3-Isobutyl-2-methoxypyrazine

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3-Isobutyl-2-methoxypyrazine
2-Isobutyl-3-methoxypyrazine.svg
Names
Preferred IUPAC name
2-Methoxy-3-(2-methylpropyl)pyrazine
Other names
2-Isobutyl-3-methoxypyrazine; IBMP

Grindstaff pyrazine

Bell pepper pyrazine
Identifiers
3D model (JSmol)
ECHA InfoCard 100.042.169 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C9H14N2O/c1-7(2)6-8-9(12-3)11-5-4-10-8/h4-5,7H,6H2,1-3H3
    Key: UXFSPRAGHGMRSQ-UHFFFAOYSA-N
  • CC(C)CC1=NC=CN=C1OC
Properties
C9H14N2O
Molar mass 166.224 g·mol−1
AppearanceLiquid
Hazards
Flash point 80 °C (176 °F; 353 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3-Isobutyl-2-methoxypyrazine (2-isobutyl-3-methoxypyrazine [1] also known as Grindstaff pyrazine) is a methoxypyrazine that is very similar to isopropyl methoxy pyrazine except that the alkyl side-group contains an isobutyl group attached to the carbon alpha to the methoxy sidegroup instead of an isopropyl side-group at that same carbon position.

Contents

Natural Occurrence

The molecule is produced by some plants and is a contributor to the aroma of several plant-based foods. [2] [3] It is also seen to be produced in some forms of blue-green algae; [4] however, it is most frequently found in members of the genus Capsicum . Specifically, it is what gives a bell pepper, along with other peppers, their distinctive smell. [5] This is to such an extent that Grindstaff pyrazine is sometimes just called the "bell pepper pyrazine." The human nose can detect concentrations of this molecule below the part per trillion level making it one of the most odor intensive compounds on earth. [6] Unlike capsaicin, which is produced and mainly stored in the placenta of the pepper, Grindstaff pyrazine is mainly contained in the flesh of the pepper. [7] This is why dried pepper flakes and other spices derived from the seeds and placenta of peppers lack the aroma of what is thought of as a "fresh pepper smell".

Uses

Illicit Drug Prevention

3-isobutyl-2-methoxypyrazine has been noted, along with a few other food flavor additives, as a possible means of preventing the use of pseudoephedrine in the production of methamphetamine. [8] A number of pharmaceutical companies have proposed various physical means of deterring such illicit uses namely by altering the method of drug delivery. However, these physical methods only make it more difficult to extract the pseudophedrine and do nothing to prevent the chemical transformation to methamphetamine. [9] The addition of 3-isobutyl-2-methoxypyrazine to pseudophedrine effectively blocks the chemical production of methamphetamine from pseudophedrine while remaining biologically inert.

Fragrance and Flavor

Since 3-isobutyl-2-methoxypyrazine has such a powerful scent, it is often used in fragrances and cleaners. It poses little threat to children or pets, making its use in detergents, candles, deodorants, gums and candies quite widespread. Even though it is not very volatile, it is often considered a top note in perfumery because the fragrance can be detected at such low levels. [5] Chemically it behaves like a base note, since it has a low volatility; however, its pungency allows it to be identified with the other top notes in the fragrance even if its relative concentration in the air is much lower. [10]

Bombyx mori pheromone binding protein bound to 3-isobutyl-2-methoxypyrazine (bell pepper odorant) PDB entry 2p70 2p70.png
Bombyx mori pheromone binding protein bound to 3-isobutyl-2-methoxypyrazine (bell pepper odorant) PDB entry 2p70

Related Research Articles

<span class="mw-page-title-main">Capsaicin</span> Pungent chemical compound in chili peppers

Capsaicin (8-methyl-N-vanillyl-6-nonenamide) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is a chemical irritant and neurotoxin for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related amides (capsaicinoids) are produced as secondary metabolites by chili peppers, probably as deterrents against certain mammals and fungi. Pure capsaicin is a hydrophobic, colorless, highly pungent, crystalline solid.

<span class="mw-page-title-main">Vanillin</span> Chemical compound

Vanillin is an organic compound with the molecular formula C8H8O3. It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the extract of the vanilla bean. Synthetic vanillin is now used more often than natural vanilla extract as a flavoring in foods, beverages, and pharmaceuticals.

