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'{{скрытый текст}} {{distinguish|Аспартат}} {{distinguish|Аспаркам}} {{Вещество | картинка = Aspartame.svg | картинка3D | картинка малая | наименование = ''N''-L-a-аспартил-L-фенилаланина<br />1-метиловый эфир | сокращения | хим. формула = CF=C₁₄H₁₈N₂O₅ | эмпирическая формула | отн. молек. масса | молярная масса = 294,301 | темп. плавления = 246–247 | темп. кипения | темп. разложения | тройная точка | критическая точка | плотность | Изоэлектрическая точка | CAS = {{CASREF|CAS=22839-47-0}} | EINECS | SMILES = S=[NH3+] [C@@H](CC([O-])=O)C(N[C@@H]<br />(CC1=CC=CC=C1)C(OC)=O)=O | растворимость | конст. диссоц. кислоты | состояние | динамическая вязкость | кинематическая вязкость | теплоёмкость | энтальпия образования | удельная теплота парообразования | удельная теплота плавления }} '''Аспартам''' (сластилин) — искусственный подсластитель, [[Заменители сахара|заменитель сахара]] ([[пищевая добавка]] E951). Метиловый [[Сложные эфиры|эфир]] [[Дипептиды|дипептида]], состоящего из [[Аминокислоты#Альфа-аминокислоты белков|стандартных аминокислот]]: [[Аспарагиновая кислота|аспарагиновой]] и [[фенилаланин]]а. == Свойства == Аспартам примерно в 160—200 раз слаще [[сахар]]а, не имеет запаха, хорошо растворяется в воде. Несмотря на то, что этот подсластитель, как и белки, имеет калорийность 4 [[ккал]]/г, для создания сладкого вкуса необходимо очень небольшое количество аспартама, поэтому его вклад в калорийность пищи не принимается в расчет. По сравнению с [[сахар]]ом вкусовое ощущение сладости от аспартама медленнее появляется и дольше остается. Аспартам начинает разрушаться при 80 °C, поэтому не пригоден для подслащивания продуктов, подвергаемых термообработке. == Применение == Аспартам выпускается под различными торговыми марками как отдельно и в составе смесей сахарозаменителей. Входит в состав примерно 6000 различных видов продуктов и напитков, часто используется в диетических напитках и не содержащих сахара жевательных резинках. Также выпускается в виде таблеток (1 таблетка по сладости соответствует 3,2 г сахара) и используется при [[сахарный диабет|сахарном диабете]], [[ожирение|ожирении]] и других заболеваниях, требующих ограничения или исключения употребления сахара. == История == Аспартам был открыт в 1965 г. Джеймсом М. Шлаттером, химиком, работавшим на компанию Сёрл (G.D. Searle & Company). Шлаттер синтезировал аспартам в ходе исследований для производства лекарств от [[язва|язвы]]. Он обнаружил сладкий вкус аспартама случайно, облизнув палец, на который попал аспартам. Первыми стали применять аспартам США и Великобритания — с 1981 года. Выпускаемый под различными торговыми марками (например, Equal, Spoonful), аспартам объявлен альтернативой сахару, позволяющей не набирать вес и не являющейся канцерогеном, как используемый ранее искусственный подсластитель — [[сахарин]]. == Метаболизм и безопасность == Аспартам в организме человека распадается на две аминокислоты и [[метанол]]. Аминокислоты являются составной частью [[белок|белка]] и не только не опасны, но даже необходимы организму. Метанол же (в больших количествах) является [[Токсикология|токсичным]] веществом, что часто дает повод для дискуссий о вреде аспартама. Однако в малых количествах метанол постоянно образуется в организме человека в результате естественных [[метаболизм|метаболических]] процессов (то есть в результате нормальной жизнедеятельности человеческого организма). Кроме того, в свежих фруктах и соках также присутствует метанол (в среднем 140 мг на литр). Всего 10 % (по массе) аспартама превращается в метанол в результате метаболизма. Таким образом, натуральный сок содержит больше метанола (140 мг на литр), чем может образоваться из напитка, подслащенного аспартамом (60 мг метанола на литр).