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Ricinoleic acid

Manufactured by Merck Group
Sourced in Sao Tome and Principe, India, United States, Germany

Ricinoleic acid is a long-chain, unsaturated fatty acid with the chemical formula C₁₈H₃₃O₃. It is the main component of castor oil, which is derived from the seeds of the castor oil plant. Ricinoleic acid is a colorless, viscous liquid with a characteristic odor. It is commonly used in the production of various industrial and pharmaceutical products.

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8 protocols using ricinoleic acid

1

Ricinine Quantification in Biological Samples

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Standard solution (100 mg/mL) of ricinine was obtained from Cerilliant (Round Rock, TX) and human urine and horse serum were purchased from Innovative Research (Novi, MI). Ethyl acetate (99.9%, HPLC grade), ricinoleic acid (≥ 99%), ricinine-(methyl-d3), (3,3,3-trifluoropropyl)-silane (99.9%, HPLC grade), methanol (99.9%, HPLC grade), formic acid (95%, reagent grade), and acetic acid (ACS reagent) were purchased from Sigma-Aldrich (St. Louis, MO). 100% Cotton spool thread was purchased from a local store (JoAnn Fabrics, Columbus, OH) and Kimble 51 expansion borosilicate glass melting point capillaries (O.D. 1.5 mm) were purchased from Kimble Chase (Rockwood, TN). Whatman filter paper (24 cm, grade 1) was purchased from Whatman (Little Chalfont, England).
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2

Lipid Membrane Fluidity Analysis

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Oxacillin sodium salt (catalog number: sc-224180B, Santa Cruz Biotechnology Inc., Dallas, TX, USA) was dissolved in distilled water. Ricinoleic acid (catalog number: R7257, Sigma-Aldrich Inc., Seoul, Republic of Korea), palmitic acid (catalog number: 129702500, Acros Organics, ThermoFisher Scientific Korea Ltd., Seoul, Republic of Korea), stearic acid (catalog number: S0163, Tokyo Chemical Industry Co., Ltd., Tokyo, Japan), linoleic acid (catalog number: L07949, ThermoFisher Scientific Korea), and oleic acid (catalog number: O0180, Tokyo Chemical Industry) were dissolved in ethanol (catalog number: 000E0243, Samchun Chemicals). Laurdan (6-Dodecanoyl-2-Dimethylaminonaphthalene, catalog number: D250) was purchased from Invitrogen (ThermoFisher Scientific Korea). Phosphate-buffered saline (PBS, catalog number: P5493-1L) was purchased from Sigma-Aldrich Inc.
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3

Ricinine Quantification in Biological Samples

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Standard solution (100 mg mL−1) of ricinine was obtained from Cerilliant (Round Rock, TX) and human urine and human serum were purchased from Innovative Research (Novi, MI). Ethyl acetate (99.9%, HPLC grade), ricinoleic acid (≥99%), ricinine-(methyl-d3), (3,3,3-trifluoropropyl)-silane (99.9%, HPLC grade), methanol (99.9%, HPLC grade), formic acid (95%, reagent grade), and acetic acid (ACS reagent) were purchased from Sigma-Aldrich (St. Louis, MO). 100% cotton spool thread was purchased from a local store (JoAnn Fabrics, Columbus, OH) and Kimble 51 expansion borosilicate glass melting point capillaries (O.D. 1.5 mm) were purchased from Kimble Chase (Rockwood, TN). Whatman filter paper (24 cm, grade 1) was purchased from Whatman (Little Chalfont, England).
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4

Synthesis of Castor Oil-based Polyurethane

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Poly(tetramethylene ether) glycol (Mw = 1000 g/mol, 98%) and castor oil (CO, Mw = 933.45, 90% ricinoleic acid) have been obtained from Sigma-Aldrich and refluxed for 3 h at 120 °C before being used. Soybean oil (SBO, Sigma-Aldrich), aliphatic isophorone diisocyanate (IPDI, 98%, Alfa Aesar), formic acid (HCOOH, ≥95%, Sigma-Aldrich), and N, N-dimethylformamide (DMF, 99.5%, Thermo Scientific™) were used without additional distillation. The diethyl ether (Et2O, ≥99.5%), dibutyltin dilaurate (DBTDL, 95%), DMG (≥99%), silver flakes (<10 µm), lactic acid (~90%), sodium chloride (≥99%), acetic acid (≥97%), citric acid monohydrate (≥98%), lipase (from Candida rugosa) were purchased from Sigma-Aldrich and used in their original forms. Stretchable TPU substrate and textile Lycra Shiny Milliskin Nylon Spandex Fabric was purchased from Spandex World. Inc, USA, and Dongguan Jiaxin Plastic Materials, respectively. Cambridge Isotope Laboratories Inc. provided deuterated solvents for NMR characterization. Double-deionized water was used throughout the study.
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5

Phytochemical Evaluation and Comparative Analysis

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Totally, 21 phytochemicals viz., citral, carvacrol, catechol, cinnamic acid, eugenol, citric acid, coumarin, pyrogallol, borneol, oleic acid, quercetin, curcumin, chlorogenic acid, ascorbic acid, gallic acid, linoleic acid, erucic acid, thymol, ricinoleic acid, phloroglucinol and cinnamaldehyde were used in the present study obtained from Sigma Aldrich (India). Metronidazole was used as positive control was purchased from Sigma Aldrich (India). The stock solutions were prepared at a final concentration of 100 mg/mL using ethanol as a solvent. Finally, the stocks were stored at 4 °C for further use.
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6

Synthesis and Characterization of Ricinoleic Lipids

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Nonradioactive fatty acids, BSA (essentially fatty acid free), G3P, phospholipase C (from Clostridium perfringens), TAG lipase (from R.miehei), phospholipase A2 (from Naja mossambica), ricinoleic acid, sn-1,2-di-18:1-DAG, CoA, sn-1-18:1-LPC, and glycerophosphocholine (GPC) were obtained from Sigma Aldrich (St. Louis, MO, USA). [14C]18:1 and [14C]G3P were purchased from Perkin Elmer, [14C]ricinoleic acids were obtained from American Radiolabeled Chemicals and tri-oleoylglycerol was purchased from Larodan (Stockholm). Acyl-CoA was synthesized in a modification of the method of Sanchez et al. (1973) (link). Sn-1,2-sn-2,3-rac-DAG with one or two ricinoleoyl groups were obtained from 2-OH-TAG from castor bean (R.communis) oil by treatment with TAG lipase and separation of resulting products TLC plates in heptane:diethyl ether:acetic acid (20:50:0.5 by vol.). Ricinoleoyl-LPC was synthesized enzymatically by acylation of GPC with ricinoleoyl-CoA in microsomes of yeast (S.cerevisiae) mutated in ALE1 (lysophospholipid acyltransferase, YOR175C) and overexpressing the GPC1 (YGR149W) gene (yeast GPC acyltransferase, GPCAT) (Glab et al., 2016 (link)). The lipids were extracted into chloroform and LPC separated from other lipids on TLC in chloroform:methanol:acetic acid:water (85:15:10:3.5 by vol.).
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7

High-Quality Pasteurized Milk Analysis

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Methanol, acetonitrile, formic acid, and ammonium formate were all of HPLC grade (HiPerSolv Chromanorm) and purchased from VWR International Ltd. Analytical standards of chloramphenicol, oleic acid, ricinoleic acid, and 18:1 lysophosphatidylethanolamine (Lyso PE) were purchased from Sigma Aldrich, and water was purified using a Milli-Q system (Millipore).
High-quality pasteurized milk was produced according to Italian Ministerial Decree No. 185 (D. M. 185/91, 1991) , which establishes the general requirements for raw milk intended for the production of high-quality pasteurized milk: raw milk must have a fat content of at least 3.5% and a protein content of 32 g/L. Concerning pasteurization, a typical example of effective applied time-temperature operative conditions is 77°C for 15 s. High-quality pasteurized milk samples were collected from batches that arrived daily, after milking and pasteurization, in our laboratory (1 sample per day was collected for each of the working days). Milk samples were supplied by a single trusted dairy, located between Cremona and Parma provinces, Italy. To increase the variability of the model, the sampling period lasted 6 wk, and the sample collection for validation was executed 4 mo later, to increase the variability and the seasonality of the set and the correspondent robustness of the study.
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8

Enzymatic Production of Palm Oil Esters

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Palm oil ester (POE) was prepared in our laboratory through enzymatic alcoholysis of palm oil with oleyl alcohol using Lipozyme RM IM as the catalyst 21) . Quercetin (purity >90%) and ricinoleic acid (RC) were purchased from Sigma-Aldrich (Germany) . Tween 80 (polyoxyethylene sorbitan monooleate) was purchased from Merck (Germany) . Pure soy bean lecithin was purchased from Lipoid GmbH (Ludwigshafen, Germany) . Glycerol was purchased from JT Baker (Philipsburg, NJ, USA) . Water was deionized using a Milli-Q filtration system, EMD Millipore (Billerica, MA, USA) .
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