Novel α-hydroxy phosphonic acids via castor oil

Cermak, Diana M.; Cermak, Steven C.; Deppe, Amy B.; Durham, Amber L.

doi:10.1016/j.indcrop.2011.12.018

Cited by 15 publications

(19 citation statements)

References 14 publications

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“…Castor oil mainly contains the esters of 12-hydroxy-9-octadecenoic acid (ricinoleic acid), which make castor oil widely used in skin and personal-care products due to its excellent lubricity, emolliency, and noncomedogenicity (Cermak et al, 2012;Hajar and Vahabzadeh, 2014;Ogunniyi, 2006). Novel castor oil-based feruloylated lipids prepared by the esterification of castor oil with FA may offer many combined potential health benefits and functional properties of both castor oil and FA.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic preparation of castor oil-based feruloylated lipids using ionic liquids as reaction medium and kinetic model

Sun

Zhu

2015

Industrial Crops and Products

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Section: Introductionmentioning

confidence: 99%

Enzymatic preparation of castor oil-based feruloylated lipids using ionic liquids as reaction medium and kinetic model

Sun

Zhu

2015

Industrial Crops and Products

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“…One synthetic route to α‐hydroxyphosphonic acids involves the hydrolysis of α‐hydroxyphosphonates in the presence of hydrochloric acid used in an excess . Another widely applied method is the fission of the C–O bond of the ester function of α‐hydroxyphosphonates using trimethylsilyl bromide, followed by hydrolysis . An oxidative method is also known, starting from α‐hydroxyalkyl‐ H ‐phosphinic acids, employing I 2 /DMSO as the oxidizing system .…”

Section: Introductionmentioning

confidence: 99%

“…[11] Another widely applied method is the fission of the C-O bond of the ester function of α-hydroxyphosphonates using trimethylsilyl bromide, followed by hydrolysis. [48][49][50] An oxidative method is also known, starting from α-hydroxyalkyl-H-phosphinic acids, employing I 2 /DMSO as the oxidizing system. [51] In most cases, the main goal was to synthesize a potentially bioactive target molecule, and the method itself represented a secondary issue.…”

Section: Introductionmentioning

confidence: 99%

Green synthesis and cytotoxic activity of dibenzyl α‐hydroxyphosphonates and α‐hydroxyphosphonic acids

Rádai

Szeles

Kiss

et al. 2018

Heteroatom Chemistry

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A series of dibenzyl α‐hydroxyphosphonates and the corresponding α‐hydroxyphosphonic acids, mostly new compounds, have been synthesized. The dibenzyl α‐hydroxyphosphonates have been obtained in the Pudovik reaction of substituted benzaldehydes and dibenzyl phosphite in the presence of triethylamine as the catalyst. The amount of the solvent was minimized during the reaction, and the workup involved crystallization from the reaction mixture. A new protocol was developed to transform the dibenzyl 1‐hydroxyphosphonates to the corresponding phosphonic acids by catalytic hydrogenation. The derivatives prepared were screened as potential cytotoxic agents against Mes‐Sa human uterine sarcoma cell line.

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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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Novel α-hydroxy phosphonic acids via castor oil

Cited by 15 publications

References 14 publications

Enzymatic preparation of castor oil-based feruloylated lipids using ionic liquids as reaction medium and kinetic model

Enzymatic preparation of castor oil-based feruloylated lipids using ionic liquids as reaction medium and kinetic model

Green synthesis and cytotoxic activity of dibenzyl α‐hydroxyphosphonates and α‐hydroxyphosphonic acids

Synthesis and Characterization of Phosphonates from Methyl Linoleate and Vegetable Oils

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