Hexadecanal (palmitic aldehyde, 16:0al) was obtained from Cayman Chemical. Phytol (cis- and trans-isomers) was obtained from Sigma Aldrich. Phytenal was synthesized by oxidation of Phytol with pyridinium chlorochromate (22 , 23 (link)). Briefly, a solution of Phytol and pyridinium chlorochromate (in a nanomolar ratio of 0.01–0.09) in dichloromethane was stirred for 90 min. The reaction mixture was passed through a silica column. The reaction product (phytenal) was collected in the flow-through and eluted with 5-ml dichloromethane. Pristanol was synthesized from pristanic acid (Larodan) as follows. Pristanic acid methyl ester was produced by methylation with 1 N methanolic HCl at 80 °C for 30 min. The methyl esters were extracted after addition of 1 ml 0.9% NaCl and 1-ml hexane. The hexane was evaporated and the methyl ester reduced to pristanol with LiAlH4 (24 ). Pristanal (pristyl aldehyde) was obtained from pristanol by oxidation with pyridinium chlorochromate as described for phytenal. Nonadecanal (19:0al), eicosanal (icosanal, 20:0al), and phytanal were produced from the corresponding fatty acids (nonadecanoic acid, eicosanoic acid, from Sigma Aldrich; phytanic acid from Larodan). The fatty acids were converted into their methyl esters and then reduced to the alcohols with LiAlH4, and the alcohols oxidized with pyridinium chlorochromate as described above.
Nonadecanoic acid
Manufactured by Merck Group
Sourced in United States
Nonadecanoic acid is a long-chain saturated fatty acid that is used as a laboratory reagent. It has the molecular formula C19H38O2.
Automatically generated - may contain errors
Lab products found in correlation
Methoxyamine hydrochloride, by Merck Group (2 mentions)
Chloroform, by Thermo Fisher Scientific (2 mentions)
Ribitol, by Merck Group (2 mentions)
Oleic acid, by Merck Group (2 mentions)
Methanol, by Merck Group (2 mentions)
Hexane, by Thermo Fisher Scientific (2 mentions)
Trace 1310 gc, by Thermo Fisher Scientific (2 mentions)
Rt 2560 capillary column, by Restek (2 mentions)
Phytanic acid, by Merck Group (1 mentions)
Phytol, by Merck Group (1 mentions)
Eicosanoic acid, by Merck Group (1 mentions)
N methyl n trimethylsilyl trifluoroacetamide, by Merck Group (1 mentions)
6 benzylaminopurine, by Merck Group (1 mentions)
Adonitol, by Merck Group (1 mentions)
Bf3 methanol, by ANPEL (1 mentions)
Cholesterol, by Merck Group (1 mentions)
Qualmix fish, by Merck Group (1 mentions)
Methyl stearate, by Merck Group (1 mentions)
1 2 dipalmitoyl rac glycero 3 phosphocholine, by Merck Group (1 mentions)
Supelco 37 component fame mix standard, by Merck Group (1 mentions)
18 protocols using nonadecanoic acid
1
Synthesis of Long-Chain Aldehydes
2
Comprehensive Metabolite Extraction Protocol
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The nonadecanoic acid, docosahexaenoic acid methyl esters, 6‐benzylaminopurine, adonitol, methoxyamine hydrochloride, N‐methyl‐N‐trimethylsilyl‐trifluoroacetamide and trimethychlorosilane were purchased from Sigma‐Aldrich (St. Louis, USA). BF3‐methanol was purchased from ANPEL Laboratory Technologies Inc. (Shanghai, China). All other chemicals were obtained from Aladdin Industrial Inc. (Shanghai, China).
3
Metabolite Extraction and Derivatization
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Methanol (High-Performance Liquid (HPLC) grade; ≥99.9%; catalog no.: A454-4) and chloroform (HPLC grade; ≥99.9%; catalog no.: C607-4) were purchased from Fisher Scientific (Hampton, NH) (
http://www.fishersci.com ). Pyridine (GC grade; ≥99.8%; catalog no.: 82704-1L),
N-methyl-
N-(trimethylsilyl)trifluoroacetamide (MSTFA reagent) (catalog no.: M7891), the methoxy amination reagent, and the internal standard. reference compounds ribitol (≥99.0%; catalog no.: A5502-5G) and nonadecanoic acid (≥99.0%; catalog no.: N5252-5G) were purchased from Sigma-Aldrich (St. Louis, MO, USA) (
http://www.sigmaal drich.com ) Distilled water was purified “in-house” using a Milli-Q system (Bedford, MA, USA) (
http://www.millipore.com ).
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Methanol (High-Performance Liquid (HPLC) grade; ≥99.9%; catalog no.: A454-4) and chloroform (HPLC grade; ≥99.9%; catalog no.: C607-4) were purchased from Fisher Scientific (Hampton, NH) (
N-methyl-
N-(trimethylsilyl)trifluoroacetamide (MSTFA reagent) (catalog no.: M7891), the methoxy amination reagent, and the internal standard. reference compounds ribitol (≥99.0%; catalog no.: A5502-5G) and nonadecanoic acid (≥99.0%; catalog no.: N5252-5G) were purchased from Sigma-Aldrich (St. Louis, MO, USA) (
4
Lipid Quantification and Characterization
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Solvents and chemical reagents used were of reagent grade and purchased from Merck (Darmstadt, Germany). The following solvents were employed: ethanol, acetone, ethyl acetate, chloroform, methanol, hexane, and toluene. The following reagents were used: ammonium molybdate, cupric acetate, pyridine, acetic acid, acetic anhydride, acetyl chloride, NaCl, anhydride sodium sulphate, sulphuric acid, ferric trichloride, perchloric acid, nitric acid, and hydroxylamine.
Quantitative standards (1,2-dipalmitoyl-rac-glycero-3-phosphocholine, oleic acid, cholesterol, methyl stearate, nonadecanoic acid) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Qualitative (Qualmix Fish) and quantitative (FAME Mix) FAME standards were obtained from Supelco, Inc. (Bellefonte, PA, USA) and Larodan (Malmo, Sweden), respectively.
Quantitative standards (1,2-dipalmitoyl-rac-glycero-3-phosphocholine, oleic acid, cholesterol, methyl stearate, nonadecanoic acid) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Qualitative (Qualmix Fish) and quantitative (FAME Mix) FAME standards were obtained from Supelco, Inc. (Bellefonte, PA, USA) and Larodan (Malmo, Sweden), respectively.
5
Fatty Acid Profiling of Brassica Seed Lipids
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Twelve seeds from different siliques were harvested at 27, 38 and 45 DAF for each biological repeat. In total, six biological repeats were used. FA extraction was performed as previously described (Woodfield et�al. 2017 (link), Woodfield et al. 2018 (link)). Seed samples were incubated in 1.2 ml of isopropanol at 70�C for 30 min to inactivate any endogenous (phospho-) lipases. Nonadecanoic acid (19:0; Sigma, St. Louis, Missouri, USA) was used as an internal standard. Fatty acid methyl esters (FAMEs) were analyzed by an Agilent GC-MS device (5,973 inert mass spectrometer combined with 6,890 N gas chromatograph) equipped with an Agilent J&W DA-WAX capillary column (30 m � 0.25 mm � 0.25 �m; Lung et�al. 2017 (link)). The oven temperature was set to 170�C for 3 min, increased to 220�C at 4�C�min−1, and held at 220�C for 15 min (Woodfield et�al. 2017 (link)). FAMEs were routinely identified by comparing the retention time of peaks with the Supelco 37 Component FAME MIX standard (Sigma) but had been identified fully in previous work (Woodfield et�al. 2017 (link)).
6
Lipid Extraction and Methyl Esterification
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Chemicals used in this study were: Yeast Extract (Biokar Diagnostics, France); Peptone (Biokar Diagnostics, France); Glucose (Sigma, Germany); Chlormaphenicol (Biomatik, USA); Ethyl Methane Sulfonate (Sigma, Germany); Sodium Thiosulfate (Sigma, Germany); Sodium Phosphate (Sigma, Germany); Sodium Chloride (Sigma, Germany); 2,6-Di-tert-butyl-4-methylphenol (BHT) (Sigma, Germany); Methanol (Carlo-Herba, France); Hydrochloric acid 37% (Carlo Herba, France); n-Hexane (VWR chemical, France); Dichloromethane (VWR chemical, France); 2,2-dimethoxypropane (Sigma, Germany); Hydrochloric acid solution (Sigma, Germany); Sodium Methoxide solution (Sigma, Germany) and Nonadecanoic acid (Sigma, Germany).
7
Quantification of Fructose Compounds
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High-fructose corn syrup (F55) was supplied by Guangzhou Shuangqiao Co., Ltd. (Guanzhou, China). Nonadecanoic acid was purchased from Sigma-Aldrich (Sigma, San Diego, USA). Methanol, hexane, and chloroform were of HPLC (High Performance Liquid Chromatography) grade and were from Merck (Darmstadt, German). Pyridine, O-methylhydroxylamine hydrochloride, N-methyl-N-(trimethylsilyl) trifluoroacetamide (MSTFA), and trimethylchlorosilane (TMCS) were from J&K Scientific Co. Ltd. (Tianjing, China).
8
Fatty Acid Composition Analysis of Oils
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The fatty acid composition of the samples was analyzed at the start of the storage test (day 0) and the end of the test (day 21) using the method previously described by Mellery et al. [37 (link)]. The fatty acids in oil were first converted to fatty acid methyl esters (FAME) via a 2-step methylation with KOH and HCl with nonadecanoic acid (C19: 0, Sigma-Aldrich) used as an internal standard. The FAMEs were then extracted in hexane and separated by gas chromatography. Fatty acids in the samples were identified and quantified by comparing the retention times and peak areas with a standard mixture of 43 pure FAME standards (Larodan, Solna, Sweden). Chromatograms were processed using Chromeleon 7 (ThermoFisher Scientific, Waltham, MA, USA), and the results are expressed as mg/g of oil.
9
Lipid Composition Analysis Protocol
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Methanol (≥99.9%), n-hexane (≥99%) and HPLC-acetonitrile (≥99.9%) were obtained from Lab-Scan (Dublin, Ireland). Nonadecanoic acid, conjugated linoleic acid (CLA) isomers, and an FA standard mixture (37 FA methyl esters [FAME] mix), α-tocopherol (αT), α-tocopheryl acetate (αTAc), cholesterol, 2,6-di-tert-butyl-pcresol, 25% aqueous 1,5-pentanedialdehyde solution, 1,1,3,3-tetramethoxy-propane (99%), sorbic acid, 2,4-dinitrophenylhydrazine (containing approximately 30% water), trichloroacetic acid and 25% BF3 in Methanol were purchased from Sigma Aldrich (St Louis, MO, USA). Chloroform, dichloromethane KOH, NaOH and Na2SO4, were obtained from Avantor Performance Materials (Gliwice, Poland). All other chemicals were of analytical grade. The vitamin and mineral premix (ID number: aPL 1405002p) was obtained from POLFAMIX OK (Poland). CA was purchased from Hunan Geneham Biomedical Technology Ltd (Changsha Road, Changsha, Hunan, China). The YSe (selenised-Saccharomyces cerevisiae) was obtained from Sel-Plex (Alltech In., Nicholasville, KY, USA). Odourless FO and RO were supplied by Company AGSOL (Pacanów, Poland). FO and RO were stored in tightly sealed containers at 4 °C in a dark place. The FA profiles in RO and FO were presented in our previous publication (Czauderna et al., 2017 ).
10
Lipid Standards Characterization Protocol
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Pentadecanoic acid (C15:0), palmitic acid (C16:0), palmitoleic acid (C16:1), heptadecanoic acid (C17:0), stearic acid (C18:0), oleic acid (C18:1), linoleicacid (C18:2), linolenic acid (C18:3), nonadecanoic acid (C19:0), arachidonic acid (C20:4), heneicosanoic acid (C21:0), docosahexaenoic acid (C22:6), L-α-phosphatidylinositol sodium salt (PI, PI(16:0/18:2)), 9-aminoacridine (9-AA), 1,8-bis(dimethylamino)naphthalene (DMAN), and N-(1-naphthyl) ethylenediamine dihydrochloride (NEDC) were purchased from Sigma-Aldrich Chemicals (St. Louis, MO, USA). 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphate (sodium salt) (PA(18:1(9Z)/18:1(9Z))), 1,2-di-(9E-octadecenoyl)-sn-glycero-3-phosphocholine (PC(18:1(9E)/18:1(9E))), 1,2-di-(9E-octadecenoyl)-sn-glycero-3-phosphoethanolamine (PE(18:1(9E)/18:1(9E))) and 1,2-dipalmitoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (sodium salt) (PG(16:0/16:0)) were purchased from Avanti Polar lipids (Alabaster, AL, USA). GO was from Nanjing JCNANO Technology Co., Ltd (Nanjing, China). HPLC-grade isopropanol and hexane were from Fisher Scientific (Pittsburg, PA, USA). Ultrapure water was purified by a Milli-Q system (Millipore, MA, USA).
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