| Revision as of 11:47, 11 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 08:52, 23 October 2024 edit undoCitation bot (talk | contribs)Bots5,423,966 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Dominic3203 | Category:Foul-smelling chemicals | #UCB_Category 10/128 |
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{{Chembox |
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{{other uses|IPMP (disambiguation)}} |
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{{chembox |
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| verifiedrevid = 427096441 |
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| verifiedrevid = 428568548 |
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| Name = Isopropyl methoxy pyrazine |
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| Name = Isopropyl methoxy pyrazine |
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| ImageFile = IPMP.png |
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| ImageFile = IPMP.png |
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| ImageSize = 200px |
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| ImageName = Chemical structure of isopropyl methoxy pyrazine |
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| ImageName = Chemical structure of isopropyl methoxy pyrazine |
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| ImageAlt = Chemical structure of isopropyl methoxy pyrazine |
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| ImageAlt = Chemical structure of isopropyl methoxypyrazine |
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| IUPACName = 2-methoxy-3-propan-2-ylpyrazine |
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| PIN = 2-Methoxy-3-(propan-2-yl)pyrazine |
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| OtherNames = IPMP<br>2-Isopropyl-3-methoxypyrazine |
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| OtherNames = 2-Isopropyl-3-methoxypyrazine |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 25773-40-4 |
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| CASNo = 25773-40-4 |
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| CASNo_Ref = |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASOther = |
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| CASNoOther = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 1FL7L111A6 |
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| PubChem = 33166 |
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| PubChem = 33166 |
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| SMILES = CC(C)C1=NC=CN=C1OC |
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| SMILES = CC(C)C1=NC=CN=C1OC |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| InChI = |
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| ChemSpiderID = 30649 |
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| InChI = 1/C8H12N2O/c1-6(2)7-8(11-3)10-5-4-9-7/h4-6H,1-3H3 |
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| InChIKey = NTOPKICPEQUPPH-UHFFFAOYAE |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C8H12N2O/c1-6(2)7-8(11-3)10-5-4-9-7/h4-6H,1-3H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = NTOPKICPEQUPPH-UHFFFAOYSA-N |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>8</sub>H<sub>12</sub>N<sub>2</sub>O |
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| Formula = C<sub>8</sub>H<sub>12</sub>N<sub>2</sub>O |
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| MolarMass = 152.19 g/mol |
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| MolarMass = 152.19 g/mol |
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| ExactMass = 152.094963 u |
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| Appearance = |
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| MeltingPt = <!-- °C --> |
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| BoilingPt = <!-- °C --> |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| GHSPictograms = {{GHS07}} |
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| RPhrases = <!-- {{R10}}, {{R23}}, {{R34}}, {{R50}} etc. --> |
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| GHSSignalWord = warning |
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| SPhrases = <!-- {{S1/2}}, {{S9}}, {{S16}}, {{S26}}, {{S36/37/39}}, {{S45}}, {{S61}} etc. --> |
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| HPhrases = {{HPhrases|H315 | H319 | H335}} |
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}} |
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| PPhrases = {{PPhrases|P302 + P352 | P305 + P351 + P338}} |
