Chemical Properties
orange crystalline solid
Uses
Furylfuramide is a synthetic nitrofuran derivative widely used as a food additive and was investigated for possible carcinogenicity.
Definition
ChEBI: A member of the class of acrylamides that is acrylamide which is substituted at positions 2 and 3 by 2-furyl and 5-nitro-2-furyl groups, respectively (the trans isomer). Formerly used as a food preservative, it was withdrawn from the marke
following suspicions of carcenogenicity.
General Description
Bright orange crystals.
Air & Water Reactions
Hydrophobic. Insoluble in water.
Reactivity Profile
A nitrated amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition 2-(2-FURYL)-3-(5-NITRO-2-FURYL)ACRYLAMIDE emits toxic fumes.
Fire Hazard
Flash point data for 2-(2-FURYL)-3-(5-NITRO-2-FURYL)ACRYLAMIDE are not available but 2-(2-FURYL)-3-(5-NITRO-2-FURYL)ACRYLAMIDE is probably combustible.
Toxicology
AF-2 was legally approved for use in Japan in 1965 and was added to soybean curd (tofu), ham, sausage, fish ham, fish sausage, and fish paste (kamaboko). The safety-testing data on which the compound was approved were those obtained for acute and chronic toxicity for two years and reproductive potential for four generations using mice and rats. At the time, no attention was paid to mutagenicity. In 1973, AF-2 was proved to be mutagenic in various microbial test systems. The mutagenicity of this food additive strongly suggested its carcinogenicity and the risk of its use as a food additive. Within a year or two after the discovery of its mutagenicity, the actual carcinogenicity of this chemical was demonstrated in animal studies.The mechanism of carcinogenesis is not yet clear, but a close relation between carcinogens and mutagens has been demonstrated. AF-2 was the first example of compound that was shown to be a carcinogen. The fact that AF-2 was discovered first to be mutagenic proved the value of mutagenicity testing as a screening method for carcinogens.
