PRODUCTS

OLEYL ALCOHOL

Oleyl alcohol /ˈoʊliˌɪl, ˈoʊliəl/,[1] octadecenol /ˌɒktəˈdɛsɪˌnɒl/, or cis-9-octadecen-1-ol, is an unsaturated fatty alcohol with the molecular formula C18H36O or the condensed structural formula CH3(CH2)7-CH=CH-(CH2)8OH. It is a colorless oil, mainly used in cosmetics.[2]
Oleyl alcohol can be produced by the hydrogenation of oleic acid esters by Bouveault–Blanc reduction, which avoids reduction of the C=C group (as would occur with usual catalytic hydrogenation). The required oleate esters are obtained from beef fat, fish oil, and, in particular, olive oil (from which it gains its name). The original procedure was reported by Louis Bouveault in 1904[3] and subsequently refined.

OLEYL ALCOHOL

CAS No. : 143-28-2
EC No. : 205-597-3

Synonyms:
(Z)-Octadec-9-en-1-ol; octadecenol; cis-9-Octadecen-1-ol; Oleic acid; Oleylamine; Oleamide;; Oleol; oleyl alcohol; oleyl alcohol, (Z)-isomer; OLEYL ALCOHOL; (Z)-octadec-9-en-1-ol; 143-28-2; cis-9-Octadecen-1-ol; Ocenol;Dermaffine; Lancol; Novol; Oceol; (Z) -OCTADEC-9-ENOL; 9-OCTADECEN-1-OL; 9-OCTADECEN-1-OL, (9Z) -; 9OCTADECEN1OL, (Z); CIS-9-OCTADECENYL ALCOHOL; HYDROXYOCTADEC-9-ENE; OLEIC ALCOHOL; 9-OCTADECEN-1-OL, CIS-; ADOL 320; ADOL 330; ADOL 34 Oleol; Satol; Oleic alcohol; Oleo alcohol; Crodacol-O; Conditioner1; Loxanol M; Atalco O; Siponol OC; Sipol O; Octadecenol;(Z)-9-Octadecen-1-ol; Cachalot O-1; Cachalot O-3; Cachalot O-8; H.D. eutanol; HD-Ocenol K; Loxanol95; Unjecol 50; Unjecol 70; Unjecol 90; Oleoyl alcohol; Olive alcohol; Cachalot O-15; Crodacol A.10; Unjecol 110; HD oleyl alcohol CG; cis-9-Octadecenylalcohol; Adol 34; Adol 80; Adol 85; Adol 90; HD-Ocenol 90/95; HD oleyl alcohol 70/75; HD oleyl alcohol 80/85; HD oleyl alcohol 90/95; (Z)-Octadec-9-enol;Witcohol 85; Witcohol 90; 9-Octadecen-1-ol, (Z)-; Adol 320; Adol 330; Adol 340; Oleyl alcohol 5 EO; (9Z)-octadec-9-en-1-ol; cis-octadecen-1-ol; Oleylalcohol; HD-Eutanol; Octadec-9Z-enol; cis-9-octadecenol; (9Z)-9-Octadecen-1-ol; (Z)-9-octadecenol; 9Z-Octadecen-1-ol; Oleyl alcohol (NF); Oleyl alcohol[NF]; Z-9-Dodecen-1-ol; ( Z)-9-octadecenol; Witcohol 85 (TN); 9-Octadecen-1-ol, (9Z)-; EINECS 205-597-3; 9-Octadecen-1-ol; 9-Octadecen-1-ol, cis-; AI3-07620; Octadec-9-en-1-ol; W-109512; 9-Octadecenol; Lipocol O; C18H36O; Anjecol 90N; Unjecol 90N; (Z)-oleyl alcohol; Anjecol 90NR; Unjecol 90NR; Francol OA-95; Fancol OA-95; cis 9 octadecen-1-ol; cis-9-0ctadecen-1-ol; 9(Z)-Octadecen-1-ol; HD-Echelon 90/95; Octadeca-9-cis-en-1-ol; EC 205-597-3; cis-.DELTA.9-Octadecenol; HD-Ocenol 90/95 V;(Z)-octadeca-9-en-1-ol; (9Z)-9-Octadecen-1-ol #; Octadec-9-en-1-ol, (Z)-; Oleyl alcohol,>=99% (GC); Oleyl alcohol, analytical standard; cis-Laquo deltaRaquo 9-Octadecenol; (9Z)-9-Octadecen-1-ol, 85%; NSC-10999; Oleyl alcohol, technical grade, 85%; Oleyl alcohol, technical, ~60% (GC); CAS-143-28-2; CC-33316; LS-97766; SC-19456; AX8146171; O0058; Oleylalcohol, technical, 80-85% 100g; OLEYL ALCOHOL; 143-28-2; (Z)-octadec-9-en-1-ol; cis-9-Octadecen-1-ol; Ocenol; Dermaffine; Lancol; Novol; Oceol; Oleol; Satol; Oleic alcohol; Oleo alcohol; (Z)-9-Octadecen-1-ol; Crodacol-O; Conditioner 1; Loxanol M; Atalco O; Siponol OC; Sipol O; Cachalot O-1; Cachalot O-3; Cachalot O-8; H.D. eutanol; HD-Ocenol K; Loxanol 95; Unjecol 50; Unjecol 70; Unjecol 90; Oleoyl alcohol; Olive alcohol; Cachalot O-15; Crodacol A.10; Unjecol 110; HD oleyl alcohol CG; cis-9-Octadecenyl alcohol; (Z)-Octadec-9-enol; Adol 34; Adol 80; Adol 85; Adol 90; HD-Ocenol 90/95; HD oleyl alcohol 70/75; HD oleyl alcohol 80/85; HD oleyl alcohol 90/95; (9Z)-octadec-9-en-1-ol; Witcohol 85; Witcohol 90; 9-Octadecen-1-ol, (Z)-; Adol 320; Adol 330; Adol 340; 0leyl alcohol; Octadecenol; cis-octadecen-1-ol; 9-Octadecen-1-ol; Oleylalcohol; HD-Eutanol; Octadec-9Z-enol; cis-9-octadecenol; (9Z)-9-Octadecen-1-ol; (Z)-9-octadecenol; 9Z-Octadecen-1-ol; Oleyl alcohol (NF); Oleyl alcohol [NF]; ( Z)-9-octadecenol; Witcohol 85 (TN); 9-Octadecen-1-ol, (9Z)-; EINECS 205-597-3; NSC 10999; 9-Octadecen-1-ol, cis-; 9-Octadecenol; Oleyl alcohol, ca. 60%, technical; cis-Oleyl alcohol; Lipocol O; C18H36O; Anjecol 90N; Unjecol 90N; (Z)-oleyl alcohol; Anjecol 90NR; Unjecol 90NR; Francol OA-95; Fancol OA-95; cis 9 octadecen-1-ol; cis-9-0ctadecen-1-ol; 9(Z)-Octadecen-1-ol; HD-Echelon 90/95; cis-octadec-9-en-1-ol; DSSTox_CID_2010; Octadeca-9-cis-en-1-ol; EC 205-597-3; cis-.DELTA.9-Octadecenol; (Z)-octadeca-9-en-1-ol; (9Z)-9-Octadecen-1-ol #; Octadec-9-en-1-ol, (Z)-; Oleyl alcohol, >=99% (GC); Oleyl alcohol, analytical standard; cis-Laquo deltaRaquo 9-Octadecenol; (9Z)-9-Octadecen-1-ol, 85%; Oleyl alcohol, technical grade, 85%; Oleyl alcohol, United States Pharmacopeia (USP) Reference Standard; cis-9-Octadecenyl alcohol

