AFCDB: Tetramethylpyrazine (FDB015495)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:52 UTC

Update date

2019-11-26 03:11:42 UTC

Primary ID

FDB015495

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Tetramethylpyrazine

Description

Tetramethylpyrazine, also known as TMP or liqustrazine, 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. Tetramethylpyrazine is a burnt, chocolate, and cocoa tasting compound. Tetramethylpyrazine has been detected, but not quantified in, several different foods, such as soy beans (Glycine max), cocoa and cocoa products, coconuts (Cocos nucifera), yellow bell peppers (Capsicum annuum), and potatos (Solanum tuberosum). This could make tetramethylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Tetramethylpyrazine.

CAS Number

1124-11-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	15 g/L	ALOGPS
logP	1.46	ALOGPS
logP	0.063	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Basic)	2.19	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	40.11 m³·mol⁻¹	ChemAxon
Polarizability	16.02 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

Chemical Formula

C8H12N2

IUPAC name

tetramethylpyrazine

InChI Identifier

InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3

InChI Key

FINHMKGKINIASC-UHFFFAOYSA-N

Isomeric SMILES

CC1=NC(C)=C(C)N=C1C

Average Molecular Weight

136.1943

Monoisotopic Molecular Weight

136.100048394

Classification

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp 190°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	1.28	YAMAGAMI,C ET AL. (1991)
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 70.55%; H 8.88%; N 20.57%	DFC
Melting Point	Mp 86° (anhyd.)	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0udr-9300000000-33fe7599448be6d9a1f0	2015-03-01	View Spectrum
GC-MS	Tetramethylpyrazine, non-derivatized, GC-MS Spectrum	splash10-0udu-9300000000-5d317f2dc804e043f2b9	Spectrum
GC-MS	Tetramethylpyrazine, non-derivatized, GC-MS Spectrum	splash10-0udu-9300000000-5d317f2dc804e043f2b9	Spectrum
Predicted GC-MS	Tetramethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-3900000000-68c7df3c47d48f17b27b	Spectrum
Predicted GC-MS	Tetramethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-000i-2900000000-825affe0aeefbf7abe2a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-052r-9800000000-0e691fbfc32545d1b1aa	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-0a4r-9300000000-bd32b31ff50928daf261	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-0pb9-9100000000-80bdd2f5e9e721213dba	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-0ue9-9000000000-a8ff866cfac430f29e97	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 9V, positive	splash10-0002-9000000000-acc42c048c36b7492ded	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 9V, positive	splash10-0a4i-9000000000-e10afcdf21ddde828d7c	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-4ea5d7454e8109b365d1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-f797c5b258bf45ed5801	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udl-9100000000-465d4f375262ee01acb3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-ca8b41e13886eb5f390f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-9c6dd6eec8dafc56f825	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kr-4900000000-a04f3b4c94a247e99232	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-ac299646e14f1770c4b5	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-3900000000-997da2b6ee4b7359f4d6	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-38545d1df73cc3f6ffdc	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1900000000-22a6232d9fbf0c94bc77	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-9800000000-d3294b56735618c40d87	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9100000000-63057d96e8a5e3139795	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

External Links

ChemSpider ID

13658

ChEMBL ID

CHEMBL303697

KEGG Compound ID

Not Available

Pubchem Compound ID

14296

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36584

CRC / DFC (Dictionary of Food Compounds) ID

KCT72-F:KCT72-F

EAFUS ID

3647

Dr. Duke ID

TETRAMETHYL-PYRAZINE|LIGUSTRAZINE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1009291

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anti aggregant			DUKE
anti anginal	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cholinergic	38323	Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons.	DUKE
anti dysmenorrheic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti embolic			DUKE
anti histaminic	37956	Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.	DUKE
anti hypertensive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti ischemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE

Showing 1 to 10 of 23 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
burnt	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
chocolate	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cocoa	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coffee	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
lard	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
nutty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
soybean	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Showing 1 to 8 of 8 entries

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Tetramethylpyrazine (FDB015495)

Structure for FDB015495 (Tetramethylpyrazine)