Glucoside, mandelonitrile

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. 

Kovacs, M. F. "Dhurrin (p-hydroxy mandelonitrile-B-O-glucoside) An allelopath Identified In johnsongrass (Sorghum halapense (L.) Fers.) rhizome exudates", Ph.D. Thesis. University of Maryland, College Park, MD. 1972. 

Salicin is an (9-glycoside of a phenol, namely salicyl alcohol. Salicin is a natural antipyretic and analgesic found in willow bark, and is the template from which aspirin (acetylsalicylic acid, see Box 7.13) was developed. Prunasin from cherry laurel is an example of a cyanogenic glycoside, hydrolysis of which leads to release of toxic HCN (see Box 7.7). It is the (9-glucoside of the alcohol mandelonitrile, the trivial name for the cyanohydrin of benzaldehyde. It is the further hydrolysis of mandelonitrile that liberates HCN. 

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

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. 

Examples of LLC phases for enzyme stabilization and bio catalysis include the micellar and LLC phases water (or glucose in water)/oclanol/octyl-/3-D-glucoside LLC system for accelerating /3-D-glucosidase-calalyzed hydrolysis of octyl-/ -n-glucoside to form glucose and octanol [108] and the use of LLC phases of numerous commercial surfactants to accelerate the (S)-hydroxynitrile lyase-catalyzed synthesis of (S)-mandelonitrile [109]. 

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°. 

Sambunigrin (D-mandelonitrile glucoside) from the leaves of the elder tree—Sambucus nigra (Caprifoliaceae)—is isomeric to prunasin. 

The isolation of the glucoside of cuminaldehyde cyanohydrin (XCVI) from the millipede Polydesmus vicinus L. [732] is of great interest since, like the established function of mandelonitrile in Apheloria corrugata [733-735] it could represent a means of delivery of hydrogen cyanide. 

The enzymic hydrolysis by almond emulsin (jS-glucosidase component) requires the preliminary hydrolysis of the gentiobiose into glucose and mandelonitrile jS-D-glucoside before the aglycon group is removed ( ), but the hydrolysis by other enzymes may follow a different course. 

Power F B, Moore C W 1909 The constituents of the bark of Prunus serotina. Isolation of 1-mandelonitrile glucoside. J Chem Soc 95 243-261... 

Mandelonitrile glucoside, under the action of prunase (another... 

Bark contains condensed tannins, prunasin (d-mandelonitrile glucoside) emulsin eudesmic acid (3,4,5-trimethoxybenzoic acid) /i-couma-ric acid scopoletin sugars andothers (karrer). Fruit skin contains capulin anthocyanins. Prunasin is a cyanogenic glucoside that is hydrolyzed by the enzyme prunase into hydrocyanic acid (HCN, prussic acid). 

Maltotetraose Malvidin chloride Mandelic acid Mandelonitrile glucoside... 

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