Oleyl Alcohol

Oleyl alcohol has uses as a nonionic surfactant, emulsifier, emollient and thickener in skin creams, lotions and many other cosmetic products including shampoos and hair conditioners. It has also been investigated as a carrier for delivering medications through the skin or mucus membranes; particularly the lungs.

Oleic acid - the corresponding fatty acid
Oleylamine - the corresponding amine
Oleamide - the corresponding amide

Oleyl alcohol, or cis-9-octadecen-1-ol, is an unsaturated fatty alcohol with the molecular formula C18H36O or the condensed structural formula CH3(CH2)7-CH=CH-(CH2)8OH.It can be produced by the hydrogenation of oleic acid esters; which can be obtained naturally from beef fat, fish oil and in particular oliveoil (from which it gains its name). Production by the Bouveault-Blanc reduction of ethyl oleate or n-butyl oleate esters was reported by Louis Bouveault in1904 and subsequently refined.It has uses as a nonionic surfactant, emulsifier, emollient and thickener in skin creams, lotions and many other cosmeticproducts including shampoos and hair conditioners. It has also been investigated as a carrier for delivering medications through the skin or mucus membranes;particularly the lungs.It is a non-ionic, unsaturated fatty alcohol. It has uses as a nonionic surfactant, emulsifier, emollient and thickener in skincreams, lotions

Oleyl alcohol and Octyldodecanol are long chain fatty alcohols. Stearyl Alcohol is a white, waxy solid with a faint odor, while Oleyl alcohol and Octyldodecanol are clear, colorless liquids. These three ingredients are found in a wide variety of products such as hair conditioners, foundations, eye makeup, skin moisturizers, skin cleansers and other skin care products.Oleyl alcohol and Octyldodecanol help to form emulsions and prevent an emulsion from separating into its oil and liquid components. These ingredients also reduce the tendency of finished products to generate foam when shaken. When used in the formulation of skin care products, Stearyl Alcohol, Oleyl alcohol and Octyldodecanol act as a lubricants on the skin surface, which gives the skin a soft, smooth appearance.

Properties
Chemical formula   C18H36O
Molar mass   268.478 g/mol
Density   0.845-0.855 g/cm3
Melting point   13 to 19 °C (55 to 66 °F; 286 to 292 K)
Boiling point   330 to 360 °C (626 to 680 °F; 603 to 633 K)
Solubility in water   Insoluble

Uses
Oleyl alcohol is a nonionic surfactant used as a hair coating in shampoos and conditioners.Oleyl alcohol is used as an emollient (skin softener), emulsifier, and thickener in creams and lotions.

Oleyl alcohol, octadecenol, or cis-9-octadecen-1-ol, is a fatty alcohol coming from inedible beef fat. It is also found in fish oil. Its chemical formula is C18H36O or CH3(CH2)7-CH=CH-(CH2)8OH. It is a non-ionic, unsaturated fatty alcohol. It has uses as a nonionic surfactant, emulsifier, emollient and thickener in skin creams, lotions and many other cosmetic products, plasticizer for softening fabrics, surfactant and hair coating in shampoos and hair conditioners, and a carrier for medications.

