Cholesterol lanolin alcohols

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... 

The ability of lanolin alcohols to deliver active substances to the skin is partly due to their surface activity.15 Lanolin alcohols, which contain a high proportion of cholesterol, have a high surface activity and are able to reduce the interfacial tension of a mineral oil-water system from 52.5 to 5.0 dyn/cm.8,53 Even at low levels, cholesterol can reduce the interfacial tension of emulsions and dispersed systems.8,54... 

Cholesterol hydrogenated lanolin lanolin, hydrous lanolin alcohols modified lanolin. 

Lanolin alcohols is a crude mixture of steroidal and triterpene alcohols, including not less than 30% cholesterol, and 10-13% isocholesterol. The USPNF 23 permits the inclusion of up to 0.1% w/w of a suitable antioxidant, while the PhEur 2005 specifies that lanolin alcohols may contain up to 200 ppm of butylated hydroxytoluene as an antioxidant. 

Lanolin alcohols is prepared by the saponification of lanolin followed by separation of the fraction containing cholesterol and other alcohols. 

Cholesterol lanolin lanolin, hydrous petrolatum and lanolin alcohols mineral oils. 

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-... 

AcetulanCi. Acetylated lanolin alcohols Prepn-Conrad, Muliuk, J. Soc. Cosmet. Chem. 6, 344 (1955), eidem. LS. pal 2,723.334 (I9S5 to American Cholesterol Prod ) Pale yellow, practically odorless liquid Sp gr at 25 0867 Neutral to litmus. Acid no 0 34 Hydroxyl no. 2.0. Saponification no 190.0 Hydrophobic, practically insol in water with no emulsification. Miscible with mineral oil, castor ml, vegetable oils, isopropanol. 95% ethanol, isopropyl mynstale. isopropyl palmiialc. hutyl stearate l F In cosmetic formulations and shampoo. 

Cholesterol and lanolin alcohols are examples of alcohols with cyclic carbon structures (w/o). Cholesterol is used as such. It is suitable in combination with the phospholipids as an emulsifier for the preparation of parenteral emulsions and in liposome technology. The lanolin alcohols are found in wool fat (Adeps lanae) and Eucerinum anhydricum. They are present as w/o-emulsifier in cutaneous preparatiOTis. 

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. 

It is not surprising that the composition of sterols varies depending on the source from which they have been derived. Table 2 shows the composition of sterols from soy oil, tall oil, and lanolin alcohol. Despite the very different sources the molecular structure is fairly similar in all types of sterols. Figure 1 depicts the structure of the most commonly found sterols it should be noted that the most abundant sterols in animal sources (cholesterol) and vegetable sources (sitosterol) differ only by an ethyl group in the hydrocarbon tail of the sterol. 

The aggregation behavior of these surfactants appears to be unusual and requires a deeper analysis. A comparison of the CMC values reported for different polyoxyethylene sterols and polyoxyethylene octylphenols, which have lipophilicities similar to that of cholesterol, is shown in Fig. 2. As the hydrophilicity of the surfactant increases, the trend in the CMC values is quite opposite the CMC values for sterol surfactants are reduced when the number of oxyethylene units is increased, which is contrary to that found for other polyoxyethylene surfactants. The observation of lanolin alcohols can be viewed as an intermediate behavior. At lower numbers of oxyethylene units the CMC trend follows the behavior of sterols, whereas at a higher degree of ethoxylation the behavior becomes dominated by the ethoxylated alcohols. These comprise only about 20% of the weight but approximately 40% of the molar composition. 

FIG. 2 Critical micelle concentration (CMQ of polyoxyethylene derivatives of (-0-) cholesterols (from [11,13]), ( ) lanolin alcohols [10], (x) phytosterol [16], ( ) cholesteryl carbonate [24], and (A) octylphenol [21]. Increasing the length of the polyoxyethylene chain causes a decrease in the CMC for the sterol derivatives, initially causes a decrease in the CMC (minimum at 15 oxyethylene imits) for the lanolin alcohols and then an increase, while for the octylphenol derivatives the CMC increases with increasing hydrophilicity. 

Examples of nonionic emulsifiers are polyoxyethylene, polyoxypropylene, fatty alcohol ether, polyethylene (or polypropylene), glycol fatty acid esters, lecithin, lanolin, cholesterol, etc... 

Cholesterol is a major component of the alcoholic fraction of lanolin.15 It is also an essential constituent of the lipids of the stratum corneum, which form the epidermal permeability barrier.29,30 However, the other stratum corneum lipids (ceramides and fatty acids) are different from those of lanolin. Clark and Steel have suggested that the a-, ()-, and m-hydroxy lanolin acids are esterified with diols to form diesters with two long acyl chains, which are similar to those found in ceramides.16,31,32... 