<span class="mw-page-title-main">Aroma compound</span> Chemical compound that has a smell or odor

An aroma compound, also known as an odorant, aroma, fragrance or flavoring, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently volatile for transmission via the air to the olfactory system in the upper part of the nose. As examples, various fragrant fruits have diverse aroma compounds, particularly strawberries which are commercially cultivated to have appealing aromas, and contain several hundred aroma compounds.

Pyrazine is a heterocyclic aromatic organic compound with the chemical formula C4H4N2. It is a symmetrical molecule with point group D2h. Pyrazine is less basic than pyridine, pyridazine and pyrimidine. It is a "deliquescent crystal or wax-like solid with a pungent, sweet, corn-like, nutty odour".

<i>cis</i>-3-Hexen-1-ol Chemical compound

cis-3-Hexen-1-ol, also known as (Z)-3-hexen-1-ol and leaf alcohol, is a colorless oily liquid with an intense grassy-green odor of freshly cut green grass and leaves. It is produced in small amounts by most plants and it acts as an attractant to many predatory insects. cis-3-Hexen-1-ol is a very important aroma compound that is used in fruit and vegetable flavors and in perfumes. The yearly production is about 30 tonnes.

<i>cis</i>-3-Hexenal Chemical compound

cis-3-Hexenal, also known as (Z)-3-hexenal and leaf aldehyde, is an organic compound with the formula CH3CH2CH=CHCH2CHO. It is classified as an unsaturated aldehyde. It is a colorless liquid and an aroma compound with an intense odor of freshly cut grass and leaves.

<span class="mw-page-title-main">Piperonal</span> Chemical compound

Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors. The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin.

<span class="mw-page-title-main">Myrcene</span> Chemical compound

Myrcene, or β-myrcene, is a monoterpene. A colorless oil, it occurs widely in essential oils. It is produced mainly semi-synthetically from Myrcia, from which it gets its name. It is an intermediate in the production of several fragrances. α-Myrcene is the name for the isomer 2-methyl-6-methylene-1,7-octadiene, which has not been found in nature.

<span class="mw-page-title-main">Zingerone</span> Chemical compound

Zingerone, also called vanillylacetone, is a major flavor component of ginger, providing the sweet flavor of cooked ginger. Zingerone is a crystalline solid that is sparingly soluble in water and soluble in ether.

<span class="mw-page-title-main">Methoxypyrazine</span> Class of chemical compounds

Methoxypyrazines are a class of chemical compounds that produce odors. The odors tend to be undesirable, as in the case of certain wines, or as defensive chemicals used by insects such as Harmonia axyridis which produces isopropyl methoxy pyrazine (IPMP). They have also been identified as additives in cigarette manufacture. Detection thresholds are very low, typically near 2 parts per trillion (1 ng/L).

<span class="mw-page-title-main">Raspberry ketone</span> Chemical compound

Raspberry ketone is a natural phenolic compound that is the primary aroma compound of red raspberries.

<span class="mw-page-title-main">3-Mercapto-3-methylbutan-1-ol</span> Chemical compound

3-Mercapto-3-methylbutan-1-ol, also known as MMB, is a common odorant found in food and cat urine. The aromas ascribed to MMB include catty, roasty, broth-like, meaty, and savory, or similar to cooked leeks.

Alkylpyrazines are chemical compounds based on pyrazine with different substitution patterns. Some alkylpyrazines are naturally occurring highly aromatic substances which often have a very low odor threshold and contribute to the taste and aroma of various foods including cocoa, baked goods, coffee and wines. Alkylpyrazines are also formed during the cooking of some foods via Maillard reactions.

<span class="mw-page-title-main">Phenylacetaldehyde</span> Chemical compound

Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes.

<span class="mw-page-title-main">2-Methoxy-4-vinylphenol</span> Chemical compound

2-Methoxy-4-vinylphenol is an aromatic substance used as a flavoring agent. It is one of the compounds responsible for the natural aroma of buckwheat.

<span class="mw-page-title-main">Odor</span> Volatile chemical compounds perceived by the sense of smell

An odor or odour is caused by one or more volatilized chemical compounds that are generally found in low concentrations that humans and many animals can perceive via their sense of smell. An odor is also called a "smell" or a "scent", which can refer to either an unpleasant or a pleasant odor.