Oleyl alcohol is classified under CAS No.143-28-2.Oleyl alcohol is also known as cis-9-octadecen-1-ol.Oleyl alcohol is a non-ionic, unsaturatedfatty alcohol, a long-chain aliphatic alcohol that occurs naturally in fish oils.Oleyl alcohol prepared by synthetic reduction of plant-derived oleic acid. Oleyl alcohol can be used in large scale applications as the softening and lubrication of textile fabrics, and in production of carbon paper,stencil paper, and printing ink.Oleyl alcohol also utilized as an antifoam agent and cutting lubricant.Oleyl alcohol also known as precursor for the preparation of its sulfuric ester derivatives, which are used in detergents and wetting agents.Oleyl alcohol has also been incorporated into various formulations for drug delivery.Oleyl alcohol can also be used as a non-ionicsurfactant, emulsifier, emollient and thickener in skin creams, lotions and many othercosmetic products. Oleyl alcohol also used as plasticizer for softening fabrics, surfactant and hair coating in shampoos and hair conditioners, and a carrier for medications. Oleyl alcohol (also octadecenol or cis-9-octadecen-1-ol) is a non-ionic, unsaturated fatty alcohol. It is an emulsion stabilizer, antifoam agent, detergent, and release agent for food applications. Oleyl alcohol is found in fish oils and inedible beef fat. It belongs to the family of fatty alcohols. These are aliphatic alcohols consisting of a chain of 8 to 22 carbon atoms (do not have to bear a carboxylic acid group

Substituents
Long chain fatty alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Stearyl Alcohol, Oleyl alcohol, and Octyl Dodecanol are long-chain saturated or unsaturated (Oleyl) fatty alcohols. They are used in numerous cosmetic product categories at concentrations of less than 0.1 percent to greater than 50 percent.The metabolism of Stearyl Alcohol and Oleyl alcohol in rats is described. The results of acute oral toxicity studies indicate a very low order of toxicity. In rabbit irritation tests, these alcohols produced minimal ocular irritation and minimal to mild cutaneous irritation. Stearyl Alcohol produced no evidence of contact sensitization or comedogenicity.Clinical patch testing indicates a very low order of skin irritation potential and sensitization. Photoreactivity studies on products containing these ingredients were negative for phototoxicity or photosensitization.Based on the available data, it is concluded that Stearyl Alcohol, Oleyl alcohol, and Octyl Dodecanol are safe as currently used in cosmetics.

Applications
Oleyl alcohol is used in softening and lubrication of textile fabrics, and in the production of carbon paper, stencil paper, and printing ink. It finds application in cosmetic products viz skin creams and lotions as a thickner, hair conditioners and hair coating shampoos. It is utilized as an antifoaming agent and cutting lubricant, as the precursor for the preparation of its sulfuric ester derivatives, which are used in detergents and wetting agents. It plays a vital role in various formulations for drug delivery. Occurs in fish oils. Emulsion stabiliser, antifoam agent, detergent and release agent for food applications Oleyl alcohol, octadecenol, or cis-9-octadecen-1 -ol, is a fatty alcohol coming from inedible beef fat. It is also found in fish oil.

Oleyl alcohol is used in softening and lubrication of textile fabrics, and in the production of carbon paper, stencil paper, and printing ink. It finds application in cosmetic products viz skin creams and lotions as a thickner, hair conditioners and hair coating shampoos. It is utilized as an antifoaming agent and cutting lubricant, as the precursor for the preparation of its sulfuric ester derivatives, which are used in detergents and wetting agents. It plays a vital role in various formulations for drug delivery.
Solubility
Miscible with alcohol and ether. Slightly miscible with carbon tetrachloride. Immiscible with water.

Oleyl alcohol is a fatty alcohol which is usually found in fish oil and beef fat. It is unsaturated and non-ionic in nature which shares a wide scope in various application as well as end-user industries. Oleyl alcohol is used in an extensive range of applications such as lotions, thickener in skin creams, emulsifiers, surfactants, hair coatings, hair conditioners, and plasticizers for softening fabrics. The global market for Oleyl alcohol has been witnessing significant growth on account of increasing demand from its application industries such as personal care. It is used in a variety of applications such as surfactants, pharmaceuticals and cosmetics. One of the major opportunities for the surfactant industry is bio-based surfactants where rising awareness among consumers towards eco-friendly products has noticeably contributed towards the growing demand for Oleyl alcohol in surfactants. Surfactants also share a broad application scope as foaming agents, emulsifiers, detergents, and wetting agents. Conditioning and detergency are some of the vital properties of surfactants due to which they share a wide application scope. Major applications of Oleyl alcohol-based surfactants include personal care, textile, pharmaceutical, soap and detergent among others. Key manufacturers have entered into several collaborations and agreements with other companies for the marketing of new products as well as garnering a larger share in the market.

Other applications of Oleyl alcohol include plasticizer for use in fabrics. The market for Oleyl alcohol in plasticizers has been witnessing noticeable growth due to changing lifestyles and emerging global economies in Asia Pacific and Latin America. Additionally, growing environmental awareness and rising legal provisions have been serving as a catalyst for the plasticizers market with developments in various emerging economies such as Brazil, Russia, China and India. Matured regions such as Europe and North America accounted for the highest demand for Oleyl alcohol due to the presence of vast hair care and skin care industries in these regions resulting in significant demand for the chemical. Moreover, emerging economies in Asia Pacific such as Japan, China and India are anticipated to witness the fastest growth rate over the forecast period on account of growing hair care, skin care and pharmaceutical industries in the region. Various factors such as rising awareness regarding healthy hair and skin among consumers as well as changing lifestyles is expected to boost the demand for personal care products which in turn is anticipated to contribute towards the demand for Oleyl alcohol.

Increased demand for personal care products such as hair care and skin care is expected to be another important factor that triggers the need for Oleyl alcohol, due to increased awareness of hair and skin. In addition, the increasing demand for drugs is also expected to contribute to the increased demand for Oleyl alcohol in the production of various drugs and ointments during the forecast period. In addition, due to low cost and ease of use, the increase in alcohol consumption in surfactants has contributed significantly to the growth of the market. However, fluctuating prices of major raw materials have been a major concern for producers and are expected to limit the growth of the market. Oleyl alcohol focusing on the commercialization and development of cost-effective bio-based surfactants, is expected to provide new opportunities for the growth of the market.

Oleyl alcohol
It is a clear, colorless liquid. It is found in a wide variety of products such as hair conditioners, skin moisturizers, skin cleansers and other skin care products.Oleyl alcohol helps to form emulsions and prevent an emulsion from separating into its oil and liquid components. When used in the formulation of skin care products, it acts as a lubricants on the skin surface, which gives the skin a soft, smooth appearance.Increasing demand for personal care products such as hair care and skin care on account of rising awareness for hair and skin is expected to be another major factor driving the demand for Oleyl alcohol. Moreover, growing demand for pharmaceuticals is also expected to contribute towards the growing demand for Oleyl alcohol in the production of various drugs and ointments within the forecast period. In addition, increasing consumption of Oleyl alcohol in surfactants due to their low cost and ease of availability has also contributed significantly towards the growth of the market. However, fluctuating prices of key feedstock materials has been major concern for the manufacturers and is expected to limit the growth of the market. Focus on commercializing and developing cost-effective bio-based surfactants using Oleyl alcohol is anticipated to provide new opportunities for the growth of the market.

Oleyl alcohol Usage
Oleyl alcohol is used in the treatment, control, prevention of the following diseases, conditions and symptoms:
Psoriasis
Seborrheic dermatitis
Skin creams and lotions thickener
Hair softening

Oleyl alcohol - Side effects
It is a list of possible side effects from the medicines containing Oleyl alcohol. This is not a comprehensive list. These side effects are likely to be seen, but not always. Some of the side effects are rare, but they can be very serious. Consult your doctor if you observe any of the following side effects, especially those that do not persist despite your waiting period.

Skin irritation
Irritation of the head skin
Skin / hair coloring
Oleyl alcohol Study, Action Mechanism and Pharmacology
Oleyl alcohol improves the condition of the patient by performing the following functions:
The skin is causing dead cells from the upper layer.
Inhibit phosphatidylcholine synthesis.

Uses
Oleyl alcohol is a nonionic surfactant used as a hair coating in shampoos and conditioners.Oleyl alcohol is used as an emollient (skin softener), emulsifier, and thickener in creams and lotions.
Oleyl alcohol, octadecenol, or cis-9-octadecen-1-ol, is a fatty alcohol coming from inedible beef fat. It is also found in fish oil. Its chemical formula is C18H36O or CH3(CH2)7-CH=CH-(CH2)8OH. It is a non-ionic, unsaturated fatty alcohol. It has uses as a nonionic surfactant, emulsifier, emollient and thickener in skin creams, lotions and many other cosmetic products, plasticizer for softening fabrics, surfactant and hair coating in shampoos and hair conditioners, and a carrier for medications.

(9Z)-octadecen-1-ol is a long chain fatty alcohol that is octadecanol containing a double bond located at position 9 (the Z-geoisomer). It has a role as a nonionic surfactant and a metabolite. It is a long-chain primary fatty alcohol and a fatty alcohol 18:1.
A mixture of cis-9[1(-14)C] octadecenol and [1(-14)C] docosanol was injected into the brains of 19-day-old rats, and incorporation of radioactivity into brain lipids was determined after 3, 12, and 24 hr. Both alcohols were metabolized by the brain but at different rates; each was oxidized to the corresponding fatty acid, but oleic acid was more readily incorporated into polar lipids. Substantial amounts of radioactivity were incorporated into 18:1 alkyl and alk-1-enyl moieties of the ethanolamine phosphoglycerides and into 18:1 alkyl moieties of the choline phosphoglycerides. Even after the disappearance of the 18:1 alcohol from the substrate mixture (12 hr), the 22:0 alcohol was not used to any measurable extent for alkyl and alk-1-enylglycerol formation.
cis-9-Octadecenyl alcohol (Oleyl alcohol), orally administered, increased the relative concentration of 18:1 alkyl and alk-1-enyl moieties in alkoxylipids of the small intestine of rats.

Farnesol (FOH) inhibits the CDP-choline pathway for PtdCho (phosphatidylcholine) synthesis, an activity that is involved in subsequent induction of apoptosis /SRP: programmed cell death/. Interestingly, the rate-limiting enzyme in this pathway, CCTalpha (CTP:phosphocholine cytidylyltransferase alpha), is rapidly activated, cleaved by caspases and exported from the nucleus during FOH-induced apoptosis. The purpose of the present study was to determine how CCTalpha activity and PtdCho synthesis contributed to induction of apoptosis by FOH and Oleyl alcohol. Contrary to previous reports, /the authors/ show that the initial effect of FOH and Oleyl alcohol was a rapid (10-30 min) and transient activation of PtdCho synthesis. During this period, the mass of DAG (diacylglycerol) decreased by 40%, indicating that subsequent CDP-choline accumulation and inhibition of PtdCho synthesis could be due to substrate depletion. At later time points (>1 h), FOH and Oleyl alcohol promoted caspase cleavage and nuclear export of CCTalpha, which was prevented by treatment with oleate or DiC8 (dioctanoylglycerol). Protection from FOH-induced apoptosis required CCTalpha activity and PtdCho synthesis since (i) DiC8 and oleate restored PtdCho synthesis, but not endogenous DAG levels, and (ii) partial resistance was conferred by stable overexpression of CCTalpha and increased PtdCho synthesis in CCTalpha-deficient MT58 cells. These results show that DAG depletion by FOH or Oleyl alcohol could be involved in inhibition of PtdCho synthesis. However, decreased DAG was not sufficient to induce apoptosis provided nuclear CCTalpha and PtdCho syntheses were sustained.

Residues of Oleyl alcohol are exempted from the requirement of a tolerance when used as a cosolvent (limit: 15%) in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest.
Hydrophilic and lipophilic formulations of naproxen were prepared, and the influence of the excipients in the formulations on the ulcerogenic potential of naproxen was investigated in rats. Doses of naproxen suspensions ranging from 3.125-100 mg/kg were administered to fasted rats and excised stomachs were examined macroscopically for the incidence and severity of lesions. Results were expressed as the 50% ulceration dose. Results of the study showed that a lipophilic formulation containing Oleyl alcohol provided the greatest gastric protection.

Long-chain fatty acids are important nutrients, but obesity is the most common nutritional disorder in humans. In this study /the authors/ investigated the effect of Oleyl alcohol on the intestinal long-chain fatty acid absorption in rats. ...[14C]Oleic acid and Oleyl alcohol /was administered/ as lipid emulsion intraduodenally in unanesthetized lymph-cannulated rats and measured the lymphatic output of oleic acid. ... Lipid emulsion /was then administered/ with a stomach tube and ... the luminal and mucosal oleic acid residues /were measured/. Furthermore, rats were fed Oleyl alcohol as a dietary component for 20 days, and fecal lipid and the weight of adipose tissues were measured. In lymph-cannulated rats, triglyceride and [14C]oleic acid output in the lymph were significantly lower in the presence of Oleyl alcohol when compared with the absence of Oleyl alcohol in a dose-dependent manner. The radioactivity remaining in the intestinal lumen was more strongly detected in rats that had been orally administered Oleyl alcohol than in the controls. The feces of rats fed an oleyl-alcohol-added diet contained much higher amounts of lipids, and the weights of their adipose tissues were significantly lower than in the control group. These results suggest that Oleyl alcohol inhibits the rat gastrointestinal absorption of long-chain fatty acids in vivo.

Studies of the influence of fatty acids, which were the component of intestinal mucosal lipids, on the permeability of several drugs across bilayer lipid membranes generated from egg phosphatidylcholine and intestinal lipid have been pursued. The permeability coefficients of p-aminobenzoic acid, salicylic acid and p-aminosalicylic acid (anionic-charged drug) increased when fatty acids such as lauric, stearic, oleic, linoleic and linolenic acid were incorporated into the bilayer lipid membranes generated from phosphatidylcholine. In the presence of methyl linoleate and Oleyl alcohol, no enhancing effect on p-aminobenzoic acid transfer was obtained. The effect of fatty acids was more marked at pH 6.5 than at pH 4.5. In contrast, upon the addition of fatty acids to intestinal lipid membranes which originally contained fatty acids, the permeability coefficient of p-aminobenzoic acid tended to decrease, though the permeability through intestinal lipid membranes was larger than that of phosphatidylcholine membranes. The permeability of p-aminobenzoic acid across bilayer lipid membranes from intestinal phospholipids was significantly decreased to about equal that of phosphatidylcholine membranes, and reverted to the value of intestinal lipid membranes when fatty acids were added to intestinal phospholipids. It seemed reasonable to assume that free fatty acids in the intestinal neutral lipid fraction could contribute to the increase in the permeability of p-aminobenzoic acid. On the basis of above results, possible mechanisms for good absorbability of weakly acidic drugs from the intestine are discussed.

The aim of this study was to investigate the frequency of sensitization to fatty alcohols in a group of patients with suspected cosmetic or medicament contact dermatitis. From May 1992 to September 1995, we patch tested a series of 5 fatty alcohols on 146 patients. These included 108 females and 38 males aged from 13 to 72 years (mean age 42.5). These patients, who had previously been tested with the GIRDCA standard series, were selected because their clinical lesions or histories indicated topical preparations as the possible source of their contact dermatitis. High-grade fatty alcohols (> 99% pure) were used for testing. 34 patients (23.2%), 25 female and 9 male aged from 14 to 72 years, showed a positive patch test to fatty alcohols, 33 of them to Oleyl alcohol. A total of 39 reactions were detected with 5 patients showing more than 1 positive reaction. Our results show that sensitization to Oleyl alcohol is not rare in patients with contact dermatitis due to cosmetics or topical medicaments.

Acute Exposure/ ... 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.
Subchronic or Prechronic Exposure/ ... In lymph-cannulated rats, triglyceride and [14C]oleic acid output in the lymph were significantly lower in the presence of Oleyl alcohol when compared with the absence of Oleyl alcohol in a dose-dependent manner. The radioactivity remaining in the intestinal lumen was more strongly detected in rats that had been orally administered Oleyl alcohol than in the controls. The feces of rats fed an oleyl-alcohol-added diet contained much higher amounts of lipids, and the weights of their adipose tissues were significantly lower than in the control group.

