Mountain ash berry

Malic acid is prepared from the juice of the mountain ash berries by precipitation as the calcium salt. 

Since parasorbic acid was previously isolated by steam distillation of the juice of mountain ash berries (.S), we steam distilled a sample of the cranberry leaf extract, but obtained little 2. The literature reports that before the ash berry juice was distilled, it was treated with calcium hydroxide to precipitate malic acid. Tschesche later showed that such treatment followed by acidification converted the glucoside of parasorbic acid, into the free acid (lactone), 2, (9). This base treatment effects a B-ellmination of the glucose fragment. In the absence of this base treatment, no free parasorbic acid was liberated from the berries. 

When the cranberry leaf extract was treated with calcium hydroxide followed by acidification and extraction with ether, parasorbic acid was indeed isolated. It was identified from the IR and HMR spectra of the crude extract and by identical retention time on two glc columns with an authentic sample of parasorbic acid. We then analyzed samples of the cranberry leaf extract by glc before and after treatment with calcium hydroxide (followed by acidification), samples of parasorbic acid alone, and extract plus parasorbic acid (in the presence of calcium hydroxide followed by acidification). Our results (Table I) show that parasorbic acid from the extract was obtained only upon calcium hydroxide treatment. This result agrees with Tschesche s observations on mountain ash berries. 

By far the most important oxidation of the hexitols is their specific biochemical transformation to ketoses. The history of this reaction dates from the fortuitous discovery of L-sorbose in mountain ash berries by Pelouze in 1852. It was not until twenty years later that Boussin-gault showed that it had arisen by bacterial oxidation of sorbitol. 

Sorbitol is a naturally occurring sugar found in a wide range of fruits. It was first isolated in 1872 from mountain ash berries, and the berries of the Sorbus genus are still the richest source of this chemical [3]. 

In 1852 Pelouze1 isolated a crystalline, sweet organic substance from the fermented and bacterially oxidized juice of the mountain ash berry... 

As early as 1852, as has been mentioned (page 99), Pelouze1 allowed the juice of the mountain ash berry (Sorbus aucuparia L) to ferment... 

Dextro tartaric acid is the ordinary tartaric acid as it is found widely distributed in nature, in grapes, mountain ash berries, pineapples, potatoes and other plants. It crystallizes without water of crystallization in transparent, mono-clinic columns which are easily soluble in water or in alcohol. 100 parts of water at 15° dissolve 132 parts of the acid. It melts at i68°-i70°. In water solution it is dextro rotatory. The chief source of tartaric acid is the juice of the grape, where it is present as the free acid and as the acid potassium salt. In this source it is mostly the dextro variety that is found. It is obtained from the vinasse, or residue which settles out from the juice after it has been expressed. When grape juice ferments, in the formation of wine, the solubility of the acid potassium salt is lessened due to the presence of alcohol and it gradually separates and settles to the bottom iii the form of what is known as lees. These lees are dried or recrystallized once and the product is then known as crude tartar or argol. The crude tartar contains, in addition to the acid potassium tartrate, free tartaric... 

Mountain ash berries parasorbic acid onion, roots ... 

Sorbic CH3CH=CHCH=CHC02H Mountain ash berries... 

According to Gmelin Scheele obtained only a thick brown uncrystallisable syrup, drying to a varnish in warm air , but Scheele does not say this pure crystalline malic acid, Gmelin says, was first prepared by Donovan from mountain-ash berries he called it sorbic acid , but Braconnot showed that it was malic acid, (The modem sorbic acid is a different substance, also present in mountain-ash berries.)... 

Donovan discovered in mountain-ash berries what he called sorbic (malic) acid, which he found in rhubarb stem he afterwards admitted the identity of sorbic and malic acids. He described the preparation of pure potash from carbonate and slaked lime, investigated whether alcohol is a product of fermentation or distillation, preparation of pure silver and of phosphorus, and denied the identity of ordinary (frictional) electricity, voltaic electricity, magneto-electricity, and thermo-electricity. He wrote on alchemical and chemical physicians and the use of hyoscyamus — both in titles only, and on smelting lead, as well as on pharmaceutical and medical subjects in the Dublin Journal of Medicine and Chemistry (1839-46). Donovan invented a gas lamp, a gas table-lamp, a hygrometer, and an apparatus for filtration out of contact with air. Donovan s solution is a i per cent solution of equal weights of arsenious and mercuric iodides used in the treatment of skin diseases. 

Vauquelin, partly in collaboration with Fourcroy, discovered several important organic compounds. They distinguished a number of proximate constituents Yourcroy %principes immediats) in vegetables, such as acids, oils, camphor, gum, resin, tannin, starch, fibre, cork, caoutchouc, and extractive (a product of extraction with cold water and evaporation). Several definite compounds which had previously been obtained but the existence of which was in doubt were confirmed. Among these was malic acid and its salts. Sodium malate (with other salts of organic acids) was obtained by Donald Monro in 1767 and the acid from apples by Scheele in 1785 (see p. 232). The acid and its salts were studied by Fourcroy and Vauquelin. Vauquelin showed that the sorbic acid isolated from mountain-ash berries by Donovan is malic acid (the modern sorbic acid is a different substance) Vauquelin s elementary analysis of malic acid was inaccurate. 

L-Iditol ( sorbi rite ) appears to be the rarest of the naturally occurring hexitols. It has been isolated only from the mother liquor after removing sorbitol by fermenting the juice of the mountain-ash berry Sorbus aucu-paria). It was at first thought to be an octitol, but Bertrand definitely established it as a hexitol 55). It has been synthesized by the reduction of L-sorbose to sorbitol and L-iditol the sorbitol was removed by fermentation with sorbose bacteria and the nonfermentable L-iditol was isolated as the tribenzylidene derivative. 

A similar family tree could be constructed for the less common ketose sugars, but only fructose, 16.43 vide supra), and sorbose are commonly encountered. Fructose is the sweetest of all the naturally occurring monosaccharides, and hence, high-fructose corn syrup, a mixture of fructose and glucose, is widely used as a sweetening agent for food. Concerns have been raised as it is linked to obesity and diabetes. The natural isomer of sorbose, unusually, is the L-isomer, 16.55 it can be isolated from mountain ash berries or prepared by oxidation of sorbitol, 16.56, and it is used in the commercial synthesis of vitamin C. 

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