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| GHS_ref = <ref>GHS: {{Webarchive|url=https://web.archive.org/web/20240501180038/https://www.sigmaaldrich.com/US/en/product/aldrich/243132 |date=2024-05-01 }}</ref> |
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'''Isopropyl methoxy pyrazine''' (IPMP) is a ], a class of chemical compounds that produce odors. The odor is rather undesirable and is produced by the ] or by the actinomycete ''] sp''.<ref>Three highly odorous metabolites from an actinomycete: 2-Isopropyl-3-methoxy-pyrazine, methylisoborneol, and geosmin. Nancy N. Gerber, Journal of chemical ecology, Volume 3, Number 4, pp. 475-482, {{doi|10.1007/BF00988190}}</ref> |
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'''Isopropyl methoxypyrazine''' ('''IPMP''') is a ], a class of chemical compounds that produce odors. The odor is rather undesirable and is produced by the ] or by the actinomycete '']'' sp.<ref>Three highly odorous metabolites from an actinomycete: 2-Isopropyl-3-methoxy-pyrazine, methylisoborneol, and geosmin. Nancy N. Gerber, Journal of Chemical Ecology, Volume 3, Number 4, pp. 475-482, {{doi|10.1007/BF00988190}}</ref> It can be detected by human taste at concentrations of as low as 2 ]s per litre.<ref>{{cite report |title=Factors affecting the presence of 3-alkyl-2- methoxypyrazines in grapes and wines. A review. |url=http://www.tesisenred.net/bitstream/handle/10803/8653/15-PaperC2.pdf |author1=Cristina Sala |author2=Olga Busto |author3=Josep Guasch |author4=Fernando Zamora |access-date=2012-04-01 |archive-date=2016-03-03 |archive-url=https://web.archive.org/web/20160303235552/http://www.tesisenred.net/bitstream/handle/10803/8653/15-PaperC2.pdf |url-status=live }}</ref> |
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== Presence in wine grapes == |
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==See also== |
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The odor of IPMP tends to be undesirable in the case of certain wines.<ref name="regional">{{Cite web |url=http://www.regional.org.au/au/roc/1991food/p-13.htm |title=Trace flavour components of grapes |access-date=2011-12-24 |archive-date=2012-02-06 |archive-url=https://web.archive.org/web/20120206142109/http://www.regional.org.au/au/roc/1991food/p-13.htm |url-status=live }}</ref> |
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] has high levels of methoxypyrazines.<ref>winepros.com.au ''Oxford Companion to Wine'' {{webarchive|url=https://web.archive.org/web/20120229141618/http://www.winepros.com.au/jsp/cda/reference/oxford_entry.jsp?entry_id=2000 |date=2012-02-29 }}</ref><ref name="Clarke pg 223">Oz Clarke ''Encyclopedia of Grapes'' pg 223 Harcourt Books 2001 {{ISBN|0-15-100714-4}}</ref> Two methoxypyrazine compounds, ] (IBMP) and 3-isopropyl-2-methoxypyrazine, are considered to be important determinants of green flavours in ] wines.<ref>Marais, J., Hunter, J.J., & Haasbroek, P.D. (1999). Effect of microclimate, season and region on Sauvignon blanc grape composition and wine quality. South African Journal of Enology and Viticulture, 20, 19-30.</ref> |
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== Presence in coffee == |
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IPMP is also an important flavour compound in coffee and is responsible for causing an off-taste called "potato taste" in East African coffee.<ref>{{Cite journal | last1 = Czerny | first1 = M. | last2 = Grosch | first2 = W. | doi = 10.1021/jf990609n | title = Potent Odorants of Raw Arabica Coffee. Their Changes during Roasting | journal = Journal of Agricultural and Food Chemistry | volume = 48 | issue = 3 | pages = 868–872 | year = 2000 | pmid = 10725165| bibcode = 2000JAFC...48..868C }}</ref> The insects '']'' are also implicated in causing the taste.<ref name=bou>{{cite journal |title=L'élimination du " goût de pomme de terre " dans le café Arabica du Burundi |language=fr |trans-title=Removing the "potato taste" from Burundian Arabica |author1=B. Bouyjou |author2=B. Decazy |author3=G. Fourny |journal=Plantations, Recherche, Développement |volume=6 |issue=2 |pages=107–115 |url=http://publications.cirad.fr/une_notice.php?dk=392315 |access-date=2012-04-01 |archive-date=2012-03-11 |archive-url=https://web.archive.org/web/20120311225751/http://publications.cirad.fr/une_notice.php?dk=392315 |url-status=live }}</ref> |
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== See also == |
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==References== |
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== References == |
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{{organic-compound-stub}} |
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