Sodium 2-(4-methoxyphenoxy)propionate

Chemical Properties

2-(4-Methoxyphenoxy)propanoate is a potent inhibitor of the sweetness of sucrose and other sweeteners.

Chemical Properties

Lactisole, the sodium salt of racemic 2(4 methoxyphenoxy) propionic acid, is a sweet-taste inhibitor marketed by Domino Sugar. It was affirmed as a GRAS flavor (FEMA no. 3773). At a concentration of 100–150 ppm, lactisole eliminates the sweet taste of a 10% sugar solution. This inhibition appears to be receptor related because lactisole also inhibits the sweet taste of aspartame. The (S) enantiomer [CAS: 4276-74-8] (38), isolated from roasted coffee beans, is the active isomer; the (R+) enantiomer is inert.

Occurrence

Reported found in coffee beans.

Uses

Sodium 2-(4-methoxyphenoxy)propanoic acid is a taste modulator that inhibits the perception of sweetness in humans, but not in rats.

Definition

ChEBI: (S)-2-(4-Methoxyphenoxy)propanoic acid is a carboxylic acid and an aromatic ether.

Biochem/physiol Actions

As a taste modulator, the sodium salt inhibits the perception of sweetness in humans, but not in rats.

Synthesis

(1) Add p-methoxyphenol (10 kg), sodium hydroxide (10 kg), potassium iodide (0.12 kg) and water (100 kg) to the reaction vessel and stir for 30 minutes at room temperature. Subsequently, the reaction mixture was heated to 60°C and the temperature was maintained in the range of 60°C to 70°C. At this temperature, methyl 2-chloropropionate (11.85 kg) was added slowly and dropwise. The reaction was catalyzed by potassium iodide and p-methoxyphenol reacted with methyl 2-chloropropionate while sodium hydroxide continued to react with the resulting acid. The reaction temperature was maintained in the range of 60°C to 90°C. The reaction was carried out for 12 hours and then completed; (2) the reaction product was cooled to room temperature, and a 30% sulfuric acid solution was slowly added, and the addition of acid was stopped after adjusting the pH of the mixture to 2.0. Subsequently, the mixture was cooled to below 45°C and centrifuged to obtain white solid 2-(4-methoxyphenoxy)propionic acid (14.28 kg).

References

[1] Patent: US4760172, 1988, A
[2] Patent: CN103922923, 2016, B. Location in patent: Paragraph 0029; 0030