83248-46-8Relevant academic research and scientific papers
ISOLATION AND STRUCTURE ELUCIDATION OF PLASMALOPENTAENE-12, THE BIOLOGICAL PRECURSOR OF PECAPENTAENE-12.
Kingston, David G. I.,Duh, C.-Y.,Piccariello, T.,Keyes, R. F.,Van Tassel, R. L.,Wilkins, T. D.
, p. 6665 - 6668 (1989)
The biological precursor of the potent fecal mutagen fecapentaene-12 has been purified and its structure elucidated as the polyunsaturated plasmalogen 2.The occurrence of 2 in germ-free animals indicates that it is a new mammalian product.
Acid-catalyzed solvolysis of polyenol ethers. II. Effect of the degree of unsaturation
Vertegaal,Van Der Gen
, p. 7301 - 7312 (2007/10/02)
The acid-catalyzed solvolysis of polyenol ethers of glycerol gradually changes with increasing unsaturation from the regular pattern into an anomalous one in which hydroxy- and methoxy-substituted aldehydes are formed.
Racemic and Enantiomeric all-trans-Fecapentaene-12 and -14.
Pfaendler, Hans Rudolf,Maier, Franz Karl,Klar, Sonja,Goeggelmann, Waltraud
, p. 449 - 454 (2007/10/02)
The syntheses of the following crystalline all-trans compounds are described: (+/-)-fecapentaene-12 (1a), natural (S)-(+)-fecapentaene-12, unnatural (R)-(-)-fecapentaene-12, (+/-)-fecapentaene-14 (1b), and (S)-(+)-fecapentaene-14.Both enantiomers and the
SYNTHESIS OF THE E- AND Z-ISOMERS OF THE POTENT MUTAGEN (S)-FECAPENTAENE-12 BY THE HORNER-WITTIG REACTION
Wit, P.P de,van der Steeg, M.,van der Gen, A.
, p. 307 - 308 (2007/10/02)
A synthesis of the E- and Z-isomers of optically pure (S)-fecapentaene-12 is described.The method is beased on the chromatographic separation of diastereomeric adducts, formed as intermediates in the Horner-Wittig reaction of an all-trans undecatetraenal,
A CONVENIENT SYNTHESIS OF FECAPENTAENE-12 BY THE HORNER-WITTIG REACTION
Wit, P. P. de,Schaik, T. A. M. van,Gen, A. van der
, p. 369 - 370 (2007/10/02)
A synthesis of racemic fecapentaene-12 and other glyceryl enol ethers has been developed based on the Horner-Wittig reaction.Coupling of the anion of the glyceryl substituted phosphine oxide 7 with unsaturated aldehydes 9a-c provided, after treatment with base, the silyl protected glyceryl enol ethers 11a-c.The silyl groups were easily removed and mixtures of E and Z isomers of glyceryl enol ethers 12a-c were obtained.The isomers could be separated upon washing with ether/hexane.
Total Synthesis of the Potent Mutagen (S)-3-(Dodeca-1,3,5,7,9-pentaenyloxy)propane-1,2-diol
Nicolaou, K. C.,Zipkin, Robert,Tanner, David
, p. 349 - 350 (2007/10/02)
A total synthesis of the mutagenic (S)-3-(dodeca-1,3,5,7,9-pentaenyloxy)propane-1,2-diol (1) from (R)-glycerol acetonide (2), potassium glutaconate (6), and the diphenylphosphine oxide (11) is reported.
SYNTHESIS OF RACEMIC FECAPENTAENE-12, A POTENT MUTAGEN FROM HUMAN FECES, AND ITS REGIOISOMER
Gunatilaka, A. A. Leslie,Hirai, Nobuhiro,Kingston, David G. I.
, p. 5457 - 5460 (2007/10/02)
Racemic fecapentaene-12 and its regioisomer 2-(1,3,5,7,9-dodecapentaenyloxy)-1,3-propanediol (2) have been synthesized.The latter compound is comparably mutagenic to 1.