Water-in-oil emulsions traditionally contain surfactants of natural origin such as cholesterol, wool fat, wool alcohols, lanolin, divalent salts of fatty acids soaps, calcium oleate and/or synthetic agents of low hydrophilic-lipophilic balance (HLB) (indicating high lipophilicity), such as Spans (fatty acid esters of sorbi-tan). An example of such a product is Oily Cream B.P. which consists of a 1 1 mixture of wool alcohols and water. 

The most familar animal wax is probably lanolin, which is obtained from the wool of the sheep. It consists primarily of esters of Cig-Cie alcohols and fatty acids, sterols (cholesterol), and terpene alcohols. It is frequently used in topical preparations. Until recently, spermaceti was another commonly used animal wax. Spermaceti is obtained through the precipitation of the head oil from the sperm whale on cooling. It consists primarily of cetyl palmitate. Because of public... 

Solubility soluble in acetone, chloroform, ethanol (95%), ethyl acetate, fats, fatty alcohols, fixed oils, liquid hydrocarbons, toluene, and waxes. Dissolves many waxes, cholesterol, or lanolin. Practically insoluble in glycerin, glycols, and water. 

Definition Mixture of organic alcohols obtained from hydrolysis of lanolin main constituents are cholesterol, lanosterol, dehydrolanosterol, various aliphatic alcohols... 

Waxes are esters formed from long-chain (16 or more carbon atoms) fatty acids and long-chain alcohols. The general formula of a wax is the same as that of a simple ester, RGOOR, with the qualification that R and R are limited to alkyl groups with a large number of carbon atoms. Natural waxes are usually mixtures of several esters. Wax coatings on leaves help to protect the leaves from disease and also help the plant to conserve water. The feathers of birds are also coated with wax. Our ears are protected by wax. Several natural waxes have been used in consumer products. These include carnauba wax (from a Brazilian pahn tree), which is used in floor waxes, automobile waxes, and shoe polishes, and lanolin (from lamb s wool), which is used in cosmetics and ointments. Lanolin also contains cholesterol. 

Fancol 707. See PPG-30 cetyl ether Fancol ACEL See Acetylated lanolin Fancol CA. See Cetyl alcohol Fancol CB Extra, Fancol CB. See Cocoa (Theobroma cacao) butter Fancol CH. See Cholesterol Fancol CH-24. See Choleth-24 Fancol CO-30. See PEG-30 castor oil Fancol DL. See DL-Panthenol Fancol HCO-25. See PEG-25 hydrogenated castor oil... 

Octyl isononanoate Octyl stearate Oleamide DEA Oleamide MIPA Oleth-3 Oleyl alcohol PEG-2 stearate PEG-8 stearate Pentaerythrityl tetracaprylate/tetracaprate Pentaerythrityl tetraisostearate lubricant, pharmaceuticals Acetylated lanolin Acetylated mono- and diglycerides of fatty acids Apricot (Prunus armeniaca) kernel oil Behenic acid Butylene glycol dicaprylate/dicaprate Butyl myristate Cl 8-36 acid glycol ester C18-36 acid triglyceride Canola oil Cl0-30 cholesterol/lanosterol esters Ceteareth-6 Ceteth-16 Ceteth-20 Cetyl lactate Cocoyl sarcosine... 

Lanolin, wool fat, wool wax the fatty or more correctly waxy substance secreted by the skin of the sheep, m-p. 36-42°C. L constitutes up to 50% of the wei t of raw wool. It is a complicated mixture of fatty adds, alcohols, fats and waxy substances. The latter are chiefly esters of steroids (cholesterol and lanoster-ol) and long chain aliphatic alcohols with higher fatty acids, which are 6-hydroxylated or carry a terminal isopropyl or isobutyl residue. L. is obtained from raw wool by extraction with organic solvents or soap solutions. It forms water-in-oil suspensions, and is used widely in the pharmaceutical and cosmetics industries (as Adeps Lanae) as an ointment base. 

The industrially important animal waxes include the wax on the surface of wool, which is obtained as a by-product of wool scouring, and after bleaching and purifiying this wax is termed lanolin. The alcohol components are mainly triterpenic (alicyclic) alcohols, such as lanosterol (see 3-92), cholesterol (see 3-114) and related steroids. Lanolin is used in the manufacture of cosmetics and pharmaceuticals. 

Wool wax, or lanolin, comes from the fleece of sheep. It is a mixture of esters and free alcohols, including the sterols cholesterol and lanosterol. 

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