Three unsaturated fatty alcohols at 35-50 microM inhibited DNA synthesis and the proliferation of tumor cells by a combination with hyperthermia to greater extents in the order: oleyl (C18:1)-> linoleyl (C18:2)-> alpha-linolenyl (C18:3) alcohol. Two saturated fatty alcohols, palmityl (C16:0)- and stearyl (C18:0) alcohols, did not inhibit at the same concentrations. At 100 microM, palmityl alcohol inhibited, whereas stearyl alcohol did not. ... The inhibition of the unsaturated fatty alcohols on DNA synthesis and proliferation was nearly proportional to the amount of their intercellular accumulation at 37 degrees C or 42 degrees C; the most inhibitory, Oleyl alcohol, was the most membrane-permeable, whilst inversely the least inhibitory, alpha-linolenyl alcohol, was the least permeable. A proportional correlation was not observed for saturated fatty alcohols

Oleyl alcohol's use as a chemical intermediate, automotive lubricant, defoamer, cosolvent and plasticizer for printing ink, and as a cosmetic emollient may result in its release to the environment through various waste streams. Oleyl alcohol is a natural product in fish oils. If released to the air, an estimated vapor pressure of 9.3X10-5 mm Hg at 25 °C indicates Oleyl alcohol will exist in both the vapor and particulate-phases in the atmosphere. Vapor-phase Oleyl alcohol will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 4.9 hours and ozone radicals in the troposphere with an estimated half-life of 2.1 hours. Particulate-phase Oleyl alcohol will be removed from the atmosphere by wet or dry deposition. If released to soil, Oleyl alcohol is expected to have no mobility based upon an estimated Koc of 1.3X10+4. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 4.6X10-4 atm-cu m/mole. However, adsorption to soil is expected to attenuate volatilization. One microbial study which used pure cultures suggests that biodegradation may be an important fate process of Oleyl alcohol in soil and water, but no rate data are available. If released to water, Oleyl alcohol is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 8 hours and 7.4 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 163 days if adsorption is considered. An estimated BCF of 420 suggests the potential for bioconcentration in aquatic organisms is high. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to Oleyl alcohol may occur through inhalation of vapors or through eye and dermal contact with this compound at workplaces where Oleyl alcohol is produced or used. The general public may be exposed to Oleyl alcohol by dermal contact during the use of cosmetics in which it is contained as a cosmetic emollient and through fish consumption.

Oleyl alcohol's use as a chemical intermediate, automotive lubricant, defoamer, cosolvent and plasticizer for printing ink, and as a cosmetic emollient(1) may result in its release to the environment through various waste streams(SRC).
Based on a classification scheme(1), an estimated Koc value of 1.3X10+4(SRC), determined from a structure estimation method(2), indicates that Oleyl alcohol is expected to be immobile in soil(SRC). Volatilization of Oleyl alcohol from moist soil surfaces may be expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.6X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Oleyl alcohol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.3X10-5 mm Hg(SRC), determined from a fragment constant method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Based on one microbial study, Oleyl alcohol was found to be utilized as the sole carbon source by bacteria, yeast, and fungi(5). Although this study provides little insight into the rate of biodegradation in soil, it suggests that biodegradation in soil may be important(SRC).

Based on a classification scheme(1), an estimated Koc value of 1.23X10+4(SRC), determined from a structure estimation method(2), indicates that Oleyl alcohol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.6X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 8 hours and 7.4 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 163 days if adsorption is considered(5). Alcohols are generally resistant to hydrolysis(6). According to a classification scheme(7), an estimated BCF of 420(SRC), from an estimated log Kow of 7.5(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Based on one microbial study, Oleyl alcohol was found to be utilized as the sole carbon source by bacteria, yeast, and fungi(10). Although this study provides little insight into the rate of biodegradation in water, it suggests that biodegradation in water may be important(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), Oleyl alcohol, which has an estimated vapor pressure of 9.3X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase Oleyl alcohol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4.5 hrs(SRC), calculated from its rate constant of 7.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase oleyl alchol may be removed from the air by wet or dry deposition(SRC). The rate constant for the vapor-phase reaction of Oleyl alcohol with ozone has been estimated as 1.3X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). This corresponds to an atmospheric half-life of about 2.1 hrs at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4).

AEROBIC: Oleyl alcohol (10 g) was found to be utilized as the sole carbon source by bacteria (Pseudomonas) in 10 days at 30 °C and pH 6.8-7.0. In the same study, 10 g Oleyl alcohol was utilized as the sole carbon source by 3 yeasts (Candida, Pichia, and an unknown) in 10 days at 30 °C and pH 6.8-7.0. It was also utilized by 3 fungi (Aspergillus, Penicillium, and an unknown) in 20 days at 20-25 °C and pH 5.5-5.6(1).
The rate constant for the vapor-phase reaction of Oleyl alcohol with photochemically-produced hydroxyl radicals has been estimated to be 7.8X10-11 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 4.9 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of Oleyl alcohol with ozone in the troposphere can be estimated to be 1.3X10-16 cu cm/molecule-sec at 25 °C which corresponds to a half-life of about 2.1 hrs at an atmospheric concn of 7X10+11 molecules per cu cm(1-2). Oleyl alcohol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3).

An estimated BCF of 420 was calculated for Oleyl alcohol(SRC), using an estimated log Kow of 7.5(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of Oleyl alcohol can be estimated to be 1.3X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that Oleyl alcohol is expected to be immobile in soil.

Oleyl alcohol is found in fish oils(1).
The Henry's Law constant for Oleyl alcohol is estimated as 4.6X10-4 atm-cu m/mole using a fragment constant estimation method(1). This Henry's Law constant indicates that Oleyl alcohol is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life of Oleyl alcohol from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 8 hrs(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 7.4 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 163 days if adsorption is considered(3). Oleyl alcohol's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Oleyl alcohol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.3X10-5 mm Hg(SRC), determined from a fragment constant method(4).

