Aspartame - Nutrasweet / Wikipedia (long)

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Aspartame

 

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Aspartame _Systematic name_

(http://en.wikipedia.org/wiki/IUPAC_nomenclature)

N-L-a-aspartyl-L-phenylalanine

1-methyl ester _Molecular formula_

(http://en.wikipedia.org/wiki/Chemical_formula) C14H18N2O5 _Molecular mass_

(http://en.wikipedia.org/wiki/Molecular_mass) 294.301 g/mol _Melting point_

(http://en.wikipedia.org/wiki/Melting_point) 246–247 °C _CAS number_

(http://en.wikipedia.org/wiki/CAS_registry_number) [22839-47-0] _[1]_

(http://webbook.nist.gov/cgi/cbook.cgi?ID=22839-47-0 & Units=SI) _SMILES_

(http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specificatio\

n) [NH3+] [C@@H](CC([O-])=O)C(N[C@@H]

(CC1=CC=CC=C1)C(OC)=O)=O (http://en.wikipedia.org/wiki/Image:Aspartam.svg)

Aspartame, (_IPA_

(http://en.wikipedia.org/wiki/International_Phonetic_Alphabet) :

/ˈæ.spɚˌteɪm/ or /əˈspɑɹˌteɪm/), is the name for an artificial,

non-_carbohydrate_ (http://en.wikipedia.org/wiki/Carbohydrate) _sweetener_

(http://en.wikipedia.org/wiki/Sweetener) , aspartyl-phenylalanine-1-methyl

ester; i.e., the methyl _ester_ (http://en.wikipedia.org/wiki/Ester) of the

_dipeptide_ (http://en.wikipedia.org/wiki/Dipeptide) of the _amino acids_

(http://en.wikipedia.org/wiki/Amino_acid) _aspartic acid_

(http://en.wikipedia.org/wiki/Aspartic_acid) and the _essential amino acid_

(http://en.wikipedia.org/wiki/Essential_amino_acid) _phenylalanine_

(http://en.wikipedia.org/wiki/Phenylalanine) .

This sweetener is marketed under a number of trademark names, such as _Equal_

(http://en.wikipedia.org/wiki/Equal_(sweetener)) , and _Canderel_

(http://en.wikipedia.org/wiki/Canderel) , and is an ingredient of approximately

6,000

consumer foods and beverages sold worldwide. It is commonly used in diet _soft

drinks_ (http://en.wikipedia.org/wiki/Soft_drink) , and is often provided as

a table condiment. It is also used in some brands of chewable _vitamin_

(http://en.wikipedia.org/wiki/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_ (http://en.wikipedia.org/wiki/E_number) (additive code) E951.

Aspartame

is also one of the sugar substitutes used by _diabetics_

(http://en.wikipedia.org/wiki/Diabetes_mellitus) . Nonetheless, aspartame has

been a subject of a

vigorous public _controversy_

(http://en.wikipedia.org/wiki/Aspartame_controversy) .

 

Contents

[_hide_ (javascript:toggleToc()) ]

* _1 Chemistry_ (http://en.wikipedia.org/wiki/Aspartame#Chemistry)

* _2 Discovery and approval_

(http://en.wikipedia.org/wiki/Aspartame#Discovery_and_approval)

* _3 Properties and use_

(http://en.wikipedia.org/wiki/Aspartame#Properties_and_use)

* _4 Metabolism_ (http://en.wikipedia.org/wiki/Aspartame#Metabolism)

* _5 Aspartame controversy_

(http://en.wikipedia.org/wiki/Aspartame#Aspartame_controversy)

* _6 References_ (http://en.wikipedia.org/wiki/Aspartame#References)

* _7 External links_

(http://en.wikipedia.org/wiki/Aspartame#External_links)

[_edit_

(http://en.wikipedia.org/w/index.php?title=Aspartame & action=edit & section=1) ]

Chemistry

Aspartame is the _methyl_ (http://en.wikipedia.org/wiki/Methyl) _ester_

(http://en.wikipedia.org/wiki/Ester) of the _dipeptide_

(http://en.wikipedia.org/wiki/Dipeptide) of the natural _amino acids_

(http://en.wikipedia.org/wiki/Amino_acid) L-_aspartic acid_

(http://en.wikipedia.org/wiki/Aspartic_acid) and

L-_phenylalanine_ (http://en.wikipedia.org/wiki/Phenylalanine) . Under

strongly _acidic_ (http://en.wikipedia.org/wiki/Acid) or _alkaline_

(http://en.wikipedia.org/wiki/Base_(chemistry)) conditions, aspartame first

generates

_methanol_ (http://en.wikipedia.org/wiki/Methanol) by _hydrolysis_

(http://en.wikipedia.org/wiki/Hydrolysis) . Under more severe conditions, the

_peptide

bonds_ (http://en.wikipedia.org/wiki/Peptide_bond) are also _hydrolyzed_

(http://en.wikipedia.org/wiki/Hydrolyzed) , resulting in the free amino acids.

[_edit_

(http://en.wikipedia.org/w/index.php?title=Aspartame & action=edit & section=2) ]

Discovery and approval

Aspartame was discovered in _1965_ (http://en.wikipedia.org/wiki/1965) by

James M. Schlatter, a chemist working for _G.D. Searle & Company_

(http://en.wikipedia.org/wiki/Searle_(company)) . Schlatter had synthesized

aspartame in

the course of producing an anti-_ulcer_ (http://en.wikipedia.org/wiki/Ulcer)

drug candidate. He discovered its sweet taste serendipitously when he licked

his finger, which had accidentally become contaminated with aspartame.

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 _U.S.

Food and Drug Administration_

(http://en.wikipedia.org/wiki/Food_and_Drug_Administration) (FDA) did not

approve its use as a food additive in the

_United States_ (http://en.wikipedia.org/wiki/United_States) for many years.

In

_1980_ (http://en.wikipedia.org/wiki/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_

(http://en.wikipedia.org/wiki/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_

(http://en.wikipedia.org/wiki/Cancer) in laboratory rats. In _1981_

(http://en.wikipedia.org/wiki/1981) , U.S.

President _Ronald Reagan_ (http://en.wikipedia.org/wiki/Ronald_Reagan)

appointed as FDA commissioner _Arthur Hull Hayes_

(http://en.wikipedia.org/w/index.php?title=Arthur_Hull_Hayes & action=edit) .

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._[1]_

(http://en.wikipedia.org/wiki/Aspartame#_note-http:.2F.2Farchive.gao.gov.2Fd28t5\

..2F133460.pdf) In _1983_

(http://en.wikipedia.org/wiki/1983) FDA further approved aspartame for use in

carbonated

beverages, and for use in other beverages, baked goods, and confections in

_1993_ (http://en.wikipedia.org/wiki/1993) . In _1996_

(http://en.wikipedia.org/wiki/1996) , the FDA removed all restrictions from

aspartame allowing it to

be used in all foods.

In _1985_ (http://en.wikipedia.org/wiki/1985) , G.D. Searle was purchased by

_Monsanto_ (http://en.wikipedia.org/wiki/Monsanto) . In this acquisition,

Searle’s aspartame business became a separate Monsanto subsidiary, the

_NutraSweet Company_ (http://en.wikipedia.org/wiki/NutraSweet) . Monsanto

subsequently

sold the NutraSweet company to J.W. Childs Equity Partners II L.P. on May

25, 2000._[2]_

(http://en.wikipedia.org/wiki/Aspartame#_note-http:.2F.2Fwww.findarticles.com.2F\

p.2Farticles.2Fmi_m0EUY.2Fis_22_6.2Fai_62920821) The U.S.

_patent_ (http://en.wikipedia.org/wiki/Patent) on aspartame expired in _1992_

(http://en.wikipedia.org/wiki/1992) , and the aspartame market is now hotly

contested between the NutraSweet Company and other manufacturers such as

_Ajinomoto_ (http://en.wikipedia.org/wiki/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. " _[3]_

(http://en.wikipedia.org/wiki/Aspartame#_note-http:.2F.2Fwww.marketwire.com.2Fmw\

..2Frelease_html_b1

..3Frelease_id.3D115447)

[_edit_

(http://en.wikipedia.org/w/index.php?title=Aspartame & action=edit & section=3) ]

Properties and use

Aspartame’s attractiveness as a sweetener comes from the fact that it is

approximately 180 times sweeter than _sugar_

(http://en.wikipedia.org/wiki/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_

(http://en.wikipedia.org/wiki/Acesulfame_potassium) are purported to have a

more sugar-like taste, and to

be more potent than either sweetener used alone.

Like many other _peptides_ (http://en.wikipedia.org/wiki/Peptide) , aspartame

may _hydrolyze_ (http://en.wikipedia.org/wiki/Hydrolyze) (break down) into

its constituent amino acids under conditions of elevated temperature or high

_pH_ (http://en.wikipedia.org/wiki/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 _fats_

(http://en.wikipedia.org/wiki/Fat) or in _maltodextrin_

(http://en.wikipedia.org/wiki/Maltodextrin) .

