Das biologische Verhalten von Fettsäuren mit Dreifachbindung II: Behenolsäure

Bernahard, K.; Yekundi, K. G.; Greub, H. R.

doi:10.1002/hlca.19670500233

Helvetica Chimica Acta

1967

DOI: 10.1002/hlca.19670500233

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Das biologische Verhalten von Fettsäuren mit Dreifachbindung II: Behenolsäure

K. Bernahard

K. G. Yekundi

H. R. Greub

Abstract: 713The conversion of bicyclo [10.3.0]-1,12-epoxy-13-pentadecanone into 4-cyclopentadecyne-1-one, effected by 9-tolylsulfonylhydrazine under mild conditions and in high yield, provides an example of a new fragmentation reaction.

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1969

1989

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Profiles in altered metabolism. IV—induction of acute dicarboxylic aciduria following 2-octynoic acid administration to the rat

Montgomery¹,

Mamer²,

Colle³

1989

Biol. Mass Spectrom.

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Rats given 2-octynoic acid by intraperitoneal injection excrete elevated amounts of medium-chain dicarboxylic acids and other acidic metabolites usually associated with human medium-chain acyl-CoA dehydrogenase deficiency. Onset of this organic acid profile is immediate and lasts for approximately 24 h. The induced acidosis in this animal model closely, acutely and transiently resembles the human disorder. The 2-octynoate load is also extensively omega- and psi-oxidized, and evidence is presented for the enzymic hydration of 2-octynoate to 3-ketooctanoic acid.

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Profiles in altered metabolism. IV—induction of acute dicarboxylic aciduria following 2-octynoic acid administration to the rat

Montgomery¹,

Mamer²,

Colle³

1989

Biol. Mass Spectrom.

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Das biologische Verhalten von Fettsäuren mit Dreifachbindung. IV. Der Abbau der Crepissäure (9‐Octadecen‐12‐insäure) im Tierkörper

Bernhard

Kaempf

1969

Helvetica Chimica Acta

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Szimmary. Crepenynic acid (9-octadeccn-12-ynoic acid) fcd t o rats as naturally occurring triglyceride is not incorporated into brain and livcr lipids, and into the dcpot f a t only t o a small amount. As a metabolite the prcviously unknown 4-clecynedioic acid W A S isolated from t h e urine.In fruheren Arbeiten I 1 1 wurde gezeigt, dass Fettsauren mit Dreifachbindung naturliclie Komponenten von Fetten und Olen aus zahlreichen pflanzlichen Samenim tierisclien Organismus nicht vollig abgebaut werden, vielmehr zu zur Ausscheidung gelangenden Metaboliten fiihren.Die 9-Octadecen-12-insaure CH,-(CH,),-C=C-CH,-CH-CH-(CH,),-COOH wurde 1964 von MIKOLAJCZAK und Mit. 1 2 1 aus dem Samenol von Crepis foetida (ComjJositae) isoliert und 1967 von BKADSHAW und Mit. 131 synthetisch hergestellt. Kurzlich bewiesen HAIGH und Mit. [4j ihre Biosyntliese aus l-l4C-0lsaure in Crepis rubra. Die Frage nach dem Verhalten der Crepissaure irn Stoffwechsel schien uns unter verschiedenen Aspekten interessant. Diese Saure ist strukturell verwandt rnit der Linolsaure (c~s-cis-9,12-Octadecadiensaure), von der BERNHARD 8. ScH6xmInim [51 zeigten, dass sie in1 Tierkorper nicht aufgebaut werden kann.Wir haben dalier an Ratten Samen von Crepis rubra und daraus erhaltenes 01 verfiittert. Nachdem es keine weitere Acetylenfettsaure enthalt, konnte auf eine Isolierung der Crepissaure verzichtet und ilire leiclit mogliclie Autoxydation vermieden werden.

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Das biologische Verhalten von Fettsäuren mit Dreifachbindung II: Behenolsäure

Abstract: 713The conversion of bicyclo [10.3.0]-1,12-epoxy-13-pentadecanone into 4-cyclopentadecyne-1-one, effected by 9-tolylsulfonylhydrazine under mild conditions and in high yield, provides an example of a new fragmentation reaction.

Cited by 2 publications

References 4 publications

Profiles in altered metabolism. IV—induction of acute dicarboxylic aciduria following 2-octynoic acid administration to the rat

Profiles in altered metabolism. IV—induction of acute dicarboxylic aciduria following 2-octynoic acid administration to the rat

Das biologische Verhalten von Fettsäuren mit Dreifachbindung. IV. Der Abbau der Crepissäure (9‐Octadecen‐12‐insäure) im Tierkörper

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