab47c39fba1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,6-dimethylpyrazine 20V, Positive-QTOF	splash10-001i-3900000000-b13c217efdf568cebaf6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,6-dimethylpyrazine 40V, Positive-QTOF	splash10-0006-9100000000-7ad1a2d738d6d7e76ad0	2021-09-22	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

FDB019680

KNApSAcK ID

Not Available

Chemspider ID

94541

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

104722

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1381291

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-Acetyl-3,6-dimethylpyrazine (HMDB0039998)

MOL for HMDB0039998 (2-Acetyl-3,6-dimethylpyrazine)

3D MOL for HMDB0039998 (2-Acetyl-3,6-dimethylpyrazine)

3D SDF for HMDB0039998 (2-Acetyl-3,6-dimethylpyrazine)

3D-SDF for HMDB0039998 (2-Acetyl-3,6-dimethylpyrazine)

PDB for HMDB0039998 (2-Acetyl-3,6-dimethylpyrazine)

3D PDB for HMDB0039998 (2-Acetyl-3,6-dimethylpyrazine)

SMILES for HMDB0039998 (2-Acetyl-3,6-dimethylpyrazine)

INCHI for HMDB0039998 (2-Acetyl-3,6-dimethylpyrazine)

Structure for HMDB0039998 (2-Acetyl-3,6-dimethylpyrazine)

3D Structure for HMDB0039998 (2-Acetyl-3,6-dimethylpyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra