Advantage

Structural formula
General
Surname	Advantage
other names	N - [ N - [3- (3-Hydroxy-4-methoxyphenyl) propyl] -α- L -aspartyl] - L -phenylalanine 1-methyl ester E  969
Molecular formula	C 24 H 30 N 2 O 7
Brief description	white to yellow solid
External identifiers / databases
CAS number 245650-17-3 714229-20-6 (monohydrate) PubChem 10389431 ChemSpider 8564873 Wikidata Q16886625
properties
Molar mass	476.52 g mol −1
Physical state	firmly
Melting point	101.5 ° C (monohydrate)
solubility	very sparingly soluble in water (0.99 g l −1 at 25 ° C) slightly soluble in ethanol (13.6 g l −1 at 25 ° C) sparingly soluble in ethyl acetate (2.79 g l −1 at 25 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Advantam is a synthetic sweetener with a high sweetening power of the Japanese company Ajinomoto Co., Inc. has been developed. The chemical structure is derived from aspartame and isovanillin .

discovery

The aim of the food company Ajinomoto was to develop a highly sweetening sweetener with a desired taste profile. The product should be derived from the sweetener aspartame. First of all, lead structures with the right properties were searched for, which were then further optimized. For this purpose, computer models were also used and the structure-activity relationships of possible molecules on the sweet receptor were examined. Through several screenings, Advantam was selected from several hundred structures. Above all, criteria such as sweetness, taste quality and possibilities of industrial production as well as the metabolism in the human body were discussed. In 2008 the structure of the Advantam was published for the first time (still under the laboratory code ANS9801).

Manufacturing

The industrial production of Advantam takes place in three stages: construction of trans-isoferulic acid (HMCA) from isovanillin over several reaction steps, hydrogenation of HMCA to 3- (3-hydroxy-4-methoxyphenyl) propanal (HMPA), conversion of HMPA with aspartame and hydrogenation by means of Hydrogen with the aid of a platinum catalyst . The product is then recrystallized and the crystals are separated off, washed and dried.

properties

Advantam is a white to yellow solid. In dry form it is very stable, but at lower pH values, such as in soft drinks, it degrades more quickly; it is similarly stable here to aspartame. The melting point is 101.5 ° C, the water solubility is moderate (approx. 1 g / liter at 25 ° C), but improves when heated.

The relative sweetness of Advantam depends on the concentration and is between approx. 7000 and 48000 (compared to a sucrose solution of the same concentration). It is between 70 and 120 times sweeter than aspartame. In descriptive taste analyzes it was found that Advantam only tastes sweet and does not have any off-flavor . The taste is similar to that of Apartam, but the aftertaste is longer lasting. Advantam also has a flavor enhancing effect, e.g. B. for mint and citrus flavors, and dampens bitter aftertaste.

The calorific value of Advantam is comparable to that of proteins (4 kcal / g), but this is negligible due to the very low amount used.

Admission

Advantam is approved in the USA and Europe (since 2014) and is marketed as a food additive E 969. The maximum permitted amounts depend on the food, there is a general maximum daily dose ( ADI ) of 5 mg per kg of body weight.

Due to the derivation of aspartame, Advantame is also a source of phenylalanine and must be considered in principle (but not strictly due to the small amount) in phenylketonuria .

Individual evidence

1. ↑ Entry on E 969: Advantame in the European database on food additives, accessed on June 27, 2020.
2. ↑ ^{a b c d e f g h i} Nabors, Lyn O'Brien: Alternative sweeteners . 4th ed. CRC Press, Boca Raton, FL 2012, ISBN 1-4398-4615-4 ( limited preview in Google Book Search).
3. ↑ ^{a b c} Data sheet Advantame, analytical standard at Sigma-Aldrich , accessed on July 19, 2019 ( PDF ).
4. ↑ Yusuke Amino, Kenich Mori, Yasuyuki Tomiyama, Hiroyuki Sakata, Takeshi Fujieda: Development of New, Low Calorie Sweetener: New Aspartame Derivative . In: Sweetness and Sweeteners . tape 979 . American Chemical Society, Washington, DC 2008, ISBN 978-0-8412-7432-7 , pp. 463-480 , doi : 10.1021 / bk-2008-0979.ch030 .
5. ↑ ^{a b} Scientific Opinion on the safety of advantame for the proposed uses as a food additive . In: EFSA Journal . tape 11 , no. 7 , 2013, ISSN  1831-4732 , p. 3301 , doi : 10.2903 / j.efsa.2013.3301 .
6. ↑ ^{a b} Sweetener Advantam approved ( Memento from July 19, 2019 in the Internet Archive )
7. ↑ Sweeteners: additives with almost calorie-free sweetening power. Retrieved July 19, 2019 . 
8. ↑ Barclay, Allan., Sandall, Philippa., Shwide-Slavin, Claudia .: The ultimate guide to sugars & sweeteners: discover the taste, use, nutrition, science, and lore of everything from agave nectar to xylitol . New York, ISBN 978-1-61519-216-8 ( limited preview in Google Book Search).
9. ↑ Advantam: EFSA publishes safety assessment. July 31, 2013, accessed July 19, 2019 . 
10. ↑ Regulation (EU) No. 497/2014 (PDF; 351 kB) .
11. ↑ Advantam | Nutritional Lexicon | ernaehrung.de. Retrieved July 19, 2019 .