Maillard Reaction

<p>Source:<a href="http://en.wikipedia.org/wiki/Maillard_Reaction">http://en.wikipedia.org/wiki/Maillard_Reaction</a></p>

<p>

The <b>Maillard reaction</b> (<small>French pronunciation: </small><a href="http://en.wikipedia.org/wiki/Wikipedia:IPA_for_French" title="Wikipedia:IPA for French" >[majaʁ]</a>, <a href="http://en.wikipedia.org/wiki/Wikipedia:Pronunciation_respelling_key" title="Wikipedia:Pronunciation respelling key" ><i>mah-<small>yar</small></i></a>) is a form of <a href="http://en.wikipedia.org/wiki/Non-enzymatic_browning" title="Non-enzymatic browning" class="mw-redirect" >nonenzymatic browning</a>similar to <a href="http://en.wikipedia.org/wiki/Caramelization" title="Caramelization" >caramelization</a>. It results from a <a href="http://en.wikipedia.org/wiki/Chemical_reaction" title="Chemical reaction" >chemical reaction</a> between an <a href="http://en.wikipedia.org/wiki/Amino_acid" title="Amino acid" >amino acid</a> and a <a href="http://en.wikipedia.org/wiki/Reducing_sugar" title="Reducing sugar" >reducing sugar</a>, usually requiring <a href="http://en.wikipedia.org/wiki/Heat" title="Heat" >heat</a>.

Vitally important in the preparation or presentation of many types of food, it is named after chemist<a href="http://en.wikipedia.org/wiki/Louis_Camille_Maillard" title="Louis Camille Maillard" >Louis-Camille Maillard</a>, who first described it in the 1910s while attempting to reproduce biological<a href="http://en.wikipedia.org/wiki/Protein_synthesis" title="Protein synthesis" class="mw-redirect" >protein synthesis</a>.<sup id="cite_ref-0" class="reference" ><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_note-0" >[1]</a></sup><sup class="reference" >(p79)</sup>

The reactive <a href="http://en.wikipedia.org/wiki/Carbonyl_group" title="Carbonyl group" class="mw-redirect" >carbonyl group</a> of the sugar reacts with the <a href="http://en.wikipedia.org/wiki/Nucleophilic" title="Nucleophilic" class="mw-redirect" >nucleophilic</a> <a href="http://en.wikipedia.org/wiki/Amine" title="Amine" >amino group</a> of the amino acid, and forms a complex mixture of poorly-characterized molecules responsible for a range of odors and flavors. This process is accelerated in an alkaline environment, as the <a href="http://en.wikipedia.org/wiki/Amine" title="Amine" >amino</a> groups are <a href="http://en.wikipedia.org/wiki/Deprotonate" title="Deprotonate" class="mw-redirect" >deprotonated</a>and, hence, have an increased <a href="http://en.wikipedia.org/wiki/Nucleophilicity" title="Nucleophilicity" class="mw-redirect" >nucleophilicity</a>. The type of the amino acid determines the resulting flavor. This reaction is the basis of the <a href="http://en.wikipedia.org/wiki/Flavoring" title="Flavoring" class="mw-redirect" >flavoring</a> industry. At high temperatures, <a href="http://en.wikipedia.org/wiki/Acrylamide" title="Acrylamide" >acrylamide</a> can be formed.

In the process, hundreds of different flavor compounds are created. These compounds, in turn, break down to form yet more new flavor compounds, and so on. Each type of food has a very distinctive set of flavor compounds that are formed during the Maillard reaction. It is these same compounds <a href="http://en.wikipedia.org/wiki/Flavorist" title="Flavorist" >flavor scientists</a> have used over the years to make <a href="http://en.wikipedia.org/wiki/Artificial_flavor" title="Artificial flavor" class="mw-redirect" >reaction flavors</a>.

