Three closely related 4-hydroxy-3(2H)-furanones have been found in a range of highly cooked foodstuffs
where they are important flavour compounds with aroma threshold values as low as 20 μg kg−1 water
(approximately 0.14 μmol l−1). The compounds are formed mainly as a result of the operation of the
Maillard reactions between sugars and amino acids during heating but one compound, 5-(or 2)-ethyl-2-(or
5)-methyl-4-hydroxy-3(2H)-furanone, appears in practice to be produced by yeast, probably from a
Maillard intermediate, during the fermentation stages in the production of soy sauce and beer. The
compounds are also important in the flavour of strawberry, raspberry, pineapple and tomato but the route
of biosynthesis is unknown. Two 3-hydroxy-2(5H)-furanones, emoxyfuranone and sotolon, which are
produced spontaneously from amino acids such as threonine and 4-hydroxy-L-leucine are major contributors
to meaty and spicy/nutty flavours in foods. The biosynthesis of 5-(1,2-dihydroxyethyl)-3,4-dihydroxy-
2(5H)-furanone (ascorbic acid, vitamin C) and 5-hydroxymethyl-3,4-dihydroxy-2(5H)-furanone (erythro-ascorbic acid) from sugars in plants and yeast, respectively, has been characterized to the enzymic level. After
treatment with chlorine, humic waters contain a range of chloro-furanones, some of which, particularly 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), are powerful mutagens. The furanones which
occur in foods are also mutagenic to bacteria and cause DNA damage in laboratory tests. However, these
compounds are, in practice, very effective anti-carcinogenic agents in the diets of animals which are being
treated with known cancer-inducing compounds such as benzo[α]pyrene or azoxymethane. Two of the food-
derived furanones have antioxidant activity comparable to that of ascorbic acid. A biological function has
been discovered for some of the furanones besides vitamin C. 5-Methyl-4-hydroxy-3(2H)-furanone is a male
pheromone in the cockroach Eurycolis florionda (Walker) and the 2,5-dimethyl derivative deters fungal growth
on strawberries and is an important component of the attractive aroma of the fruit. The red seaweed Delisea
pulchra (Greville) Montagne produces a range of brominated furanones which prevent colonisation of the
plant by bacteria by interfering with the acylated homoserine lactone (AHL) signalling system used by the
bacteria for quorum sensing. In addition, these compounds can deter grazing by marine herbivores. It is
proposed here that the evolved biological function of a number of furanones is to act as inter-organism signal
molecules in several different systems. This has resulted in two coincidental effects which are important for
humans. Firstly, the easily oxidized nature of the furanones in general, which is likely to be an important
property in their functioning as signal molecules, results in both mutagenic and anti-carcinogenic activity.
The balance of these two effects from compounds in the diet has yet to be fully established. Secondly, and
more specifically, the 4-hydroxy-3(2H)-furanones associated with fruit aromas act to attract animals to the
fruit, which ensures seed dispersal. In the case of humans, the coincidental synthesis of some of these
compounds in foods during preparation results in these foods appearing particularly attractive through the
transferred operation of the original signalling mechanisms.