Stigmasterol

From the standpoint of usefulness as a starting material for cortisone syntheses, diosgenin has the advantage over ergosterol in that its side 

The ozonization of stigmasterol (I) to the bisnorcholenic acid (V) has been described sometime ago by Femholz (1933). Chamberlin et al. (1951) succeeded in converting V via the A -Mienic acid (VI) and A -diene (VII) to methyl 3 9-acetoxy-ll-ketobisnorallocholanate (VIII) through precisely the same type of intermediates as outlined in Fig. 14 (VIII — VII — V VI — XII) for ergosterol. Furthermore, Butenandt et oZ. 

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Stigmasterol from soy bean extracts can be selectively ozonolyzed on the side-chain double bond. The 20-formyl group formed is converted to the enamine with piperidine. This can be oxidized to progesterone. 

In milk fat, cholesterol is associated with Hpoproteins in the milk fat globule. It is also a component of animal membranes and controls rigidity and permeabihty of the membranes. Cholesterol has interesting surface properties and can occur in Hquid crystalline forms. Plants contain sterols such as P-sitosterol [83-46-5] (4b) or stigmasterol [83-48-7] (4c). Their functions in plant metaboHsm are not yet well understood. Analysis of sterols has proven useful for detection of adulteration of edible fats (9). 

Oil CAS Registry Campesteiot Number [474-62-4] Stigmasterol [83-48-7] p-Sitosterol [83-46-5] A -Avenasterol A -Stigmasterol [83-45-4]... 

Many selective epoxidations are possible with polyunsaturated steroids. In general, oc, -unsaturated ketones are not attacked by peracid, although linear dienones react slowly at the y,5-double bond. Aw-Chloroperbenzoic acid is the reagent of choice for this reaction.When two isolated double bonds are present in the steroid nucleus, e.g. (27) and (30), the most highly substituted double bond reacts preferentially with the peracid. Selective epoxidation of the nuclear double bond of stigmasterol can likewise be achieved.However, one exception to this general rule has been reported [See (33) (34)]. ... 

A. Molecular Ion Because of low volatility, most steriods are derivatized before analysis by GC/MS. Molecular ions are usually observed for steriods sufficiently volatile to be analyzed underivatized by GC/MS (see Figure 31.1) Some important steroids in urine include estrone, estradiol, estriol, pregnanediol, and 17-ketosteroids. which can be analyzed by GC/MS as the TMS or the MO-TMS derivatives. The plant steroids, such as camposterol, ergosterol. stigmasterol, cholestanol, and sitosterol, are generally analyzed as the TMS derivatives. 

Fig. 1. Relative composition of root microsomal membranes from 24 land races, varieties and breeding lines of rice which differ in their salt resistance. Campesterol, Stigmasterol and Sitosterol as % of total sterols 16 0, 18 1, 18 2 and 18 3 fatty acids as % of total fatty acids Na transport on a relative scale from (1) lowest to (9) highest. Data of D.R. Lachno, T.J. Flowers A.R. Yeo (unpublished).

Tenerife and La Palma, revealed the existence of luteolin and an array of simple phenolic derivatives as well as three known phytosterols, B-amyrin, sitosterol, and stigmasterol. The phenols identified comprised a set of phenylpropanoids myristicin [566] (see Fig. 6.16 for structures 566-573), methyleugenol [567], todadiol [568], todatriol [569], crocatone [570], elemicin [571], apiole [572], and the coumarin scopoletin [573]. The occurrence of these compounds is recorded in Table 6.5. The differences between the two profiles were taken by Gonzalez and his co-workers... 

If simple sample pretreatment procedures are insufficient to simplify the complex matrix often observed in process mixtures, multidimensional chromatography may be required. Manual fraction collection from one separation mode and re-injection into a second mode are impractical, so automatic collection and reinjection techniques are preferred. For example, a programmed temperature vaporizer has been used to transfer fractions of sterols such as cholesterol and stigmasterol from a reversed phase HPLC system to a gas chromatographic system.11 Interfacing gel permeation HPLC and supercritical fluid chromatography is useful for nonvolatile or thermally unstable analytes and was demonstrated to be extremely useful for separation of compounds such as pentaerythritol tetrastearate and a C36 hydrocarbon standard.12... 

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