Aspartame

Aspartame^[1]
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
CAS Number	22839-47-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	2223850
ChEBI	CHEBI:2877 ;
ChEMBL	ChEMBL171679 ;
ChemSpider	118630 ;
DrugBank	DB00168 ;
ECHA InfoCard	100.041.132
EC Number	245-261-3;
E number	E951 (glazing agents, ...)
KEGG	C11045 ;
PubChem CID	134601;
UNII	Z0H242BBR1 ;
CompTox Dashboard (EPA)	DTXSID0020107 ;
	InChI 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 Key: IAOZJIPTCAWIRG-QWRGUYRKSA-N ; 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;
	SMILES O=C(O)C[C@H](N)C(=O)N[C@H](C(=O)OC)Cc1ccccc1;
Properties
Chemical formula	C14H18N2O5
Molar mass	294.307 g·mol−1
Density	1.347 g/cm3
Melting point	246.5 °C (475.7 °F; 519.6 K)
Boiling point	Decomposes
Solubility in water	Sparingly soluble
Solubility	Slightly soluble in ethanol
Acidity (pKa)	4.5–6.0
Hazards
NFPA 704 (fire diamond)	1 1 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Aspartame is an artificial non-saccharide sweetener commonly used as a sugar substitute in foods and beverages.^[4] 200 times sweeter than sucrose, it is a methyl ester of the aspartic acid/phenylalanine dipeptide with brand names NutraSweet, Equal, and Canderel.^[4] Discovered in 1965, aspartame was approved by the US Food and Drug Administration (FDA) in 1974 and re-approved in 1981 after its initial approval was briefly revoked.^[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.^[14]

^ Budavari S, ed. (1989). "861. Aspartame". The Merck Index (11th ed.). Rahway, NJ: Merck & Co. p. 859. ISBN 978-0-911910-28-5.
^ Rowe RC (2009). "Aspartame". Handbook of Pharmaceutical Excipients. Pharmaceutical Press. pp. 11–12. ISBN 978-1-58212-058-4.
^ Haynes WM, ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.30. ISBN 978-1498754293.
^ ^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.
^ Cite error: The named reference fda-timeline was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference EFSAExperts was invoked but never defined (see the help page).
^ ^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.
^ Kay O'Donnel (2012). Mitchell H (ed.). Sweeteners and sugar alternatives in food technology. Oxford, UK: Wiley-Blackwell. p. 126.
^ Cite error: The named reference cfr was invoked but never defined (see the help page).
^ 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.
^ 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.
^ 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.
^ 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.
^ ^[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.

[pubch-4] "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.

[fda-timeline-5] Cite error: The named reference fda-timeline was invoked but never defined (see the help page).

[EFSAExperts-6] Cite error: The named reference EFSAExperts was invoked but never defined (see the help page).

[fda7-14-7] "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.

[Mitchell_2006_943-8] Kay O'Donnel (2012). Mitchell H (ed.). Sweeteners and sugar alternatives in food technology. Oxford, UK: Wiley-Blackwell. p. 126.

[cfr-9] Cite error: The named reference cfr was invoked but never defined (see the help page).

[Magnuson-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.

[FSANZ2-11] 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.

[Butchko-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.

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