Isostearic Acid Research Articles

Inhibition of DNA methyltransferase by microbial inhibitors and fatty acids.

Streptomyces sp. strain No. 560 produces four kinds of DNA methyltransferase inhibitors in the culture filtrate. One of them, DMI-4 was distinguished from DMI-1, -2 and -3 previously reported with respect to certain properties, DMI-4 is considered to be a triglyceride consisting of the fatty acids anteisopentadecanoic acid (C15:0), isopalmitic acid (C16:0) and isostearic acid (C18:0) from the results of gas chromatography analysis. Since DMI-4 contains three molecules of fatty acid, and the previously reported DMI-1, 8-methylpentadecanoic acid, is analogous to a fatty acid, the inhibitory activity has been examined of various fatty acids and their methyl esters against Eco RI DNA methyltransferase (M. Eco RI). Oleic acid (C18:1) was found to be a potent inhibiton of M. Eco RI. The inhibitory activity of oleic acid was shown to be pH- and temperature-dependent and inhibited M. Eco RI in a noncompetitive manner with respect to DNA or S-adenosylmethionine (SAM). The number of carbon atoms and double bonds in the fatty acid molecule affected the inhibitory activity, but their methyl esters were not inhibitors. Our results suggest that the length of the carbon chain, the number of double bonds and the presence of a carboxyl group and branched methyl group in the fatty acid molecule may play an important role in the inhibition of DNA methyltransferase.

Curcumin in a Model Skin Lotion Formulation

A lamellar liquid crystalline region was identified in a typical skin lotion formulation system composed of a mixture of isostearic acid and triethanolamine (TEA) at 65:35 (w/w), decane, and water (the temperature was controlled at 30 °C). The interlayer spacings were determined by a small‐angle X‐ray diffraction technique. Incorporation of a natural dye, curcumin, resulted in lower interlayer spacings and higher penetration of water into the layered structure. However, the higher penetration of water was not apparent at all compositions of isostearic acid:TEA, decane, and water.

Effect of vehicles on diclofenac permeation across excised rat skin.

The in vitro percutaneous permeation of diclofenac from various vehicles was examined using rat abdominal skin as a model membrane. The oleaginous vehicles used in this study consisted of three components: i.e. fatty acid, fatty acid ester and nonpolar oil. The solubilities of sodium diclofenac in formulated vehicles were above 0.2 M. The effect of each oleaginous component in the vehicle on the permeation of diclofenac across the skin was in the following order: oleic acid > isostearic acid, diisopropyl adipate = diethyl sebacate > Panasate 875 and squalane > liquid paraffin. To clarify the reason for the differences in permeation among the fatty acid esters, the release of diclofenac through either porous or lipoidal membranes from these vehicles in vitro and the solubility of sodium diclofenac in the vehicles were studied. However, no relationship was observed between the release rate or solubility and skin permeability. The skin permeation of diclofenac increased following pretreatment with diisopropyl adipate or diethyl sebacate, but not with middle chain triglyceride (Panasate 875). These results suggested that the main reason may be the enhancement effect of fatty acid esters. Emulsions and creams containing 3% sodium diclofenac were prepared using the above oleaginous vehicles. A large flux and short lag time were observed in these preparations compared with an aqueous suspension of sodium diclofenac. The incorporation of urea significantly enhanced the permeation of diclofenac from these preparations. These results suggest that the emulsion and cream prepared in this study are useful for development for practical purposes.

High resolution 13C NMR study of synthetic branched-chain acids and of wool wax acids and isostearic acid

The 13C NMR spectra of 28 branched-chain acids (including two from the literature) have been recorded and assigned. These range from C 6 to C 18 in chain length. They are mainly methyl-branched but include also C 2, C 3, C 4, C 5, C 6, and C 16 branches. On the basis of these results the branched-chain acids in wool grease and the industrially produced isostearic acid have been examined.

3 Final Report on the Safety Assessment of Isopropyl Isostearate

Isopropyl Isostearate, the ester of isopropyl alcohol and isostearic acid, is used as a skin conditioning agent-emollient in cosmetic products. Undiluted Isopropyl Isostearate was classified as a slight ocular irritant. Repeated applications of a 10.0% aqueous suspension of Isopropyl Isostearate to the skin of albino rabbits was well-tolerated. Based upon the safety test data on chemically similar isopropyl esters that is summarized in the report, it is concluded that Isopropyl Isostearate is safe as a cosmetic ingredient in the present practices of use and concentration.

Some Candidate Replacement Materials for Dioctyl Phthalate in “Hot Smoke” Aerosol Penetrometer Machines

For many decades dioctyl phthalate (DOP), a common industrial material, has been used by the U.S. Army and other agencies to simulate aerosol behavior in nondestructive gas mask and filter serviceability testing, and for related test purposes. Techniques are completely standardized. But DOP is now considered to be a potentially hazardous material. The research reported here, which was performed using ATI Q-127 and TDA-100 “hot smoke” aerosol penetrometer test machines, identified relatively innocuous, inexpensive replacement materials for DOP. One of these, a synthetic hydrocarbon (poly-alpha olefin [PAO]), can be used to replace DOP directly with minimum impact upon existing hardware and procedures. Of more than two dozen candidate replacement materials that were tested, isostearic acid and oleic acid also performed well as DOP replacements. All three materials also show promise for cold smoke testing applications

Isolation and Partial Identification of Lactones from Technical Isostearic Acid

AbstractUsing the techniques of clathrate formation with urea and chromatographic separation on silicagel, lactone fractions (about 6–8%) were isolated from technical isostearic acid. The lactones were partially identified (GC/MS) as a range of γ‐lactones which included branched and unbranched isomers and homologs, besides other compounds. A mechanism is proposed for the formation of these lactones, relating them to the bulk of the isostearic acid isomers.

Failure to detect beta-leucine in human blood or leucine 2,3-aminomutase in rat liver using capillary gas chromatography-mass spectrometry.

It has been reported (Poston, J. (1976) J. Biol. Chem. 251, 1859-1863; (1982) 255, 10067-10072; (1984) 259, 2059-2061) that mammalian tissues contain an adenosylcobalamin-dependent enzyme, leucine 2,3-aminomutase, which catalyzes the interconversion of beta-leucine and leucine. It was also reported that beta-leucine is detectable in normal human serum (mean = 4.8 mumol/liter, n = 37) and is elevated in serum from patients with cobalamin deficiency (mean = 24.7 mumol/liter, n = 17). Serum levels of leucine were claimed to be decreased in the cobalamin deficient patients (mean = 52 mumol/liter) as compared with the normal subjects (mean = 81 mumol/liter). It was also reported that rat liver supernatant catalyzed the formation of beta-leucine, leucine, or both amino acids from iso-fatty acids, and that the generation of leucine from iso-fatty acids was stimulated by adenosylcobalamin and inhibited by unsaturated cobalamin-binding protein. We have synthesized t-butyldimethylsilyl derivatives of beta-leucine and leucine and have used capillary gas chromatography-mass spectrometry for their analysis. Using forms of beta-leucine and leucine that contain several deuterium atoms in place of several hydrogen atoms as internal standards, techniques have been developed which make it possible to detect and quantitate as little as 0.1 mumol/liter of beta-leucine or leucine in human serum and in incubations containing rat liver supernatant. beta-Leucine was not detectable, i.e. less than 0.1 mumol/liter, in any sera from 50 normal human subjects or in any sera from 50 cobalamin-deficient patients. The mean level of leucine in the 50 cobalamin-deficient sera was 219 mumol/liter, which was not decreased with respect to that in the 50 control sera (167 mumol/liter). Experiments in which beta-leucine, leucine, isostearic acid, or isocaproic acid were incubated with rat liver supernatant in the presence or absence of adenosylcobalamin or cobalamin-binding protein failed to demonstrate the formation of leucine or beta-leucine or their interconversion under any of the conditions studied. We conclude that beta-leucine is not present in human blood and that the existence of leucine 2,3-aminomutase in mammalian tissues remains to be established.

Friction properties of C18-fatty acids.

The friction properties of C18-fatty acids (stearic acid, oleic acid and isostearic acid) were investigated using a pendulum type friction tester. These fatty acids gave different antifriction properties owing to their different molecular structures, in spite of their having the same polar group (carboxylic group) and the C18-hydrocarbon chain. The order of antifriction properties of these C18-fatty acids was: stearic acid >oleic acid>isostearic acid. This suggests the difference of the state of the adsorbed films formed on the frictional surfaces as lubricating films. The states of the adsorbed films were examined from the surface pressure-area isotherms obtained for these fatty acid monolayers at the air/water interface.

4 Final Report on the Safety Assessment of Isostearic Acid

Isostearic Acid is a mixture of fatty esters consisting mainly of methyl branched isomers of octadecanoic acid and is used at concentrations up to 10% in a wide variety of cosmetic products. In rats, the acute oral LD50 is estimated to be greater than 32 ml/kg. The raw ingredient produced no significant skin or eye irritation in Draize rabbit irritation tests. In clinical studies, 100 subjects showed no signs of irritation after a 24 h single insult skin patch with undiluted Isostearic Acid. Thirty-four percent Isostearic Acid was neither an irritant nor a sensitizer in 168 subjects, and gave no indication of phototoxicity in a subset of this population. It is concluded that Isostearic Acid is safe as a cosmetic ingredient in the present practices of use. Consideration for the compound's potential for production of human comedogenicity is noted.

Analysis of sorbitan fatty acid esters by HPLC

AbstractSorbitan esters of several fatty acids have been analyzed by high pressure liquid chromatography (HPLC) using an RP‐18 column. No derivatization was necessary. Mono‐, di‐ and trisorbitan esters of palmitic, stearic, oleic, isostearic and sesquioleic acid have been separated using isopropanol/water as the elution mixture.

Novel Alkanecarboxylic Acids via the Koch Reaction. A Route To Replace Isostearic Acid

Novel Alkanecarboxylic Acids via the Koch Reaction. A Route To Replace Isostearic Acid

Effects of Selected Psychrophilic Bacteria on the Fatty Acid Composition of Chicken Breast Meat ,

To determine the effects of psychrophilic microorganisms on the fatty acid composition of chicken breast meat, aseptically procured samples were inoculated with an Alcaligenes sp., a Flavobacterium sp., or Pseudomonas putrefaciens, and stored at 3°C, for periods of time up to 14 days. Following storage, the samples were analyzed for total bacterial numbers. The pH of each sample was determined and the meat was then heat-treated.Butyl esters of fatty acids were prepared from lipids extracted from the chicken meat. The fatty acid composition of these samples was determined using gas-liquid chromatography.Eighteen fatty acids were detected and tentatively identified in chicken breast meat. The fatty acid composition of aseptically procured uninoculated meat remained relatively constant throughout the 14 day storage period. However, in chicken meat inoculated with psychrophilic spoilage bacteria, the proportion of “lower” fatty acids (C-14 through C-17, plus isostearic acid and stearic acid) tended to increase with storage time. This change in fatty acid composition was particularly pronounced as spoilage occurred in the chicken meat.

Lubricants from Mixed Pentaerythritol Esters of 2-Ethylhexanoic and Isostearic Acids

A mixed pentaerythritol ester composed of 25 mole percent 2-ethylhexanoic and 75 mole percent of isostearic acid substituents was synthesized and characterized. By means of the synthetic and analytical procedures developed, this mixed ester can be prepared in a highly reproducible manner. Oxidation and thermal stabilities, corrosivity, and wetting characteristics are reported. The ester is of interest in instrument and bearing applications where a viscous lubricant having excellent low-temperature properties is required. Presented at the 26th ASLE Annual Meeting in Boston, Massachusetts, May 3—6, 1971

Emery 875-D Isostearic Acid imparts unusual properties to cosmetics.

Emery 875-D Isostearic Acid imparts unusual properties to cosmetics.

Dispersing Performance of Ashless Dispersants

An iron powder-bed procedure used by Clayfield has been developed to investigate the dispersing performance of engine oil dispersants. The main purpose of this investigation was to find out the relationship between chemical structure and the dispersing ability of dispersants.From the results, it appeared that the dispersant additives could be divided into the following three groups:(1) Those having free amino or imino groups in the polar side chain show an excellent dispersing performance. Such compounds are derived from polyamine compounds and polybutenylsuccinic anhydride, polybutenyl (thio) phosphoric acid, naphthenic acid or isostearic acid.(2) Those having free hydroxy groups in the polar side chain show a fairly good dispersing performance. Such compounds are derived from polyhydroxy compounds and polybutenylsuccinic acid or naphthenic acid.(3) Those having acid anhydride group or alkaline earth metal salt group in the polar side chain show a medium dispersing performance.It was concluded that the excellent dispersing performance of polybutenylsuccinimides depends on their basic amino groups rather than their high molecular weight oleophillic groups.

Incorporation of branched-chain fatty acids into myxoviruses.

The incorporation of free fatty acids into myxoviruses was shown, using branched-chain fatty acids as molecular markers. The presence of isostearic or phytanic acid was detected by gas-liquid chromatography in the phospholipid fraction of the A(0)/PR8/34 strain of influenza virus. Uptake of free fatty acids into the virus varied from 8 to 11 per cent and was accompanied by a shift in the fatty acid profile. Infected allantoic fluids from eggs treated with branched-chain acids possessed higher hemagglutinin activity when compared to fluids infected under normal conditions. Attempts to detect branched-chain acids in Sendai virus were unsuccessful. Shifts in acyl chain composition persisted after three passages of modified viruses in the absence of branched-chain acids. Force-area curves at an air-water interface revealed the cross-sectional area of branched-chain acids to be greater than their straight-chain homologs. It is suggested that hydrophobic interactions can alter the configuration of envelope proteins. Such changes may have an important role in the selection of fragments of influenza viral genome and can conceivably alter viral genotype.

No other isostearic acid can equal new Emery 3101-D......Except Emery 3185-D...it's the latest with many attractive refinements

No other isostearic acid can equal new Emery 3101-D......Except Emery 3185-D...it's the latest with many attractive refinements

Isostearic Acid—First Real Breakthrough in Fatty Acid Technology

Isostearic Acid—First Real Breakthrough in Fatty Acid Technology

The branched-chain fatty acids of mutton fat. 3. The isolation of 16-methylheptadecanoic acid (isostearic acid).

Research Article| October 01 1956 The branched-chain fatty acids of mutton fat. 3. The isolation of 16-methylheptadecanoic acid (isostearic acid)* R. P. Hansen; R. P. Hansen 1Fats Research Laboratory, Department of Scientific and Industrial Research, Wellington, New Zealand Search for other works by this author on: This Site PubMed Google Scholar F. B. Shorland; F. B. Shorland 1Fats Research Laboratory, Department of Scientific and Industrial Research, Wellington, New Zealand Search for other works by this author on: This Site PubMed Google Scholar N. J. Cooke N. J. Cooke 1Fats Research Laboratory, Department of Scientific and Industrial Research, Wellington, New Zealand Search for other works by this author on: This Site PubMed Google Scholar Biochem J (1956) 64 (2): 214–216. https://doi.org/10.1042/bj0640214 Views Icon Views Article contents Figures & tables Video Audio Supplementary Data Peer Review Share Icon Share Facebook Twitter LinkedIn MailTo Cite Icon Cite Get Permissions Citation R. P. Hansen, F. B. Shorland, N. J. Cooke; The branched-chain fatty acids of mutton fat. 3. The isolation of 16-methylheptadecanoic acid (isostearic acid). Biochem J 1 October 1956; 64 (2): 214–216. doi: https://doi.org/10.1042/bj0640214 Download citation file: Ris (Zotero) Reference Manager EasyBib Bookends Mendeley Papers EndNote RefWorks BibTex toolbar search Search Dropdown Menu toolbar search search input Search input auto suggest filter your search All ContentAll JournalsBiochemical Journal Search Advanced Search This content is only available as a PDF. © 1956 CAMBRIDGE UNIVERSITY PRESS1956 Article PDF first page preview Close Modal You do not currently have access to this content.