Ox bile

Initial steroid research involved isolation of sterols and bile acids from natural sources. DeFourcroy is generally credited with the discovery of cholesterol [57-88-5] (2) in 1789 (3). In 1848, choHc acid [81-25-4] (3) was isolated from the saponification of ox bile and its elementary composition deterrnined as... 

Choline was isolated from ox bile in 1849 by Strecker. During 1900 to 1920, observations led to interest in the vasodepressor properties of the esters of choline, and in the 1920s it was shown that acetylcholine was presumably the "vagus-substance." The nutritional importance of choline was recognized in the 1930s, when it was found that choline would prevent fatty infiltration of the Hver in rats. Subsequent observations showed that choline deficiency could produce cirrhosis (1) or hemorrhagic kidneys (2) in experimental animals under various conditions. 

Glycocholic Acid.—Fresh ox bile (2-0-2 5 1.) is obtained from a... 

The two most important bile acids, cholic acid C24H40Os and desoxy-cholic acid C24H40O4, occur in ox bile in combination, partly with glycine and partly with taurine as glyco- and taurocholic and glyco- and tauro-desoxycholic acids. The linkage between the amino acids and the bile acids is of an amide nature. On hydrolysis the nitrogenous constituents are split off. 

Ox bile, which contains cholic acid as its principal constituent, provided one of the earliest mammalian sources of steroid raw materials for the commercial manufacture of the androgens. In nature, cholesterol itself is the mammalian precursor of the androgens, the biosynthesis passing through progesterone (XII). 

Ox Bile Extract occurs as a yellow-green powder. It contains ox bile acids, chiefly glycocholic and taurocholic, as sodium salts, equivalent to not less than 45.0% cholic acid, C24H40O5. It is the purified portion of the bile of an ox, obtained by evaporating the alcohol extract of concentrated bile. It is soluble in water and in alcohol. 

Taurine was discovered in 1827 in ox bile, where it is conjugated with the bile acids. It was later shown to be a major excretory product of the sulfur amino acids methionine emd cysteine. Until about 1976, it was assumed that it was a metabolic end-product whose only function was the conjugation of bile acids. In the rat, taurine synthesis accounts for 70% to 85% of total cj teine catabolism. 

Derivation Isolated from ox bile, organic synthesis. 

OX BILE, Fel taurisOn bile is obtained from cattle in slaughterhouses, and contains sodium salts of some 20 conjugated bile acids. Among these, cholic acid and desoxy-cholic acid occur in the ratio 10 1. 

Morphins and derivatives A -methylpiperazine Oils, vegetable and animal medicinal grade—refined and concentrated Opium derivatives Ox bile salts and derivatives bulk, uncompounded Penicillin bulk, uncompounded Physostigmine and derivatives Pituitary gland derivatives bulk, uncompounded Procaine and derivatives bulk, uncompounded Quinine and derivatives Reserpines... 

One such synthesis began with desoxycholic acid (from ox bile), which was laboriously converted to cortisone in 32 steps, many of which were required to transpose the oxygen function from the 12 to the 11 position, to introduce the 17 a-hydroxyl and to construct the a,P-keto arrangement in ring A. Over a 3-year period (1946-1949) some 1,200 pounds of the bile acid laboriously yielded less than 1 kg of cortisone. Workers at the Mayo Clinic (Hensch et al., 1949) reported on their dramatic success in controlling rheumatoid arthritis pain with cortisone. This gave the impetus to find a better way to provide cortisone than by the 32-step synthesis from desoxycholic acid or the laborious extraction from ox adrenals. 

It may be obtained from ox-bile, in which it exists as tlie salt of a conjugate acid from uric acid by the action of hydriodic acid and by the union of formic aldehyde, hydrocyanic acid, and water. It is isomeric with giycolamide ... 

Sodium salt, CMHj,NaOj, sodium cholale. Crystals. Soly in water at t5° > 568.9 g/l. Caution The names "sodium cholate and sodium choleate" are sometimes used for mixtures of bile sails. The term "sodium choleate" is to be preferred for bile salts, see Ox Bile Extract. 

USE Sodium salt is a lipase accelerator. See also Ox Bile Extract. 

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