Aliphatic alcohols sterols

Unsaponifiable Matter in Fats and Oils, Including Marine Oils (Ca bb-5, 3) determines substances dissolved in fats and oils that cannot be saponified (turned into sodium salts) by the usual caustic treatment, including higher aliphatic alcohols, sterols, pigments, and hydrocarbons. This method is not suitable for marine oils or feed grade fats. 

Chemically wool wax is a complex mixture of esters, diesters and hydroxy esters of high molecular weight lanolin alcohol and acids. The lanolin alcohol consists of three main types - aliphatic alcohols, sterols (such as cholesterol) and trimethyl sterols (such as lanosterols). The lanolin acid consists of four main types - normal, iso, anteiso and hydroxy acids. On exposure to the environment wool readily undergoes auto-oxidation. The reaction product (oxidised wool wax) be-... 

R Lanuzza, G. Micali and G. Calabro, On-line HPLC-HRGC coupling and simultaneous transfer of two different LC fractions determination of aliphatic alcohols and sterols in olive oil , 7. High Resolut. Chromatogr. 19 444-448 (1996). 

The active constituents in saw palmetto berries are not well defined. Phytosterols (eg, B-sitosterol), aliphatic alcohols, polyprenic compounds, and flavonoids are all present. Marketed preparations are dried lipophilic extracts that are generally standardized to contain 85-95% fatty acids and sterols. 

Recently Amelio et al. (7) described a method which may find routine applications and which makes use of SPE for the separation and clean-up of the unsaponifiable from olive oil, from which the aliphatic alcohols are separated by means of HPLC (besides sterols and the two triterpenic dialcohols erythrodiol and uvaol). The alkanols are then derivatized and analyzed by means of HRGC. The use of an autosampler and a fraction collector for use with HPLC permits a considerable automatization of the analysis. (Reprinted from Ref. 1, p. 581, by courtesy of Marcel Dekker Inc.)... 

The analysis of lanolin has concentrated on the lanolin alcohols (the unsaponifiable fraction of lanolin) and lanolin acids produced by hydrolysis rather than the esters in lanolin itself.20 Lanolin alcohols belong to three major groups (1) 69 aliphatic alcohols from C12 to C36, (2) sterols (cholesterol and dihydrocholesterol), and (3) trimethyl sterols (lanesterol, dihydrolanesterol, agnosterol, and dihydroagenosterol).21 The latter have been incorrectly termed triterpenoids. The relative proportion of each group is 22% (w/w) aliphatic alcohols, 35% (w/w) sterols, and 38% (w/w) trimethyl sterols.8... 

Three other GC analyses now used in authentication, largely for olive and other oils which should not be refined or solvent extracted, are the determination of waxes, aliphatic alcohols, triterpene alcohols (uvaol and erythrodiol), and stigmastadiene and other sterol-dehydration products (EEC, 1991). These analyses are used at present not to detect adulteration with other oils, but with solvent-extracted or refined oils. However, it is possible that, with solvent-extracted oils, wax, aliphatic alcohol and terpene alcohol compositions, could prove useful in differentiating or detecting different oils. 

The method applied consists in a prior, basic hydrolysis (saponification) of the oil sample, followed by thin layer chromatography (TLC) fractionation of the classes of compounds, namely hydrocarbons, tocopherols, long-chain aliphatic alcohols, triterpenic alcohols, methyl sterols, sterols and triterpenic dialcohols. This procedure loses all information about the combination of polycyclic triter-penes with fatty acids. 

The lipophilic fraction, extractable with nonpolar solvents (ethyl ether, dichloromethane, etc.) consists mainly of fats, waxes, terpenes and terpenoids, and higher aliphatic alcohols (cf. Sections 5.3.1 and 5.3.2). Terpenes, resin acids, and sterols are located in the resin canals present in the bark and also occur in the cork cells and in the pathological exudate (oleore-sin) of wounded bark. Triterpenoids are abundant in bark /3-sitosterol occurs in waxes, as an alcohol component, and the cork cells in the outer bark (periderm) of birch contain large amounts of betulinol (cf. Fig. 5-6). 

