Fatty Alcohols

Project ID

2760

Category

OPPT

Added on

Oct. 23, 2018, 8:28 a.m.

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Journal Article

Abstract  EfudixA cream or topical 5% 5-fluorouracil (5-FU) is an antimitotic cream used to treat premalignant and malignant skin lesions (1). Although it commonly causes cutaneous irritation, allergic contact dermatitis is uncommon (2). There is only 1 previous report of contact sensitivity from stearyl alcohol in EfudixA cream (3).

Journal Article

Abstract  To evaluate the importance of the terminal carboxy group of the oleic acid molecule in the release of secretin and cholecystokinin (CCK) to plasma, six normal persons were stimulated twice with duodenal perfusates containing either 20 mM oleic acid or 20 mM oleyl alcohol. Oleic acid increased the pancreatic secretion of bicarbonate and amylase and the concentrations of secretin and CCK in plasma and provoked gallbladder emptying. Oleyl alcohol only increased the amylase output slightly, but significantly. It is concluded that the carboxy group of the fat molecule has an important role in triggering the release of secretin and CCK to plasma.

DOI
Journal Article

Abstract  Fifteen organic solvents were examined to determine their biocompatibility for in situ extraction of fermentation products from cultures of the thermophilic anaerobe Clostridium thermohydrosulfuricum . Five solvents (hexadecane, isooctane, kerosene, oleyl alcohol, Shellsol TD) were found to be non-toxic to Clostridium thermohydrosulfuricum . Interfacial tension, phase separation and partition coefficients for ethanol of the biocompatible solvents were compared. With the exception of kerosene, these solvents showed good separation from the aqueous phase. Oleyl alcohol had the highest partition coefficient for ethanol (K sub(D) = 0.34 at 65 degree C) and appears to be suitable for extractive ethanol fermentation.

Journal Article

Abstract  Minimal inhibitory concentrations (MICs) of a series of fatty acids and fatty alcohols against a cariogenic bacterium, Streptococcus mutans, were determined by a tube dilution technique. Among saturated fatty alcohols, tetradecanol and pentadecanol had the highest activity (MIC, 1.56 μg/ml), while among monounsaturated fatty alcohols, 10Z-pentadecenol had the strongest activity (MIC, 0.78 μg/ml). Saturated fatty acids showed relatively weak activity; tridecanoic acid had the highest activity among them (MIC, 12.5 μg/ml). Among unsaturated fatty acids, 10Z-heptadecenoic, 6Z-octadecenoic, 11 Z-octadecenoic and 9Z, 12Z-octadecadienoic acids had potent activity (MIC, 3.13 μg/ml). The antibacterial activities of methyl-branched and hydroxyl fatty acids as well as long chain dicarboxylic acids were also investigated.

Journal Article

Abstract  Animal studies have been carried out on a series of highly branched primary aliphatic alcohols. The alcohols were amyl, hexyl, isooctyl, 2-ethylhexyl, isononyl, decyl, tri-decyl, and hexadecyl. The tests included oral and dermal LD50, eye and skin irritation, and 6-hour vapor exposure. Oral LD50 values in rats ranged from 1.5 to greater than 8.4 gm/kg and did not show a consistent increase with increased molecular weight. Signs of effect were associated with central nervous system depression. Dermal LD50 values in rabbits were all greater than 2.6 or 3.2 gm/kg, the highest dose tested, although percutaneous absorption was seen. Skim irritation was slight to severe and generally inversely related to molecular weight. The C5 through C13 alcohols produced moderate to severe eye irritation; the C16 alcohol produced only slight irritation. Inhalation toxicity was low, with systemic effects seen only with amyl, 2-ethylhexyl, and isononyl alcohols. Some eye, nose, throat, or respiratory tract irritation was seen with each alcohol.

Journal Article

Abstract  1. Several series of structurally related radioactively labelled compounds were administered intraduodenally to rats with cannulated thoracic ducts and the radioactivity appearing in 24-hour thoracic duct lymph measured and identified. 2. Radioactivity appeared in lymph following treatment with simple aromatic compounds, a series of short- and long-chain aliphatic compounds, steroids, a group of drugs, and DDT. In most cases this radioactivity was only a small percentage of the total amount absorbed from the intestinal tract. It is suggested that this appearance of radioactivity in the lymph is due to the distribution of the compounds in the total body water, of which lymph is a part. 3. For compounds which enter lymph more readily (cholesterol, octadecanoic acid, octadecanol and p, p'-DDT), lipid solubility appears to be an important factor, and metabolic alterations affecting lipid solubility can affect the distribution of these compounds within the lipid and aqueous fractions of lymph. The lymphatic absorption of p, p'-DDT is dependent upon the concomitant absorption of lipids from the intestinal tract, and most of the DDT absorbed into lymph is carried in the lipid core of the chyiomicrons.

Journal Article

Abstract  Importance of the field: Recurrent herpes labialis (RHL) is a significant disorder with social and health consequences that affects upwards of 20 – 40% of the adult population. Docosanol is the only FDA-approved topical agent that is available over the counter for management of RHL. Its mechanism of action is unique compared with other available antiviral agents. Areas covered in this review: The authors conducted a comprehensive search of the published preclinical and clinical literature on topical docosanol for RHL. All of the published literature relating to docosanol and its use for the management of recurrent herpes labialis was reviewed, from the first report of docosanol to 31 January 2010. What the reader will gain: The objective of this review was to summarize and critically evaluate the available literature with respect to topical docosanol's mechanism, safety and efficacy in the management of RHL. Take home message: Ten percent docosanol cream is a safe and effective topical treatment for the management of RHL in immunocompetent adults, with essentially equivalent efficacy compared with other available prescription topical antiviral agents. Owing to its unique mechanism of action, there is little to no risk of developing resistance.

Journal Article

Abstract  Repeat applications of an artificial monolayer to the interfacial boundary layer of large agricultural water storages during periods of high evaporative demand remains the most commercially feasible water conservation strategy. However, the interfacial boundary layer (or microlayer) is ecologically distinct from subsurface water, and repeat monolayer applications may adversely affect microlayer processes. In this study, the natural cleansing mechanisms operating within the microlayer were investigated to compare the biodegradability of two fatty alcohol (C16OH and C18OH) and one glycol ether (C18E1) monolayer compound. The C16OH and C18OH compounds were more susceptible to microbial degradation, but the C18E1 compound was most susceptible to indirect photodegradation. On clean water the surface pressure and evaporation reduction achieved with a compressed C18E1 monolayer was superior to the C18OH monolayer, but on brown water the surface pressure dropped rapidly. These results suggest artificial monolayers are readily degraded by the synergy between photo and microbial degradation. The residence time of C18OH and C18E1 monolayers on clear water is sufficient for cost-effective water conservation. However, the susceptibility of C18E1 to photodegradation indicates the application of this monolayer to brown water may not be cost-effective.

Journal Article

Abstract  A 65-year-old non-atopic man presented in 1 July 2012 to the emergency department of our hospital with a well-demarcated severe oedematous and vesicular reaction on the back of his right hand, extending to his wrist and forearm (Fig. 1); on the back of his left hand, he showed only a very discrete papulovesicular itching reaction. Three days previously, he had cleaned his garden shed with ammonia diluted in water by use of a sponge, thereby wearing a rubber glove on his right hand only (Vileda Comfort and Care, Comfort plus, extra-absorbent®; Vileda, Verviers, Belgium), the interior side being coated with a moisturizer, said to contain perfume and chamomile. With the left (ungloved) hand, he had occasionally held the wet sponge. He had noticed that some of the ammonia solution had spilled into the glove, but he had continued cleaning for ∼2 hr without taking it off, without any discomfort. It was only on the next day that the itching, redness and swelling started to develop. The lesions had become really severe, despite using a corticosteroid cream (Fucicort®; Leo, Wilrijk, Belgium). At the emergency unit, the patient received treatment with oral steroids, application of a wet dressing for 15 min twice daily, Diprosone® cream (Schering-Plough, Heist-op-den-Berg, Belgium), and systemic antihistamines and ibuprofen; this was followed by gradual improvement of the skin lesions after 2 weeks; the treatment was further reduced, and a moisturizer was prescribed. However, the patient was seen by us in October, and mentioned that he had stopped using the moisturizer, as it had again produced worsening of his skin lesions. The patient had been patch tested in 2009, and had been shown to be allergic to cetrimide, (a quaternary ammonium compound), isopropanol, iodine, and povidone iodine, which had been considered to be relevant to skin lesions that he had developed during wound treatment of his left elbow following osteosynthesis. The dermatitis had been treated with Fucicort® cream. Later on, he had experienced a skin reaction on his knee following the application of an ointment, the name of which he could not recall. As a retired endive farmer, he had been wearing rubber gloves for > 20 years without any skin problems.

Meetings & Symposia

Abstract  Long-chain alcohols are known to be the precursors of both alkyl and alk-1-enyl moieties of ether lipids in biological systems including the mammalian brain. In recent investigations on the levels of free longchain alcohols in rat brain at different stages of postnatal development, we detected relatively large amounts of 1-docosanol, comprising up to 20% of the total alcohols. Since rat brain ether lipids do not contain alkyl or alk-1 enyl moieties of more than 18 carbon atoms, the metabolism of docosanol relative to other fatty alcohols was investigated. Simultaneous intracerebral injection of (1-14cJdocosanol and [l-14c]octadecenol showed that both alcohols were oxidized to the corresponding fatty acids. However, only octadecenol served as substrate for alkylglycerol synthesis within a 24 hr period. Subcellular preparations of developing rat brain were used to study the reduction of fatty acids of different chain lengths to the corresponding alcohols, and the formation of the ether bond from such alcohols in vitro. Although previous work from this laboratory has shown that a variety of structural analogs of fatty alcohols can serve as alkyl donors in ether lipid biosynthesis, the present data indicate a distinct chain-length specificity for this reaction.

Journal Article

Abstract  The role of oleic acid in the modulation of gap junction permeability was studied in cultured rat astrocytes by the scrape-loading/Lucifer yellow transfer technique. Incubation with oleic acid caused a dose-dependent inhibition of gap junction permeability by 79.5% at 50 mu M, and no further inhibition was observed by increasing the oleic acid concentration to 100 mu M. The oleic acid-mediated inhibition of gap junction permeability was reversible and was prevented by bovine serum albumin. The potency of oleic acid-related compounds in inhibiting gap junction permeability was arachidonic acid > oleic acid > oleyl alcohol > palmitoleic acid > stearic acid > octanol > caprylic acid > palmitic acid > methyloleyl ester. Oleic acid and arachidonic acid, but not methyloleyl ester, increased glucose uptake by astrocytes. Neither-oleic acid nor arachidonic acid increased glucose uptake in the poorly coupled glioma C6 cells. These results support that the inhibition of gap junction permeability is associated with the increase in glucose uptake. We suggest that oleic acid may be a physiological mediator of the transduction pathway leading to the inhibition of intercellular communication.

DOI
Journal Article

Abstract  A 84-days-long experiment was conducted with a view to observe the effects of different feeds on growth and survival of Channa striatus grow-outs to develop a rearing technique for promoting its aquaculture. There were seven treatments (L3HUF, H3HUF, MUSOL, LINOL, MIXOL, SATOL and NATFO), each having two replications, stocked with 20 grow-out having an initial average weight 27.36 +/- A 0.09 to 32.54 +/- A 0.41 g in a circular plastic pools (300 l capacity). The six feeds were formulated with basic ingredients (soybean meal, 41 %; soluble starch, 25 %; casein, 20 %; carboxy methyl cellulose, 2 %; papain, 0.5 %; vitamin and mineral mix, 3.5 %) with iso-energetic (19.3 kJ/g, F1-F6) diets and results were compared with natural food fed fishes. Each diet was hand fed two times daily for 84 days to triplicate homogenous groups of 20 fishes. The fishes fed with live tubificid worms showed significantly better results in terms of weight gain and specific growth rate (%) compared to the rest six treatments. The survival was recorded cent percent in all the treatments. Results showed that the feed efficiency and growth performance significantly (p < 0.05) changed with various types of dietary lipid. At the end of the 84 days study the weight gain was recorded as 51.65 +/- A 0.35, 51.15 +/- A 0.21, 50.95 +/- A 0.35, 53.20 +/- A 0.28, 59.15 +/- A 0.21, 55.53 +/- A 0.41 and 61.44 +/- A 0.24 g for L3HUF, H3HUF, MUSOL, LINOL, MIXOL, SATOL and NATFO respectively. The best growth recorded in natural food fed fishes followed by MIXOL, SATOL, H3HUF, LINOL, L3HUF and MUSOL. The hepatosomatic and viscerosomatic indices ranged between 2.1-2.5 and 3.4-4.3 respectively in F1-F7. The feed efficiency in terms of feed conversion ratio recorded as 2.02-3.04 among all the feeding trials. It could be concluded, based on the results of this trial, that a diet formulated with a gross energy of 19.3 kJ/g is sufficient to promote good feed efficiency and growth performance in C. striatus grow-out however, the best growth recorded in mixed oil (MIXOL) containing 50 % mustard oil and 50 % linseed oil.

DOI
Journal Article

Abstract  Near surface sediments from an abyssal northeast Atlantic site were sectioned using a newly designed Precision Core Extruder (PCE). Downcore profiles of excess Pb-210 and sterols showed pronounced millimeter-scale variability reflecting specific degradation and bioturbation processes. Excess Pb-210 and sterol concentrations decreased sharply in the uppermost 5 mm, and pronounced subsurface maxima were present. Stanol/stenol ratios, and the relative abundance of cholesterol, increased below 10 mm, indicating biodegradation involving Delta(5) double bond hydrogenation, C-24 dealkylation and/or de novo synthesis. Sterol profiles indicate that early diagenesis of labile compounds is dominated by processes operating near the sediment/water interface, and that the penetration of labile material into oxic sediments is largely controlled by advective processes, associated with infaunal feeding rather than diffusive-like mixing.

Journal Article

Abstract  Eighteen potential penetration enhancers, some at concentrations that might be used for that purpose, have been examined to evaluate their irritancy potential on nude mouse skin. A biopsy technique was employed followed by histological examination. Up to 50% glycerol, 10% hydroxyethyl lactamide (HELA), 10% oleyl alcohol, 10% Solketal, 10% glycofurol, 100% tetrahydrofurfuryl alcohol (THFA) and 10% urea induced no discernible change in the histological appearance of the skin whereas 100% dimethyl sulphoxide (DMSO), 100% dimethyl formamide (DMF), 100% N-methyl-2-pyrrolidone, 10% Azone, 10% oleic acid, 10% methyl laurate, 10% benzyl alcohol and 10% glycerol formal caused severe skin irritation.

WoS
Journal Article

Abstract  The Oleth family of ingredients are the polyethylene glycol (PEG) ethers of oleyl alcohol. They are manufactured by the ethoxylation of oleyl alcohol with the number of moles of ethylene oxide corresponding to the average polyethylene glycol chain length desired. Not all of the polymer chain lengths covered in this assessment are currently reported to be used, but all are listed as cosmetic ingredients and may have been used in the past and could be used in the future. Oleths are surfactants used as emulsifying, cleansing, and solubilizing agents in cosmetic formulations. Limited safety test data are available on ingredients in the Oleth family, all consistent with surfactant properties. In feeding studies, Oleth-20 was associated with reduced body weight gain. Hepatic lesions in one exposure group were not found in any other exposure group, but were found in the controls. Oleth-20 and Oleth-10 were found to have moderate ocular irritation potential, and Oleth-10 was considered to be a cumulative skin irritant. Toxicity data, including reproductive and developmental toxicity, carcinogenesis data, and clinical testing data, available from previous safety assessments on Polyethylene Glycol and Oleyl Alcohol, were summarized. The principal finding related to PEGs, based on clinical data in burn patients, is that PEGs were mild irritant/sensitizers and there was evidence of nephrotoxicity. No such effects were seen in animal studies on intact skin. Cosmetic manufacturers should adjust product formulations containing Polyethylene Glycol to minimize any untoward effects when products are used on damaged skin. Although metabolites of ethylene glycol monoalkyl ethers are reproductive and developmental toxins, it was considered unlikely that the relevant metabolites would be found in or produced from the use of Oleths in cosmetic formulations. Of concern was the possible presence of 1,4-dioxane and ethylene oxide impurities. The importance of using the necessary purification procedures to remove these impurities was stressed. Based on particle size and cosmetic use considerations, it was not considered that these ingredients, in formulation, are respirable. Based in part on the limited data available on Oleths included in the report and on the previous reviews of Polyethylene Glycol and Oleyl Alcohol, it was concluded that Oleth-2, -3, -4, -5, -6,-7,-8,-9,-10,-11,-12,-15,-16,-20,-23, -25, -30, -40, -44, and, -50 are safe in the present practices of use.

