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Palm oil‐based fatty alcohol is a basic oleochemical with many different applications depending on its carbon chain length. The carbon chain distribution using a GC‐flame ionization detector (GC‐FID) is a quality control tool for monitoring the composition of either single or blended fatty alcohol. There is a published GC‐FID method but it requires a derivatization step. The objective of this work is to develop a derivatization‐free method with simple preparation steps. It can be used for routine analysis of the carbon chain distribution to determine the composition of palm‐based fatty alcohol. The GC‐FID method developed used a ZB‐FFAP (60 m × 0.25 mm i.d., 0.25 μm film thickness) consisting of polyethylene glycol bonded nitroterephthalic acid phase for separation of eight types of fatty alcohol with a run time of 40 min. The method showed good validation parameters performance in terms of accuracy (as compared with FAL standards), linearity (R2 > 0.9999) and intraday and intermediate precision (CV < 0.05% for retention time and CV < 1.5% for peak area). Monitoring of commercial FAL from local manufacturers showed that the composition was consistent with the required specifications. [ABSTRACT FROM AUTHOR]

Various lipids (mainly meibum lipids secreted by the meibomian glands) are present in the tear film lipid layer and play important roles in tear stability and the health of the cornea and conjunctiva. Many meibum lipids contain fatty alcohols (FAls) with chain lengths ≥C24, but the fatty acyl‐CoA reductases (FARs) that produce them remain unclear. Here, using cell‐based assays, we found that the two FAR isozymes (FAR1 and FAR2) show different substrate specificities: FAR1 and FAR2 are involved in the production of C16–C18 and ≥C20 FAls, respectively. Next, we generated Far2 knockout (KO) mice and examined their dry eye phenotype and meibum lipid composition. These mice showed a severe dry eye phenotype, characterized by plugged meibomian gland orifices, corneal damage, and tear film instability. The plugging was attributed to an increase in the melting point of the meibum lipids. Liquid chromatography coupled with tandem mass spectrometry revealed that FAl‐containing meibum lipids (wax monoesters and types 1ω, 2α, and 2ω wax diesters) with a hydroxyl group at position 1 were almost completely absent in Far2 KO mice. The levels of di‐unsaturated (O‐acyl)‐ω‐hydroxy fatty acids were higher in Far2 KO mice than in wild type mice, but those of tri‐unsaturated ones were comparable, suggesting the presence of two synthesis pathways for type 1ω wax diesters. These results indicate the importance of FAl‐containing meibum lipids in the formation of a functional tear film lipid layer. In addition, our study provides clues to the molecular mechanism of the biosynthesis of meibum lipids. [ABSTRACT FROM AUTHOR]

Fatty alcohol‐polysorbate 60‐water ternary systems were used as models to represent the continuous phases of the respective semisolid oil‐in‐water emulsions for topical delivery of cosmetic and medicinal agents. The influence of batch variation of polysorbate 60 and fatty alcohol on structure and consistency of these systems was investigated using microscopy, rheology, differential scanning calorimetry and X‐ray scattering techniques. The polysorbate 60 : cetostearyl alcohol mixed emulsifying wax showed swelling in water, that is, the lamellar repeat distance continually augmented from 93 to 125 Å with water percentage 20–90%. Cetostearyl alcohol ternary systems were thicker than cetyl alcohol ones independently of polysorbate 60 batches used. All the ternary systems showed an initial increase in consistency over the first 2 weeks of storage, which was followed by slight changes in consistency (cetostearyl alcohol systems) due to the re‐allocation of polysorbate 60 molecules in the gel network or significant breakdown of structure (cetyl alcohol systems) due to the transformation of swollen α‐lamellar gel phase into β, γ crystals on 25°C storage. With all fatty alcohols, the consistency of polysorbate 60 ternary system was directly dependent upon interlamellar water thickness as governed by the length and distribution of polyoxyethylene groups within polysorbate 60 molecules. In relation with the composition of polysorbate 60 batches used, the consistency of ternary systems was higher when prepared with the polysorbate 60 batch containing a greater amount of sorbitan polyoxyethylene monoesters. It was proposed that the swollen α‐crystalline gel phase could be better formed by sorbitan polyoxyethylene monoesters rather than sorbitan polyoxyethylene diesters. [ABSTRACT FROM AUTHOR]

