Abstract: Methods for preparing and purifying 2-monoacylglyceride compounds are disclosed. In one method, an unsaturated triglyceride is reacted with water, a C1-C8 alcohol, or a mixture thereof in the presence of a lipase to produce a mixture comprising a 1,3-dihydroxy-2-monoacylglyceride and fatty esters or acids. Reaction of the 1,3-dihydroxy-2-monoacylglyceride with an aldehyde or ketone gives a mixture comprising a 2-monoacylglyceride acetal or ketal. Fatty esters or acids are removed from the mixture as an overhead product by distillation or wiped-film evaporation to isolate a purified 2-monoacylglyceride acetal or ketal. The inventive methods provide a 2-monoacylglyceride protected at the 1- and 3-positions such that the acyl unit remains at the 2-position. The products are enriched in unsaturated fatty acid content when compared with the unsaturated fatty acid content of the original unsaturated triglyceride.

Abstract: Methods for preparing and purifying 2-monoacylglyceride compounds are disclosed. In one method, an unsaturated triglyceride is reacted with water, a C1-C8 alcohol, or a mixture thereof in the presence of a lipase to produce a mixture comprising a 1,3-dihydroxy-2-monoacylglyceride and fatty esters or acids. Reaction of the 1,3-dihydroxy-2-monoacylglyceride with an aldehyde or ketone gives a mixture comprising a 2-monoacylglyceride acetal or ketal. Fatty esters or acids are removed from the mixture as an overhead product by distillation or wiped-film evaporation to isolate a purified 2-monoacylglyceride acetal or ketal. The inventive methods provide a 2-monoacylglyceride protected at the 1- and 3-positions such that the acyl unit remains at the 2-position. The products are enriched in unsaturated fatty acid content when compared with the unsaturated fatty acid content of the original unsaturated triglyceride.

Abstract: The present technology provides a process of reducing, removing or eliminating organohalo, glycidol, and oxirane species from carboxylic acid esters streams and crude and refined triglyceride oils to provide a carboxylic acid ester stream or triglyceride oil with reduced levels or essentially free of organohalo, glycidyl or other oxirane species. The process includes adding to the carboxylic acid ester stream or triglyceride oil an amount of a carboxylate anion and a cation counterion sufficient to react with the organohalo, glycidyl and oxirane species present.

Abstract: The present technology provides a process of reducing, removing or eliminating organohalo, glycidol, and oxirane species from carboxylic acid esters streams and crude and refined triglyceride oils to provide a carboxylic acid ester stream or triglyceride oil with reduced levels or essentially free of organohalo, glycidyl or other oxirane species. The process includes adding to the carboxylic acid ester stream or triglyceride oil an amount of a carboxylate anion and a cation counterion sufficient to react with the organohalo, glycidyl and oxirane species present.

Abstract: A process for preparing conjugated linoleic acid (CLA) or derivatives thereof from ricinoleic acid, lower alkyl esters of ricinoleic acid, or salts thereof. The CLA is formed by reacting a carboxylic acid, or anhydride, anhydride equivalent, or ester thereof with the ricinoleic acid or derivative to form an intermediate having a carboxylic ester at the 12-hydroxy position of the ricinoleic acid or derivative, and reacting the intermediate with a base to form a cis-9, trans-11 conjugated linoleic acid.

Abstract: Provided are alternative sources of ketone bodies for reducing or eliminating symptoms of Parkinson's disease, amyotrophic lateral sclerosis (ALS, also called Lou Gehrig's disease), Alzheimer's disease, Huntington's disease, epilepsy and other diseases or disorders characterized by impaired glucose metabolism. The alternative sources of ketone bodies include mono-, di- and triglyceride esters of acetoacetate and mixtures thereof, and/or mono-, di- and triglyceride esters of 3-hydroxybutyrate and mixtures thereof. These glyceride esters can be administered orally as a dietary supplement or in a nutritional composition.

Abstract: A process for preparing conjugated linoleic acid (CLA) or derivatives thereof from ricinoleic acid, lower alkyl esters of ricinoleic acid, or salts thereof. The CLA is formed by reacting a carboxylic acid, or anhydride, anhydride equivalent, or ester thereof with the ricinoleic acid or derivative to form an intermediate having a carboxylic ester at the 12-hydroxy position of the ricinoleic acid or derivative, and reacting the intermediate with a base to form a cis-9, trans-11 conjugated linoleic acid.

Abstract: Provided are alternative sources of ketone bodies for reducing or eliminating symptoms of Parkinson's disease, amyotrophic lateral sclerosis (ALS, also called Lou Gehrig's disease), Alzheimer's disease, Huntington's disease, epilepsy and other diseases or disorders characterized by impaired glucose metabolism. The alternative sources of ketone bodies include mono-, di- and triglyceride esters of acetoacetate and mixtures thereof, and/or mono-, di- and triglyceride esters of 3-hydroxybutyrate and mixtures thereof. These glyceride esters can be administered orally as a dietary supplement or in a nutritional composition.

Abstract: A process to manufacture conjugated linoleic acid (CLA)-containing materials such as conjugated linoleic salts and acids that are enriched in desirable cis-9, trans-11- and trans-10, cis-12-CLA isomers and are low in certain undesirable isomers. The process generally entails isomerization of an alkyl ester of a linoleic acid-containing material at a temperature typically between about 90 to 140° C. to effectuate conjugation of the double bonds, followed by saponification of the resultant CLA-containing fatty acid ester to produce a CLA-containing fatty acid salt, optionally followed by neutralization of the CLA-containing fatty acid salt with an acid source to produce a CLA-containing fatty acid.

Abstract: A process to manufacture conjugated linoleic acid (CLA)-containing materials such as conjugated linoleic salts and acids that are enriched in desirable cis-9, trans-11- and trans-10, cis-12-CLA isomers and are low in certain undesirable isomers. The process generally entails isomerization of an alkyl ester of a linoleic acid-containing material at a temperature typically between about 90 to 140° C. to effectuate conjugation of the double bonds, followed by saponification of the resultant CLA-containing fatty acid ester to produce a CLA-containing fatty acid salt, optionally followed by neutralization of the CLA-containing fatty acid salt with an acid source to produce a CLA-containing fatty acid.

Abstract: A process to manufacture conjugated linoleic acid (CLA)-containing materials such as conjugated linoleic salts and acids that are enriched in desirable cis-9, trans-11- and trans-10, cis-12-CLA isomers and are low in certain undesirable isomers. The process generally entails isomerization of an alkyl ester of a linoleic acid-containing material at a temperature typically between about 90 to 140° C. to effectuate conjugation of the double bonds, followed by saponification of the resultant CLA-containing fatty acid ester to produce a CLA-containing fatty acid salt, followed by neutralization of the CLA-containing fatty acid salt with an acid source to produce a CLA-containing fatty acid.

Abstract: Omapatrilat (I) is a potent inhibitor of angiotensin-converting enzyme (ACE) and neutral endopeptidase (NEP) both in vitro and in vivo and is currently undergoing large scale clinical trials as an anti-hypertensive. Omapatrilat may be synthesized using the S-stereoisomer of compound (V). Compound (V) may be prepared from a novel hydantoin (III). The hydantoin may be prepared from a monoacetal (XI) or via a dinitrile (V).

Abstract: Omapatrilat (I) is a potent inhibitor of angiotensin-converting enzyme (ACE) and neutral endopeptidase (NEP) both in vitro and in vivo and is currently undergoing large scale clinical trials as an anti-hypertensive. Omapatrilat may be synthesized using the S-stereoisomer of a racemic mixture. The racemic mixture may be prepared from a hydantoin (III). The hydantoin may be prepared from a novel dinitrile compound (IV): The dinitrile may be produced by reacting a monoacetal with a non-carbonate ammonium salt and an alkali cyanide.

Abstract: A process of producing compounds containing an acyloxyalkoxy group from an alcohol consists of reacting the alcohol with a formaldehyde donor until a compound of the formula:R--O--CH.sub.2 (OCH.sub.2).sub.X OR (V)is generated, wherein x is between about 1 to about 5 and R is an organic moiety. This product is then reacted with a carboxylic acid anhydride. The resulting product has the formula:R--O--CH.sub.2 O--COR.sup.1wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group. The invention further relates to intermediates used in the production of such acyloxyalkoxylated compounds.

Abstract: The present technology provides a process of reducing, removing or eliminating organohalo, glycidol, and oxirane species from carboxylic acid esters streams and crude and refined triglyceride oils to provide a carboxylic acid ester stream or triglyceride oil with reduced levels or essentially free of organohalo, glycidyl or other oxirane species. The process includes adding to the carboxylic acid ester stream or triglyceride oil an amount of a carboxylate anion and a cation counterion sufficient to react with the organohalo, glycidyl and oxirane species present.