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Sophorolipids (SL) are glycolipids composed of a sophorose head‐group linked to a hydroxy‐fatty acid tail which makes them a potential source of structurally unique biobased hydroxy fatty acids. Furthermore, Lesquerella is a native southwestern plant that has been commercially cultivated as a replacement for castor seed oil due to high seed oil concentrations of 14‐hydroxy‐eicosenoic acid (14‐OH‐C20:1c11). In this study, SL‐derived hydroxy fatty acids and methyl esters containing 15‐hydroxy‐palmitic acid (15‐OH‐C16), 17‐hydroxy‐stearic acid (17‐OH‐C18), 15‐hydroxy‐palmitic acid methyl ester (15‐OH‐C16ME), 17‐hydroxy‐stearic acid methyl ester (17‐OH‐C18ME), and 13‐hydroxy‐behenic acid methyl ester (13OH‐C22ME) were obtained from the SL produced by two yeast strains. In addition, hydrogenated Lesquerella oil (HLO) was made with ~62% 14‐OH‐eicosanoic (C20) acid (14‐OH‐C20). These materials, along with 12‐hydroxy‐stearic acid (12‐OH‐C18) as a standard for comparison were used to make soybean oil oleogels, and their properties determined. The minimum gelation concentration (MGC) of 12‐OH‐C18 was 1% (wt/wt), while the MGC of 15‐OH‐C16 and 17‐OH‐C18 were 5% and 10%, respectively. The MGC for 15‐OH‐C16ME was 5%, but 17‐OH‐C18ME was unable to form a stable gel at concentrations up to 10%. HLO formed a viscous solution rather than an oleogel, but its crystal morphology underwent a large transformation during storage over a 2.5‐month period, after which it was able to form a stable gel. SL‐based hydroxy fatty acids were able to form oleogels in soybean oil and have the potential to be considered as a new source of low‐molecular weight oleogelators as well as biobased hydroxy fatty acids. [ABSTRACT FROM AUTHOR]

Soybean oil is an abundant commodity crop that has garnered attention for its use as a feedstock for sustainable materials. Soybean oil is high in polyunsaturated fatty acid content, which can promote undesirable properties in biodiesel and lubricant applications. In this work, we characterized the fatty acid composition of commercial soybean oil along with two other soybean oil varieties, Ellis and TN18‐4110. Ellis and commercial soybean oils had similar fatty acid compositions, while TN18‐4110 was enriched in the monounsaturated oleic acid. Biodiesel and estolides were prepared from the three varieties and the relevant physical properties were measured. In comparison to commercial soybean diesel, both Ellis and TN18‐4110 exhibited unique advantages. As estolide‐based lubricants, all three varieties had advantageous cold flow properties, but TN18‐4110 also possessed excellent oxidative stability and lower viscosity. The physical properties and structural property relationships of the biodiesel and estolides are discussed. [ABSTRACT FROM AUTHOR]

Hydroxy fatty acids (HFAs) have found wide use in today's market, ranging from industrial materials to pharmaceuticals. Castor oil, which is obtained from castor seeds, has served as a primary source of the most common HFA, ricinoleic acid, but also contains several undesirable compounds which pose severe health risks, the most notable being ricin, an unusually stable, toxic protein. A promising HFA alternative is lesquerella oil, an oil obtained from seeds of the Lesquerella fendleri species. Lesquerella oil is mainly comprised of lesquerolic acid, an HFA that is structurally similar to ricinoleic acid, the only difference being that lesquerolic acid possesses two additional methylene groups on the carboxyl end of the molecule. In addition, the bisphosphonate moiety has been shown to display interesting biological activities, primarily as osteoporosis drugs and anti‐cancer therapeutics. The synthesis of lesquerella‐based bisphosphonates, both an unsaturated and saturated series, have been produced in high yields and high purity and are reported here. [ABSTRACT FROM AUTHOR]

Hydroxy fatty acids (HFAs) have long been a staple component of feedstock oils with uses ranging from motor oils to food to pharmaceuticals. Castor oil, which contains the HFA ricinoleic acid as its principal component, is the most widely used source of HFA in the world. In addition, bisphosphonates are a functional moiety that has been shown to display a variety of industrial applications, ranging from use in water softeners to osteoporosis drugs, primarily due to their affinity for the calcium ion. We have long been interested in the modification of ricinoleic acid from castor oil to phosphorus derivatives, including α‐hydroxy phosphonates and phosphonic acids, and have now accomplished the synthesis of a family of ricinoleic‐derived bisphosphonates: one that retains the cis alkene found in ricinoleic acid and one where the alkene has undergone hydrogenation. These compounds have been produced in high yields and high purity and the synthesis of these compounds is reported. [ABSTRACT FROM AUTHOR]

Silphium integrifolium Michx. (Silflower) has been a promising subject for domestication as a perennial oilseed crop. This work was carried out to investigate the seed processing aspect of this effort. Thousand seed weight, densities, and dimension of the seeds were evaluated, seed milling to obtain enriched kernel fraction was conducted, and initial characterization of the seed protein was performed. There was wide variation in flat seed length (11.5–20.8 mm), width (4.6–11.8 mm), and thickness (0.9–1.6 mm). The thousand seed weight was 23.8 g but the tapped bulk density was only 189.6 g/L due to the presence of wing around the seed's periphery. The kernel accounted for 56.1% of the seed weight and contained 31.0% oil. A kernel‐enriched fraction with 79.6% purity was obtained by roller‐milling, sifting, and air classification. Linoleic (62.3%) and oleic (19.6%) acids were the major fatty acids in the oil. The defatted enriched kernel fraction contained 63.41% crude protein. Globulin, glutelin, albumin, and prolamin accounted for 55.6%, 19.3%, 16.4%, and 8.7% of the soluble proteins, respectively. At an extraction pH of 9, protein solubility was 62%. Maximum solubility (70%) was obtained at pH 10 while minimum solubility of 9% occurred between pH 4 and 5.5. Aside from the oil, the dehulling of silflower seeds also produced a high‐protein defatted meal, which may be used as is or as a starting material for enriching the protein further into a protein isolate. [ABSTRACT FROM AUTHOR]