Arachidic acid

Manufactured by Merck Group

Sourced in United States, Germany, United Kingdom

Arachidic acid is a long-chain saturated fatty acid. It is a white, crystalline solid at room temperature. Arachidic acid is commonly used in the manufacturing of various laboratory and industrial products.

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Arachidic

24 protocols using arachidic acid

Synthesis and Characterization of Deuterated Lipids

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Chol, CholS, and Cer[NS] were purchased from Avanti Polar Lipids (Alabaster, AL). Deuterated Chol (²H-2,2,3,4,4,6) (Chol-d₆) was purchased from Cambridge Isotope Laboratories, Inc (Tewksbury, MA), and perdeuterated lignoceric acid-d₄₇ (LA-d₄₇) was purchased from Cayman Chemical (Ann Arbor, MI). The synthesis of deuterated N-lignoceroyl-d-erythro-sphingosine-d₄₇ (Cer[NS]-d₄₇) was a one-step reaction of the sphingosine with LA as previously described (25 ). Palmitic acid, stearic acid, arachidic acid, behenic acid, and LA (all analytical or HPLC grade) were purchased from Sigma-Aldrich Chemie GmbH (Schnelldorf, Germany).

Fandrei F., Engberg O., Opálka L., Jančálková P., Pullmannová P., Steinhart M., Kováčik A., Vávrová K, & Huster D. (2022). Cholesterol sulfate fluidizes the sterol fraction of the stratum corneum lipid phase and increases its permeability. Journal of Lipid Research, 63(3), 100177.

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Catalytic Decarboxylation of Fatty Acids

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Nickel nitrate hexahydrate (98%), aluminium nitrate hydrate(98%), cobalt nitrate hydrate(99%), cupric nitrate hydrate(99%) and zirconyl nitrate hydrate (99%) were purchased from Aladdin Industrial Corporation, Shanghai, China. 5% Pt/C and activated carbon were obtained from Sigma–Aldrich, USA, 40% Ni/SiO₂ were purchased from Gansu Zhongkeyaoyuan Biological Engineering Co., Ltd, China. 20% Ni/Al₂O₃, 20% Cu/ZrO₂, 20% Co/ZrO₂ and 20% Ni/ZrO₂ were synthesized in lab by the co-precipitation method. 10% Ni/C, 20% Ni/C and 30% Ni/C were synthesized in lab by the impregnation method. Stearic acid (>99%), lauric acid (>99%), myristic acid (>99%), palmitic acid (>99%), arachidic acid (>99%) and behenic acid (>99%) were all purchased from Sigma-Aldrich, USA. Acetone (analytic reagent grade) was obtained from Hangzhou Chemical Reagent Co., Ltd, China. The XRD results for all the catalysts were presented in Figure S1 or the section of “effects of nickel loadings on decarboxylation”.

Wu J., Shi J., Fu J., Leidl J.A., Hou Z, & Lu X. (2016). Catalytic Decarboxylation of Fatty Acids to Aviation Fuels over Nickel Supported on Activated Carbon. Scientific Reports, 6, 27820.

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Partially Deuterated Ceramide Synthesis

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CER EOS (C30) as well as shorter CERs, including
CER NS (C24), N-(tetracosanoyl)-phytosphingosine
(CER NP (C24 and C16)), N-(2R-hydroxy-tetracosanoyl)-sphingosine
(CER AS (C24)), and N-(2R-hydroxy-tetracosanoyl)-phytosphingosine
(CER AP (C24)), was all kindly donated by Evonik, Essen, Germany.
Palmitic acid (C16), stearic acid (C18), arachidic acid (C20), behenic
acid (C22), tricosylic acid (C23), lignoceric acid (C24), cerotic
acid (C26), and CHOL were purchased from Sigma-Aldrich Chemie GmbH,
Schnelldorf, Germany. The structures of both partially deuterated
CER NS (C24), which are substituted into the models, are shown in Figure 1. These included:
when hydrogens on the terminal three carbons of the sphingosine chain
were replaced with deuterium (CER NS-d7, purchased from Avanti Polar
Lipids, Alabama) and when the hydrogen atoms along the entire acyl
chain were also replaced (CER NS-d47, kindly provided by Evonik, Essen,
Germany). All solvents used were of analytical grade and supplied
by Labscan, Dublin, Ireland. The water was of Millipore quality produced
by a Milli-Q water filtration system with a resistivity of 18 MΩ
cm at 25 °C. Nucleopore polycarbonate filters, with 0.05 μm
pore size, were purchased from Whatman, Kent, U.K.

Beddoes C.M., Gooris G.S., Foglia F., Ahmadi D., Barlow D.J., Lawrence M.J., Demé B, & Bouwstra J.A. (2020). Arrangement of Ceramides in the Skin: Sphingosine Chains Localize at a Single Position in Stratum Corneum Lipid Matrix Models. Langmuir, 36(34), 10270-10278.

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Synthesis and Characterization of Deuterium-Labeled Lipids

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Chol and Cer[NS] were purchased from Avanti Polar Lipids (Alabaster, AL). Chol(2,2,3,4,4,6)-d₆ was purchased from Cambridge Isotope Laboratories, Inc. (Tewksbury, MA) and lignoceric acid-d₄₇ (LA-d₄₇), 1,12-dibromododecane-d₂₄ and γ-butyrolactone-d₆ were purchased from C/D/N Isotopes, Inc. (Pointe-Claire, Canada). N-(32-linoleoyloxy)dotriacontanoyl-D-erythro-sphingosine (Cer[EOS]) (Fig. 1) was synthesized as described in the literature (25 (link)). Cer[EOS]-sphing-d₉ was purchased from Matreya LLC (State College, PA). The synthesis of Cer[NS]-d₄₇ was a one-step reaction of the sphingosine with LA as similarly performed before (26 ). Palmitic acid, stearic acid, arachidic acid, behenic acid and LA (all analytical or HPLC grade) were purchased from Sigma-Aldrich Chemie GmbH (Schnelldorf, Germany). Chemicals and solvents for synthesis were purchased from Merck (Darmstadt, Germany), VWR International (Stribrna Skalice, Czech Republic), and Penta Chemicals (Prague, Czech Republic) and were used without further purification. Linoleic acid-d₃₂ and ¹³C₁₈ were purchased from Merck (Darmstadt, Germany).

Fandrei F., Havrišák T., Opálka L., Engberg O., Smith A.A., Pullmannová P., Kučerka N., Ondrejčeková V., Demé B., Nováková L., Steinhart M., Vávrová K, & Huster D. (2023). The intriguing molecular dynamics of Cer[EOS] in rigid skin barrier lipid layers requires improvement of the model. Journal of Lipid Research, 64(5), 100356.

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Lipid Signaling Pathway Compounds Protocol

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GGA, phytenic acid, farnesoic acid and geranoic acid were generous gifts from Kuraray (Okayama, Japan). All-trans retinoic acid (ATRA) and 9-cis retinoic acid (9CRA) were obtained from Wako, Osaka, Japan. (S)-2,3-dihydroGGA, (R)-2,3-dihydroGGA and dolichoic acid were synthesized and provided by Dr. Sagami of Tohoku University, Sendai, Japan. Geranylgeraniol (GGOH), phytanic acid, arachidic acid, palmitic acid, oleic acid, fatty acid-free bovine serum albumin (BSA) and tunicamycin were purchased from Sigma Aldrich, St. Louis, MO, USA. IRE1 inhibitor III, 4μ8C (#412512), was from Calbiochem, Merck Millipore Japan, Tokyo, Japan.

Iwao C, & Shidoji Y. (2015). Polyunsaturated Branched-Chain Fatty Acid Geranylgeranoic Acid Induces Unfolded Protein Response in Human Hepatoma Cells. PLoS ONE, 10(7), e0132761.

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Fatty Acid Quantification by LC-MS/MS

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The following chemicals were purchased from Tokyo Chemical Industry (Tokyo, Japan): n-octanoic acid (C8:0), lauric acid (C12:0), myristic acid (C14:0), palmitic acid (C16:0), cis-9-hexadecenoic acid (C16:1), stearic acid (C18:0), γ-linolenic acid (C18:3), cis-5,8,11,14,17-eicosapentaenoic acid (EPA; C20:5) and arachidonic acid (C20:4). Decanoic acid (C10:0), 9-decenoic acid (C10:1), oleic acid (C18:1), arachidic acid (C20:0), all-cis-7,10,13,16,19-docosapentaenoic acid (DPA, C22:5), docosanoic acid (C22:0), tetracosanoic acid (C24:0), hexacosanoic acid (C26:0), DAABD-AE, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), 4-(dimethylamino) pyridine (DMAP) and perfluorooctanoic acid (PFOA) were purchased from Sigma-Aldrich (Taufkirchen, Germany). The following deuterium or ¹³C labeled analogs used as IS were purchased from Cambridge Isotopes Laboratories (Tewksbury, MA, USA): ¹³C₄-C8:0, d₃-C10:0, d₃-C12:0, d₃-C14:0, d₄-C16:0 and d₃-C18:0. PRA, PHA, d₃-PRA, d₃-PHA, d₄-C22:0, d₄-C24:0, and d₄-C26:0 were obtained from Dr. H. J. Ten Brink (Vrije Universiteit Medical Center, Amsterdam, The Netherlands). LC-MS/MS grade acetonitrile and water were purchased from Merck (Darmstadt, Germany). Merck also supplied us with HPLC grade hexane, toluene, and heptane.

Aidaros A.A., Sharma C., Langhans C.D., G. Okun J., Hoffmann G.F., Dasouki M., Chakraborty P., Aljasmi F, & Y. Al-Dirbashi O. (2020). Targeted Metabolomic Profiling of Total Fatty Acids in Human Plasma by Liquid Chromatography-Tandem Mass Spectrometry. Metabolites, 10(10), 400.

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Investigating Apoptosis Pathways

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MSU, phorbol 12-myristate 13-acetate (PMA) and free fatty acids (palmitic acid, palmit oleic acid, myristic acid, myrist oleic acid, stearic acid, oleic acid, arachidic acid, arachidonic acid) were obtained from Sigma-Aldrich. Caspase inhibitors Z-VAD-FMK, Z-IETD-FMK, Z-LEHD-FMK were purchased from Calbiochem. Short interfering RNA human PYCARD and anti-rabbit human PYCARD were purchased from Invitrogen and Cell Signaling Technology.

Kong W.S., Tsuyama N., Inoue H., Guo Y., Mokuda S., Nobukiyo A., Nakatani N., Yamaide F., Nakano T., Kohno Y., Ikeda K., Nakanishi Y., Ohno H., Arita M., Shimojo N, & Kanno M. (2021). Long-chain saturated fatty acids in breast milk are associated with the pathogenesis of atopic dermatitis via induction of inflammatory ILC3s. Scientific Reports, 11, 13109.

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Fatty Acid and Methyl Ester Standards for Lipid Analysis

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The following fatty acid and fatty acid methyl ester standards were purchased from Sigma Aldrich (Gillingham, Dorset, UK): tricosanoic acid (C23:0), behenic acid (C22:0), cis-11,14-eicosadienoic acid (C20:2 Δ11,14), heptadecanoic acid (C17:0), cis-10-pentadecanoic acid (C15:1Δ10), pentadecanoic acid methyl ester (C15:0) (PDA), palmitic acid methyl ester (C16:0), palmitoleic acid methyl ester (C16:1Δ9), cis-10-heptadecanoic acid methyl ester (C17:1Δ10), stearic acid methyl ester (C18:0), elaidic acid methyl ester (t-C18:1Δ9), oleic acid methyl ester (C18:1Δ9), linolelaidic acid methyl ester (t-C18:2 Δ9, 12) linoleic acid methyl ester (C18:2 Δ9,12), arachidic acid methyl ester (C20:0), linolenic acid methyl ester (C18:3 Δ9,12,15), heneicosanoic acid methyl ester (C21:0), all-cis-11,14,17-eicosatrienoic acid methyl ester (C20:3 Δ11,14,17), arachidonic acid methyl ester (C20:4 Δ5,8,11,14), all-cis-13,16-docosadienoic acid methyl ester (C22:2 Δ13,16), lignoceric acid methyl ester (C24:0), nervonic acid methyl ester (C21:1 Δ15), docosahexanoic acid methyl ester (C22:6 Δ4,7,10,13,16,19) (DHA), all-cis-8,11,14-eicosaterinoic acid methyl ester (C20:3 Δ8,11,14), erucic acid methyl ester (C22:1 Δ13). All solvents used (methanol n-hexane and dichloromethane) were CHROMASOLV HPLC grade (Sigma Aldrich, UK). Hydrogen chloride (1.25 M) in methanol was purchased from Fluka Analytical (UK).