{{нет АИ|14|09|2009}} Большое количество токсикологических и клинических исследований аспартама подтвердили его безвредность, если дневная доза не превышает 50 мг на килограмм веса.<ref name=CritReview>{{cite journal |author=Magnuson BA, Burdock GA, Doull J, ''et al'' |title=Aspartame: a safety evaluation based on current use levels, regulations, and toxicological and epidemiological studies |journal=Crit. Rev. Toxicol. |volume=37 |issue=8 |pages=629–727 |year=2007 |pmid=17828671 |doi=10.1080/10408440701516184 |url=}}</ref><ref name=GAO87>GAO 1987. [http://www.gao.gov/docdblite/info.php?rptno=HRD-87-46 «Food Additive Approval Process Followed for Aspartame»] United States General Accounting Office, GAO/HRD-87-46, June 18, 1987</ref><ref name=GAO86>GAO 1986. [http://archive.gao.gov/d4t4/130780.pdf «Six Former HHS Employees' Involvement in Aspartame’s Approval.»] United States General Accounting Office, GAO/HRD-86-109BR, July 1986.</ref><ref name="Health Canada">[[Health Canada]]: {{cite web |url=http://www.hc-sc.gc.ca/fn-an/securit/addit/sweeten-edulcor/aspartame-eng.php |title=Aspartame - Artificial Sweeteners |accessdate=2008-11-08}}</ref><ref name=FSANZ>[[Food Standards Australia New Zealand]]: {{cite web |url=http://www.foodstandards.gov.au/newsroom/factsheets/factsheets2007/aspartameseptember203703.cfm |title=Food Standards Australia New Zealand: Aspartame (September 2007) |accessdate=2008-11-08}}</ref><ref>{{cite news | url = http://www.fda.gov/fdac/features/1999/699_sugar.html | title = Sugar Substitutes: Americans Opt for Sweetness and Lite | work = [[FDA Consumer]] | date = November–December 1999 | accessdate = January 29, 2009 | first = John | last = Henkel}}</ref> В Европе установлен максимум: 40 мг на килограмм веса в день. Практически 40 мг/кг веса тела для человека весом 70 кг значат примерно 266 таблеток синтетического подслащивающего средства, или 26,6 л колы, в один день. Потребление продуктов, содержащих аминокислоту [[фенилаланин]] противопоказано людям с наследственным заболеванием [[фенилкетонурия]], поэтому во многих странах, включая Россию, продукты, содержащие аспартам, должны иметь предупреждение «Содержит источник фенилаланина». == Внешние ссылки == <!-- Для перевода из англовики: ''aspartyl-phenylalanine-1-methyl ester''; i.e., the methyl [[ester]] of the [[dipeptide]] of the [[amino acid]]s [[aspartic acid]] and the [[essential amino acid]] [[phenylalanine]]. It is marketed under a number of trademark names, such as [[Equal (sweetener)|Equal]], and [[Canderel]], and is an ingredient of approximately 6,000 consumer foods and beverages sold worldwide. It is commonly used in diet [[soft drink]]s, and is often provided as a table condiment. It is also used in some brands of chewable [[vitamin]] supplements. However, aspartame is not always suitable for baking, because it often breaks down when heated and loses much of its sweetness. In the European Union, it is also known under the [[E number]] (additive code) '''E951'''. Aspartame is also one of the sugar substitutes used by [[diabetes mellitus|diabetics]]. Nonetheless, aspartame has been a subject of a vigorous public [[aspartame controversy|controversy]]. ==Chemistry== Aspartame is the [[methyl]] [[ester]] of the [[dipeptide]] of the natural [[amino acid]]s L-[[aspartic acid]] and L-[[phenylalanine]]. Under strongly [[acid]]ic or [[Base (chemistry)|alkaline]] conditions, aspartame first generates [[methanol]] by [[hydrolysis]]. Under more severe conditions, the [[peptide bond]]s are also [[hydrolyzed]], resulting in the free amino acids. ==Discovery and approval== ... Following initial safety testing, there was debate as to whether these tests had indicated that aspartame may cause cancer in rats; as a result, the [[Food and Drug Administration|U.S. Food