Advantame

Advantame

Names
IUPAC name (3S)-3-[3-(3-Hydroxy-4-methoxyphenyl)propylamino]-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid
Systematic IUPAC name N-[N-[3-(3-hydroxy-4-methoxyphenyl)propyl]-α-L-aspartyl]-L-phenylalanine 1-methyl ester
Identifiers
CAS Number	714229-20-6 monohydrate 245650-17-3 anhydrous
ChemSpider	8564873
Jmol interactive 3D	Image
PubChem	10389431
InChI InChI=1S/C24H30N2O7/c1-32-21-11-10-17(14-20(21)27)9-6-12-25-18(15-22(28)29)23(30)26-19(24(31)33-2)13-16-7-4-3-5-8-16/h3-5,7-8,10-11,14,18-19,25,27H,6,9,12-13,15H2,1-2H3,(H,26,30)(H,28,29)/t18-,19-/m0/s1 Key: YTKBWWKAVMSYHE-OALUTQOASA-N InChI=1/C24H30N2O7/c1-32-21-11-10-17(14-20(21)27)9-6-12-25-18(15-22(28)29)23(30)26-19(24(31)33-2)13-16-7-4-3-5-8-16/h3-5,7-8,10-11,14,18-19,25,27H,6,9,12-13,15H2,1-2H3,(H,26,30)(H,28,29)/t18-,19-/m0/s1 Key: YTKBWWKAVMSYHE-OALUTQOABU
SMILES COC1=C(C=C(C=C1)CCCN[C@@H](CC(=O)O)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)OC)O
Properties
Chemical formula	C24H30N2O7
Molar mass	458.51 g·mol^−1
Appearance	white to yellow powder
Melting point	99.3–101.5 °C (210.7–214.7 °F; 372.4–374.6 K)
Solubility in water	Slightly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Advantame is a non-caloric sweetener from Japan's Ajinomoto Co.^[1] The U.S. Food and Drug Administration has approved advantame for general use in foods and beverages except meat and poultry as a food additive. It is synthesized from isovanillin and aspartame.^[2]

Advantame is classified as generally recognized as safe (GRAS) by the Flavor and Extract Manufacturers Association for use in dairy, frozen desserts, beverages, and chewing gum (FEMA #: 4716).^[3]

Animal studies have found no evidence for carcinogenicity or developmental toxicity.^[4]

References

1. "FDA Approves New No-Calorie Sweetener". Medscape. May 21, 2014. Retrieved 22 May 2014.
2. http://www.efsa.europa.eu/en/topics/topic/sweeteners
3. "Ajinomoto - Advantame Home". Advantame.
4. Otabe, A.; Fujieda, T.; Masuyama, T.; Ubukata, K.; Lee, C. (November 2011). "Advantame – An overview of the toxicity data". Food and Chemical Toxicology 49: S2–S7. doi:10.1016/j.fct.2011.06.046.