Nasaruddin M.L., Pan X., McGuinness B., Passmore P., Kehoe P.G., Hölscher C., Graham S.F, & Green B.D. (2018). Evidence That Parietal Lobe Fatty Acids May Be More Profoundly Affected in Moderate Alzheimer’s Disease (AD) Pathology Than in Severe AD Pathology. Metabolites, 8(4), 69.

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Fatty Acid Profiling Protocol

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Ethyl acetate (EtOAc), methanol (MeOH), acetonitrile (ACN), chloroform (CHCl₃), sulfuric acid 96% (H₂SO₄) and propan-2-ol were purchased from Carlo Erba (Val de Reuil, France). Ammonium formate and the following standards were purchased from Sigma Aldrich (Saint-Quentin Fallavier, France): do decanoic acid, myristic acid, palmitic acid, palmit oleic acid, stearic acid, oleic acid, linoleic acid, γ-linolenic acid, arachidic acid, arachidonic acid, nervonic acid, eicosapentaenoic acid and eicosatrienoic acid. Dimethyl carbonate (DMC) and lauric acid 99% were purchased from Acros Organics (Geel, Belgium). Formic acid was purchased from Fisher Scientific SAS (Illkirch, France). Nonanoic acid 98% and decanoic acid 99% were purchased from Alfa Aesar (Haverhill, MA, USA). Water was purified using a Milli-Q system (Millipore Corporation, Bedford, MA, USA). Phosphoric acid 85–90% (H₃PO₄) and Formic acid were purchased from Fisher Scientific SAS (Illkirch, France). Vanillin was purchased from Extrasynthese (Genay, France).

Wils L., Yagmur M., Phelippe M., Montigny B., Clément-Larosière B., Jacquemin J, & Boudesocque-Delaye L. (2022). Alternative Solvents for the Biorefinery of Spirulina: Impact of Pretreatment on Free Fatty Acids with High Added Value. Marine Drugs, 20(10), 600.

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Preparation and Characterization of Lipid-based Nanoparticles

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Stearic acid and SPAN 80 were purchased from Merck (Merck KGaA, Darmstadt, Germany). Arachidic acid, Tween 60, Tween 80, poly(vinyl alcohol), L-lysine monohydrochloride, lithium carbonate, dansyl chloride, methylamine hydrochloride, triethylamine and sodium acetate were purchased from Sigma-Aldrich (St. Louis, MO, USA) and Miglyol 812 was purchased from Caelo (Caesar & Loretz GmbH, Hilden, Germany). Precirol ATO 5 and Compritol 888 ATO were kindly provided by Gattefossé (Saint Priest Cedex, France). L-Phenylalanine ethyl-ester hydrochloride was purchased from Fluka (Fluka Chemie GmbH, Buchs, Switzerland), acetic acid was obtained from VWR Chemicals (VWR International S.A.S., Fontenay-sous-Bois, France) and acetonitrile and methanol were obtained from Honeywell (Honeywell Riedel-de Häen AG, Seelze, Germany). Aqueous solutions were prepared with double-deionized water (Arium Pro, Sartorius AG, Göttingen, Germany).

Albuquerque J., Casal S., Páscoa R.N., Van Dorpe I., Fonseca A.J., Cabrita A.R., Neves A.R, & Reis S. (2020). Applying nanotechnology to increase the rumen protection of amino acids in dairy cows. Scientific Reports, 10, 6830.

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