| Field | Specification |
|---|---|
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C24H32N2O8 |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Advantame is an N-substituted derivative of aspartame that acts as a high-intensity, low-calorie sweetener and can interact with plasma protein. It has the potential to produce hypotension and to inhibit the hERG K+ channel, raising cardiotoxicity risk, and it binds the T1R2/T1R3 taste GPCR to form an oligomeric functional-selectivity complex of biased heteromers with NMBR that induces marked sialidase activity in vitro. In a prenatal developmental toxicity study, Advantame produced maternal toxicity, including gastrointestinal disturbances, in rabbits[1][2][3]. It is supplied as a white to off-white solid (C24H32N2O8, MW 476.52) at 99.27% purity.
Physical & Chemical Properties
| CAS Number | 714229-20-6 |
|---|---|
| Molecular Formula | C24H32N2O8 |
| Molecular Weight | 476.52 g/mol |
| Purity | 99.27% |
| Appearance | Solid |
| Color | White to off-white |
| SMILES | OC1=C(OC)C=CC(CCCN[C@@H](CC(O)=O)C(N[C@H](C(OC)=O)CC2=CC=CC=C2)=O)=C1.O |
| Signaling Pathway | GPCR/G Protein |
| Solubility | In Vitro: DMSO: 100 mg/mL (209.85 mM; Requires sonication; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) |
| Storage | -20°C, sealed storage, away from moisture. In solvent: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
[2]. DENISA IOANA VOICULESCU, et al., (2021) COMPUTATIONAL ASSESSMENT OF THE PHARMACOKINETICS AND TOXICITY OF THE INTENSIVE SWEETENERS: Farmacia, 69, 6.
[3]. EFSA Panel on Food Additives and Nutrient Sources added to Food (ANS), (2013), Scientific Opinion on the safety of advantame for the proposed uses as a food additive, 11(7).
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 100 mg/mL (209.85 mM) | requires sonication; use freshly opened DMSO (absorbed moisture lowers solubility) |
Aliquot the stock solution and store it at -80°C (up to 6 months) or -20°C (up to 1 month); sealed storage, away from moisture; avoid repeated freeze-thaw cycles.
Data provided by the manufacturer.
In Vitro
In simulated intestinal fluid containing Pancreatin, Advantame (120 min) is rapidly hydrolyzed (99.4%) to ANS9801-acid within 5 minutes[3]. Advantame binds the T1R2/T1R3 taste GPCR, forming an oligomeric functional selectivity of biased heteromers with NMBR and inducing significant sialidase activity in live PANC-1 pancreatic cancer cells[4]. Advantame (1-100 mg/mL, 22 h) drives N-cadherin expression for PANC-1 invasion and metastasis (EC50 = 9.899 mg/mL, 72.7 mM)[4].
In Vivo
Advantame (2000 mg/kg, i.g., bw/day) gives a systemic exposure 5 to 25 times higher than dietary administration in rabbit models[3]. In rats, Advantame (50000 mg/kg, in diet, 13 weeks) lowers body weight/body weight gain[3]. In dogs, Advantame (50000 mg/kg, in diet, 1 year) lowers body weight/body weight gain[3].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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