 </p>

<h2 >Foods and products with Maillard reactions</h2>

6-Acetyl-2,3,4,5-tetrahydropyridine</div>

</div>

2-Acetylpyrroline</div>

</div>

<p >The Maillard reaction is responsible for many colors and flavors in foods:</p>

<ul >

<li >The <a href="http://en.wikipedia.org/wiki/Browning_(food_process)" title="Browning (food process)" >browning</a> of various meats like <a href="http://en.wikipedia.org/wiki/Steak" title="Steak" >steak</a></li>

<li ><a href="http://en.wikipedia.org/wiki/Toast" title="Toast" >Toasted bread</a></li>

<li ><a href="http://en.wikipedia.org/wiki/Biscuits" title="Biscuits" class="mw-redirect" >Biscuits</a></li>

<li ><a href="http://en.wikipedia.org/wiki/French_Fries" title="French Fries" class="mw-redirect" >French Fries</a></li>

<li ><a href="http://en.wikipedia.org/wiki/Malted_barley" title="Malted barley" class="mw-redirect" >Malted barley</a> as in <a href="http://en.wikipedia.org/wiki/Malt" title="Malt" >malt</a> <a href="http://en.wikipedia.org/wiki/Whiskey" title="Whiskey" class="mw-redirect" >whiskey</a> or <a href="http://en.wikipedia.org/wiki/Beer" title="Beer" >beer</a></li>

<li >Fried <a href="http://en.wikipedia.org/wiki/Onion" title="Onion" >onions</a></li>

<li ><a href="http://en.wikipedia.org/wiki/Dry_milk" title="Dry milk" class="mw-redirect" >Dried</a> or <a href="http://en.wikipedia.org/wiki/Condensed_milk" title="Condensed milk" >condensed milk</a></li>

<li >Roasted <a href="http://en.wikipedia.org/wiki/Coffee" title="Coffee" >coffee</a></li>

<li ><i><a href="http://en.wikipedia.org/wiki/Dulce_de_leche" title="Dulce de leche" >Dulce de leche</a></i></li>

<li >The burnished surface (crust) of <a href="http://en.wikipedia.org/wiki/Brioche" title="Brioche" >brioche</a>, cakes, yeast, and quick <a href="http://en.wikipedia.org/wiki/Bread" title="Bread" >breads</a></li>

<li >Roasted <a href="http://en.wikipedia.org/wiki/Meat" title="Meat" >meat</a><sup id="cite_ref-McGee.2C_Harold_2004_p.778-9_1-0" class="reference" ><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_note-McGee.2C_Harold_2004_p.778-9-1" >[2]</a></sup></li>

<li >Maple syrup</li>

</ul>

<p ><a href="http://en.wikipedia.org/wiki/6-Acetyl-2,3,4,5-tetrahydropyridine" title="6-Acetyl-2,3,4,5-tetrahydropyridine" >6-Acetyl-2,3,4,5-tetrahydropyridine</a> is responsible for the biscuit or cracker-like flavor present in baked goods like <a href="http://en.wikipedia.org/wiki/Bread" title="Bread" >bread</a>,<a href="http://en.wikipedia.org/wiki/Popcorn" title="Popcorn" >popcorn</a>, and <a href="http://en.wikipedia.org/wiki/Tortilla" title="Tortilla" >tortilla</a> products. The structurally-related compound <a href="http://en.wikipedia.org/wiki/2-acetyl-1-pyrroline" title="2-acetyl-1-pyrroline" class="mw-redirect" >2-acetyl-1-pyrroline</a> has a similar smell, and occurs also naturally without heating and gives varieties of cooked <a href="http://en.wikipedia.org/wiki/Rice" title="Rice" >rice</a> and the <a href="http://en.wikipedia.org/wiki/Spice" title="Spice" >spice</a> <i>pandan</i> (<i><a href="http://en.wikipedia.org/wiki/Pandanus_amaryllifolius" title="Pandanus amaryllifolius" >Pandanus amaryllifolius</a></i>) their typical smells. Both compounds have <a href="http://en.wikipedia.org/wiki/Odor_thresholds" title="Odor thresholds" class="mw-redirect" >odor thresholds</a> below 0.06 <a href="http://en.wikipedia.org/wiki/Nanogram" title="Nanogram" class="mw-redirect" >ng</a>/<a href="http://en.wikipedia.org/wiki/Liter" title="Liter" class="mw-redirect" >l</a>.<sup id="cite_ref-2" class="reference" ><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_note-2" >[3]</a></sup>

The browning reactions that occur when meat is roasted or seared are complicated, and occur mostly by Maillard browning<sup id="cite_ref-McGee.2C_Harold_2004_p.778-9_1-1" class="reference" ><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_note-McGee.2C_Harold_2004_p.778-9-1" >[2]</a></sup> with contributions from other chemical reactions, including the breakdown of the tetrapyrrole rings of the muscle protein <a href="http://en.wikipedia.org/wiki/Myoglobin" title="Myoglobin" >myoglobin</a>.

