Maple lactone

In addition to mating-disruption pheromones, there are a number of naturally occurring, nonpheromonal attractants and repellents. Many are typically used as food additives or in cosmetics or perfumes, and are derived from diverse plant and animal sources. Capsaicin [44], the spicy component of chili peppers, is used in several bird, deer, and rodent repellents. Maple lactone [45], a common food additive and flavoring, is used in traps to attract cockroaches with its stale beer odor. Methyl... 

Figure 12.6 Structures of capsaicin, maple lactone, and methyl anthranilate.

USEPA (2009) Maple lactone (2-cyclopenten-1-one, 2-hydroxy-3-methyl) (004049) Fact Sheet http //www.epa.gov/ oppbppdl /biopesticides / ingredients / factsheets/factsheet 0040 49.htm (last accessed 30 April 2010). 

D.68) 2-Cyclopenten-l-one, 2-hydroxy-3-methyl-, 2-hydroxy-3-methylcyclopent-2-en-l-one, 3-methylcyclopent-2-en-2-ol-l-one 80-71-7] 1,2-cyclopentanedione, 3-methyl-, 3-methylcyclopentane-l,2-dione, cyclotene, corylone, maple lactone, nussol [765-70-8] FEMA 2700... 

Synonyms cas 80-71-7 corylon corylone cycloten maple lactone 3-methylcyclopentane-i,2-dione... 

Mapeg S-100. See PEG-100 stearate Mapeg S-150. See PEG-150 stearate Mapeg TAO-15. See PEG-660 tallate Maple lactone. See 3-Methyl-2-cyclopenten-2-ol-1-one... 

Synonyms 2-Cyclopenten-1-one, 2-hydroxy-3-methyl- Cyclotene 2-Hydroxy-3-methylcyclopent-2-enone 2-Hydroxy-3-methyl-2-cyclopenten-1-one Hydroxy-3-methylcyclopent-2-en-1 -one Kentonarome Maple lactone 3-Methylcyclopentan-1,2-dione 3-Methylcyclopentane-1,2-dione 3-Methyl-2-cycl opentene-2-ol-one Methyl cyclopentenolone Methyl-2-cyclopenten-2-ol-1-one Empirical C6Hs02... 

This lactone is the flavoring compound formed by the aging of a-ketobutyric acid (Sulser et al., 1967). The flavor is described as malt, molasses, maple, burnt sugar (Chemisis, 1965), with a strong seasoninglike aroma at a concentration of 0.1 ppm and a taste threshold of 1-5 ppb for Sulser et al. (1972). Manley et al. (1980) reported a maple-like, remarkably persistent curry-like odor and wondered if the enolization or the instability of the compound could be responsible for the two notes. It is a potent odorant of roasted powder and brew of arabica coffee with odor descriptions similar to those of G.12, and an odor threshold of 2-4ng/m , air (Blank et al., 1992a,b), of 7.5 ppb in water (Semmelroch et al., 1995). 

The most Important use of body odors in disease diagnosis relates to the infant diseases involving errors in amino acid metabolism. Strong and unusual odors are manifest in the breath, sweat, and urine of these individuals. Table II summarizes several known acidurias, the amino acids that are not properly metabolized, and the odors associated with the compounds which accumulate and can be detected in the urine ( ). In the case of the Maple Syrup Urine and Oasthouse syndrome, the keto- and hydroxy- acids which have been identified may not be responsible for the observed maple and celery/yeast odors (.9). Alternatively, these odors could be the result of conversion of 2-keto-butyrlc acid to methyl-ethyl-tetronlc acid (Slusser s lactone) which is used as an extender in maple and celery flavors and has a maple syrup-like odor (R. Soukup, personal communication). With these acidurias it is imperative that an immediate diagnosis is made, since corrective diet can prevent the brain damage that results from these diseases. This is readily done on an olfactory basis which can subsequently be supported by gas chromatographic... 

Certain 2-hydroxy substituted y-lactones (3-hydroxy furan-2-ones) derived from ycrotonolactone, however, have a specific odour. Typically 3-hydroxy-4,5-dimethyl-5//-furan-2-one (sotolon) has an aroma resembling fenugreek or curry at higher concentrations, and caramel, maple syrup or burnt sugar at lower concentrations. Sotolon occurs as a mixture of -)- R)-and (-F)-(S)-enantiomers (8-111). The perception threshold of (S)-sotolon (0.8 (xg/1) in a model wine solution was 100 times lower than that of the (l )-enantiomer (89 p-g/l), indicating that mainly (S)-sotolon contributes to the characteristic aroma of wines. The key component of acid protein hydrolysates is the higher... 

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