and Drug Administration]] (FDA) did not approve its use as a food additive in the [[United States]] for many years. In [[1980]], the FDA convened a Public Board of Inquiry (PBOI) consisting of independent advisors charged with examining the purported relationship between aspartame and [[brain cancer]]. The PBOI concluded that aspartame does not cause brain damage, but it recommended against approving aspartame at that time, citing unanswered questions about [[cancer]] in laboratory rats. In [[1981]], U.S. President [[Ronald Reagan]] appointed as FDA commissioner [[Arthur Hull Hayes]]. This appointment proved to be favorable to the approval of aspartame, since the CEO of [[G.D. Searle]], [[Donald Rumsfeld]], the current [[Secretary of Defense]] was a good friend of Hayes. Citing data from a single Japanese study that had not been available to the members of the PBOI, Hayes approved aspartame for use in dry goods.<ref name="http://archive.gao.gov/d28t5/133460.pdf">[http://archive.gao.gov/d28t5/133460.pdf http://archive.gao.gov/d28t5/133460.pdf]</ref> In [[1983]] FDA further approved aspartame for use in carbonated beverages, and for use in other beverages, baked goods, and confections in [[1993]]. In [[1996]], the FDA removed all restrictions from aspartame allowing it to be used in all foods. In [[1985]], G.D. Searle was purchased by [[Monsanto]]. In this acquisition, Searle’s aspartame business became a separate Monsanto subsidiary, the [[NutraSweet|NutraSweet Company]]. Monsanto subsequently sold the Nutrasweet company to J.W. Childs Equity Partners II L.P. on May 25, 2000.<ref name="http://www.findarticles.com/p/articles/mi_m0EUY/is_22_6/ai_62920821">[http://www.findarticles.com/p/articles/mi_m0EUY/is_22_6/ai_62920821 http://www.findarticles.com/p/articles/mi_m0EUY/is_22_6/ai_62920821]</ref> The U.S. [[patent]] on aspartame expired in [[1992]], and the aspartame market is now hotly contested between the NutraSweet Company and other manufacturers such as [[Ajinomoto]], Merisant and the Holland Sweetener Company — the latter of which is exiting the business in the fourth quarter of 2006 due to a "persistently unprofitable business position" because "global aspartame markets are facing structural oversupply, which has caused worldwide strong price erosion over the last 5 years."<ref name="http://www.marketwire.com/mw/release_html_b1?release_id=115447">[http://www.marketwire.com/mw/release_html_b1?release_id=115447 http://www.marketwire.com/mw/release html b1?release id=115447]</ref> == Properties and use == Aspartame’s attractiveness as a sweetener comes from the fact that it is approximately 180 times sweeter than [[sugar]] in typical concentrations without the high energy value of sugar. While aspartame, like other peptides, has a caloric value of 4 kilocalories (17 kilojoules) per gram, the quantity of aspartame needed to produce a sweet taste is so small that its caloric contribution is negligible, which makes it a popular sweetener for those trying to avoid calories from sugar. The taste of aspartame is not identical to that of sugar: aspartame’s sweetness has a slower onset and longer duration than sugar’s, and some consumers find it unappealing. Blends of aspartame with [[acesulfame potassium]] are purported to have a more sugar-like taste, and to be more potent than either sweetener used alone. Like many other [[peptide]]s, aspartame may [[hydrolyze]] (break down) into its constituent amino acids under conditions of elevated temperature or high [[pH]]. This makes aspartame undesirable as a baking sweetener, and prone to degradation in products hosting a high-pH, as required for a long shelf life. Aspartame’s stability under heating can be improved to some extent by encasing it in [[fat]]s or in [[maltodextrin]]. Aspartame’s