Epsilon-polylysine is a homopolymer of L-lysine, containing approximately 30 L-lysine subunits, as synthesized in aerobic bacterial fermentation by Streptomyces albulus. epsilon -Polylysine is approved for food use in Japan as an antimicrobial preservative. A series of pharmacokinetic and metabolic profile studies on epsilon -polylysine have been conducted in rats in order to provide a better understanding of the reason for its lack of toxicological effects in subchronic and chronic feeding bioassays using relatively high concentrations in the diet up to 50000 ppm. As reported in this article, epsilon -polylysine was practically non-toxic in an acute oral toxicity study in rats, with no mortality up to 5 g/kg and was not mutagenic in bacterial reversion assays. Absorption, distribution, metabolism and excretion (ADME) studies on 14C-radiolabeled epsilon -polylysine, given in a single dose to fasted male rats at 100mg/kg, revealed low absorption from the gastrointestinal tract. All but trace amounts of the dosed radioactivity was eliminated by excretion within 168 h and over 97% was accounted for in urine (1.2%), feces (92.9%), or expired air (3%) by 48 h. The sum of the cumulative excretion with routes associated with absorption in urine, expired air and carcass was 6.4% of total recovered radioactivity; approximately 94% of the dose of epsilon -polylysine passed unabsorbed through the gastrointestinal tract in the feces. Whole body autoradiography did not show concentration of absorbed epsilon -polylysine in any tissue or organ. Excretion half-lives of epsilon -polylysine equivalents in blood and plasma were 20 and 3.9 days, likely prolonged by the incorporation into protein of cleaved L-lysine. Metabolic profiles by HPLC analysis of plasma samples suggest that L-lysine is the predominant early metabolic by-product, likely from protease activity in the upper GI tract; only 0.2% of the administered parent compound was found in plasma. At 8-72 h, HPLC profiles show diminishing levels of epsilon -polylysine and L-lysine in plasma, accompanied by a shift to larger peaks of homopolymer fragments of varying subunit length, presumably from microbial degradation of epsilon -polylysine in the lower gut. HPLC profiles of urine and feces collected from 0 to 24 h post-dosing revealed three distinct peaks in urine, the first peak likely to be epsilon -polylysine and epsilon -polylysine less a few amino acid subunits, and the second, L-lysine and the third, a metabolite of L-lysine. Radiolabeled L-lysine was reduced from 67.2% of the radioactivity in plasma at 30 min to 7.5% at 4 h, indicating that L-lysine is readily removed from plasma from essential amino acid incorporation into protein. Based on the findings of the ADME studies and lack of toxicity in safety studies, the proposed use of epsilon -polylysine as a preservative in foods is considered to be safe.

In the quantitative mononitration of anisole in 54–82% sulphuric acid at 25° the o : p ratio varies from 1.8 to 0.7. It is suggested that the rate-limiting step is the formation of an encounter pair between the nitronium ion and an anisole molecule which is hydrogen-bonded to a hydronium ion. The change in the o : p ratio may be due to competition between direct formation of Wheland intermediates from the hydrogen-bonded encounter pair, and loss of the hydronium ion to give a nitroniurn ion–anisole encounter pair, with subsequent formation of Wheland intermediates. With o- and p-methylanisole the products, and changes in product ratios with acidity are interpreted by considering the fates of the ipso-Wheland intermediates formed at C–Me. 4-Methyl-2-nitrophenol is an important product of the nitration of p-methylanisole, and results from ipso-attack by nitronium at C–Me, followed by attack of water and loss of methoxy.

AbstractDie Photochlorierung der Titelverbindung ergab primär ein Gemisch von Dichloriden, aus dem bei weiterer Chlorierung 1‐Chlor‐naphthalin‐tetrachloride hervorgingen.