Aspartame’s stability when dissolved in water depends markedly on _pH_

(http://en.wikipedia.org/wiki/PH) . At room temperature, it is most stable at

pH 4.3,

where its _half-life_ (http://en.wikipedia.org/wiki/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 _fountain beverages_

(http://en.wikipedia.org/wiki/Soda_fountain) , aspartame is sometimes blended

with a more stable sweetener, such as _saccharin_

(http://en.wikipedia.org/wiki/Saccharin) . [_citation needed_

(http://en.wikipedia.org/wiki/Wikipedia:Citing_sources) ]

In products such as powdered beverages, aspartame’s amino group can undergo a

_Maillard reaction_ (http://en.wikipedia.org/wiki/Maillard_reaction) with

the _aldehyde_ (http://en.wikipedia.org/wiki/Aldehyde) groups present in

certain _aroma compounds_ (http://en.wikipedia.org/wiki/Aroma_compound) . The

ensuing loss of both flavor and sweetness can be prevented by protecting the

aldehyde as an _acetal_ (http://en.wikipedia.org/wiki/Acetal) .

[_edit_

(http://en.wikipedia.org/w/index.php?title=Aspartame & action=edit & section=4) ]

Metabolism

Upon ingestion, aspartame breaks down into several constituent chemicals,

including the naturally occurring _essential amino acid_

(http://en.wikipedia.org/wiki/Essential_amino_acid) _phenylalanine_

(http://en.wikipedia.org/wiki/Phenylalanine) which is a health hazard to the

few people born with

_phenylketonuria_ (http://en.wikipedia.org/wiki/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)[_citation needed_

(http://en.wikipedia.org/wiki/Wikipedia:Citing_sources) ], raising

concerns as to its safe containment and elimination.

[_edit_

(http://en.wikipedia.org/w/index.php?title=Aspartame & action=edit & section=5) ]

Aspartame controversy

 

Main article: _Aspartame controversy_

(http://en.wikipedia.org/wiki/Aspartame_controversy)

 

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 tumors_ (http://en.wikipedia.org/wiki/Brain_tumor) ,

_brain

lesions_ (http://en.wikipedia.org/wiki/Lesion) , and _lymphoma_

(http://en.wikipedia.org/wiki/Lymphoma) .[_citation needed_

(http://en.wikipedia.org/wiki/Wikipedia:Citing_sources) ] These findings,

combined with notable conflicts of

interest in the approval process, have engendered vocal activism regarding

the possible risks of aspartame.[_citation needed_

(http://en.wikipedia.org/wiki/Wikipedia:Citing_sources) ]

[_edit_

(http://en.wikipedia.org/w/index.php?title=Aspartame & action=edit & section=6) ]

References

1. _^_

(http://en.wikipedia.org/wiki/Aspartame#_ref-http:.2F.2Farchive.gao.gov.2Fd28t5.\

2F133460.pdf_0) _http://archive.gao.gov/d28t5/133460.pdf_

(http://archive.gao.gov/d28t5/133460.pdf)

2. _^_

(http://en.wikipedia.org/wiki/Aspartame#_ref-http:.2F.2Fwww.findarticles.com.2Fp\

..2Farticles.2Fmi_m0EUY.2Fis_22_6.2Fai_62920821_0)

_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)

3. _^_

(http://en.wikipedia.org/wiki/Aspartame#_ref-http:.2F.2Fwww.marketwire.com.2Fmw.\

2Frelease_html_b1.3Frelease_id.3D115447_0)

_http://www.marketwire.com/mw/release html b1?release id=115447_

(http://www.marketwire.com/mw/release_html_b1?release_id=115447)

[_edit_

(http://en.wikipedia.org/w/index.php?title=Aspartame & action=edit & section=7) ]

External links

* _Link page to external chemical sources_

(http://en.wikipedia.org/wiki/Wikipedia:Chemical_sources) .

 

 

_v_ (http://en.wikipedia.org/wiki/Template:E_number_infobox_950-969) · _d_

(http://en.wikipedia.org/w/index.php?title=Template_talk:E_number_infobox_950-96

9 & action=edit) · _e_

(http://en.wikipedia.org/w/index.php?title=Template:E_number_infobox_950-969 & act\

ion=edit)

 

_E numbers_ (http://en.wikipedia.org/wiki/E_numbers) _Colours_

(http://en.wikipedia.org/wiki/Food_colouring) (E100-199) • _Preservatives_

(http://en.wikipedia.org/wiki/Preservative) (E200-299) • _Antioxidants_

(http://en.wikipedia.org/wiki/Antioxidant) & _Acidity regulators_

(http://en.wikipedia.org/wiki/Acidity_regulator) (E300-399) • _Thickeners_

(http://en.wikipedia.org/wiki/Thickener) , _stabilisers_

(http://en.wikipedia.org/wiki/Stabiliser) &

_emulsifiers_ (http://en.wikipedia.org/wiki/Emulsifier) (E400-499) • _pH_

(http://en.wikipedia.org/wiki/PH) _regulators_

(http://en.wikipedia.org/wiki/Acidity_regulator) & _anti-caking agents_

(http://en.wikipedia.org/wiki/Anti-caking_agent) (E500-599) • _Flavour

enhancers_

(http://en.wikipedia.org/wiki/Flavour_enhancer) (E600-699) • Miscellaneous

(E900-999) • Additional

chemicals (E1100-1599)