Oleyl alcohol was qualitatively detected in adult lake trout (Salvelinus namaycush) collected in 1977 from Lake Michigan in Charlevoix, MI and it was qualitatively detected in walleye (Stizostedion v. vitreum) from Lake St. Clair Anchor Bay, MI and Lake Erie Dunkirk, PA(1).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 78,925 workers (49,124 of these are female) are potentially exposed to Oleyl alcohol in the US(1). Occupational exposure to Oleyl alcohol may occur through inhalation and dermal contact with this compound at workplaces where Oleyl alcohol is produced or used(SRC). Monitoring data indicate that the general population may be exposed to Oleyl alcohol via ingestion of food products containing fish oil(SRC).

What Is It?
Stearyl Alcohol, Oleyl alcohol and Octyldodecanol are long chain fatty alcohols. Stearyl Alcohol is a white, waxy solid with a faint odor, while Oleyl alcohol and Octyldodecanol are clear, colorless liquids. These three ingredients are found in a wide variety of products such as hair conditioners, foundations, eye makeup, skin moisturizers, skin cleansers and other skin care products.

Why is it used in cosmetics and personal care products?
Stearyl Alcohol, Oleyl alcohol and Octyldodecanol help to form emulsions and prevent an emulsion from separating into its oil and liquid components. These ingredients also reduce the tendency of finished products to generate foam when shaken. When used in the formulation of skin care products, Stearyl Alcohol, Oleyl alcohol and Octyldodecanol act as a lubricants on the skin surface, which gives the skin a soft, smooth appearance.

Scientific Facts:
Stearyl Alcohol and Oleyl alcohol are mixtures of long-chain fatty alcohols. Stearyl Alcohol consists primarily of n-octadecanol, while Oleyl alcohol is primarily unsaturated 9-n-octadecenol. Octyldodecanol is a branched chain fatty alcohol. Fatty alcohols are higher molecular weight nonvolatile alcohols. They are produced from natural fats and oils by reduction of the fatty acid (-COOH) grouping to the hydroxyl function (-OH). Alternately, several completely synthetic routes yield fatty alcohols which may be structurally identical or similar to the naturally-derived alcohols.

Use: specialty Oleyl/LinOleyl alcohol provides exceptionally high levels of unsaturation (110-135 I.V.) for specialty ethoxylation and esterification reactions. JARCOL 110BJ has significantly higher levels than can be found with standard mono-unsaturated Oleyl alcohols.
Membrane-Based Recovery Such As Pervaporation
Pervaporation is a simple technique that allows selective removal of volatiles from model solutions/fermentation broths using a membrane. The volatile organic component (AB in this case) diffuses through the membrane as a vapor followed by recovery by condensation. During this process, a phase change occurs from liquid to vapor. Since it is a selective removal process, the desired component requires a heat of vaporization at the feed temperature. In pervaporation, the effectiveness of separation of a volatile is measured by two parameters called selectivity (a measure of selective removal of volatile) and flux (the rate at which an organic volatile passes through the membrane per m2 membrane area). A schematic diagram of the pervaporation process is shown in Figure 5(c). Application of pervaporation to batch butanol fermentation has been described by numerous investigators. Pervaporation has also been applied for the removal of butanol from the fermentation broth in fed-batch reactors. In the fed-batch reactors, concentrated sugar solutions have been used to reduce the volume of process streams. It is interesting to note that acids did not diffuse through some of the membranes.

In an attempt to improve membrane selectivity, the two techniques known as liquid–liquid extraction and pervaporation were combined to recover butanol. The extraction solvent used for this process was Oleyl alcohol, which formed a thin liquid layer (known as a thin membrane) on a microporous 25 μm thick polypropylene flat sheet. The Oleyl alcohol got impregnated into the sheet pores. In this combination of liquid–solid membrane, Oleyl alcohol dissolved butanol relatively quickly followed by diffusion through the polypropylene membrane. The advantage of combining the liquid (Oleyl alcohol) and solid membrane was that a high butanol selectivity (180) was achieved in comparison to a low selectivity (10–15) when using polypropylene film alone. Note that a membrane with selectivity 180 would concentrate 5 g l−1 feed butanol to 475 g l−1 butanol in a single pass, while a membrane of selectivity 15 would concentrate the same feed to 70 g l−1 butanol. A product containing 475 g l−1 butanol is 6.79 times more concentrated than 70 g l−1. It was estimated that if this solid–liquid pervaporation membrane with a selectivity of 180 were used for butanol separation, the energy requirement would be only 10% of that required in a conventional distillation. Unfortunately, the membrane was not stable as the Oleyl alcohol that formed a thin film and was impregnated into the polypropylene film pores diffused out of the membrane during the recovery process.

Extraction of PDO from fermentation broth is theoretically promising as the high energy demand of water evaporation could be avoided and the various by-products could be separated simultaneously. A large number of organic solvents were investigated for this purpose, which did not result in success. The partition coefficient for PDO in the solvents increases with polarity but does not reach an acceptable value for an economically feasible PDO extraction. The unavoidable dilution of PDO in the extract would annihilate the advantages to the first route due to rising energy demand during solvent recovery.30 Nevertheless, several patents have been published that claim different solvents and their feasibilities for PDO extraction, including pentanol, propanol, hexanol, Oleyl alcohol, 4-methyl-2-pentanone, isopropyl acetate, tributyl phosphate, oleic acid, soya oil, and castor oil.

Most studies of CKD patients have been carried out in dialysis-dependent patients. They can be divided into two main categories: studies that used systemic vitamin E and studies that used vitamin E-coated hemodialysis membranes. Among the latter (Table 65-1), only two studies used reasonable surrogate clinical endpoints of CVD, namely the progression of aortic calcification25 and changes in carotid intimal thickness.26 The remainder used biochemical parameters of OS or immunologic parameters related to inflammatory responses to the hemodialysis membrane exposure, which is a measure of membrane biocompatibility.27–29 Exposure of the patient's blood to an artificial membrane (and possibly back-diffusion of pyrogens or endotoxins in the dialysate) elicits a strong cellular immunologic response, manifested by leukopenia, complement activation, and production of free oxygen radicals by the activated white blood cells.30 The hemodialysis procedure itself can contribute to OS and endothelial dysfunction.31 To ameliorate hemodialysis-induced OS, many manufacturers offer vitamin E-coated dialyzers. In these dialyzers α-tocopherol is bonded to a cellulose- or polysulfone-based membrane. The membrane has other modifications that affect its function and biocompatibility.32 The inner surface of the hollow fiber is bound, via an acrylic polymer, to a complement-inhibiting fluororesin polymer and to an Oleyl alcohol chain that inhibits platelet aggregation. The Oleyl alcohol chain itself is bonded to α-tocopherol by hydrophobic-hydrophobic bonds. These modifications decrease the number of hydroxyl groups in the cellulose membrane and thereby increase its biocompatibility. Several studies have shown a beneficial effect of vitamin E-coated dialyzers on various parameters of OS and immunologic reaction to hemodialysis. Most of these studies, however, are small, unblinded, and poorly controlled; a critical flaw is that most have used less biocompatible membranes as controls. Furthermore, the clinical relevance of the measured biomarkers in these studies is not known. Although the concept of vitamin E-coated membranes is interesting, larger randomized, controlled studies with hard clinical endpoints are needed to prove their utility; current evidence does not support their use in routine clinical practice at present.

Silicone elastomeric devices display a high degree of biocompatibility and are quite flexible, yet mechanically strong. The material is often used for manufacturing urinary catheters. However, the lack of inherent lubricity of the material poses a major disadvantage as it causes discomfort and irritation to the patient. Self-lubricating silicone elastomers may be advantageous in this respect. Thus, novel tetra-functional compounds were developed for the condensation crosslinking of hydroxyl terminated PDMS chains to yield lubricious silicone elastomeric biomaterials. Lubricity was due to the higher alcohol, non-volatile condensation by-product formed during the crosslinking (vulcanisation) of linear PDMS. The alcohol, for example Oleyl alcohol, was found to permeate to the surface and produce a liquid, oily film on the surface. The coefficients of friction of these elastomers were examined and it was found that the novel elastomers exhibited a greater lubricity, with substantially reduced coefficients of friction, when compared with a standard RTV silicone elastomer.

Tweet et al. recently reported that vitamin K1 is an efficient quencher for chlorophyll fluorescence in a monolayer diluted with Oleyl alcohol (28). In Fig. 6, the relative fluorescence (the ratio of the fluorescence yields in the presence and in the absence of vitamin K1) in the diluted monolayer is plotted as a function of vitamin K1 concentration expressed in numbers of molecules per unit area. Over a chlorophyll concentration range corresponding to a chlorophyll area fraction from 0.003 to 0.026 in the mixed layer, or a chlorophyll-chlorophyll separation from 175 to 75 Å, the agreement was within 10%. The solid line represents values calculated from the Stern-Volmer equation ϕ(Q)/φ0 = l/(1 + kQCQ), with the quenching constant kQ = 3.4 × 1013 cm2/molecule. The quenching of chlorophyll fluorescence by the nonfluorescent copper pheophytin a is shown in the same figure by the dashed curve. As with vitamin K1, the chlorophyll fluorescence is progressively quenched with increasing copper pheophytin concentration.

The direct carboxylation of unsaturated fatty acids to dibasic acids, in the absence of a metal catalyst, was demonstrated by Kirkpatrick,200 who reacted oleic acid with CO in the presence of boron trifluoride and water at high temperatures (100–250 °C) and pressures (400–1000 atm). Subsequently, Koch described a technically feasible route to carboxylic acids,201 catalyzed by a large excess of a Brnsted acid, which acted as a protonating agent as well as a solvent,201 and it is now known as the ‘Koch reaction’. Unsaturated compounds can be directly carboxylated at low pressures and temperatures, in the presence of concentrated sulfuric acid, such as the formation of a mixture of C12 dicarboxylic acids from undecylenic acid, in which the newly formed carboxyl group is secondary or tertiary.202,203

The Koch reaction was used to add CO to the double bonds of oleic acid, Oleyl alcohol, linoleic acid, and methyl ricinoleate,204 which included a modification where CO was prepared in situ from formic acid and concentrated sulfuric acid.203 The best yield of carboxylated oleic acid was obtained with 97% sulfuric acid that had 5 mol. of water per mole of oleic acid. No carboxylation took place in 91% sulfuric acid or in 100% sulfuric acid, demonstrating the importance of the right concentration of sulfuric acid and water.204,205 The use of liquid hydrogen fluoride as the catalyst and solvent enables almost quantitative recovery of the catalyst by distillation, while yielding carboxylated products in high yield.206 Metal catalysts, such as monovalent group IB metals (e.g., Cu2O), can also be used.