The photochemical chlorination of 1-chloronaphthalene gives a mixture of dichlorides, which on further chlorination give several new 1-chloronaphthalene tetrachlorides. The structures of the latter have been elucidated by using 1H n.m.r. spectroscopy and by isomerisation with aluminium trichloride as the 1,1,r-2,t-3,c-4- and 1,1,r-2,-c-3,t-4-pentachlorotetralins; and the r-1,t-2,t-3,c-4,5-; r-1,t-2,c-3,c-4,5-; and r-1,t-2,c-3,t-4,5-pentachlorotetralins. Evidence is presented to suggest that the last compound, because of internal non-bonding strain, exists predominantly in an unusual ‘half-boat’ conformation. The results are compared with those obtained by heterocyclic chlorination, from which another isomer, r-1,c-2,t-3,t-4,5-pentachlorotetralin, is a minor product. The course and products of alkaline dehydrochlorination have been used to support some of the assignments of structure. The heterolytic chlorination of 1,2-dichloronaphthalene has been examined also; the major product is r-1,t-2,c-3,t-4,5,6-hexachlorotetralin, which also exists in a ‘half-boat’ conformation.

Chemischer InformationsdienstVolume 4, Issue 44 Article ChemInform Abstract: SPEKTROPHOTOMETRIC DETERMINATION OF BASICITY CONSTANTS, BENZAMIDES AND PHENYLUREAS JAMES W. BARNETT, JAMES W. BARNETTSearch for more papers by this authorCHARMIAN J. O'CONNOR, CHARMIAN J. O'CONNORSearch for more papers by this author JAMES W. BARNETT, JAMES W. BARNETTSearch for more papers by this authorCHARMIAN J. O'CONNOR, CHARMIAN J. O'CONNORSearch for more papers by this author First published: October 30, 1973 https://doi.org/10.1002/chin.197344114Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume4, Issue44October 30, 1973 RelatedInformation

Chemischer InformationsdienstVolume 4, Issue 29 Preparative Organic Chemistry ChemInform Abstract: SAEUREKATALYSIERTE HYDROLYSE VON ACETYLGLYCIN UND GLYCYLTYROSIN JAMES W. BARNETT, JAMES W. BARNETTSearch for more papers by this authorCHARMIAN J. O'CONNOR, CHARMIAN J. O'CONNORSearch for more papers by this author JAMES W. BARNETT, JAMES W. BARNETTSearch for more papers by this authorCHARMIAN J. O'CONNOR, CHARMIAN J. O'CONNORSearch for more papers by this author First published: July 17, 1973 https://doi.org/10.1002/chin.197329147AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume4, Issue29July 17, 1973 RelatedInformation

Chemischer InformationsdienstVolume 4, Issue 44 Preparative Organic Chemistry ChemInform Abstract: ACID HYDROLYSIS OF PHENYLUREA, 4-FLUOROPHENYLUREA, AND 3-METHYLPHENYLUREA CHARMIAN J. O'CONNOR, CHARMIAN J. O'CONNORSearch for more papers by this authorJAMES W. BARNETT, JAMES W. BARNETTSearch for more papers by this author CHARMIAN J. O'CONNOR, CHARMIAN J. O'CONNORSearch for more papers by this authorJAMES W. BARNETT, JAMES W. BARNETTSearch for more papers by this author First published: October 30, 1973 https://doi.org/10.1002/chin.197344130AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume4, Issue44October 30, 1973 RelatedInformation

Chemischer Informationsdienst. Organische ChemieVolume 2, Issue 34 Preparative Organic Chemistry ChemInform Abstract: LOESUNGSMITTELEINFLUESSE AUF DIE SAEURE-KATALYSIERTE ROHRZUCKER-INVERSION J. W. BARNETT, J. W. BARNETTSearch for more papers by this authorCHARMIAN J. O'CONNOR, CHARMIAN J. O'CONNORSearch for more papers by this author J. W. BARNETT, J. W. BARNETTSearch for more papers by this authorCHARMIAN J. O'CONNOR, CHARMIAN J. O'CONNORSearch for more papers by this author First published: August 24, 1971 https://doi.org/10.1002/chin.197134159Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume2, Issue34August 24, 1971 RelatedInformation