stability when dissolved in water depends markedly on [[pH]]. At room temperature, it is most stable at pH 4.3, where its [[half-life]] is nearly 300 days. At pH 7, however, its half-life is only a few days. Most soft-drinks have a pH between 3 and 5, where aspartame is reasonably stable. In products that may require a longer shelf life, such as syrups for [[soda fountain|fountain beverages]], aspartame is sometimes blended with a more stable sweetener, such as [[saccharin]]. {{Fact|date={{subst:CURRENTMONTHNAME}} {{subst:CURRENTYEAR}}}} In products such as powdered beverages, aspartame’s amino group can undergo a [[Maillard reaction]] with the [[aldehyde]] groups present in certain [[aroma compound]]s. The ensuing loss of both flavor and sweetness can be prevented by protecting the aldehyde as an [[acetal]]. == Metabolism == Upon ingestion, aspartame breaks down into several constituent chemicals, including the naturally occurring [[essential amino acid]] [[phenylalanine]] which is a health hazard to the few people born with [[phenylketonuria]], a congenital inability to process phenylalanine. Aspartame products generally include a warning label related to Phenylketonuria to help protect these people. It is safer for those with the disease to monitor their diets and to attempt to avoid such products. Phenylketonuria (PKU) is a rare inherited disease that prevents the essential amino acid phenylalanine from being properly metabolized. Because of this, phenylalanine can accumulate in the body and cause health problems including mental retardation. People with PKU are placed on a special diet with a severe restriction of phenylalanine from birth to adolescence or after. Women with PKU must remain on the special diet throughout pregnancy. Since individuals with PKU must consider aspartame as an additional source of phenylalanine, aspartame-containing foods must state «Phenylketonurics: Contains Phenylalanine» in the U.S. Some point to the rapid breakdown of aspartame causing spikes of phenylalanine and aspartic acid which can upset chemical balances and cross the blood-brain barrier, as well as unnatural spikes in levels of methanol in places the body does not normally encounter it (like within metabolic processes), raising concerns as to its safe containment and elimination. == Aspartame controversy == {{main|Aspartame controversy}} Before editing this section, please realize that all Aspartame Health Risk Controversy information (other than the intro below) is on the «Aspartame controversy» subject for the time being … unless Editors choose to recombine. Aspartame has been the subject of a vigorous public controversy regarding its safety and the circumstances around its approval. Some studies have also recommended further investigation into connections between aspartame and diseases such as [[brain tumor]]s, [[lesion|brain lesions]], and [[lymphoma]]. These findings, combined with notable conflicts of interest in the approval process, have engendered vocal activism regarding the possible risks of aspartame. {{E number infobox 950-969}} --> {{reflist|2}} {{Пищевые добавки}} [[Категория:Пищевые добавки]] [[Категория:Подсластители и заменители сахара]] [[ar:أسبرتام]] [[be:Аспартам]] [[be-x-old:Аспартам]] [[bg:Аспартам]] [[ca:Aspartam]] [[cs:Aspartam]] [[da:Aspartam]] [[de:Aspartam]] [[en:Aspartame]] [[es:Aspartamo]] [[fa:آسپارتام]] [[fi:Aspartaami]] [[fr:Aspartame]] [[gl:Aspartamo]] [[he:אספרטם]] [[hu:Aszpartám]] [[id:Aspartam]] [[is:Aspartam]] [[it:Aspartame]] [[ja:アスパルテーム]] [[ko:아스파탐]] [[lt:Aspartamas]] [[nl:Aspartaam]] [[no:Aspartam]] [[pl:Aspartam]] [[pt:Aspartame]] [[ro:Aspartam]] [[simple:Aspartame]] [[sk:Aspartam]] [[sl:Aspartam]] [[sv:Aspartam]] [[th:แอสปาร์แตม]] [[tr:Aspartam]] [[uk:Аспартам]] [[zh:阿斯巴甜]]'