<span class="mw-page-title-main">Isopropyl methoxypyrazine</span> Chemical compound

Isopropyl methoxypyrazine (IPMP) is a methoxypyrazine, a class of chemical compounds that produce odors. The odor is rather undesirable and is produced by the Asian lady beetle or by the actinomycete Streptomyces sp. It can be detected by human taste at concentrations of as low as 2 nanograms per litre.

<span class="mw-page-title-main">6-Nonenal</span> Chemical compound

6-Nonenal is an organic compound with the formula C2H5CH=CH(CH2)4CHO. Other isomeric nonenal compounds are also known to exist naturally, e.g. 2-nonenal. The cis-isomer of 6-nonenal is often listed as the principal component in the aromas of muskmelon fruits. The trans-isomer is listed as an off-flavor aroma of milk foams, and thought to be a possible polypropylene odorant.

<span class="mw-page-title-main">4-Methylcyclohexanemethanol</span> Chemical compound

4-Methylcyclohexanemethanol (MCHM, systematic name 4-methylcyclohexylmethanol) is an organic compound with the formula CH3C6H10CH2OH. Classified as a saturated higher alicyclic primary alcohol. Both cis and trans isomers exist, depending on the relative positions of the methyl (CH3) and hydroxymethyl (CH2OH) groups on the cyclohexane ring. Commercial samples of MCHM consists of a mixture of these isomers as well as other components that vary with the supplier.

References

  1. ↑ 2-Isobutyl-3-methoxypyrazine in Sigma-Aldrich Catalogue
  2. ↑ Kaneko, S.; Sakai, R.; Kumazawa, K.; Usuki, M.; Nishimura, O. (2013). "Key aroma compounds in roasted in-shell peanuts". Bioscience, Biotechnology, and Biochemistry. 77 (7): 1467–1473. doi: 10.1271/bbb.130112 . PMID   23832337.
  3. ↑ Koch, A.; Doyle, C. L.; Matthews, M. A.; Williams, L. E.; Ebeler, S. E. (2010). "2-Methoxy-3-isobutylpyrazine in grape berries and its dependence on genotype". Phytochemistry. 71 (17–18): 2190–2198. Bibcode:2010PChem..71.2190K. doi:10.1016/j.phytochem.2010.09.006. PMID   20965529.
  4. ↑ Peter, Andreas; Köster, Oliver; Schildknecht, Andrea; von Gunten, Urs (2009-05-01). "Occurrence of dissolved and particle-bound taste and odor compounds in Swiss lake waters". Water Research. 43 (8): 2191–2200. Bibcode:2009WatRe..43.2191P. doi:10.1016/j.watres.2009.02.016. PMID   19303129.
  5. 1 2 Roth, Klaus (2014). "The Biochemistry of Peppers". ChemViews. doi:10.1002/chemv.201400031.
  6. ↑ Roth, Klaus (2009-04-01). "Allerlei vom Frühstücksei. Eine Oologisch-chemische Osterbetrachtung". Chemie in unserer Zeit. 43 (2): 100–114. doi:10.1002/ciuz.200900485. ISSN   1521-3781.
  7. ↑ Camara, Bilal; Monéger, René (1978-01-01). "Free and esterified carotenoids in green and red fruits of Capsicum annuum". Phytochemistry. 17 (1): 91–93. Bibcode:1978PChem..17...91C. doi:10.1016/S0031-9422(00)89686-7.
  8. ↑ Rajagopalan, Raghavan (March 31, 2016). "Prevention of Illicit Manufacture of Methamphetamine from Pseudoephedrine Using Food Flavor Excipients". United States Patent Application WO/2015/048597.
  9. ↑ Skinner, H.F. (1990). "Methamphetamine synthesis via hydriodic acid/red phosphorus reduction of ephedrine". Forensic Science International. 48 (2): 123–134. doi:10.1016/0379-0738(90)90104-7.
  10. ↑ Adams, T. B.; et al. (2002). "The FEMA GRAS assessment of pyrazine derivatives used as flavor ingredients". Food and Chemical Toxicology. 40 (4): 429–451. doi:10.1016/s0278-6915(01)00123-5. PMID   11893403.
  11. ↑ Lautenschlager, C.; Leal, W. S.; Clardy, J. (2007). "Bombyx mori Pheromone-Binding Protein Binding Nonpheromone Ligands: Implications for Pheromone Recognition". Structure. 15 (9): 1148–1154. doi:10.1016/j.str.2007.07.013. PMC   2072049 . PMID   17850754.
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