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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:44:31 UTC
Update Date2023-02-21 17:25:26 UTC
HMDB IDHMDB0036584
Secondary Accession Numbers
  • HMDB36584
Metabolite Identification
Common NameTetramethylpyrazine
DescriptionTetramethylpyrazine, or 2,3,5,6-tetramethylpyrazine, or TMP and also known as FEMA 3237, is an alkylpyrazine and 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 moderately basic compound with white crystals that are soluble in alcohol, fixed oils, propylene glycol and water. Its odor is described as nutty, musty and vanilla with dry, brown cocoa nuances and it taste is described as nutty, musty, cocoa, drying, peanut-like with raw coffee notes. Tetramethylpyrazine has been detected in roasted beef, cheddar cheese, dairy products, red and yellow bell peppers (c. annuum), potato, filberts, boiled egg, coconut endosperm, cocoa products, green tea, tea leaf, soybean products, soybean seed, macadamia nut, peanut, meat, guava fruit, shrimp, rum and whiskey. This could make tetramethylpyrazine a potential biomarker for the consumption of these foods. It has been used as a perfuming agent in soaps, detergents, toiletries, fabric softeners, bleach, alcoholic beverages, and fine fragrances. Its biosynthesis in Bacillus involves the amination of acetoin, the latter being derived from pyruvate (doi:10.1038/1951103a0). It exhibits potential nootropic (improved executive function PMID:23916742 ) and anti-inflammatory activities against induced cerebral ischemic in rats (PMID:23644042 ).
Structure
Thumb
Synonyms
Chemical FormulaC8H12N2
Average Molecular Weight136.1943
Monoisotopic Molecular Weight136.100048394
IUPAC Nametetramethylpyrazine
Traditional Namepyrazine, tetramethyl-
CAS Registry Number1124-11-4
SMILES
CC1=NC(C)=C(C)N=C1C
InChI Identifier
InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
InChI KeyFINHMKGKINIASC-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrazines
Direct ParentPyrazines
Alternative Parents
Substituents
  • Pyrazine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point86 °CNot Available
Boiling Point190.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility7007 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.28Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015495
KNApSAcK IDC00056171
Chemspider ID13658
KEGG Compound IDNot Available
BioCyc IDCPD-15901
BiGG IDNot Available
Wikipedia LinkTetramethylpyrazine
METLIN IDNot Available
PubChem Compound14296
PDB IDNot Available
ChEBI ID133246
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1009291
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhu XL, Xiong LZ, Wang Q, Liu ZG, Ma X, Zhu ZH, Hu S, Gong G, Chen SY: Therapeutic time window and mechanism of tetramethylpyrazine on transient focal cerebral ischemia/reperfusion injury in rats. Neurosci Lett. 2009 Jan 2;449(1):24-7. doi: 10.1016/j.neulet.2008.09.007. Epub 2008 Sep 6. [PubMed:18790005 ]
  2. Dai XZ, Bache RJ: Coronary and systemic hemodynamic effects of tetramethylpyrazine in the dog. J Cardiovasc Pharmacol. 1985 Sep-Oct;7(5):841-9. [PubMed:2413290 ]
  3. Li M, Handa S, Ikeda Y, Goto S: Specific inhibiting characteristics of tetramethylpyrazine, one of the active ingredients of the Chinese herbal medicine 'Chuanxiong,' on platelet thrombus formation under high shear rates. Thromb Res. 2001 Oct 1;104(1):15-28. [PubMed:11583735 ]
  4. Wu W, Yu X, Luo XP, Yang SH, Zheng D: Tetramethylpyrazine protects against scopolamine-induced memory impairments in rats by reversing the cAMP/PKA/CREB pathway. Behav Brain Res. 2013 Sep 15;253:212-6. doi: 10.1016/j.bbr.2013.07.052. Epub 2013 Aug 2. [PubMed:23916742 ]
  5. Kao TK, Chang CY, Ou YC, Chen WY, Kuan YH, Pan HC, Liao SL, Li GZ, Chen CJ: Tetramethylpyrazine reduces cellular inflammatory response following permanent focal cerebral ischemia in rats. Exp Neurol. 2013 Sep;247:188-201. doi: 10.1016/j.expneurol.2013.04.010. Epub 2013 Apr 30. [PubMed:23644042 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .