Mandelonitrile amygdalin

Glucose mandelonitrile Amygdalin Yeast maltase Emulsin Emmerling (1901) Fischer Armstrong (1902)... 

U8 C, (-l-)-or (-)- m.p. 133X. Occurs combined in the glucoside amygdalin. Prepared by hydrolysis of mandelonitrile (ben-zaldehyde cyanohydrin). It is administered in large doses in the treatment of urinary infections. 

Benzaldehyde Cyanohydrin. This cyanohydrin, also known as mandelonitrile [532-28-5] is a yellow, oily Hquid, insoluble in water, but soluble in alcohol and diethyl ether. Mandelonitrile is a component of the glycoside amygdalin [29883-15-6] a precursor of laetdle [1332-94-7] found in the leaves and seeds on most Prunus species (plum, peach, apricot, etc). In 1832, mandelonitrile was the first cyanohydrin to be synthesized. 

Mandelic acid is best prepared by the hydrolysis of mandeloni-trile with hydrochloric acid. The mandelonitrile has been prepared from amygdalin, by the action of hydrocyanic acid on benzaldehyde, and by the action of sodium or potassium cyanide on the sodium bisulfite addition product of benzaldehyde. ... 

Mandelonitrile glycosides (cyanoglycosides) e.g. amygdalin, pninasin, taxiphyllin, vicianin... 

Prunus armeniaca L. Xing Ren (Apricot) (kernel) Amygdalin, prunasin, fatty acids, mandelonitrile (enzyme amygdalase can hydrolyze amygdalin to produce cyanic acid).33 53 Stimulate respiratory center reflexively and produce a tranquilizing effect. 

Numerous oligosaccharides occur naturally,170 an example being amygdalin (D-mandelonitrile-/3-glucosido-6-/3-D-glucoside) obtained from... 

Note. The name iaetrile is frequently used to describe amygdalin but it has also been used to describe /-mandelonitrile-) -glucuronide, a substance which may be derived from amygdalin. 0-(6-0-)5-D-Glucopyranosyl-)S-D-glucopyranosyl)-D-mandelo-nitrile... 

During the late 1950s, and for about 20 years afterwards, laetrile (1-mandelonitrile-beta-glucuronoside), which is related to amygdalin, was touted as a cure for cancer (http //www.quackwatch.org/01QuackeryRelatedTopics/ Cancer/laetrile.html). However, in 1982 Arnold Reiman, then Editor of the New England Journal of Medicine, pronounced that Laetrile has had its day in court. The evidence, beyond reasonable doubt, is that it doesn t benefit patients with advanced cancer, and there is no reason to believe that it would be any more effective in... 

Emxdsin (synaptase), found in the seeds of the Bitter Almond, Cherry Laurel leaves, in the barks of the Wild Black Cherry and Choke Cherry and in other Rosaceous plant parts, in Manihot utilissima, Polygala species, etc., hydrolyzes the glucoside present (either amygdalin or 1-mandelonitrile glucoside) to hydrocyanic acid, benzaldehyde and glucose. 

The addition of hydrogen cyanide to benzaldehyde forms a compound called mandelonitrile. (Rj-Mandelonitrile is formed from the hydrolysis of amygdalin, a compound found in the pits of peaches and apricots. Amygdalin is the principal constituent of laetrile, a compound that was once highly touted as a treatment for cancer. The drug was subsequently found to be ineffective. Is (R)-mandelonitrile formed by attack of cyanide ion on the Re face or the Si face of benzaldehyde ... 

Laetrile is a levorotatoiy mandelonitrile beta-diglucoside that has often been used as a synonym for chemically related amygdahn. Amygdalin was first isolated from bitter almonds by two French scientists in 1830. It is also a constituent of lentils, lima beans, cashews, brown rice, and millet. The kernels of the apricot, peach, or bitter almond are the commercial source for its productioir It was known as a cancer medicine in Russia as early as 1845, and its first reported use in the U.S. was during the 1920s. " ... 

Treatment of racemic mandelonitrile with UDP-glucosyl transferase from the fruits and leaves of black cherry, Prums serotina, produces only (/ )-prunasin (19). These preparations did not convert prunasin to the diglycoside amygdalin (20) (Dewick, 1984). 

C14H15NO7 309.275 Obt. by hydrol. of Amygdalin (see 2-Hydroxy-2-phenylacetonitrile) and oxidn. of the resulting L-Mandelonitrile-p-glucoside. Claimed to be an anticancer agent, but there is no rigorous scientific evidence for this. Mp 214-216°. 

Four cyanogenic glycosides (amygdalin, linamarin, prunasin, mandelonitrile) were extracted from apricots and separated on a C g column (2 = 200 nm or pulsed amperometric detection, ] = 0.00 V for 240 ms, = 0.60 V for 60 ms, ) = —0.80 V for 60 ms). For the amperometric analysis, a 0.5 M NaOH solution was fed into the effluent postcolumn. An isocratic 12 min 82/12 water/acetonitrile run or an 8-min 100/0- 40/60 water/acetonitrile gradient was used [1259]. Baseline resolution was achieved using the gradient... 

Since the amygdalin may be synthesized 41) from hepta-O-acetyl-gentiobiosyl bromide and ethyl DL-mandelate by the procedure outlined above, the glycoside is undoubtedly D(levo)-mandelonitrile iS-D-gentio-bioside 42),... 

Similar arguments apply to the asymmetric catalytic racemization of amygdalin, recorded by Smith (133). Amygdalin is the gentiobioside of (-l-)-mandelonitrile. The extreme optical lability of the latter is reflected in the great precautions which have to be taken to avoid its racemization, for the pure crystalline (-b) nitrile is readily racemized by the presence of even a trace of water, probably by a mechanism of the type suggested by Fischer and Bergmann (40) ... 

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