Product Code Database
Advantame is a non-caloric artificial sweetener and aspartame analog by Ajinomoto. By mass, it is about 20,000 times sweeter than sucrose and about 110 times sweeter than aspartame.Nabors 2012, p. 2–3 It has no notable off-flavors when compared to sucrose and tastes sweet a bit longer than aspartame and is chemically more stable. It can be blended with many other natural and artificial sweeteners.Nabors 2012, p. 31–44
Advantame can be used as a table top sweetener and in certain , flavored drinks, , and confectionery among other things.
In 2013, it was approved for use in foods within EU with the E number E969. In 2014, FDA approved advantame as a non-nutritive sweetener and flavor enhancer within United States in foods generally, except meat and poultry.
The Center for Science in the Public Interest ranks advantame as safe and as generally recognized as safe.
Advantame has 2 and 4 stereoisomers.
Advantame can be made from aspartame and vanillin. Vanillin is transformed to HMPA in 4 steps. 3-hydroxy-4-methoxycinnamaldehyde (HMCA) is formed in the third step. HMCA is hydrogenated to HMPA in the final step. HMPA is selectively hydrogenated with palladium on aluminium oxide and platinum on carbon in one step to advantame in methanol with aspartame. Product is crystallized. Crude crystals are washed, recrystallized, washed and dried.
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.
Advantame as a dry powder degrades very slowly at 25 °C and 60% relative humidity and can last for years under such conditions. It can last for more than a year in aqueous solutions at pH 3.2. This corresponds to the typical pH of soft drinks. It degrades faster at higher temperatures and humidity, but is generally more stable than aspartame. Unlike aspartame, advantame doesn't form a diketopiperazine via intra-molecular cyclization due to steric hindrance by the vanillyl group.
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.
|
|
