Aspartame

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Aspartame[1]
Aspartame
Ball-and-stick model of aspartame
Names
Pronunciation /ˈæspərteɪm/ or
/əˈspɑːrteɪm/
IUPAC name
Methyl L-α-aspartyl-L-phenylalaninate
Systematic IUPAC name
(3S)-3-amino-4-「[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino」-4-oxobutanoic acid
Other names
  • N-(L-α-Aspartyl)-L-phenylalanine,
    1-methyl ester
Identifiers
3D model (JSmol)
2223850
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.041.132 Edit this at Wikidata
EC Number
  • 245-261-3
E number E951 (glazing agents, ...)
KEGG
UNII
  • InChI=1S/C14H18N2O5/c1-21-14(20)11(7-9-5-3-2-4-6-9)16-13(19)10(15)8-12(17)18/h2-6,10-11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t10-,11-/m0/s1 checkY
    Key: IAOZJIPTCAWIRG-QWRGUYRKSA-N checkY
  • InChI=1/C14H18N2O5/c1-21-14(20)11(7-9-5-3-2-4-6-9)16-13(19)10(15)8-12(17)18/h2-6,10-11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t10-,11-/m0/s1
    Key: IAOZJIPTCAWIRG-QWRGUYRKBV
  • O=C(O)C[C@H](N)C(=O)N[C@H](C(=O)OC)Cc1ccccc1
Properties
C14H18N2O5
Molar mass 294.307 g·mol−1
Density 1.347 g/cm3
Melting point 246.5 °C (475.7 °F; 519.6 K)[3]
Boiling point Decomposes
Sparingly soluble
Solubility Slightly soluble in ethanol
Acidity (pKa) 4.5–6.0[2]
Hazards[4]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose and is commonly used as a sugar substitute in foods and beverages.[4] It is a methyl ester of the aspartic acid/phenylalanine dipeptide with brand names NutraSweet, Equal, and Canderel.[4] Aspartame was approved by the US Food and Drug Administration (FDA) in 1974, and then again in 1981, after approval was revoked in 1980.[4][5][6]

Aspartame is one of the most studied food additives in the human food supply.[7][8] Reviews by over 100 governmental regulatory bodies found the ingredient safe for consumption at the normal acceptable daily intake limit.[6][7][9][10][11][12][13]

  1. ^ Budavari S, ed. (1989). "861. Aspartame". The Merck Index (11th ed.). Rahway, NJ: Merck & Co. p. 859. ISBN 978-0-911910-28-5.
  2. ^ Rowe RC (2009). "Aspartame". Handbook of Pharmaceutical Excipients. Pharmaceutical Press. pp. 11–12. ISBN 978-1-58212-058-4.
  3. ^ Haynes WM, ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.30. ISBN 978-1498754293.
  4. ^ a b c d "Aspartame". PubChem, National Library of Medicine, US National Institutes of Health. 27 May 2023. Archived from the original on 17 August 2017. Retrieved 2 June 2023.
  5. ^ Cite error: The named reference fda-timeline was invoked but never defined (see the help page).
  6. ^ a b Cite error: The named reference EFSAExperts was invoked but never defined (see the help page).
  7. ^ a b "Aspartame and Other Sweeteners in Food". US Food and Drug Administration. 14 July 2023. Archived from the original on 29 June 2023. Retrieved 14 July 2023.
  8. ^ Kay O'Donnel (2012). Mitchell H (ed.). Sweeteners and sugar alternatives in food technology. Oxford, UK: Wiley-Blackwell. p. 126.
  9. ^ Cite error: The named reference cfr was invoked but never defined (see the help page).
  10. ^ Magnuson BA, Burdock GA, Doull J, Kroes RM, Marsh GM, Pariza MW, et al. (2007). "Aspartame: a safety evaluation based on current use levels, regulations, and toxicological and epidemiological studies". Critical Reviews in Toxicology. 37 (8): 629–727. doi:10.1080/10408440701516184. PMID 17828671. S2CID 7316097.
  11. ^ Food Standards Australia New Zealand: "Food Standards Australia New Zealand: Aspartame – what it is and why it's used in our food". Archived from the original on 16 December 2008. Retrieved 9 December 2008.
  12. ^ Butchko HH, Stargel WW, Comer CP, Mayhew DA, Benninger C, Blackburn GL, et al. (April 2002). "Aspartame: review of safety". Regulatory Toxicology and Pharmacology. 35 (2 Pt 2): S1–93. doi:10.1006/rtph.2002.1542. PMID 12180494.
  13. ^ Rios-Leyvraz M, Montez J (12 April 2022). Health effects of the use of non-sugar sweeteners: a systematic review and meta-analysis (Report). World Health Organization (WHO). hdl:10665/353064. ISBN 978-92-4-004642-9.