ADDA

Acid Chlorides and Acid Anhydrides of Aromatic Adda, Table IV, 187. Aliphatic Esters, Table III, 106. 

Readions. — i. Adda few chops of the acid solution or solution of the calcium salt to a few c.c. of ammonia-silver nitrate and warm in hot water. A silver mirror is deposited. 

Nodularia spwnigena has also been shown to produce a peptide with hepato-toxic activity. The more recent reports come from Australia (76), the German Democratic Republic (77), Denmark (78), Sweden (79), and Finland (80,81). Recently structure information on Nodularia toxin has been presented by Rinehart (97) for waterbloom material collected in Lake Forsythe, New Zealand, in 1984 by Eriksson et al. (81) from waterbloom material collected in the Baltic Sea in 1986, and Runnegar et al. (82) for a field isolate from the Peel Inlet, Perth, Australia. Structure work by Rinehart, Eriksson, and Runnegar all indicate that the peptide is smaller than the heptapeptide toxins. Rinehart s work (97) indicates the toxin is a pentapeptide with a similar structure to the heptapeptides and containing fi-methylaspartic acid, glutamic acid, arginine, dehydrobutyrine, and ADDA (MW 824). 

ADDA = 3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid... 

Wright CW, Addae-Kyereme J, Breen AG, Brown JE, Cox MF, Croft SL, Gokcek Y, Kendrick H, Phillips RM, Pollet PL (2001) J Med Chem 44 3187... 

Phenol has been reported at concentrations of 7 and 28.6 ppm in smoked summer sausage and smoked pork belly, respectively (EPA 1980), and was identified but not quantified in mountain cheese (Dumont and Adda 1978), fried bacon (Ho et al. 1983), fried chicken (Tang et al. 1983), and black fermented tea (Kaiser 1967). Phenol has also been found in honey at concentrations ranging from 0 (detection limit 0.1 ppm) to 19 ppm (Spoms 1981). It was present each time the honey was collected with phenol-treated boards. 

Dumont JP, Adda J. 1978. Occurrence of sesquiterpenes in mountain cheese volatiles. J Agric Food Chem 26 364-367. 

The most convenient synthetic approach to compound 1, acrylamidobutyraldehyde dialkyl acetal (ADDA), Is shown In Scheme 2. 

Honomer Selection. In practice the amide/blocked aldehyde precursor 1 (ADDA) proved more readily accessible than 2. The two forms were completely Interconvertible and equally useful as self-and substrate reactive crosslinkers (6). In our addition polymer systems, the acrylamide derivative 1 (R=CH3) provided a good blend of accessibility, physical properties, and ready copolymerizablllty with most commercially Important monomers. Structure/property relationships for other related monomers will be reported elsewhere. 

Hexanone has been identified among the natural volatile components of several foods including blue and Beaufort cheeses, nectarines, roasted filberts, and chicken muscle (Day and Anderson 1965 Dumont and Adda 1978 Grey and Shrimpton 1967 Kinlin et al. 1972 Takeoka et al. 1988) levels were not stated in these reports. It has also been detected in milk and cream at concentrations ranging from 0.007 to 0.018 ppm (7-18 ppb) and in bread (Lande et al. 1976). Because few quantitative data are available, it is not known if food is an important source of human exposure to 2-hexanone. 

Pyridine has been isolated in the volatile components from cooked beef ( sukiyaki ) in Japan (Shibamoto etal., 1981), fried chicken in the United States (Tang et al., 1983), fried bacon (Ho et al., 1983), Beaufort cheese (Dumont Adda, 1978), black tea aroma (Vitzthum et al., 1975) and coffee aroma (Aeschbacher et al., 1989). 

These natural toxins are heptapeptides produced by cyanobacteria, which are associated with algal blooms. These substances are a hazard to wild and farm animals and sometimes humans who come in contact with contaminated water. There are a number of these toxins, some of which such as microcystin LR are hepatotoxic, causing damage to both hepatocytes and endothelial cells. The toxins have some unusual structural features, incorporating three D-amino acids and two very unusual ones, namely, methyldehydro alanine (Mdha) and amino-methoxy-trimethyl-phenyl-decadi-enoic acid (Adda) (Fig. 7.26). 

Figure 7.26 The structure of the hepatotoxic cyclic heptapeptide microcystin LR. L-Arginine and L-leucine are variable amino acids. The reactive unsaturated group is indicated by the star. Abbreviations Adda, amino-methoxy-trimethyl-phenyl-decadienoic acid Mdha, methyldehydro-alanine Masp, methyl D-/so-aspartate D-Glu, D-/soglutamate D-Ala, D-alanine.

Adda, J., Blane-Platin, E., Jeuenet, R Grappin, R., Mocquot, G., Paujardieu, B. and Ricordeau, G. 1968. Trial of the infrared milk analyzer. Lait 48, 145-154. 

Amino acids are generally not considered to be important flavor components of several varieties of cheese, although they are important precursors of a variety of flavor components volatile sulfur compounds, amines, aldehydes, and ammonia (Adda et al. 1982 Aston and Dulley 1982 Forss 1979 Langsrud and Reinbold 1973). Free proline levels in Swiss cheese are important in producing the typical sweet cheese flavor. Cheeses with a proline content of < 100 mg/100 g cheese lacked the sweet flavor, while levels of >300 mg/100 g produced a cheese of excessive sweetness (Mitchell 1981). 

Adda, J., Gripon, J. C. and Vassal, L. 1982. The chemistry of flavour and texture generation in cheese. Food Chem. 9, 115-129. 

Dumont, J. P., Roger, S. and Adda, J. 1975. Identification of a nitrogenous heterocyclic compound responsible for a potato-like off-flavor in Gruyere de Comte. Lait 55, 479-487. 

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