Trimethylpyrazine (YMDB01442)

Identification

YMDB ID

YMDB01442

Name

Trimethylpyrazine

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Trimethylpyrazine 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. Trimethylpyrazine exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on Trimethylpyrazine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2,3,5-Trimethylpyrazine
2,3,6-Trimethylpyrazine
pyrazine, 2,3,5-trimethyl
235-Trimethyl-pyrazine
2,3,5-TRIMETHYL pyrazine
2,3,5-Trimethyl-pyrazine
FEMA 3244
Trimethyl-pyrazine

CAS number

14667-55-1

Weight

Average: 122.1677
Monoisotopic: 122.08439833

InChI Key

IAEGWXHKWJGQAZ-UHFFFAOYSA-N

InChI

InChI=1S/C7H10N2/c1-5-4-8-6(2)7(3)9-5/h4H,1-3H3

IUPAC Name

2,3,5-trimethylpyrazine

Traditional IUPAC Name

pyrazine, trimethyl-

Chemical Formula

C₇H₁₀N₂

SMILES

CC1=CN=C(C)C(C)=N1

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

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	0.95 [YAMAGAMI,C ET AL. (1991)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	51.6 g/L	ALOGPS
logP	1.11	ALOGPS
logP	-0.068	ChemAxon
logS	-0.37	ALOGPS
pKa (Strongest Basic)	2.08	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	35.52 m³·mol⁻¹	ChemAxon
Polarizability	13.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Cocoa	FDB008527
Earthy	FDB008527
Hazelnut	FDB008527
Must	FDB008527
Musty	FDB008527
Nutty	FDB008527
Peanut	FDB008527
Potato	FDB008527
Powdery	FDB008527
Roast	FDB008527
Roasted	FDB008527

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-006x-9200000000-9f6faed991931d5ad1ee	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9200000000-40504210dd3941e2c04a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-006x-9200000000-9f6faed991931d5ad1ee	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9200000000-40504210dd3941e2c04a	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-8900000000-a14528e7d6edd51f8dc6	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-00di-2900000000-76363ef0f48afd63a91a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-00di-7900000000-e98f2f5a6e323c824048	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-0ab9-9400000000-35d807ba9ebeef9ae55c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-0pb9-9100000000-fff3de03d74c83ae57e0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-0zfr-9000000000-715231eb0f6256a14836	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 8V, positive	splash10-001i-9000000000-9b38357d8213dfc04a21	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 8V, positive	splash10-0a4i-9000000000-5c4795e954d5c3e9b74e	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-9fd5c695f7b8a4cfe63d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2900000000-bb37b6ad64235815e0f4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zgl-9000000000-8acc5bf685bbdae5968f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-434c116a57f2e3b72058	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-65f5a51dc79dd6ae5de8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pi0-9800000000-dfd2d2cc903cdbd80f8e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-1fbfd2b4b0ef1b9b6fee	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9400000000-a6ecdcbe708aeefa02c5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-100u-9000000000-7d5a8bbe136aa07e5c95	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1900000000-7b36c336b1384f9bab4b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-9300000000-49f0534d4a86e681b444	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-b33164d500a1075f7e25	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-006x-9300000000-0bf83855966f2520d689	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Mahadevan, K., Farmer, L. (2006). "Key odor impact compounds in three yeast extract pastes." J Agric Food Chem 54:7242-7250.16968089

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	HMDB0031844
Pubchem Compound ID	26808
Kegg ID	Not Available
ChemSpider ID	24972
FOODB ID	FDB008527
Wikipedia ID	Alkylpyrazine
BioCyc ID	Not Available

Structure for #<Compound:0xa5c117f4>