SUMMARY: Suberin is a complex hydrophobic polymer of aliphatic and phenolic compounds which controls the movement of gases, water, and solutes and protects plants from environmental stresses and pathogenic infection. The synthesis and regulatory pathways of suberin remain unknown in Brachypodium distachyon. Here we describe the identification of a B. distachyon gene, BdFAR4, encoding a fatty acyl‐coenzyme A reductase (FAR) by a reverse genetic approach, and investigate the molecular relevance of BdFAR4 in the root suberin synthesis of B. distachyon. BdFAR4 is specifically expressed throughout root development. Heterologous expression of BdFAR4 in yeast (Saccharomyces cerevisiae) afforded the production of C20:0 and C22:0 fatty alcohols. The loss‐of‐function knockout of BdFAR4 by CRISPR/Cas9‐mediated gene editing significantly reduced the content of C20:0 and C22:0 fatty alcohols associated with root suberin. In contrast, overexpression of BdFAR4 in B. distachyon and tomato (Solanum lycopersicum) resulted in the accumulation of root suberin‐associated C20:0 and C22:0 fatty alcohols, suggesting that BdFAR4 preferentially accepts C20:0 and C22:0 fatty acyl‐CoAs as substrates. The BdFAR4 protein was localized to the endoplasmic reticulum in Arabidopsis thaliana protoplasts and Nicotiana benthamiana leaf epidermal cells. BdFAR4 transcript levels can be increased by abiotic stresses and abscisic acid treatment. Furthermore, yeast one‐hybrid, dual‐luciferase activity, and electrophoretic mobility shift assays indicated that the R2R3‐MYB transcription factor BdMYB41 directly binds to the promoter of BdFAR4. Taken together, these results imply that BdFAR4 is essential for the production of root suberin‐associated fatty alcohols, especially under stress conditions, and that its activity is transcriptionally regulated by the BdMYB41 transcription factor. [ABSTRACT FROM AUTHOR]

Fatty alcohols are widely used for various applications and are found in products ranging from detergents to cosmetics and cleaning agents. Currently, over 3 million tonnes of fatty alcohols are produced per year from bio‐based and petroleum‐based feedstocks through chemical conversion and synthetic processes. However, the environmental impact of current fatty alcohol production processes has become a major concern, and several bioprocesses have emerged as alternative methods for synthesis. These biological processes are environmentally friendly due to their metal‐free nature, low consumption of energy, and mild reaction conditions. This review overviews the current status of fatty alcohol production – both chemical and biological approaches. Our focus is on biological synthesis approaches using biocatalysis and metabolic engineering due to their proven efficacy. Potential downstream processing for these bioprocesses is also presented. © 2020 Society of Chemical Industry and John Wiley & Sons, Ltd [ABSTRACT FROM AUTHOR]

Fatty alcohols (FOHs) are important feedstocks in the chemical industry to produce detergents, cosmetics, and lubricants. Microbial production of FOHs has become an attractive alternative to production in plants and animals due to growing energy demands and environmental concerns. However, inhibition of cell growth caused by intracellular FOH accumulation is one major issue that limits FOH titers in microbial hosts. In addition, identification of FOH‐specific exporters remains a challenge and previous studies towards this end are limited. To alleviate the toxicity issue, we exploited nonionic surfactants to promote the export of FOHs in Rhodosporidium toruloides, an oleaginous yeast that is considered an attractive next‐generation host for the production of fatty acid‐derived chemicals. Our results showed FOH export efficiency was dramatically improved and the growth inhibition was alleviated in the presence of small amounts of tergitol and other surfactants. As a result, FOH titers increase by 4.3‐fold at bench scale to 352.6 mg/L. With further process optimization in a 2‐L bioreactor, the titer was further increased to 1.6 g/L. The method we show here can potentially be applied to other microbial hosts and may facilitate the commercialization of microbial FOH production. [ABSTRACT FROM AUTHOR]

This study reports on a marine bacterium that accumulates fatty alcohols (C14,16,18) at more than 1% (w/w) of the dry cell weight. This unique bacterium, designated as strain 1–4, is related to the genus Reinekea. A novel gene cluster for fatty alcohol synthesis, phsAB, is identified from strain 1–4. The phsA product shows significant homology to fatty acyl‐CoA reductase (51% identity), whereas the phsB product shows very low homology to lipases. Interestingly, phsA alone causes Escherichia coli to accumulate fatty alcohols at 19% (w/w) of the dry cell weight. Moreover, the phsA‐containing E. coli accumulate more fatty alcohols (24%) and grow faster after phsB is introduced, indicating that phsAB could greatly assist the mass production of fatty alcohols. [ABSTRACT FROM AUTHOR]

Abstract: Fatty acid–derived hydrocarbons attract increasing attention as biofuels due to their immiscibility with water, high‐energy content, low freezing point, and high compatibility with existing refineries and end‐user infrastructures. Yeast Saccharomyces cerevisiae has advantages for production of fatty acid–derived hydrocarbons as its native routes toward fatty acid synthesis involve only a few reactions that allow more efficient conversion of carbon substrates. Here we describe major biosynthetic pathways of fatty acid–derived hydrocarbons in yeast, and summarize key metabolic engineering strategies, including enhancing precursor supply, eliminating competing pathways, and expressing heterologous pathways. With recent advances in yeast production of fatty acid–derived hydrocarbons, our review identifies key research challenges and opportunities for future optimization, and concludes with perspectives and outlooks for further research directions. [ABSTRACT FROM AUTHOR]

