Synthesis of lesquerella α-hydroxy phosphonates

Cusimano, John S.; Hart, Margaret M.; Cermak, Diana M.; Cermak, Steven C.; Durham, Amber L.

doi:10.1016/j.indcrop.2013.12.031

Cited by 5 publications

(9 citation statements)

References 25 publications

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“…Because of the health implications associated with castor, castor oil is not grown in the United States but instead is a major import for the United States as well as many European and Asian countries, and the price of castor oil varies greatly based on the current state of the world market. This has led to researchers having an interest in identifying a new plant that could be a domestically grown source of HFAs to supplement or replace the use of castor oil for industrial purposes (Cusimano et al, 2014). This would benefit the United States economy by decreasing the amount of castor oil imported and thus decreasing the impact of Mention of trade names or commercial products in this publication is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the U.S. Department of Agriculture.…”

Section: Introductionmentioning

confidence: 99%

“…The only HFA that is in enough supply for industrial use is ricinoleic acid (C18:1‐OH, 1 , Figure 1), which is the principal component of the oil found in castor seeds (Cusimano et al, 2014; Naik et al, 2018; Salywon et al, 2005). The castor plant is native to Africa but can be successfully grown worldwide.…”

Section: Introductionmentioning

confidence: 99%

“…Up until the 1970s, castor was grown in the United States but this was discontinued due to health and safety concerns because castor seeds contain ricin, ricinine, and other dangerous allergens. Ricin is a highly toxic protein, ricinine is a poisonous alkaloid, and CB‐1A allergens are released upon processing, making it dangerous for workers to harvest and process the seeds (Chen et al, 2016; Cusimano et al, 2014; Lee et al, 2019). Because of the health implications associated with castor, castor oil is not grown in the United States but instead is a major import for the United States as well as many European and Asian countries, and the price of castor oil varies greatly based on the current state of the world market.…”

Section: Introductionmentioning

confidence: 99%

“…In our ongoing studies of phosphorus derivatives of castor and lesquerella oils, we have previously shown that ricinoleic and lesquerolic acids can be chemically modified to produce α‐hydroxy phosphonates and phosphonic acids (Cermak et al, 2012; Cusimano et al, 2014). We are now interested in the synthesis of a family of lesquerella‐based bisphosphonates: monounsaturated bisphosphonate 11a and saturated lesquerolic acid bisphosphonate 11b (as shown in Figure 5).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of lesquerella‐based bisphosphonates

Boon,

Bamert,

Fayer

et al. 2023

J Americ Oil Chem Soc

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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.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of lesquerella‐based bisphosphonates

Boon,

Bamert,

Fayer

et al. 2023

J Americ Oil Chem Soc

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“…Biobased phosphonates have good low temperature properties [1], act as plasticizers [2], and have corrosion-inhibition [3] and flame retardant properties [4]. α-Hydroxy phosphonate derivatives of fatty acids have been synthesized for their biological activities [5,6]. Triglyceride derivatives with incorporated phosphorus atoms (phosphine oxide and phosphonate groups) possess a flame retardant property [7,8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Phosphonates from Methyl Linoleate and Vegetable Oils

Bantchev

Moser

Murray

et al. 2016

J Americ Oil Chem Soc

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Phosphonates were synthesized on a medium scale (~200 g) from three lipids—methyl linoleate (MeLin), high‐oleic sunflower oil (HOSO) and soybean oil (SBO), and three dialkyl phosphites—methyl, ethyl and n‐butyl, using a radical initiator. A staged addition of the lipid and the initiator was used to achieve good yields. Good results were observed with MeLin (94–99% conversions of the double bonds, as determined by NMR, and 83–99% isolated yields) and HOSO (99–100% NMR conversions, 87–96% isolated yields) using tert‐butyl perbenzoate as the initiator. With SBO, benzoyl peroxide was used as the initiator, due to its capability to generate radicals at a higher rate at slightly lower temperatures, and thus to shorten the reaction time. Conversions of 91–93% (by NMR) and isolated yields of 80–94% were achieved. The progress of the reaction was monitored with GC–MS. The products were characterized using 1H, 13C and 31P NMR, IR and gel permeation chromatography. A prolonged reaction led to some transesterification between the carboxylic and phosphite ester groups. Conditions favoring higher reaction rates led to the formation of more oligomers and benzoate fatty ester byproducts. The benzoate fatty ester byproducts were formed by the attack of a benzoate radical on a double bond. The more double bonds that were present per lipid molecule, the more oligomers were formed: MeLin 2–8%, HOSO 3–9% and SBO 8–29%.

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