Journal Article

Abstract  A young woman being treated for linear scleroderma became allergic to fluocinonide (Lidex) cream while using it with occlusion. She was able to continue treatment with fluocinonide ointment without an adverse reaction. Patch testing with the ingredients of the cream demonstrated sensitization to an impurity in commercial stearyl alcohol and irritation from propylene glycol. The woman had no adverse reactions to fluocinonide ointment because this preparation contains no stearyl alcohol and very little propylene glycol. This case reemphasizes the important role of vehicles in contact allergy and indicates that allergic sensitization may be induced despite the presence of a potent topical steroid.

DOI
Book/Book Chapter

Abstract  Industrially, the most important alcohols are methanol, ethanol, 1‐propanol, 1‐butanol, 2‐methyl‐1‐propanol (isobutyl alcohol), the plasticizer alcohols (C6–C11), and the fatty alcohols (C12–C18), used for detergents. They are prepared mainly from synthesis gas alone (methanol), from olefins via the oxo synthesis, or by the Ziegler process. Apart from the applications mentioned above, alcohols are used as solvents and diluents for paints (mainly C1–C6 alcohols) 1, as intermediates in the manufacture of esters and a whole range of organic compounds, as flotation agents, as lubricants, and as fuel or fuel additives, e.g., methanol, ethanol, tert‐butyl alcohol. For industrial purposes, isomeric mixtures often are preferred because the pure alcohols are too expensive. Moreover, mixtures of alcohols with differing numbers of carbon atoms can be advantageous for certain purposes. Therefore, the amounts of alcohol mixtures available on the market are similar to the quantities of the pure, individual alcohols.

Journal Article

Abstract  Effectiveness of certain long carbon chain aliphatic alcohols as ovicides and larvicides was investigated under laboratory conditions against eggs and larvae of Aedes aegypti and Aedes scutellaris. Out of the eight alcohols tested, three (1-decanol, 1-undecanol and 1-dodecanol) proved to be very effective. The hatching of mosquito eggs was inhibited at a dosage of 5 to 7 litres/hectare. First, third and fourth instar larvae were killed at a dosage of 3 to 7 litres/hectare. First instar larvae were more sensitive to the alcohols than the older larvae. The shorter carbon chain alcohols (2-mercapto-ethanol, 1-butanol, benzyl alcohol and 2-octanol) proved unsatisfactory due to their volatility and solubility. Longer carbon chain alcohols (1-tetradecanol, 1-hexadecanol and 1-octadecanol), Which are solid and wax-like at room temperature, proved unsatisfactory when dissolved in hexane and applied to eggs and larvae.

Technical Report

Abstract  A 96 h LC50 value of >0.4 mg/L was determined for the effect of the test substance on mortality of the fish O. mykiss. The water solubility of octadecanol is 0.0011 mg/L at 25oC [SIDS dossier on 1-octadecanol, 1993b; Budavari, 1996], therefore the LC50 value is >0.0011 mg/L, The water solubility of octadecanol is 0.0011 mg/L at 25oC [SIDS dossier on 1-octadecanol, 1993b; Budavari, 1996], therefore the LC50 value is >0.0011 mg/L (>LoS), i.e. the test substance was not toxic at the LoS.

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