Objective The objective of this work was to create a shampoo formula that contains a stable ordered gel network structure that delivers fatty alcohols inside hair. Methods X-ray diffraction ( SAXS and WAXS), SEM and DSC have been used to confirm formation of the ordered Lβ gel network with fatty alcohol (cetyl and stearyl alcohols) and an anionic surfactant ( SLE1S). Micro-autoradiography and extraction methods using GC- MS were used to confirm penetration of fatty alcohols into hair, and cyclic fatigue testing was used to measure hair strength. Results In this work, evidence of a stable Lβ ordered gel network structure created from cetyl and stearyl alcohols and anionic surfactant ( SLE1S) is presented, and this is confirmed via scanning electron microscopy images showing lamella layers and differential scanning calorimetry ( DSC) showing new melting peaks vs the starting fatty alcohols. Hair washed for 16 repeat cycles with this shampoo showed penetration of fatty alcohols from the gel network into hair as confirmed by a differential extraction method with GC- MS and by radiolabelling of stearyl alcohol and showing its presence inside hair cross-sections. The gel network role in delivering fatty alcohol inside hair is demonstrated by comparing with a shampoo with added fatty alcohol not in an ordered gel network structure. The hair containing fatty alcohol was measured via the Dia-stron cyclic fatigue instrument and showed a significantly higher number of cycles to break vs control. Conclusions The formation of a stable gel network was confirmed in the formulated shampoo, and it was demonstrated that this gel network is important to deliver cetyl and stearyl alcohols into hair. The presence of fatty alcohol inside hair was shown to deliver a hair strength benefit via cyclic fatigue testing. [ABSTRACT FROM AUTHOR]

Alcohol ethoxylates surfactants are produced via ethoxylation of fatty alcohol (FA) with ethylene oxide. The source of FA could be either palm kernel oil (PKO) or petrochemicals. The study aimed to compare the potential environmental impacts for PKO-derived FA (PKO-FA) and petrochemicals-derived FA (petro-FA). Cradle-to-gate life cycle assessment has been performed for this purpose because it enables understanding of the impacts across the life cycle and impact categories. The results show that petro-FA has overall lower average greenhouse gas (GHG) emissions (~2.97 kg COe) compared to PKO-FA (~5.27 kg COe). (1) The practices in land use change for palm plantations, (2) end-of-life treatment for palm oil mill wastewater effluent and (3) end-of-life treatment for empty fruit bunches are the three determining factors for the environmental impacts of PKO-FA. For petro-FA, n-olefin production, ethylene production and thermal energy production are the main factors. We found the judicious decisions on land use change, effluent treatment and solid waste treatment are key to making PKO-FA environmentally sustainable. The sensitivity results show the broad distribution for PKO-FA due to varying practices in palm cultivation. PKO-FA has higher impacts on average for 12 out of 18 impact categories evaluated. For the base case, when accounted for uncertainty and sensitivity analyses results, the study finds that marine eutrophication, agricultural land occupation, natural land occupation, fossil depletion, particulate matter formation, and water depletion are affected by the sourcing decision. The sourcing of FA involves trade-offs and depends on the specific practices through the PKO life cycle from an environmental impact perspective. [ABSTRACT FROM AUTHOR]

The development of specific regulatory persistence criteria and a growing need to conduct risk assessments in sediment have increased the need to better understand fate in this compartment. A simplified test approach was developed to assess the fate of chemicals in aerobic sediments and used to evaluate the biodegradation of 14C-labeled representative analogs of alcohol sulfate, alcohol ethoxylate, alcohol ethoxy sulfate, linear alkylbenzene sulfonate, and tetradecanol in 2 different sediments. The method provides kinetic data on primary and ultimate biodegradation in sediments as well as information on biodegradation pathways and metabolites. All test materials exhibited extensive biodegradation in both sediments; disappearance of parent exhibited biphasic kinetics, described by a 2-compartment model, and mineralization was coupled to parent disappearance with little accumulation of metabolites. The first-compartment decay rates ranged from 10.8 d−1 to 17.1 d−1 for tetradecanol, 2.54 d−1 to 24.8 d−1 for alcohol sulfate, 0.17 d−1 to 0.75 d−1 for alcohol ethoxylate, 0.41 d−1 to 0.71 d−1 for alcohol ethoxy sulfate, and 0.26 d−1 to 1.25 d−1 for linear alkylbenzene sulfonate. These rates corresponded to half-lives ranging from 0.041 d to 4.08 d. This method's simplicity and focus on only sediment-associated processes offer potential benefits over the current Organisation for Economic Co-operation and Development 308 aerobic sediment-water test. Environ Toxicol Chem 2016;35:2199-2208. © 2016 SETAC [ABSTRACT FROM AUTHOR]

Many moth pheromones are composed of mixtures of acetates of long-chain (≥10 carbon) fatty alcohols. Moth pheromone precursors such as fatty acids and fatty alcohols can be produced in yeast by the heterologous expression of genes involved in insect pheromone production. Acetyltransferases that subsequently catalyze the formation of acetates by transfer of the acetate unit from acetyl-CoA to a fatty alcohol have been postulated in pheromone biosynthesis. However, so far no fatty alcohol acetyltransferases responsible for the production of straight chain alkyl acetate pheromone components in insects have been identified. In search for a non-insect acetyltransferase alternative, we expressed a plant-derived diacylglycerol acetyltransferase (EaDAcT) (EC 2.3.1.20) cloned from the seed of the burning bush ( Euonymus alatus) in a yeast system. EaDAcT transformed various fatty alcohol insect pheromone precursors into acetates but we also found high background acetylation activities. Only one enzyme in yeast was shown to be responsible for the majority of that background activity, the acetyltransferase ATF1 (EC 2.3.1.84). We further investigated the usefulness of ATF1 for the conversion of moth pheromone alcohols into acetates in comparison with Ea DAcT. Overexpression of ATF1 revealed that it was capable of acetylating these fatty alcohols with chain lengths from 10 to 18 carbons with up to 27- and 10-fold higher in vivo and in vitro efficiency, respectively, compared to Ea DAcT. The ATF1 enzyme thus has the potential to serve as the missing enzyme in the reconstruction of the biosynthetic pathway of insect acetate pheromones from precursor fatty acids in yeast. [ABSTRACT FROM AUTHOR]

Sulfonated acrylate esters have been synthesized by using renewable raw materials such as fatty alcohols of Al-Ceder oil. Mixed fatty acids were isolated from Al-Ceder oil by hydrolysis; both saturated and unsaturated fatty acids were isolated from the mixed fatty acids. The methyl esters of mixed fatty acid, saturated and unsaturated acids of Al-Cedre oil were subjected to reduction with (LiAlH4) to give the corresponding fatty alcohols. The products of the reduction process were saponified and the hydroxyl values were estimated to further confirm the reduction occurrence. The acrylate esters were synthesized by esterification of acrylic acid with fatty alcohols of C, C, C, and C mixed saturated, mixed unsaturated and mixed fatty acids of Al-Cedre oil, respectively. This esterification was followed by addition of NaHSO to form bisulfite adducts. The structures of the prepared surfactants were characterized by IR and HNMR spectroscopy. A series of useful surface parameters, stability towards acids and base hydrolysis and calcium stability have been determined. [ABSTRACT FROM AUTHOR]

The present paper describes the synthesis and evaluation of surface properties of a novel series of anionic surfactant, namely sodium 3-(3-alkyloxy-3-oxopropoxy)-3-oxopropane-1-sulfonate with varying alkyl chain length (C8-C16). Synthesis involves initial formation of the 3-alkyloxy-3-oxopropyl acrylate along with fatty acrylate during the direct esterification of fatty alcohol with acrylic acid in the presence of 0.5 % NaHSO at 110 °C followed by sulfonation of the terminal double bond of the 3-alkyloxy-3-oxopropyl acrylate. Synthesized compounds were evaluated for surface and thermodynamic properties such as critical micelle concentration (CMC), surface tension at CMC (γ), efficiency of surface adsorption (pC), surface excess (Γ), minimum area per molecule at the air-water interface ( A), free energy of adsorption (∆ G°), free energy of micellization (∆ G°), wetting time, emulsifying properties, foaming power and calcium tolerance. Effect of chain length on CMC follows the classic trend, i.e. decrease in CMC with the increase in alkyl chain length. High pC (>3) value indicates higher hydrophobic character of the surfactant. These surfactants showed very poor wetting time and calcium tolerance, but exhibited good emulsion stability and excellent foamability. Foaming power and foam stability of C14-sulfonate were found to be the best among the studied compounds. Foam stability of C14-sulfonate was also studied at different concentrations over time and excellent foam stability was obtained at a concentration of 0.075 %. Thus this novel class of surfactant may find applications as foam boosters in combination with other suitable surfactants. [ABSTRACT FROM AUTHOR]

Arachidonyl alcohol rarely occurs in natural oils. It can be used as a substrate for production of several ether lipids possessing beneficial functions. Although arachidonyl alcohol has been produced on a laboratory scale by the chemical reduction of arachidonic acid, it will be difficult to scale up this process for industrial application. The aim of this study was to develop a new bioprocess for converting arachidonic acid to arachidonyl alcohol. Screening was conducted using 11 wax ester- (esters of fatty acids and fatty alcohols) producing strains reported in our previous study, and a single-cell oil containing arachidonic acid. A new strain, Acinetobacter species N-476-2, most effectively converted arachidonic acid to arachidonyl alcohol, which accumulated inside the cells as a wax ester. GC-MS, FT-IR, and NMR analyses showed that this strain reduced the carboxyl group of 5- cis,8- cis,11- cis,14- cis-arachidonic acid to a hydroxyl group without altering the position or configuration of the double bonds; the product was identified as 5- cis,8- cis,11- cis,14- cis-arachidonyl alcohol. A time-course study of cultivation showed that the amount of arachidonyl alcohol produced by the strain after 4 days was 2.2 mg/mL culture. The bioprocess using Acinetobacter sp. N-476-2 can be applied to the large-scale production of arachidonyl alcohol. [ABSTRACT FROM AUTHOR]

Structuring liquid oils has become an active area of research in the past decade, mainly due to pressures to reduce saturated fat intake and eliminate trans fats from our diets. However, replacing hard fats with liquid oil can lead to major changes in the quality of food products. Recent strategies to impart solid-fat functionality to liquid oils include the addition of unusual compounds to oil, leading to its gelation. These include small-molecule organogelators such as phytosterols and 12-hydroxystearic acid, which self-assemble into crystalline fibers which trap oil. Other crystalline additives include waxes, ceramides, monoacylglycerides, and other surfactants. Recently, the polymer ethyl cellulose was reported to form a polymer gel in triacylglyceride (TAG) oils. Other non-conventional strategies also include the formation of protein-stabilized cellular solids with oil trapped within the cells. In this review, we summarize the research on each one of these components in order to provide a comprehensive overview of the state of the area in oleogel research and provide future perspectives. [ABSTRACT FROM AUTHOR]

Abstract: The reduction of acyl-CoA or acyl-ACP to fatty alcohol occurs via a fatty aldehyde intermediate. In prokaryotes this reaction is thought to be performed by separate enzymes for each reduction step while in eukaryotes these reactions are performed by a single enzyme without the release of the intermediate fatty aldehyde. However, here we report that a purified fatty acyl reductase from Marinobacter aquaeolei VT8, evolutionarily related to the fatty acyl reductases in eukaryotes, catalysed both reduction steps. Thus, there are at least two pathways existing among prokaryotes for the reduction of activated acyl substrates to fatty alcohol. The Marinobacter fatty acyl reductase studied has a wide substrate range in comparison to what can be found among enzymes so far studied in eukaryotes. [Copyright &y& Elsevier]

Euglena gracilis, a unicellular phytoflagellate, can accumulate a large amount of medium-chain wax esters under anaerobic growth conditions. Here we report the identification and characterization of two genes involved in the biosynthesis of wax esters in E. gracilis. The first gene encodes a fatty acyl-CoA reductase ( EgFAR) involved in the conversion of fatty acyl-CoAs to fatty alcohols and the second gene codes for a wax synthase ( EgWS) catalyzing esterification of fatty acyl-CoAs and fatty alcohols, yielding wax esters. When expressed in yeast ( Saccharomyces cerevisiae), EgFAR converted myristic acid (14:0) and palmitic acid (16:0) to their corresponding alcohols (14:0Alc and 16:0Alc) with myristic acid as the preferred substrate. EgWS utilized a broad range of fatty acyl-CoAs and fatty alcohols as substrates with the preference towards myristic acid and palmitoleyl alcohol. The wax biosynthetic pathway was reconstituted by co-expressing EgFAR and EgWS in yeast. When myristic acid was fed to the yeast, myristyl myristate (14:0–14:0), myristyl palmitoleate (14:0–16:1), myristyl palmitate (14:0–16:0) and palmityl myristate (16:0–14:0) were produced. These results indicate EgFAR and EgWS are likely the two enzymes involved in the biosynthesis of medium-chain wax esters in E. gracilis. [ABSTRACT FROM AUTHOR]

2-Chlorohexadecanal (2-ClHDA), a 16-carbon chain chlorinated fatty aldehyde that is produced by reactive chlorinating species attack of plasmalogens, is elevated in atherosclerotic plaques, infarcted myocardium, and activated leukocytes. We tested the hypothesis that 2-ClHDA and its metabolites, 2-chlorohexadecanoic acid (2-ClHA) and 2-chlorohexadecanol (2-ClHOH), induce COX-2 expression in human coronary artery endothelial cells (HCAEC). COX-2 protein expression increased in response to 2-ClHDA treatments at 8 and 20 h. 2-ClHA also increased COX-2 expression following an 8 h treatment. Quantitative PCR showed that 2-ClHDA treatment increased COX-2 mRNA over 8 h, while 2-ClHA treatment led to a modest increase by 1 h and those levels remained constant over 8 h. 2-ClHDA led to a significant increase in 6-keto-PGF1α release (a measure of PGI2 release) by HCAEC. These data suggest that 2-ClHDA and its metabolite 2-ClHA, which are produced during leukocyte activation, may alter vascular endothelial cell function by upregulation of COX-2 expression. [ABSTRACT FROM AUTHOR]

Conversion of oils into gels generally involves altering the chemical characteristics of the liquid. We describe here the gelling of vegetable oils, essential oils, and hydrocarbons at ambient temperature, without changing the chemical characteristics of the liquids, using saturated FA having carbon chain lengths of 10 to 31. The gelling ability of the added FA increased linearly with their chain lengths. Structure-function studies demonstrated that the carboxyl group, position of an additional hydroxyl group, and acyl chain length played an important role in gelation. Long-chain saturated fatty alcohols, wax esters, and dicarboxylic acids also had the ability to gel plant oils and hydrocarbons. [ABSTRACT FROM AUTHOR]

Amination of fatty alcohols by hydrogenation and dehydrogenation catalysis is one of the main commercial processes for the production of dimethylalkylamines. The key factor in this process is the preparation of catalysts with high selectivity. A study of amination catalyzed by Cu−Ni catalysts supported on CaCO3 is reported in this paper. Selectivity of the catalysts was adjustable by varying the ratio of Cu to Ni or by adding a third element (Zn or Mg). The promotion of catalyst selectivity was mainly attributable to the effect of the components on the reducibility of Ni2+ in the catalysts. Lower reducibility of Ni2− led to higher catalyst selectivity. [ABSTRACT FROM AUTHOR]

Summary Bread wheat (hexaploid AABBDD genome; 16 billion basepairs) is a genetically complex, self-pollinating plant with bisexual flowers that produce short-lived pollen. Very little is known about the molecular biology of its gametophyte development despite a longstanding interest in hybrid seeds. We present here a comprehensive characterization of three apparently homeologous genes (TAA1a , TAA1b and TAA1c ) and demonstrate their anther-specific biochemical function. These eight-exon genes, found at only one copy per haploid complement in this large genome, express specifically within the sporophytic tapetum cells. The presence of TAA1 mRNA and protein was evident only at specific stages of pollen development as the microspore wall thickened during the progression of free microspores into vacuolated-microspores. This temporal regulation matched the assembly of wall-impregnated sporopollenin, a phenylpropanoid-lipid polymer containing very long chain fatty alcohols (VLCFAlc), described in the literature. Our results establish that sporophytic genes contribute to the production of fatty alcohols: Transgenic expression of TAA1 afforded production of long/VLCFAlc in tobacco seeds (18 : 1; 20 : 1; 22 : 1; 24 : 0; 26 : 0) and in Escherichia coli (14 : 0; 16 : 0; 18 : 1), suggesting biochemical versatility of TAA1 with respect to cellular milieu and substrate spectrum. Pollen walls additionally contain fatty alcohols in the form of wax esters and other lipids, and some of these lipids are known to play a role in the highly specific sexual interactions at the pollen–pistil interface. This study provides a handle to study these and to manipulate pollen traits, and, furthermore, to understand the molecular biology of fatty alcohol metabolism in general. [ABSTRACT FROM AUTHOR]

The present work demonstrates the rate-limiting effect of varying levels of both glycerine and monoglyceride through a series of batch hydrogenations of fatty dodecyl methyl ester, using copper chromite as the catalyst. Reactions were carried out at 3000 psig H2, 280°C with catalyst levels varying between 1.25 and 1.80%. With increasing contaminant levels of glycerine (0.0, 0.1, 0.5, 5 wt%), conversion of fatty methyl ester to alcohol is correspondingly reduced (95, 89, 80, 2 wt%). On a molar basis of contaminant, monoglyceride equally reduces the conversion of methyl ester to alcohol. In both cases the latent appearance of fatty-fatty ester results from the slower hydrogenation rate. Chemistry is proposed outlining the thermal decomposition of glycerine or glyceride to intermediate components (acetol and acrolein), leading to the generation of propanediols. Experimental studies indicate that diols effectively deactivate the copper chromite catalyst, limiting the rate of fatty methyl ester hydrogenation. Catalyst deactivation is not permanent, suggesting catalyst site blockage by physical adsorption of the polyhydroxyl components. The complete understanding of this interaction holds promise for the development of glycerine/monoglyceride-insensitive catalysts. In addition, a brief overview of methyl ester hydrogenation inhibition effects of some heteroelements, water, and soap is presented. [ABSTRACT FROM AUTHOR]

Fatty alcohols are produced by hydrogenating fatty methyl esters in slurry phase in the presence of copper chromite catalyst at temperatures of 250–300°C and hydrogen pressures of 2000–3000 psi. The fatty methyl ester, catalyst, and hydrogen are fed to the reactor cocurrently. The product slurry is passed through gas-liquid separators and then through a continuous filtration system for removal of the catalyst. A portion of the used catalyst in crude alcohol is recycled to the hydrogenator. The overall efficiency of the process depends upon the intrinsic activity, life, and filterability of the catalyst. The fatty alcohol producer therefore requires a catalyst with high activity, long life, and good separation properties. The main goal of the present laboratory investigation was to develop a superior copper chromite catalyst for the slurry-phase process. Two copper chromite catalysts, prepared by different procedures, were tested for methyl ester hydrogenolysis activity, reusability, and filtration characteristics. The reaction was carried out in a batch autoclave at 280°C and 2000–3000 psi hydrogen pressure. The reaction rates were calculated by assuming a kinetic mechanism that was first-order in methyl ester concentration. The catalyst with the narrower particle size distribution was 30% more active, filtered faster, and maintained activity for several more uses than the catalyst with the broader particle size distribution. X-ray photoelectron spectroscopy data showed higher surface copper concentrations for the former catalyst. [ABSTRACT FROM AUTHOR]

Fatty alcohols, derived from natural sources, are commercially produced by hydrogenation of fatty acids or methyl esters in slurry-phase or fixed-bed reactors. One slurry-phase hydrogenation of methyl ester process flows methyl esters and powdered copper chromite catalyst into tubular reactors under high hydrogen pressure and elevated temperature. In the present investigation, slurry-phase hydrogenations of C12 methyl ester were carried out in semi-batch reactions at nonoptimal conditions (i.e., low hydrogen pressure and elevated temperature). These conditions were used to accentuate the host of side reactions that occur during the hydrogenation. Some 14 side reaction routes are outlined. As an extension of this study, copper chromite catalyst was produced under a number of varying calcination temperatures. Differences in catalytic activity and selectivity were determined by closely following side reaction products. Both activity and selectivity correlate well with the crystallinity of the copper chromite surface; they increase with decreasing crystallinity. The ability to follow the wide variety of side reactions may well provide an additional tool for the optimized design of hydrogenation catalysts. [ABSTRACT FROM AUTHOR]

To purify docosahexaenoic acid (DHA), we attempted the selective esterification of fatty acids originating from tuna oil with lipases. Tuna oil was hydrolyzed in NaOH-ethanol solution, and the resulting fatty acid mixture [DHA, 23.2%; named tuna-free fatty acid (FFA)] was used as a starting material. Rhizopus delemar which acted lightly on DHA, was a suitable catalyst for the selective esterification of tuna-FFA, and lauryl alcohol was the best substrate. The reaction proceeded most effectively when a mixture of 2.4 g lauryl alcohol/tuna-FFA (2:1, mol/mol), 0.6 g water, and 600 U Rhizopus lipase was incubated at 30°C for 20 h with stirring at 500 rpm. Under these conditions 72% of tuna-FFA was esterified, and 84% of DHA was recovered in the unesterified fatty acid fraction. The DHA content in the fatty acid fraction rose from 23 to 73% with this reaction. To further elevate the DHA content, the unesterified fatty acids were extracted, and then esterified again under the same conditions. By this repeated esterification, DHA was purified to 89% with a recovery of 71% of its initial content. [ABSTRACT FROM AUTHOR]

Knowing that dimethiconols or silanols condense under acid or alkaline catalysis, a study was undertaken to determine if these compounds could be successfully ethoxylated under conditions similar to those used to ethoxylate fatty alcohols and acids. It was anticipated that the condensation reaction would take precedent over ethoxylation reaction. We determined that ethoxylation reaction occurs preferentially to condensation reaction. In addition, kinetics of ethoxylation are similar to kinetics observed when fatty alcohols are ethoxylated. This reaction gives rise to a new class of hydrolyzable silicone compounds that have applications in industrial as well as in personal-care products. [ABSTRACT FROM AUTHOR]

The wax esters of the roe oil of the amber fish, Seriola aureovittata, have been resolved by high-performance liquid chromatography (HPLC) in the silver-ion mode. Each of the fractions collected was transmethylated, and the fatty acids and alcohols were identified by gas chromatography/mass spectrometry (GC/MS) as the picolinyl esters and nicotinates, respectively. Their compositions were determined by GC. The fatty acid composition is complex, and the main components are C18:1n-9 (35.5 mol%), C22:6n-3 (20.3 mol%), and C16:1n-7 (10.7 mol%), while fatty alcohols are limited to saturated (C16:0, 60.3 mol%; C18:0, 15.3 mol%; C14:0, 5.1 mol%) and monoenoic alcohols (C18:1n-9, 6.5 mol%; C16:1n-7, 4.5 mol%) with traces (<0.1 mol%) of polyunsaturated fatty alcohols such as C20:3n-3, C20:4n-6, C20:5n-3, and C22:5n-3. Silver-ion HPLC exhibited excellent resolution in which fractions were resolved on the basis of the number and configuration of double bonds as well as the distribution pattern between the acid and alcohol moieties of the molecules with a given number of double bonds. The main wax ester fraction are those of monoenoic acid-saturated alcohol species, hexaenoic acid/saturated alcohol species, and pentaenoic acid/saturated alcohol species. Appreciable specificity was observed in the esterification of fatty acids with alcohols, and surprisingly, no saturated acid-monoenoic alcohol species were detected. [ABSTRACT FROM AUTHOR]

Fatty acid diesters based upon polyoxyethylene glycol (PEG diesters) find applications in many diverse segments of thechemical industry. PEG diesters contain both a water-soluble and an oil-soluble portion, resulting in a surface-active product. These surfactants exhibit emulsification properties. A study of PEG diesters was undertaken to determine the effect of the following variables in the fatty portion of the molecule: (i) number of carbon atoms present, (ii) branching or lack of branching, and (iii) presence of unsaturation. The objective was to compare titer point, solubilities and emulsification properties of various PEG-600 based diesters that were synthesized using high-purity linear saturated, Guerbet-branched, and unsaturated acids. Included in the test was a series of esters based upon meadowfoam oil, a high-molecular-weight unsaturated oil. [ABSTRACT FROM AUTHOR]

Lipase-catalyzed conversions of some minor oils and fats like mowrah (Madhuca latifolia), mango (Mangifera indica) kernel, and sal (Shorea robusta) fats into low, medium, and high molecular weight alcohol esters have been investigated. In solvent-free medium, alcoholysis of the above-mentioned fats with 10% (w/w) Mucor miehei lipase produced alcohol esters in good yield. The percentage molar conversions of C4, C8, C10, C12, C14, C16, C18, and C18:1 alcohols into corresponding alcohol esters ranged from 86.8 to 99.2, while the percentage molar conversions on the basis of oil were in the range of 108.0 to 123.5. [ABSTRACT FROM AUTHOR]

Polymer scale inhibitors have been widely used to reduce the loss caused by mineral scaling in circulating cooling water systems. In this article, four maleic acid‐based copolymers [hydrolyzed polymaleic anhydride (HPMA)‐AEO] containing different fatty alcohol polyoxyethylene ether (such as AEO‐9, AEO‐10, AEO‐15, and AEO‐20) are prepared by the way of free‐radical copolymerization and characterized using Fourier transform infrared (FTIR), 1H NMR, and gel permeation chromatographic (GPC) techniques. The effects of HPMA‐AEO on CaCO3 scale are studied in several aspects (such as dose, Ca2+ concentration, temperature, inhibition time, pH, the ratio of EO:carboxyl, and the relative supersaturation of CaCO3 solution) by static experiments. The CaCO3 scaling process with dosing of HPMA‐AEO‐9 is investigated under dynamic tests. CaCO3 deposits and precipitate in the presence of HPMA‐AEO‐9 are analyzed using scanning electronic microscope (SEM) and X‐ray diffraction (XRD). The results show that the performance of HPMA‐AEO against CaCO3 scale highly depends upon the ratio of EO:carboxyl; the introduction of AEO group can significantly improve the performance of HPMA‐AEO to tolerate high alkalinity, high hardness, and high temperature; the presence of HPMA‐AEO‐9 can obviously affect the CaCO3 scaling process on the tube wall through interfering with nucleation process and crystal growth process and significantly alter the surface morphology and crystal form of CaCO3 deposits. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47470 [ABSTRACT FROM AUTHOR]

The article presents a study pertaining to the allergic contact dermatitis to phytantriol in Germany. Phytantriol is believed to be a an ingredient in cosmetic products that provides moisture whenever applied, however, predicted not a sensitizer as yet. Meanwhile, highlight on a case report of a certain 44-year-old woman having an acute eczematous skin reaction on her face after using a new facial cream and pure almond oil, is likewise provided.