Citric acid, organic structure

Citric Acid. Citric acid, whose structure is shown below, is the most important organic acid produced by means of fermentation. 

Alkaloids vary widely in structure, from the simple to the enormously complex. The odor of rotting fish, for example, is caused largely by methylamine, CH3NH2, a simple relative of ammonia in which one of the NH3 hydrogens has been replaced by an organic CH3 group. In fact, the use of lemon juice to mask fish odors is simply an acid-base reaction of the citric acid in lemons with methylamine base in the fish. 

FIGURE 1.1 Structures of organic compounds referred to in the text (a) sucrose (also known as saccharose), (b) dimethyl sulfoxide (DMSO), (c) dimethylformamide (DMF), (d) sorbitol, (e) mannitol, (f) nitrilotriacetic acid (NTA), (g) citric acid, (h) N,N,N, N -fran,s-1,2-diaminocyclohexane-tetraacetic acid (CyTA), (i) saccharic acid, (j) glutamic acid. 

You find them in citrus fruits (citric acid), vinegar (acetic acid), aspirin (acetylsalicylic acid), and numerous other natural and synthetic compounds, as well on numerous organic exams. In this chapter you explore the structure, synthesis, and reactions of these acids and acids like them. 

Two of the three attractant pheromones identified to date are very close structurally to those used in primary metabolism. The biosynthesis of the estolide 5 probably starts from 3-hydroxybutyric acid (4), an intermediate in fatty acid biosynthesis (Fig. 4.3). Condensation of two units furnishes the pheromone 5. The formation of cupilure (3 Fig. 4.2) can be easily explained by two methylations from ubiquitous citric acid. Both compounds are unlike any known insect pheromones, whereas the third known attractant pheromone (ketone 1 Fig. 4.1), bears some resemblance to some insect pheromones. A proper comparison of the differences and similarities between insect and arachnid pheromones will require the identification of representative compounds from most of the families of both groups of organisms. 

The principal organic acids in grape are L(+)-tartaric, L(—)-malic, shikimic and citric acid. Gluconic, 2-keto-D-gluconic and mucic acids are present in rot grapes as metabolites of Botrytis Cinerea. The structures of these compounds are reported in Figure 1.2. 

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