__

_Waxes_ (http://en.wikipedia.org/wiki/Wax) (E900-909) • _Synthetic

glazes_ (http://en.wikipedia.org/wiki/Glazing_agent) (E910-919) • _Improving

agents_ (http://en.wikipedia.org/wiki/Improving_agent) (E920-929) •

_Packaging

gases_ (http://en.wikipedia.org/wiki/Packaging_gas) (E930-949) •

_Sweeteners_

(http://en.wikipedia.org/wiki/Sugar_substitute) (E950-969) • _Foaming

agents_ (http://en.wikipedia.org/wiki/Foaming_agent) (E990-999)

__

Aspartame (E951) • _Cyclamate_ (http://en.wikipedia.org/wiki/Cyclamate)

(E952) • _Isomalt_ (http://en.wikipedia.org/wiki/Isomalt) (E953) •

_Saccharin_ (http://en.wikipedia.org/wiki/Saccharin) (E954) • _Sucralose_

(http://en.wikipedia.org/wiki/Sucralose) (E955) • _Thaumatin_

(http://en.wikipedia.org/wiki/Thaumatin) (E957) • _Neohesperidin

dihydrochalcone_

(http://en.wikipedia.org/wiki/Neohesperidin_dihydrochalcone) (E959) •

_Maltitol_

(http://en.wikipedia.org/wiki/Maltitol) (E965) • _Lactitol_

(http://en.wikipedia.org/wiki/Lactitol) (E966) • _Xylitol_

(http://en.wikipedia.org/wiki/Xylitol) (E967)

Retrieved from " _http://en.wikipedia.org/wiki/Aspartame_

(http://en.wikipedia.org/wiki/Aspartame) "

 

_Categories_ (http://en.wikipedia.org/wiki/Special:Categories) : _Articles

with unsourced statements_

(http://en.wikipedia.org/wiki/Category:Articles_with_unsourced_statements) |

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(http://en.wikipedia.org/wiki/Category:Carboxylate_esters) | _Sweeteners_

(http://en.wikipedia.org/wiki/Category:Sweeteners)

 

 

 

 

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59)

 

 

 

In other languages

 

* _БеларуÑкаÑ_ (http://be.wikipedia.org/wiki/ÐÑпартам)

* _ÄŒesky_ (http://cs.wikipedia.org/wiki/Aspartam)

* _Dansk_ (http://da.wikipedia.org/wiki/Aspartam)

* _Deutsch_ (http://de.wikipedia.org/wiki/Aspartam)

* _Español_ (http://es.wikipedia.org/wiki/Aspartamo)

* _Français_ (http://fr.wikipedia.org/wiki/Aspartame)

* _Galego_ (http://gl.wikipedia.org/wiki/Aspartamo)

* _한국어_ (http://ko.wikipedia.org/wiki/아스파íƒ)

* _Italiano_ (http://it.wikipedia.org/wiki/Aspartame)

* _עברית_ (http://he.wikipedia.org/wiki/×ספרט×)

* _Magyar_ (http://hu.wikipedia.org/wiki/Aszpartám)

* _Nederlands_ (http://nl.wikipedia.org/wiki/Aspartaam)

* _日本語_ (http://ja.wikipedia.org/wiki/アスパルテーム)

* _Norsk (bokmål)_ (http://no.wikipedia.org/wiki/Aspartam)

* _Polski_ (http://pl.wikipedia.org/wiki/Aspartam)

* _Português_ (http://pt.wikipedia.org/wiki/Aspartame)

* _Română_ (http://ro.wikipedia.org/wiki/Aspartam)

* _РуÑÑкий_ (http://ru.wikipedia.org/wiki/ÐÑпартам)

* _SlovenÄina_ (http://sk.wikipedia.org/wiki/Aspartam)

* _Suomi_ (http://fi.wikipedia.org/wiki/Aspartaami)

* _Svenska_ (http://sv.wikipedia.org/wiki/Aspartam)

* _ไทย_

(http://th.wikipedia.org/wiki/à¹à¸­à¸ªà¸›à¸²à¸£à¹Œà¹à¸•à¸¡)

* _Türkçe_ (http://tr.wikipedia.org/wiki/Aspartam)

* _中文_ (http://zh.wikipedia.org/wiki/阿斯巴甜)

 

 

 

 

 

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