The unsaponifiable fraction of fats consists of sterols, terpenic alcohols, aliphatic alcohols, squalene, and hydrocarbons. The distribution of the various components of the unsaponifiable fraction in some fats and oils is given in Table 2-19. In most fats the major components of the unsaponifiable fraction are sterols. Animal fats contain cholesterol... 

Oils Hydrocarbons Squalene Aliphatic Alcohols Terpenic Alcohols Sterols... 

The replacement of OH by F in aliphatic alcohols has been extended to sterols.24 The trimethylsilyl ether (62) of pregnenolone on treatment with PhPF4 in methylene chloride produced as the sole isolated product (70%) the A5-3/3-fluoride (63). Pregnenolone acetate (64) reacted with a lead tetra-acetate-hydrogen fluoride mixture [Pb(OAc)4-12HF] in methylene chloride at — 50 °C to yield the 5a,6a-difluoride (65) (20%) and a product (66) of rearrangement (70%).25... 

Minor Components. The carotenoids, tocopherols, sterols, phosphatides, triterpe-nic, and aliphatic alcohols form the minor constitutents of palm oil. Though present in less than 1 % altogether in palm oil, nevertheless they play a signihcant role in the stability and rehnability of the oil, in addition to increasing the nutritive value of the oil. 

Other Components of the Unsaponifiable Matter The unsaponifiable matter in a cmde regular sunflower oil is usually in the range of 0.5-1.5% (9, 17), or lower than 15 g/kg according to the Codex-Stan 210-1999. In addition to sterols (around 2.4. 6 g/kg) and tocopherols and tocotrienols (0.4-1.5 g/kg), there are minor components of sunflower oil. Aliphatic compounds and terpenoids occur naturally in oils. Of the terpenoid family, squalene is the most widely occurring compound. The occurrence of squalene in regular sunflower oil is fairly low 0.008-0.019% (5) or 15-20 mg/100 g (9). The aliphatic alcohol content is 100-mg/lOO-g oil (9). 

High aliphatic alcohols and wax esters in which aliphatic alcohols or sterols are esterified to fatty or phenolic acids are also present in cmde vegetable oils at low levels and are partially removed in the winterization process during oil refining. Waxes, mainly esters of long-chain saturated fatty acids and a monounsaturated alcohol, especially eicosenoic alcohol, are found in crude vegetable oils such as olive, sunflower, soybean or peanut but are absent from com or rice bran oils... 

Crude palm oil is rich in minor components such as carotenoids, tocopherols, tocotrienols, sterols, phospholipids, triterpene alcohols, squalene, aliphatic alcohols and aliphatic hydrocarbons (Goh et al. 1985). The major components of interest are the carotenes, tocopherols, tocotrienols, sterols and squalene (Table 3.10). Carotenes and tocopherols are antioxidants and stabilise the oil against oxidation. During refining, the bleaching and steam deodorisation processes partially remove some of these valuable components. The amounts retained in the refined oils depend on the conditions of refining. 

The various classes of minor constituents can be divided into two groups. The first group consists of fatty acid derivatives such as mono- and diacylglycerols, phospholipids, waxes and esters of sterols. The second group includes classes of compounds not related chemically to fatty acids hydrocarbons, aliphatic alcohols, free sterols, tocopherols, chlorophylls, carotenoids and polar compounds such as tyrosol and hydroxytyrosol. 

It was of interest to examine how the vegetation which grows in polluted wetlands contributes to their additional purification. For that purpose plant samples, after preliminary preparation, were extracted in an Soxlet s apparatus using a mixture of methanol/chloroform. After that the extracts were let through a column filled with aluminum oxide and by Thin Layer Chromatography were separated to three fractions sterols, terpenic and aliphatic alcohols and hydrocarbons. The hydrocarbon fractions were analyzed by Gas Chromatography and Mass Spectrometry. 

In his 1968 review, Stedman (3797) divided the alcohols into three categories, namely, alcohols, sterols, and oxygenated isoprenoid constituents. The latter category contained constituents other than those with an alcoholic hydroxyl group, for example, farnesyl acetone (a ketone), solanach-romene (a phenol), the tocopherols (phenols), and the levan-tanolides and levantenolide (ether-lactone combinations). In the category usually considered alcohols, Stedman listed a total of twenty-five alcohols (fifteen aliphatic, two aromatic, five polyols, and three cyclic). 

Olive oil is often illegally adulterated with other less expensive vegetable oils. Oils widely used for this purpose include olive pomace oil, corn oil, peanut oil, cottonseed oil, sunflower oil, soybean oil, and poppy seed oil. °° Among the varions chemical and physical methods employed toward the detection of the adulteration of olive oil by low-grade olive oils and seed oils are (a) Sterol analysis (presence of stigmasterol and 3-sitosterol), (b) alkane analysis (C27, C29, and C31), (c) wax and aliphatic alcohol analysis, (d) fatty acids/(with HPLC) trans fatty acid, and (e) Triacylglycerol. 

Nasri, N., Fady, B., and Triki, S., Quantification of sterols and aliphatic alcohols in Mediterranean stone pine Pinus pinea L.) populations, J. Agric. Food Chem., 55, 2251-2255, 2007. 

The triglyceride composition is summarized in Tables 3.142 and 3.143. Unsaponifiable components occur at levels of 0.2-1% of the oil and include hydrocarbons, aliphatic alcohols, triterpene alcohols (Table 3.147), sterols (Tables 3.145, 3.146 and 3.50) and tocopherols (Table 3.51). jS-Carotene and lutein are the major pigments, their level decreasing in the oil as the seed matures. Changes in the major lipid classes during maturation have been studied (Pattee et aL,1969 Sanders, 1980). Oleic acid increases as maturation progresses. 

The unsaponifiable matter includes lipids of natural origin such as sterols, higher aliphatic alcohols, pigments, hydrocarbons as well as any foreign organic matter non-volatile at 103 °C (e.g. mineral oils). 

Lanolin steryl ester determinations Lanolin is the wool grease secreted by the sheep sebaceous glands, and represents a complex mixture of high molecular mass lipids, including fatty acids and alcohols, sterols, hydroxyacids, diols, and aliphatic and steryl esters. Lanolin is widely used in cosmetic and pharmaceutical formulations. The study of minor lipids... 

Terpenic and aliphatic alcohols are also present in grapeseed oil from about 7 to 24% of the unsaponifiable matter. The straight chain alcohols from 20 to 28 carbons have been identified as well as p-amyrin, cycloartenol, a-amyrin and 24-methylenecycloartanol (Capella et al., 1979b). Methyl sterols are present from 7 to 13% of the unsaponihables and contain among others obtusifoliol, gramisterol and citrostadienol. Sterol and terpenic dialcohols comprise up to about 45% of the unsaponifiable material. The major sterols identified are campesterol, stigmasterol (about... 

Sterols from animal sources are dominated by cholesterol, which is obtained from the alcohols in wool wax (lanolin) [5]. This alcohol contains numerous products of which sterols compose approximately 80% the rest made up of various aliphatic alcohols. The lanolin alcohols are used in many different applications, including raw materials for surfactants. However, it appears that in only a few cases the cholesterol is isolated and used for surfactant production. 

Description. This class of surfactants essentially covers ethoxylated derivatives of lanolin (wool fat) and castor oil. Lanolin is the generic name of a wax containing a complex mixture of esters and polyesters of high-molecular-weight alcohols (aliphatic, steroid, and triterpenoid) and fatty acids (saturated, unsaturated, hydroxylated, and non-hydroxylated). The ethoxylation is carried out on fractionation products of lanolin (lower aliphatic alcohols and sterols). 

Com oil is primarily consists of triacylglycerols (> 95%) and secondarily free fatty acids, mono- and diacylglycerols, and several lipid compoimds such as hydrocarbons, sterols, aliphatic alcohols, tocopherols, and pigments (Gunstone, 2011). 

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