Advantame
Names | |
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IUPAC name
Methyl N-[3-(3-Hydroxy-4-methoxyphenyl)propyl]aspartylphenylalaninate
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Systematic IUPAC name
(3S)-3-{[3-(3-Hydroxy-4-methoxyphenyl)propyl]amino}-4-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino}-4-oxobutanoic acid | |
Other names
N-[N-[3-(3-Hydroxy-4-methoxyphenyl)propyl]-α-L-aspartyl]-L-phenylalanine 1-methyl ester
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Identifiers | |
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3D model (
JSmol ) |
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ChemSpider | |
E number | E969 (glazing agents, ...) |
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
C24H30N2O7 | |
Molar mass | 458.511 g·mol−1 |
Appearance | white to yellow powder[1] |
Melting point | 101.5 °C (214.7 °F; 374.6 K)[1] |
0.99 g/L at 25 °C[2] | |
Hazards | |
Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Advantame is a non-caloric
Advantame can be used as a table top sweetener and in certain bubblegums, flavored drinks, milk products, jams and confectionery among other things.[4]
In 2013, it was approved for use in foods within
Safety
The
The Center for Science in the Public Interest ranks advantame as safe[7] and as generally recognized as safe.[8]
Sweetness
Relative sweetness of advantame varies. It depends on the concentration and food/matrix in which it is used. In water solutions of advantame, that are equivalently sweet to water solutions of 3–14 percentage sucrose by weight (wt%), advantame is 7000–47700 times sweeter. Relative sweetness of advantame increases
Chemistry
Advantame is formally a
Advantame has 2
Advantame can be made from aspartame and
At 15 °C the solubility of advantame is 0.76 g/L in water, 7.98 g/L in ethanol and 1.65 g/L in ethyl acetate. At 25 °C the solubilities are 0.99 g/L, 13.58 g/L and 2.79 g/L, respectively. At 40 °C the solubilities are 2.10 g/L, 38.27 g/L and 7.96 g/L, respectively. At 50 °C the solubilities are 3.10 g/L, 98.68 g/L and 16.00 g/L, respectively.[2]
Advantame as a dry powder degrades very slowly at 25 °C and 60%
Metabolism
In humans, 89% of the ingested advantame is excreted in feces and 6.2% in urine. Some is excreted unchanged, but most as metabolites. Advantame is poorly absorbed, rapidly metabolized and only small amounts of it and its metabolites can be detected in blood shortly after ingestion.[1]
52% of the ingested dose is excreted in feces as de-esterified advantame and 30% as N-(3-(3-hydroxy-4-methoxyphenyl))propyl-L-aspartic acid and as an equivalent molar amount of phenylalanine. 1% of the ingested dose is excreted in urine as the aforementioned aspartic acid analog, 1.9% as 5-(3-aminopropyl)-2-methoxyphenyl and 2.3% as de-esterified advantame. Methanol forms in de-esterification, but this is considered insignificant at advantame concentrations intended to be used in foods, and in comparison to methanol naturally formed in body and to methanol naturally found in foods.[1]
History
Ajinomoto developed advantame and announced its structure publicly in print in 2008. At first advantame was identified by the laboratory code ANS9801. Aspartame, neotame and aspartame N-substituted with asparagine via amide bond (covered in US patent 5,286,509) were selected as the lead compounds for research that lead to advantame.[9]
Notes
- ^ ISSN 1831-4732.
- ^ a b c d e f g h Nabors 2012, p. 31–44
- ^ Nabors 2012, p. 2–3
- ^ a b "EUR-Lex - 32014R0497 - EN - EUR-Lex". eur-lex.europa.eu. Retrieved 2019-09-14.
- ^ "Food Additives Permitted for Direct Addition to Food for Human Consumption; Advantame". Federal Register. 2014-05-21. Archived from the original on 2017-06-03. Retrieved 2019-09-14.
- ^ "Additional Information about High-Intensity Sweeteners Permitted for Use in Food in the United States". FDA. 2019-02-09.
- ^ "Chemical Cuisine | Center for Science in the Public Interest". cspinet.org. Retrieved 2019-09-14.
- S2CID 100599854.
- ^ OCLC 173368780.
References
- Nabors LO, et al. (2012). Alternative sweeteners (4th ed.). CRC Press. OCLC 760056415.
External links
- Media related to Advantame at Wikimedia Commons