<a href="http://en.wikipedia.org/wiki/Caramelization" title="Caramelization" >Caramelization</a> is an entirely different process from Maillard browning, though the results of the two processes are sometimes similar to the naked eye (and tastebuds). Caramelization may sometimes cause browning in the same foods in which the Maillard reaction occurs, but the two processes are distinct. They both are promoted by heating, but the Maillard reaction involves amino acids, as discussed above, whereas caramelization is simply the <a href="http://en.wikipedia.org/wiki/Pyrolysis" title="Pyrolysis" >pyrolysis</a> of certain sugars. The following things are a result of the Maillard browning reaction:</p>

<ul >

<li ><a href="http://en.wikipedia.org/wiki/Caramel" title="Caramel" >Caramel</a> made from <a href="http://en.wikipedia.org/wiki/Milk" title="Milk" >milk</a> and <a href="http://en.wikipedia.org/wiki/Sugar" title="Sugar" >sugar</a>, especially in candies: Milk is high in protein (amino acids), and browning of food involving this complex ingredient would most likely include Maillard reactions. See references below.</li>

<li ><a href="http://en.wikipedia.org/wiki/Chocolate" title="Chocolate" >Chocolate</a> and <a href="http://en.wikipedia.org/wiki/Maple_syrup" title="Maple syrup" >maple syrup</a></li>

<li >Lightly roasted <a href="http://en.wikipedia.org/wiki/Peanut" title="Peanut" >peanuts</a></li>

</ul>

<p >In making <a href="http://en.wikipedia.org/wiki/Silage" title="Silage" >silage</a>, excess heat causes the Maillard reaction to occur, which reduces the amount of energy and protein available to the animals who feed on it.</p>

<h2 >[<a href="http://en.wikipedia.org/w/index.php?title=Maillard_reaction&action=edit&section=2" title="Edit section: The process" >edit</a>]The process</h2>

<ol >

<li >The <a href="http://en.wikipedia.org/wiki/Carbonyl_group" title="Carbonyl group" class="mw-redirect" >carbonyl group</a> of the sugar reacts with the <a href="http://en.wikipedia.org/wiki/Amino" title="Amino" class="mw-redirect" >amino group</a> of the <a href="http://en.wikipedia.org/wiki/Amino_acid" title="Amino acid" >amino acid</a>, producing N-substituted <a href="http://en.wikipedia.org/wiki/Glycosylamine" title="Glycosylamine" >glycosylamine</a> and water</li>

<li >The unstable glycosylamine undergoes <a href="http://en.wikipedia.org/wiki/Amadori_rearrangement" title="Amadori rearrangement" >Amadori rearrangement</a>, forming <a href="http://en.wikipedia.org/wiki/Ketosamine" title="Ketosamine" >ketosamines</a></li>

<li >There are several ways for the ketosamines to react further:

<ul >

<li >Produce 2 water and <a href="http://en.wikipedia.org/wiki/Reductone" title="Reductone" class="mw-redirect" >reductones</a></li>

<li ><a href="http://en.wikipedia.org/wiki/Diacetyl" title="Diacetyl" >Diacetyl</a>, <a href="http://en.wikipedia.org/wiki/Aspirin" title="Aspirin" >aspirin</a>, <a href="http://en.wikipedia.org/wiki/Pyruvaldehyde" title="Pyruvaldehyde" class="mw-redirect" >pyruvaldehyde</a> and other short-chain <a href="http://en.wikipedia.org/wiki/Hydrolytic" title="Hydrolytic" class="mw-redirect" >hydrolytic</a> fission products can be formed</li>

<li >Produce brown nitrogenous polymers and <a href="http://en.wikipedia.org/wiki/Melanoidin" title="Melanoidin" >melanoidins</a></li>

</ul>

</li>

</ol>

<h2 >[<a href="http://en.wikipedia.org/w/index.php?title=Maillard_reaction&action=edit&section=3" title="Edit section: Factors" >edit</a>]Factors</h2>

<p >High temperature, intermediate moisture levels, and alkaline conditions all promote the Maillard reaction.<sup id="cite_ref-3" class="reference" ><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_note-3" >[4]</a></sup> In cooking, low moisture levels are necessary mainly because water boils into steam at 100 °C (212 °F), whereas the Maillard reaction happens noticeably around 154 °C (309 °F): significant browning of food does not occur until all surface water is vaporized.

The rate of Maillard reactions increases as the <a href="http://en.wikipedia.org/wiki/Water_activity" title="Water activity" >water activity</a> increases from 0.0 or as it decreases from 1.0, reaching a maximum at water activities in the range of 0.6 to 0.7. Since the Maillard reaction produces water, further increases in water activity may inhibit Maillard reactions.<sup id="cite_ref-4" class="reference" ><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_note-4" >[5]</a></sup>

<a href="http://en.wikipedia.org/wiki/Pentose" title="Pentose" >Pentose</a> reducing sugars react more than <a href="http://en.wikipedia.org/wiki/Hexose" title="Hexose" >hexoses</a>, which react more than <a href="http://en.wikipedia.org/wiki/Disaccharide" title="Disaccharide" >disaccharides</a>. Different amino acids produce different amounts of browning.</p>

<h2 >[<a href="http://en.wikipedia.org/w/index.php?title=Maillard_reaction&action=edit&section=4" title="Edit section: Physiology" >edit</a>]Physiology</h2>

<p >The Maillard reaction also occurs in the human body. It is a step in the formation of <a href="http://en.wikipedia.org/wiki/Advanced_glycation_endproduct" title="Advanced glycation endproduct" class="mw-redirect" >advanced glycation endproducts</a> (AGEs).<sup id="cite_ref-Grandhee_5-0" class="reference" ><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_note-Grandhee-5" >[6]</a></sup> It is tracked by measuring <a href="http://en.wikipedia.org/wiki/Pentosidine" title="Pentosidine" >pentosidine</a>. Although the Maillard reaction has been studied most extensively in foods, it has also shown a correlation in numerous different diseases in the human body, in particular degenerative eye diseases. In general, these diseases are due to the accumulation of AGEs on <a href="http://en.wikipedia.org/wiki/Nucleic_acids" title="Nucleic acids" class="mw-redirect" >nucleic acids</a>, <a href="http://en.wikipedia.org/wiki/Proteins" title="Proteins" class="mw-redirect" >proteins</a>, and <a href="http://en.wikipedia.org/wiki/Lipids" title="Lipids" class="mw-redirect" >lipids</a>. Though AGEs have numerous origins, they can form from the oxidation and dehydration of Amadori adducts, which themselves are products of nonenzymatic Maillard reactions. Apart from ocular diseases, whose correlation with Maillard chemistry has been more recently studied, the formation of AGEs has also proven to contribute to a wide range of human diseases that include<a href="http://en.wikipedia.org/wiki/Diabetes_mellitus" title="Diabetes mellitus" >diabetic complications</a>, <a href="http://en.wikipedia.org/wiki/Pulmonary_fibrosis" title="Pulmonary fibrosis" >pulmonary fibrosis</a>, and <a href="http://en.wikipedia.org/wiki/Neurodegeneration" title="Neurodegeneration" >neurodegeneration</a>.

Receptor systems in the body have been suggested to have evolved to remove glycation-modified molecules, such as AGEs, to eliminate their effects. The adverse effects of AGE accumulation appear to be mediated by numerous different AGE receptors. Examples include AGE-R1, galectin-3, CD36, and, most noted, RAGE, the receptor for AGEs.

Advanced glycation in numerous different locations within the eye can prove detrimental. In the <a href="http://en.wikipedia.org/wiki/Cornea" title="Cornea" >cornea</a>, whose endothelial cells have been known to express RAGE and galectin-3, the accumulation of AGEs is associated with thickened corneal stroma, corneal edema, and morphological changes within patients with diabetes. Within the lens, Maillard chemistry has been studied extensively in the context of cataract formation. Advanced glycation is known to alter fiber membrane integrity in the lens, and dicarbonyl compounds are known to cause increased aggregate formation within the lens. This effect is exacerbated by both diabetes and aging. Furthermore, it is thought that AGE-inhibiting compounds are effective in preventing cataract formation in diabetics.

Glycation in Maillard reactions may lead to destabilization of the vitreous gel structure within the eye via unnecessary cross-linking between collagen fibrils. Again, this process is more strongly observed within diabetic patients. Within the <a href="http://en.wikipedia.org/wiki/Retina" title="Retina" >retina</a>, the accumulation of AGEs in the Drusen and Bruch’s membrane has been associated with age, and has also been observed at a higher level among patients with age-related macular degeneration (AMD). This is manifested by the thickening of the Bruch’s membrane. Furthermore, it has been observed that AGE levels increase with age within the lamina cribosa, and the products of the Maillard reaction have been observed there, as well.

A wide range of ocular diseases, particularly diabetic retinopathy, may be prevented by the inhibition of the Maillard reaction. This may be achieved in numerous ways: preventing the formation of AGEs, reducing the effectiveness of the AGE signaling pathway and the receptor-ligand interactions, or breaking the AGE crosslinks. This latter method has already been achieved to some extent by the breaker ALT-711, though its effectiveness against retinopathy is unknown. Another method is by the use of amadorins, which are able to prevent the reaction of Amadori intermediates, which form into AGEs by scavenging the reactive carbonyls.<sup id="cite_ref-6" class="reference" ><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_note-6" >[7]</a></sup></p>

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<td ><i><b><a href="http://en.wikipedia.org/wiki/Portal:Food" title="Portal:Food" >Food portal</a></b></i></td>

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<ul >

<li ><a href="http://en.wikipedia.org/wiki/Advanced_glycation_end-product" title="Advanced glycation end-product" >Advanced glycation end-product</a></li>

<li ><a href="http://en.wikipedia.org/wiki/Baking" title="Baking" >Baking</a></li>

</ul>

<h2 >[<a href="http://en.wikipedia.org/w/index.php?title=Maillard_reaction&action=edit&section=6" title="Edit section: References" >edit</a>]References</h2>

<li id="cite_note-0" ><b><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_ref-0" >^{</a></b> Chichester}, C. O. (1986). <i>Advances in Food Research (Advances in Food and Nutrition Research)</i>. Boston: Academic Press. <a href="http://en.wikipedia.org/wiki/International_Standard_Book_Number" title="International Standard Book Number" >ISBN</a> <a href="http://en.wikipedia.org/wiki/Special:BookSources/0-12-016430-2" title="Special:BookSources/0-12-016430-2" >0-12-016430-2</a>.</li>

<li id="cite_note-McGee.2C_Harold_2004_p.778-9-1" >^ <a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_ref-McGee.2C_Harold_2004_p.778-9_1-0" ><sup ><i><b>a</b></i></sup></a> <a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_ref-McGee.2C_Harold_2004_p._778-9_1-1" ><sup ><i><b>b</b></i></sup></a> McGee, Harold (2004). <i>On Food and Cooking: The Science and Lore of the Kitchen</i>, p. 778-9. Scribner, New York. <a href="http://en.wikipedia.org/wiki/Special:BookSources/9780684800011" class="internal mw-magiclink-isbn" >ISBN 978-0-684-80001-1</a>.</li>

<li id="cite_note-2" ><b><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_ref-2" >^{</a></b> T}. J. Harrison, G. R. Dake (2005). "An expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline". <i><a href="http://en.wikipedia.org/wiki/J.Org.Chem." title="J. Org. Chem." class="mw-redirect" >J. Org. Chem.</a></i> <b>70</b> (26): 10872–10874. <a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier" >doi</a>:<a rel="nofollow" class="external text" href="http://dx.doi.org/10.1021%2Fjo051940a" >10.1021/jo051940a</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier" class="mw-redirect" >PMID</a> <a rel="nofollow" class="external text" href="http://www.ncbi.nlm.nih.gov/pubmed/16356012" >16356012</a>.</li>

<li id="cite_note-3" ><b><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_ref-3" >^{</a></b> }<a rel="nofollow" class="external text" href="http://albumen.conservation-us.org/library/c20/reilly1982a.html" >"Albumen Photography"</a>. American Institute for Conservation.</li>

<li id="cite_note-4" ><b><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_ref-4" >^{</a></b> }<a rel="nofollow" class="external text" href="http://www.decagon.com/food_science/info/safety.php" >"A beginner's course in water activity"</a>. Decagon Devices.</li>

<li id="cite_note-Grandhee-5" ><b><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_ref-Grandhee_5-0" >^{</a></b>&nbsp};SK Grandhee and VM Monnier (June 25, 1991). <a rel="nofollow" class="external text" href="http://www.jbc.org/cgi/content/abstract/266/18/11649" >"Mechanism of formation of the Maillard protein cross-link pentosidine. Glucose, fructose, and ascorbate as pentosidine precursors"</a>. <i>J. Biol. Chem.</i> <b>266</b> (18): 11649–11653. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier" class="mw-redirect" >PMID</a> <a rel="nofollow" class="external text" href="http://www.ncbi.nlm.nih.gov/pubmed/1904866" >1904866</a>. Retrieved 2007-12-14.</li>

<li id="cite_note-6" ><b><a href="http://en.wikipedia.org/wiki/Maillard_Reaction#cite_ref-6" >^{</a></b>&nbsp};Alan W. Stitt (2005). "The Maillard Reaction in Eye Diseases". <i>Annals of the New York Academy of Science</i> <b>1043</b>: 582–597.<a href="http://en.wikipedia.org/wiki/Digital_object_identifier" title="Digital object identifier" >doi</a>:<a rel="nofollow" class="external text" href="http://dx.doi.org/10.1196%2Fannals.1338.066" >10.1196/annals.1338.066</a>. <a href="http://en.wikipedia.org/wiki/PubMed_Identifier" title="PubMed Identifier" class="mw-redirect" >PMID</a> <a rel="nofollow" class="external text" href="http://www.ncbi.nlm.nih.gov/pubmed/16037281" >16037281</a>.</li>

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<td class="mbox-text" >This article includes a <a href="http://en.wikipedia.org/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources" >list of references</a>, related reading or <a href="http://en.wikipedia.org/wiki/Wikipedia:External_links" title="Wikipedia:External links" >external links</a>, but <b>its sources remain unclear because it lacks <a href="http://en.wikipedia.org/wiki/Wikipedia:Citing_sources#Inline_citations" title="Wikipedia:Citing sources" >inline citations</a></b>. Please <a href="http://en.wikipedia.org/wiki/Wikipedia:WikiProject_Fact_and_Reference_Check" title="Wikipedia:WikiProject Fact and Reference Check" >improve</a> this article by introducing more precise citations. <small><i>(January 2011)</i></small></td>

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<ul >

<li >Peter J. Van Soest, 1982. Nutritional Ecology of the Ruminant published by Cornell University Press</li>

</ul>

<h2 >[<a href="http://en.wikipedia.org/w/index.php?title=Maillard_reaction&action=edit&section=7" title="Edit section: External links" >edit</a>]External links</h2>

<ul >

<li ><a rel="nofollow" class="external text" href="http://web.archive.org/web/20041029235215/http://www.agsci.ubc.ca/courses/fnh/410/colour/3_82.htm" >Course website on Maillard reaction (archived copy)</a></li>

<li ><a rel="nofollow" class="external text" href="http://www.chm.bris.ac.uk/webprojects2002/rakotomalala/maillard.htm" >Diagram of the Maillard Reaction</a></li>

<li ><a rel="nofollow" class="external text" href="http://www.imars.org/" >Official Website of the International Maillard Reaction Society</a></li>

<li ><a rel="nofollow" class="external text" href="http://www.wired.com/wired/archive/12.06/cooking.html" >The Thermochemical Joy of Cooking</a></li>

<li ><a rel="nofollow" class="external text" href="http://blogs.zdnet.com/emergingtech/?p=942" >The secret of fresh beer</a>: the Maillard reaction</li>

</ul>