2-Acetyl-1-pyrroline Structure and properties References Navigation menu85213-22-5Interactive...
FlavorsKetonesIminesPyrrolines
aroma compoundflavorwhite breadjasmine ricebasmati ricebinturonghomolog6-acetyl-2,3,4,5-tetrahydropyridineMaillard reactionsodor thresholdsnglsubstitutedpyrrolineimineketone
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Preferred IUPAC name 1-(3,4-Dihydro-2H-pyrrol-5-yl)ethan-1-one | |
| Other names 1-(3,4-Dihydro-2H-pyrrol-5-yl)ethanone 2-Acetyl-1-pyrroline | |
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MeSH | 2-Acetyl-1-pyrroline |
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Chemical formula | C6H9NO |
Molar mass | 7002111144000000000♠111.144 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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2-Acetyl-1-pyrroline (2AP) is an aroma compound and flavor that gives white bread, jasmine rice and basmati rice, the spice pandan (Pandanus amaryllifolius), and bread flowers (Vallaris glabra) their customary smell.[1] Many observers describe the smell as similar to "hot, buttered popcorn", and it is credited for lending this odor to the scent of binturong (bearcat) urine.[2] Fresh MF (Marking fluid) and urine of the tiger (Indian, Amur or Siberian) and Indian leopard also have a strong aroma due 2AP.[3]
2AP and its structural homolog, 6-acetyl-2,3,4,5-tetrahydropyridine of similar smell, can be formed by Maillard reactions during heating of food such as the baking of bread dough. Both compounds have odor thresholds below 0.06 ng/l.[4]
The chemical has a boiling point of 104–105 °C (219–221 °F).[5]
Structure and properties
2AP is a substituted pyrroline and a cyclic imine as well as a ketone.
References
^ S. Wongpornchai; T. Sriseadka; S. Choonvisase (2003). "Identification and quantitation of the rice aroma compound, 2-acetyl-1-pyrroline, in bread flowers (Vallaris glabra Ktze)". J. Agric. Food Chem. 51 (2): 457–462. doi:10.1021/jf025856x. PMID 12517110..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output .citation q{quotes:"""""""'""'"}.mw-parser-output .citation .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-maint{display:none;color:#33aa33;margin-left:0.3em}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
^ "Why bearcats smell like buttered popcorn". Duke University/Eurekalert. 2016-04-13.
^ Brahmachary, Poddar-Sarkar. "Fifty years of tiger pheromone research" (PDF). Archived (PDF) from the original on 2015-06-27. Retrieved 2017-03-25.
^ 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". J. Org. Chem. 70 (26): 10872–10874. doi:10.1021/jo051940a. PMID 16356012.
^ https://www.sigmaaldrich.com/catalog/product/aldrich/381055
