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Record Information
StatusExpected but not Quantified
Creation Date2012-09-11 17:54:04 UTC
Update Date2019-07-23 06:12:40 UTC
Secondary Accession Numbers
  • HMDB33156
Metabolite Identification
Common NameMethoxypyrazine
DescriptionMethoxypyrazine, also known as fema 3302, belongs to the class of organic compounds known as methoxypyrazines. These are pyrazines containing a methoxyl group attached to the pyrazine ring. They have also been identified as additives in cigarette manufacture. Two methoxypyrazine compounds, 3-isobutyl-2-methoxypyrazine (IBMP) and 3-isopropyl-2-methoxypyrazine (IPMP), are considered to be important determinants of green flavours in Sauvignon blanc wines. Cabernet Sauvignon has high levels of methoxypyrazines. Methoxypyrazine is an extremely weak basic (essentially neutral) compound (based on its pKa). Methoxypyrazine is a sweet, cocoa, and nutty tasting compound. Outside of the human body, Methoxypyrazine has been detected, but not quantified in, cocoa and cocoa products. This could make methoxypyrazine a potential biomarker for the consumption of these foods. The odors tend to be undesirable, as in the case of certain wines, or as in the case of the Asian Lady Beetle which produces isopropyl methoxy pyrazine (IPMP). Detection thresholds are very low, typically near 2 parts per trillion (1 ng/L). Methoxypyrazines are a class of chemical compounds that produce odors.
Chemical FormulaC5H6N2O
Average Molecular Weight110.1139
Monoisotopic Molecular Weight110.048012824
IUPAC Name2-methoxypyrazine
Traditional Name2-methoxypyrazine
CAS Registry Number3149-28-8
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxypyrazines. These are pyrazines containing a methoxyl group attached to the pyrazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
Sub ClassPyrazines
Direct ParentMethoxypyrazines
Alternative Parents
  • Methoxypyrazine
  • Alkyl aryl ether
  • Heteroaromatic compound
  • Azacycle
  • Ether
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Route of exposure:


Biological location:


Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.73Not Available
Predicted Properties
Water Solubility353 g/LALOGPS
pKa (Strongest Basic)0.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.01 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.52 m³·mol⁻¹ChemAxon
Polarizability10.56 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-9400000000-f0d7b83cc2264eebf07cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-fda081551167973cfbaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-590033940c7cc1a5d4d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-9000000000-c1c5d52afd364d2b9fa6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-f0b30191136c63b9dcabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-dc05a18814c746076634Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1b5a0b27beee51867795Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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 IDFDB011162
KNApSAcK IDNot Available
Chemspider ID17443
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethoxypyrazines
METLIN IDNot Available
PubChem Compound18467
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Vallarino JG, Lopez-Cortes XA, Dunlevy JD, Boss PK, Gonzalez-Nilo FD, Moreno YM: Biosynthesis of methoxypyrazines: elucidating the structural/functional relationship of two Vitis viniferaO-methyltransferases capable of catalyzing the putative final step of the biosynthesis of 3-alkyl-2-methoxypyrazine. J Agric Food Chem. 2011 Jul 13;59(13):7310-6. doi: 10.1021/jf200542w. Epub 2011 Jun 9. [PubMed:21591781 ]
  2. Kogel S, Eben A, Hoffmann C, Gross J: Influence of diet on fecundity, immune defense and content of 2-isopropyl-3-methoxypyrazine in Harmonia axyridis Pallas. J Chem Ecol. 2012 Jul;38(7):854-64. doi: 10.1007/s10886-012-0139-1. Epub 2012 May 31. [PubMed:22648506 ]
  3. Sun Q, Gates MJ, Lavin EH, Acree TE, Sacks GL: Comparison of odor-active compounds in grapes and wines from vitis vinifera and non-foxy American grape species. J Agric Food Chem. 2011 Oct 12;59(19):10657-64. doi: 10.1021/jf2026204. Epub 2011 Sep 13. [PubMed:21879766 ]
  4. van Leeuwen C, Roby JP, Alonso-Villaverde V, Gindro K: Impact of clonal variability in Vitis vinifera Cabernet franc on grape composition, wine quality, leaf blade stilbene content, and downy mildew resistance. J Agric Food Chem. 2013 Jan 9;61(1):19-24. doi: 10.1021/jf304687c. Epub 2012 Dec 14. [PubMed:23205623 ]
  5. Suklje K, Lisjak K, Cesnik HB, Janes L, Du Toit W, Coetzee Z, Vanzo A, Deloire A: Classification of grape berries according to diameter and total soluble solids to study the effect of light and temperature on methoxypyrazine, glutathione, and hydroxycinnamate evolution during ripening of Sauvignon blanc (Vitis vinifera L.). J Agric Food Chem. 2012 Sep 19;60(37):9454-61. Epub 2012 Sep 10. [PubMed:22946638 ]
  6. Kaneko S, Kumazawa K, Nishimura O: Studies on the key aroma compounds in soy milk made from three different soybean cultivars. J Agric Food Chem. 2011 Nov 23;59(22):12204-9. doi: 10.1021/jf202942h. Epub 2011 Oct 24. [PubMed:21981068 ]
  7. Botezatu A, Pickering GJ: Determination of ortho- and retronasal detection thresholds and odor impact of 2,5-dimethyl-3-methoxypyrazine in wine. J Food Sci. 2012 Nov;77(11):S394-8. doi: 10.1111/j.1750-3841.2012.02942.x. Epub 2012 Oct 11. [PubMed:23057415 ]
  8. Camara M, Gharbi N, Lenouvel A, Behr M, Guignard C, Orlewski P, Evers D: Detection and quantification of natural contaminants of wine by gas chromatography-differential ion mobility spectrometry (GC-DMS). J Agric Food Chem. 2013 Feb 6;61(5):1036-43. doi: 10.1021/jf303418q. Epub 2013 Jan 28. [PubMed:23356506 ]
  9. Botezatu AI, Kotseridis Y, Inglis D, Pickering GJ: Occurrence and contribution of alkyl methoxypyrazines in wine tainted by Harmonia axyridis and Coccinella septempunctata. J Sci Food Agric. 2013 Mar 15;93(4):803-10. doi: 10.1002/jsfa.5800. Epub 2012 Oct 19. [PubMed:23079938 ]
  10. Ma K, Zhang JN, Zhao M, He YJ: Accurate analysis of trace earthy-musty odorants in water by headspace solid phase microextraction gas chromatography-mass spectrometry. J Sep Sci. 2012 Jun;35(12):1494-501. doi: 10.1002/jssc.201200029. [PubMed:22740259 ]
  11. Harris SA, Ryona I, Sacks GL: Behavior of 3-isobutyl-2-hydroxypyrazine (IBHP), a key intermediate in 3-isobutyl-2-methoxypyrazine (IBMP) metabolism, in ripening wine grapes. J Agric Food Chem. 2012 Dec 5;60(48):11901-8. doi: 10.1021/jf302990m. Epub 2012 Nov 26. [PubMed:23163527 ]
  12. Bindon K, Varela C, Kennedy J, Holt H, Herderich M: Relationships between harvest time and wine composition in Vitis vinifera L. cv. Cabernet Sauvignon 1. Grape and wine chemistry. Food Chem. 2013 Jun 1;138(2-3):1696-705. doi: 10.1016/j.foodchem.2012.09.146. Epub 2012 Nov 10. [PubMed:23411300 ]
  13. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .