Furan Fatty Acids Research Articles

Steroids contents of wound healing preparations from the skin of the Arabian Gulf catfish (Arius bilineatus, Val.) (1001.7)

The Arabian Gulf catfish secretes copious amounts of epidermal gel‐like material when threatened or injured. The freeze dried gel contained 85% proteins, 14.4% lipids 2.6% nucleic acid components and carbohydrates.Preparations from the skin of the catfish were found to accelerate the rate of wound healing, as well as being potent anti‐inflammatory. The lipids were composed of non‐polar lipids, glycolipids and phospholipids. Analysis of the lipids for steroids using TLC, FTIR, 1HNMR, 13CNMR, GC/MS, and GC/MS/MS showed them to contain 14 steroids, including 12 oxysterols. The following compounds were characterized: cholesterol, 7α‐hydroxy cholesterol, 7β‐hydroxycholesterol, 5,6 epoxycholesterol, 3β‐hydroxycholest‐5‐ene‐7‐one, cholest‐3,5‐diene and cholesta‐3,5‐dien‐7‐one. Progesterone, cholest‐3,5,6‐triol and 4‐cholesten‐3‐one were found as minor components, and were identified by comparing their MS, 1HNMR and FTIR spectral data with those of standards and library data. Cholest‐3,6‐dione, cholesta‐4,6‐diene‐3‐one, cholesta‐2,4‐diene, and cholesta‐5,20(22)‐dien‐3‐ol were found only in trace amounts and were identified by GC/MS and MS and their spectral data were compared with library data. The bile of the catfish was found to contain 6 bile acids and salts. The presence of the oxysteroids together with eicosanoids, platelet activating factors, furan fatty acids and unsaturated fatty acids in the skin secretion may help understand the pharmacological and therapeutic activities of the preparations from the skin of the catfish.Grant Funding Source: This project is supported by Research Administration, Kuwait University Grant No. SL04/09

The Furan Fatty Acid Metabolite CMPF Is Elevated in Diabetes and Induces β Cell Dysfunction

Gestational diabetes (GDM) results from failure of the β cells to adapt to increased metabolic demands; however, the cause of GDM and the extremely high rate of progression to type 2 diabetes (T2D) remains unknown. Using metabolomics, we show that the furan fatty acid metabolite 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid (CMPF) is elevated in the plasma of humans with GDM, as well as impaired glucose-tolerant and T2D patients. In mice, diabetic levels of plasma CMPF induced glucose intolerance, impaired glucose-stimulated insulin secretion, and decreased glucose utilization. Mechanistically, we show that CMPF acts directly on the β cell, causing impaired mitochondrial function, decreasing glucose-induced ATP accumulation, and inducing oxidative stress, resulting in dysregulation of key transcription factors and ultimately reduced insulin biosynthesis. Importantly, specifically blocking its transport through OAT3 or antioxidant treatment could prevent CMPF-induced β cell dysfunction. Thus, CMPF provides a link between β cell dysfunction and GDM/T2D that could be targeted therapeutically.

Lipotoxicity, β Cell Dysfunction, and Gestational Diabetes

Gestational diabetes (GDM) is caused by failure of islet β cells to meet the increased insulin requirements of pregnancy. Recently, Prentice etal. (2014) discovered a 7-fold elevation of the furan fatty acid metabolite 3-carboxy-4-methyl-5-propyl-2-furanopropanoic acid (CMPF) in plasma of women with GDM and showed that CMPF directly induces β cell dysfunction.

Volatile compounds as indicators of conjugated and unconjugated linoleic acid thermal oxidation

In this research, volatiles arising from heating of conjugated (CLA) and unconjugated (LA) linoleic acid, in different chemical forms (free acids, methyl esters, and homogeneous TAGs) have been studied. A solid phase micro‐extraction (SPME) coupled with GC–MS was used to analyze the volatile compounds produced during heating at 180°C for different times (15, 30, 45, and 60 min). Numerous types of volatiles have been identified such as aldehydes, furan fatty acids (FA), alcohols, methyl esters, and methyl‐oxoacids. Results showed that aldehydes were the main volatile compounds both in CLA and LA, even if some differences were found between conjugated and unconjugated systems. In particular, heptanal and trans‐2‐octenal were detected mainly in CLA forms, while trans‐2‐heptenal in LA. Among furan FA, 2‐pentyl‐furan content was higher in LA than in CLA at all treatment times, while 2‐hexyl‐furan was detected in free fatty acid and methyl ester forms of CLA and it was never detected in LA model systems. Among alcohols, 1‐octen‐3‐ol was found only in LA forms. Methylated forms of CLA and LA provided high contents of methyl esters, among which methyl octanoate was the most represented. Therefore heptanal, trans‐2‐octenal, 2‐hexyl‐furan could be considered as characteristic compounds produced during CLA‐rich sample oxidation.Practical applications: Nowadays CLA, known for its interesting beneficial health effects both on animals and humans, is widely used as functional component in numerous foods and nutritional supplements. Besides the more common TAG form, CLA is used also as free fatty acids and methyl esters. To date, studies on CLA oxidation are scarce and the results are sometimes contradictory. For this reason, the comparison of the volatile compounds obtained from different model systems of CLA and LA could be useful to deepen knowledge on secondary oxidation products of some chemical forms of interest for pharmaceutical formulae and CLA‐rich oils. In fact, it is very important to know the secondary products typical of CLA‐ and LA‐based matrices to identify characteristic oxidation compounds of CLA and LA products.

Characterization of the Lipid Fraction of Wild Sea Urchin from the Sardinian Sea (Western Mediterranean)

The fatty acid (FA) composition of Spatangus purpureus, Echinus melo, Sphaerechinus granularis, and Paracentrotus lividus, sea urchins, has been studied. Sea urchins were collected at different depth along Sardinia coast in the Mediterranean sea, and their gonad was measured, separated, and analyzed for FA composition by gas chromatography-mass spectrometry. A total of 53 FAs were detected, 16 saturated (SFA), 10 monounsaturated (MUFA), 9 polyunsaturated (PUFA), and 13 highly unsaturated (HUFA). Moreover, 5 furan FAs (FFAs) were revealed for the first time in sea urchin. The HUFA and PUFA classes were the most represented accounting for almost 80% of total FAs. Among these compounds, C20:4 n6 (19.64, 20.52, 23.37, and 8.48 mg/g, respectively) and C22:6 n3 (19.68, 20.05, 3.83, and 1.78 mg/g, respectively) were the most abundant. The results of principal component analysis indicated that the sea urchin samples could be clearly discriminated with respect to their FAs composition.

Bioactive Fish Fatty Acids: Health Effects and Their Use as Functional Food Ingredients

The nutritional benefits of fish or fish oil consumption lies predominantly in its advantageous fatty acid profile, which is rich in long chain omega-3 polyunsaturated fatty acids (ω3 PUFA). Evidence from a large number of epidemiological studies, clinical studies and intervention trials have established the protective effect of ω3 PUFA against several diseases. New experimental evidence also indicates the presence in fish oils of other class of bioactive fatty acids, such as the furan fatty acid (F-acids). Dietary recommendations suggest that the consumption of ω3 PUFA should be increased. The great variability of fatty acid composition of fish species throughout the year should be considered when fish are suggested as a means of improving health or used for oil extraction. The fish oil remains the principal source of ω3 PUFA as an ingredient into conventional food products enrichment and in ω3 PUFA concentrates production (i.e. integrator, nutraceutical), even if a variety of alternative ω3 PUFA sources, such as bacteria, fungi, plants and microalgae are currently being explored for commercial production. The present review summarizes the beneficial effects of ω3 PUFA dietary supplementation on cardiovascular disease, neurological disorder and type 2 diabetes as well as the biological actions of F-acids. Furthermore, in order to present the fish as a dietary source of bioactive fatty acids, differences in fatty acid composition of various fish species are recognized. The alternative ways to ensure an optimal ω3 PUFA intake are also provided by illustrating the possible applications of fish oil on the ω3 PUFA enrichment of functional foods. Keywords: Bioactive foods, docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA), fish oil, food enrichment, functional food, furan fatty acids, omega-3 polyunsaturated fatty acids.

Effect of Rubber Clone on Fatty Acid Composition and Properties of Air Dried Sheet

Properties of air dried sheet (ADS) made from four different clones of Hevea brasiliensis (BPM24, RRIM600, PR255 and PB235) were investigated. BPM24, RRIM600 and PR255 rubbers show a bimodal molar mass distribution (MMD) while PB235 rubber has quasi-unimodal molar mass distribution. It was found that ADS from rubber clone with bimodal MMD (BPM24, RRIM600 and PR255) displayed lower original plasticity (P0) but higher plasticity retention index (PRI). Those rubber samples with bimodal MMD show higher accelerated storage hardening test (ASHT) values than ADS from PB235. Within bimodal rubbers, ADS from PR255 displayed lower PRI and P than the 2 other clones, i.e. RRIM600 and BPM24. ADS made from BPM24 and RRIM600 presented similar fatty acid composition with 3 major fatty acids namely linoleic acid (C18:2), stearic acid (C18:0) and oleic acid (C18:1). In contrast, major fatty acids of ADS made from PR255 were linoleic acid (C18:2) and furan fatty acid. Moreover, ADS from PB235 showed the highest amount of furan fatty acid which confirmed the results of Liengprayoon et al. [1]. Relationship between mesostructure, fatty acids composition and ADS properties are discussed.

Effect of Spawning on Furan Fatty Acid Profile of Edible Muscle and Organ Tissues from Sardine (Sardina pilchardus) and Anchovy (Engraulis encrasicolus)

The total fatty acid compositions, especially the furan fatty acid (F-acids) profile, from edible muscle (fillet) and organ tissues (brain, eye, ovaries, and testes) of spawning and nonspawning sardine and anchovy were examined. The spawning season had no effect on F-acid profiles of the fillet and all organ tissues, for both fishes. However, differences among the F-acid fraction of the organ tissues were revealed. The F-acid portion was less than 1% of total fatty acid in all samples. Five F-acid congeners were detected in the fillet, eye, and gonads, while the brain contained only four F-acids. Unlike the F-acids, spawning season affected the docosahexaenoic acid (DHA) abundance in fillet and gonads. DHA enrichment occurred in fillets and gonads from spawning sardine and anchovy. The ratio ω3 PUFA/ω6 PUFA decreases between spawning and nonspawning fillets, thus the fillets from spawning fish have higher nutritional value.

Detection of 430 Fatty Acid Methyl Esters from a Transesterified Butter Sample

AbstractMilk fat is known to contain one of the highest number of fatty acids of all edible oils. Some of these fatty acids are known to be valuable (e.g. conjugated linoleic acids, furan fatty acid) and other as undesirable (e.g. saturated and some trans‐fatty acids) food ingredients. However, a comprehensive picture on the presence of many trace fatty acids has not been achieved. For this reason we have developed an analysis scheme based on the conversion of the fatty acids into methyl esters. The fatty acid methyl esters were then fractionated by urea complexation. Both the filtrate of the urea complexation (~4 % of the sample weight) and the original sample were fractionated by high‐speed counter‐current chromatography (HSCCC). The resulting fractions were analyzed by GC/MS analysis. With this method 430 fatty acids were detected in one single butter sample. More than 230 fatty acids had two or more double bonds. In addition to the widely known spectrum of fatty acids we also detected a range of cyclohexyl fatty acids (five homologues) and methyl‐branched fatty acids (including short chain and even‐numbered anteiso‐fatty acids), conjugated tetradecadienoic acids along with the novel ω‐oxo‐fatty acids (seven homologues). The reported relative retention time on the polar column may serve as a data base for the screening of other samples for this profusion of fatty acids.

Furan fatty acids – valuable minor fatty acids in food

AbstractFuran fatty acids (F‐acids) are heterocyclic lipid components with a furan moiety in the centre of the molecule. Reports on F‐acids in the literature are rather scarce, although they are considered as particularly valuable food ingredients. F‐acids occur as minor compounds in the lipids of different food samples. Despite the low concentrations, some studies produced evidence that the F‐acids are excellent radical scavengers and thus are able to protect polyunsaturated fatty acids from lipid peroxidation. Accordingly, they may play a currently underrated and largely overlooked positive role in human nutrition. The limited data available result from difficulties in the analysis of these trace compounds. F‐acids in food can hardly be determined without selective enrichment and the use of gas chromatography with mass spectrometry for their determination. The lack of reference standards is a further drawback that hampers the exact assessment of the actual relevance of F‐acids in human nutrition.

Furan fatty acids efficiently rescue brain cells from cell death induced by oxidative stress

Treatment of rat brain C6 astroglioma cells with furan fatty acid F6 prior to exposure to hydrogen peroxide shows a strong protective effect of F6 against cell death resulting from oxidative stress. This protective effect is obtained only for F6 administered as a free fatty acid and with an intact furan ring. It is proposed that brain cells are rescued by F6 scavenging radicals elicited by lipid peroxidation within the cell membrane. Oxidative processes outside the cell membrane, such as protein carbonylation, are not affected by F6. Furan fatty acids such as those present in fish oils and marine organisms are likely beneficial for consumption in reducing the risk of diseases that have been implicated to arise from oxidative stress, such as Alzheimer's disease.

In‐Vitro Toxicological and Proteomic Analysis of Furan Fatty Acids Which are Oxidative Metabolites of Conjugated Linoleic Acids

Furan fatty acids (furan-FA) are oxidative products of conjugated linoleic acids (CLA) and may therefore be ingested when CLA-containing food or food-additives are consumed. Due to the presence of a furan ring structure the question arises whether furan-FA may have toxic properties on enterocytes and liver cells. Here we show that furan-FA neither have toxic effects in human colon cancer cell line Caco-2 nor in human hepatoma cell line HepG2 at concentrations that could be relevant for humans. At concentrations up to 100 μM, all tested furan-FA isomers showed no pronounced cytotoxicity and did not affect cellular proliferation or apoptosis up to concentrations of 500 μM. In addition, furan-FA was neither genotoxic in the micronucleus test using Chinese hamster lung fibroblasts (V79) nor in the Ames test independent of the presence or absence of rat liver homogenate for enzymatic activation of the furan ring structure. A proteomic approach revealed that 48 proteins were differentially expressed when Caco-2 cells were incubated with up to 1 mM of 10,13-epoxy-10,12-octadecadienoic acid (10,12-furan-FA). Three of the 30 proteins that could be identified by MALDI-TOF analysis were upregulated and were associated with lipid droplet biogenesis. The remaining 27 proteins were downregulated and were considered to be associated with general cellular processes such as DNA replication and transcription, protein biosynthesis and protein processing, lipid and energy metabolism. From the proteomic data we conclude that furan-FA is predominantly stored in lipid droplets thereby downregulating cellular metabolic activity and driving the cells into a state of rest.

A uremic toxin, 3-carboxy-4-methyl-5-propyl-2-furanpropionate induces cell damage to proximal tubular cells via the generation of a radical intermediate

3-Carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF), a furan fatty acid uremic toxin (UT) and a substrate for organic ion transporters, contributes to the accumulation of CMPF in renal tubular cells. Although oxidative stress induced by UTs has been proposed as a mechanism of its toxicity in chronic kidney disease, little information is available regarding the redox property of CMPF and its relation to renal cell damage. The findings herein show that CMPF enhances the production of reactive oxygen species (ROS) in HK-2 cells in the presence of angiotensin II (A-II), an inducer of O2−. When iron is also present, CMPF and A-II induce the Fenton reaction, resulting in a further increase in ROS production. Such CMPF-induced oxidative stress increases TGF-β1secretion in HK-2 cells, and a positive correlation between CMPF-induced ROS production and the secretion of active TGF-β1 was observed. CMPF caused a reduction in cell viability which was negatively correlated with intracellular ROS production. These negative effects of CMPF in HK-2 cells were completely suppressed by probenecid, an inhibitor of organic anion transport. Interestingly, in vitro ROS assays indicate that CMPF directly interacts with superoxide anion radicals (O2−) and peroxy radicals (LOO) to produce CMPF radicals. The subsequent interaction of CMPF radicals with dissolved oxygen leads to the overproduction of O2−. Based on these findings, we conclude that CMPF, which accumulates in the renal cells, appears to play a prominent role as a pro-oxidant which subsequently leads to renal cellular damage via the overproduction of O2−.

Dehalococcoides mccartyi gen. nov., sp. nov., obligately organohalide-respiring anaerobic bacteria relevant to halogen cycling and bioremediation, belong to a novel bacterial class, Dehalococcoidia classis nov., order Dehalococcoidales ord. nov. and family Dehalococcoidaceae fam. nov., within the phylum Chloroflexi

Six obligately anaerobic bacterial isolates (195(T), CBDB1, BAV1, VS, FL2 and GT) with strictly organohalide-respiring metabolisms were obtained from chlorinated solvent-contaminated aquifers, contaminated and uncontaminated river sediments or anoxic digester sludge. Cells were non-motile with a disc-shaped morphology, 0.3-1 µm in diameter and 0.1-0.2 µm thick, and characteristic indentations on opposite flat sides of the cell. Growth occurred in completely synthetic, reduced medium amended with a haloorganic electron acceptor (mostly chlorinated but also some brominated compounds), hydrogen as electron donor, acetate as carbon source, and vitamins. No other growth-supporting redox couples were identified. Aqueous hydrogen consumption threshold concentrations were <1 nM. Growth ceased when vitamin B(12) was omitted from the medium. Addition of sterile cell-free supernatant of Dehalococcoides-containing enrichment cultures enhanced dechlorination and growth of strains 195 and FL2, suggesting the existence of so-far unidentified stimulants. Dechlorination occurred between pH 6.5 and 8.0 and over a temperature range of 15-35 °C, with an optimum growth temperature between 25 and 30 °C. The major phospholipid fatty acids were 14 : 0 (15.7 mol%), br15 : 0 (6.2 mol%), 16 : 0 (22.7 mol%), 10-methyl 16 : 0 (25.8 mol%) and 18 : 0 (16.6 mol%). Unusual furan fatty acids including 9-(5-pentyl-2-furyl)-nonanoate and 8-(5-hexyl-2-furyl)-octanoate were detected in strains FL2, BAV1 and GT, but not in strains 195(T) and CBDB1. The 16S rRNA gene sequences of the six isolates shared more than 98 % identity, and phylogenetic analysis revealed an affiliation with the phylum Chloroflexi and more than 10 % sequence divergence from other described isolates. The genome sizes and G+C contents ranged from 1.34 to 1.47 Mbp and 47 to 48.9 mol% G+C, respectively. Based on 16S rRNA gene sequence comparisons, genome-wide average nucleotide identity and phenotypic characteristics, the organohalide-respiring isolates represent a new genus and species, for which the name Dehalococcoides mccartyi gen. nov., sp. nov. is proposed. Isolates BAV1 ( = ATCC BAA-2100 = JCM 16839 = KCTC 5957), FL2 ( = ATCC BAA-2098 = DSM 23585 = JCM 16840 = KCTC 5959), GT ( = ATCC BAA-2099 = JCM 16841 = KCTC 5958), CBDB1, 195(T) ( = ATCC BAA-2266(T) = KCTC 15142(T)) and VS are considered strains of Dehalococcoides mccartyi, with strain 195(T) as the type strain. The new class Dehalococcoidia classis nov., order Dehalococcoidales ord. nov. and family Dehalococcoidaceae fam. nov. are described to accommodate the new taxon.

ChemInform Abstract: Optimized Syntheses of the Furan Fatty Acids F5 and F6 Featuring Convertion of a β‐Iodofuran into a β‐Methylfuran in a Single Operation.

AbstractOptimized syntheses of the furan fatty acids F5 (XI) and F6 (XV) are presented which comprise the conversion of the β‐iodofuran (XII) into the β‐methylfuran (XIV) in a single operation.

Determination of Furan Fatty Acids in Food Samples

AbstractFuran fatty acids (F‐acids) are valuable bioactive compounds found at low concentrations in food. A method for the quantitative determination of saturated F‐acids in food is reported. The sample preparation is based on accelerated solvent extraction, transesterification into methyl esters and silver ion chromatography (20% AgNO3 in silica, 1% deactivated) of the resulting methyl esters. There then follows determination of the enriched F‐acid methyl (or ethyl) esters by GC/EI‐MS in the selected ion monitoring (SIM) mode. The 9‐(3‐methyl‐5‐pentylfuran‐2‐yl)‐nonanoic acid ethyl ester (9M5‐EE) was used as an internal standard for recovery checks. The limit of detection was 11 pg, and the recovery rate of the silver ion chromatography was 85% (n = 5). Further F‐acid standards were used for evaluation of individual SIM‐responses. Application of the method to various biological samples gave the following results: champignons (n = 2) contained 1.7 or 2.5 mg/100 g dry weight F‐acids, while fish oil capsules (n = 5) contained between 18 and 234 mg/100 g oil F‐acids distributed over up to seven F‐acids. The concentrations and patterns were different to fresh fish. Accordingly, fish oil supplements seem to be a minor source for F‐acids compared to (fresh) fish. Organic butter samples (n = 4) contained about twice the amount of F‐acids when compared with conventional butter (n = 5).

Absorption and Metabolism of cis‐9,trans‐11‐CLA and of Its Oxidation Product 9,11‐Furan Fatty Acid by Caco‐2 Cells

Furan fatty acids (furan-FA) can be formed by auto-oxidation of conjugated linoleic acids (CLA) and may therefore be ingested when CLA-containing foodstuff is consumed. Due to the presence of a furan ring structure, furan-FA may have toxic properties, however, these substances are toxicologically not well characterized so far. Here we show that 9,11-furan-FA, the oxidation product of the major CLA isomer cis-9,trans-11-CLA (c9,t11-CLA), is not toxic to human intestinal Caco-2 cells up to a level of 100 μM. Oil-Red-O staining indicated that 9,11-furan-FA as well as c9,t11-CLA and linoleic acid are taken up by the cells and stored in the form of triglycerides in lipid droplets. Chemical analysis of total cellular lipids revealed that 9,11-furan-FA is partially elongated probably by the enzymatic activity of cellular fatty acid elongases whereas c9,t11-CLA is partially converted to other isomers such as c9,c11-CLA or t9,t11-CLA. In the case of 9,11-furan-FA, there is no indication for any modification or activation of the furan ring system. From these results, we conclude that 9,11-furan-FA has no properties of toxicological relevance at least for Caco-2 cells which serve as a model for enterocytes of the human small intestine.

Optimized Syntheses of the Furan Fatty Acids F5 and F6 Featuring Convertion of a β-Iodofuran into a β-Methylfuran in a Single Operation

Optimized syntheses of the furan fatty acids F5 1a and F6 1b are described, which give >60% overall yields over 7 or 8 steps respectively starting from 10-undecenal 6. The F6 approach also features a conversion of a β-iodofuran into the corresponding β-methyl derivative in a single operation.

Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus

A lipid extract of Perna canaliculus (New Zealand green-lipped mussel) has reportedly displayed anti-inflammatory effects in animal models and in human controlled studies. However, the anti-inflammatory lipid components have not been investigated in detail due to the instability of the lipid extract, which has made the identification of the distinct active components a formidable task. Considering the instability of the active component, we carefully fractionated a lipid extract of Perna canaliculus (Lyprinol) and detected furan fatty acids (F-acids). These naturally but rarely detected fatty acids show potent radical-scavenging ability and are essential constituents of plants and algae. Based on these data, it has been proposed that F-acids could be potential antioxidants, which may contribute to the protective properties of fish and fish oil diets against chronic inflammatory diseases. However, to date, in vivo data to support the hypothesis have not been obtained, presumably due to the limited availability of F-acids. To confirm the in vivo anti-inflammatory effect of F-acids in comparison with that of eicosapentaenoic acid (EPA), we developed a semisynthetic preparation and examined its anti-inflammatory activity in a rat model of adjuvant-induced arthritis. Indeed, the F-acid ethyl ester exhibited more potent anti-inflammatory activity than that of the EPA ethyl ester. We report on the in vivo activity of F-acids, confirming that the lipid extract of the green-lipped mussel includes an unstable fatty acid that is more effective than EPA.

One-Step Production of a Biologically Active Novel Furan Fatty Acid from 7,10-Dihydroxy-8(E)-octadecenoic Acid

Furan fatty acids (F-acids) gain special attention because they are known to play important roles in biological systems including humans. Specifically, F-acids are known to have strong antioxidant activitis such as radical scavenging activity. Although widely distributed in most biological systems, F-acids are trace components and their biosynthesis is complicated and quite different by sources. On the basis of biochemical study, they are considered to be an essential nutritional factor for mammals and should be provided through the diet. Hence, several studies reported the chemical synthesis of F-acids using chemical catalysts. However, chemical synthesis required complicated multiple steps. In this study was developed a simple one-step synthesis of a novel F-acid, 7,10-epoxyoctadeca-7,9-dienoic acid (EODA), from a dihydroxyl fatty acid, 7,10-dihydroxy-8(E)-octadecenoic acid (DOD), by heat treatment. The structure of EODA was confirmed by GC-MS, NMR, and FTIR analyses, and maximum production yield under the reaction conditions of 90 °C and 24 h reached 80%.