Myristoleic acid

Manufactured by Merck Group

Sourced in United States

Myristoleic acid is a 14-carbon unsaturated fatty acid used in various laboratory applications. It serves as a standard and reference compound for analytical procedures.

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Lab products found in correlation

9 protocols using myristoleic acid

Identification of Ae. aegypti Compounds

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Chemical compounds used for electroantennography (EAG) and oviposition bioassays were previously identified from extracts of immature stages of Ae. aegypti (3^rd and 4^th larval instars and pupae) [27 (link)]. The isovaleric acid, myristoleic acid, myristic acid and pentadecanoic acid synthetic compounds (purity ≥ 99%; Sigma Aldrich Inc., St-Louis, MO, USA) were diluted in n-hexane (HPLC grade; Carlo Erba reagents, Milano, Italy).

Boullis A., Mulatier M., Delannay C., Héry L., Verheggen F, & Vega-Rúa A. (2021). Behavioural and antennal responses of Aedes aegypti (l.) (Diptera: Culicidae) gravid females to chemical cues from conspecific larvae. PLoS ONE, 16(2), e0247657.

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Quantification of Mycotoxins and Phytochemicals

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Aflatoxin B1, B2 G1 and G2, were purchased from Supelco (Bellefonte, Pennsylvania, USA), apigenin (>99%), luteolin (>97%), rutin hydrate (>94%), quercetin dehydrate (>98%), octadecanoic acid (>98.5%), glutamic acid, myrist oleic acid, tetradecanoic acid, hexadecanoic acid, (Z)-9-hexadecenoic acid, lin oleic acid, (Z)-9-octadecenoic acid, octadecanoic acid, (Z,Z)-9,12-0ctadecadienoic acid, oleic acid, eicosanoic acid and amino acid standard solution (AAS 18) were purchased from Sigma-Aldrich (Chemie GmbH Munich, Germany).

Shumo M., Osuga I.M., Khamis F.M., Tanga C.M., Fiaboe K.K., Subramanian S., Ekesi S., van Huis A, & Borgemeister C. (2019). The nutritive value of black soldier fly larvae reared on common organic waste streams in Kenya. Scientific Reports, 9, 10110.

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Fatty Acid Standards for Analytical LC-MS

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All solvents used were of LC–MS analytical grade. Acetonitrile was purchased from Carlo Erba (Val De Reuil, France), isopropanol and methanol from Fisher Scientific (Laughborough, UK) and formic acid 98–100% from Chem-Lab (Zedelgem, Belgium). Lauric acid was purchased from Acros Organics (>99%), myristic acid from Sigma Aldrich (>99.5%), myristoleic acid from Sigma Aldrich (>99%), pentadecanoic acid from Sigma Aldrich (>99%), palmitic acid from Fluka (analytical standard), 9-palmitoleic acid from Fluka (analytical standard), margaric acid from Sigma Aldrich (>98%), 10-Z-heptadecenoic acid from Cayman Chemical Company (>98%), stearic acid from Fluka (analytical standard), oleic acid from Fluka (analytical standard), linoleic acid from Sigma Aldrich (>99%), linolenic acid from Sigma Aldrich (>99%), arachidic acid from Cayman Chemical Company (>98%), bihomo-γ-linolenic acid from Cayman Chemical Company (>98%), arachidonic acid from Sigma Aldrich (>99), 5,8,11,14,17-cis-eicosapentanoic acid from Fluka (analytical standard), 7,10,13,16,19-cis-docosapentaenoic acid from Cayman Chemical Company (>98%), 4,7,10,13,16,19-cis-docosahexaenoic acid from Sigma Aldrich (>98%) and lignoceric acid from Cayman Chemical Company (>98%).

Mantzourani C, & Kokotou M.G. (2023). Targeted and Suspect Fatty Acid Profiling of Royal Jelly by Liquid Chromatography—High Resolution Mass Spectrometry. Biomolecules, 13(3), 424.

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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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Comprehensive Analysis of Plant Compounds

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The synthetic standards including (1R)-(+)-α-pinene, (-)-β-pinene, β-myrcene, (S)-(-)-limonene, linalool, octanal, nonanal, decanal, benzaldehyde, butylated hydroxytoluene, methyl benzoate, (-)-bornyl acetate, 6-methyl-5-hepten-2-one, geranyl acetone, decanoic acid, undecanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, myrist oleic acid, palmit oleic acid, lin oleic acid, oleic acid, (+)-longifolene, caryophyllene oxide, (E)–β-caryophyllene, undecane, dodecane, pentadecane, hexadecane and quercetin were obtained from Sigma-Aldrich (>98% purity).

Murungi L.K., Kirwa H., Salifu D, & Torto B. (2016). Opposing Roles of Foliar and Glandular Trichome Volatile Components in Cultivated Nightshade Interaction with a Specialist Herbivore. PLoS ONE, 11(8), e0160383.

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Profiling Aflatoxins and Fatty Acids

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Aflatoxins B₁, B_2, G₁ and G₂ were purchased from Supelco (Bellefonte, Pennsylvania, USA), apigenin (≥ 99%), luteolin (≥ 97%), rutin hydrate (≥ 94%) quercetin dehydrate (≥ 98%), octadecanoic acid (≥ 98.5%), glutamic acid, myrist oleic acid, tetradecanoic acid, hexadecanoic acid, (Z)-9-hexadecenoic acid, lin oleic acid, (Z)-9-octadecenoic acid, octadecanoic acid, (Z, Z)-9,12-octadecadienoic acid, oleic acid, eicosanoic acid and amino acid standard solution (AAS 18) were purchased from Sigma-Aldrich (Chemie GmbH, Munich, Germany).

Musundire R., Osuga I.M., Cheseto X., Irungu J, & Torto B. (2016). Aflatoxin Contamination Detected in Nutrient and Anti-Oxidant Rich Edible Stink Bug Stored in Recycled Grain Containers. PLoS ONE, 11(1), e0145914.

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Avasimibe Lipid Nanoparticle Synthesis

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Avasimin was prepared following the protocol described previously (26 (link)). Avasimibe, DMSO, human albumin, cholesteryl oleate, glyceryl tri oleate, myristoleic acid, palmitic acid, palmitoleic acid, stearate, oleate, linoleic acid, arachidonic acid, and docosahexaenoic acid were purchased from Sigma-Aldrich. IWP-2 was purchased from Abcam. Recombinant human Wnt3a was purchased from Bio-Techne Corporation. Luciferin was purchased from Perkin Elmer.

Lee H.J., Li J., Vickman R.E., Li J., Liu R., Durkes A.C., Elzey B.D., Yue S., Liu X., Ratliff T.L, & Cheng J.X. (2018). Cholesterol Esterification Inhibition Suppresses Prostate Cancer Metastasis by Impairing the Wnt/β-catenin Pathway. Molecular cancer research : MCR, 16(6), 974-985.

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Fatty Acid Profiling by GC-MS

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All FA standards, including lauric acid (C12:0), myristic acid (C14:0), pentadecanoic acid (C15:0), palmitic acid (C16:0), heptadecanoic acid (C17:0), stearic acid (C18:0), arachidic acid (C20:0), lignoceric acid (C24:0), myrist oleic acid (C14:1), palmit oleic acid (C16:1), oleic acid (C18: 1n -9), vaccenic acid (C18:1), linoleic acid (C18: 2n -6), 8-eicosenoic acid (C20:1), α-linolenic acid (C18: 3n -3), eicosadienoic acid (C20: 2n -6), brassidic acid (C22: 1n -9), erucic acid (C22: 1n -9), 11,14,17-eicosatrienoic acid (C20:3 n-3), arachidonic acid (C20: 4n -6), docosadienoic acid (C22: 2n -6), eicosapentaenoic acid (C20: 5n -3), nervonic acid (C24: 1n -9), and DHA (C22: 6n -3), were purchased from Sigma (St. Louis, MO). The reagents used were methanol (67-56-1, Honeywell Research Chemicals, Charlotte, NC), n-hexane (110-54-3, Honeywell), chloroform (67-66-3, Sinopharm Chemical Reagent Co. Ltd., Shanghai, China), and diazomethane Sigma) . We made a standard solution by dissolving 5 mg of the FA standards in 100 mL of chloroform. The solution (100 μL) was added to a derivatization reagent (diazomethane) and incubated for 1 h, followed by drying. We added 1,000 μL of n-hexane to reconstitute it, giving a final constituted standard with the initial concentration of 5 μg/mL. The gradient was diluted to 2, 1, 0.5, 0.2, 0.1, and 0.05 μg/mL.

Li M., Liu Y., Li Q., Yang M., Pi Y., Yang N., Zheng Y, & Yue X. (2020). Comparative exploration of free fatty acids in donkey colostrum and mature milk based on a metabolomics approach. Journal of dairy science, 103(7).

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Fatty Acid Characterization Protocol

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Lauric acid (LA) 12:0, tridecanoic acid (TA) 13:0, myristoleic acid (MOA) 14:1, palmitoleic acid (POA) 16:1, α-linolenic acid (ALA) 18:3 and internal standard (IS) pentadecanoic acid (15:0) were purchased from Sigma (Sigma Aldrich, UK); all standards were of purity ≥99 % (GC). The derivatisation reagent, BCl₃-methanol, 12 % w/w (12 % boron trichloride in methanol), n-hexane (HPLC grade, purity, ≥99 %), Tween 80, PEG 400 and anhydrous sodium sulphate were also purchased from Sigma (Sigma-Aldrich, UK).

Butt U., ElShaer A., Snyder L.A., Chaidemenou A, & Alany R.G. (2016). Fatty acid microemulsion for the treatment of neonatal conjunctivitis: quantification, characterisation and evaluation of antimicrobial activity. Drug Delivery and Translational Research, 6(6), 722-734.

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