Journal of Japan Oil Chemists' Society

Some New Organic Reactions in Oil Chemistry

Ryohei ODA

1980 Volume 29 Issue 11 Pages 779-787
Published: November 20, 1980
Released on J-STAGE: November 10, 2009

DOIhttps://doi.org/10.5650/jos1956.29.779

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Recent Progress of the Halogenation Reactions of Aliphatic Compounds

Yoshiro OGATA, Makoto KIMURA

1980 Volume 29 Issue 11 Pages 788-795
Published: November 20, 1980
Released on J-STAGE: November 10, 2009

DOIhttps://doi.org/10.5650/jos1956.29.788

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Synthetic Uses of Oligomers of Conjugated Dienes

Jiro TSUJI

1980 Volume 29 Issue 11 Pages 796-805
Published: November 20, 1980
Released on J-STAGE: November 10, 2009

DOIhttps://doi.org/10.5650/jos1956.29.796

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Electrochemical Functionalization of Aliphatic Compounds for Organic Synthesis

Sigeru TORII

1980 Volume 29 Issue 11 Pages 806-813
Published: November 20, 1980
Released on J-STAGE: November 10, 2009

DOIhttps://doi.org/10.5650/jos1956.29.806

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Present Technical Situation of Terpenoids Industry

Yoshiji FUJITA, Takuji NISHIDA

1980 Volume 29 Issue 11 Pages 814-821
Published: November 20, 1980
Released on J-STAGE: November 10, 2009

DOIhttps://doi.org/10.5650/jos1956.29.814

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Asymmetrically Modified Nickel Catalyst Its Application to the Preparation of Optically Active 3-Hydroxyacid

Akira TAI

1980 Volume 29 Issue 11 Pages 822-831
Published: November 20, 1980
Released on J-STAGE: November 10, 2009

DOIhttps://doi.org/10.5650/jos1956.29.822

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Preparations and Synthetic Applications of Cyclic α, β-Unsaturated Ethers

Mutsuo ISHII, Masaaki KUBO

1980 Volume 29 Issue 11 Pages 832-840
Published: November 20, 1980
Released on J-STAGE: November 10, 2009

DOIhttps://doi.org/10.5650/jos1956.29.832

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Effect of Inorganic Anions on the Catalysis in Micellar System

Cleavage of the S-S Bond in Bis (3-carboxy-4-nitrophenyl) Disulfide in the Presence of a Cationic Surfactant

Koichi HIRAMATSU, Mitsuru HIDAKA, Koichiro AOKI

1980 Volume 29 Issue 11 Pages 841-843
Published: November 20, 1980
Released on J-STAGE: November 10, 2009

DOIhttps://doi.org/10.5650/jos1956.29.841

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The effect of added inorganic anions on the cleavage of S-S bond in bis (3-carboxy-4-nitrophenyl) disulfide was studied in the presence of tetradecyltrimethylammonium bromide at 25°C. The effect of retardation was in the order Cl^-<Br^-<NO₃^-. The effect of divalent anion SO₄^2- was more remarkable. The trend is in agreement with the result, for example, on the alkaline hydrolysis of p-nitrophenyl hexanoate in the presence of tetradecyltrimethylammonium chloride by Romsted and Cordes.

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Synergism between γ-Tocopherol and Tri-n-octylamine in the Inhibition of the Autoxidation of Methyl Linoleate

Yukihiro ISHIKAWA

1980 Volume 29 Issue 11 Pages 844-848
Published: November 20, 1980
Released on J-STAGE: November 10, 2009

DOIhttps://doi.org/10.5650/jos1956.29.844

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The synergistic effect of tri-n-octylamine (TOA) on the antioxidative activity of γ-tocopherol (γ-Toc) to inhibit the autoxidation of methyl linoleate was investigated.
Remarkable synergism was observed when higher concentrations of γ-Toc and TOA were used. In the presence of TOA, the amount of reducing dimers of γ-Toc markedly increased with the decrease in the amount of γ-Toc, and the total amounts of them were maintained at a level of about 50% (weight proportion to the initial weight of γ-Toc) within the period tested. An isomeric mixture of methyl oxooctadecadienoates was characteristically formed as a main oxidation product from methyl linoleate. The peroxide and total carbonyl values of methyl linoleate incubated with γ-Toc and TOA were maintained constant after 40 days of reaction, and in appearance the oil stopped to autoxidize.
From these results, it may be concluded that TOA derivative (s) having a strong antioxidative activity is formed and plays an important role in remarkable synergism between γ-Toc and TOA.

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Studies on Complex Lipids of Sea Squirts (Ascidiacea), Pyura michaelseni. I.

The Phospholipids of Viscera

Masanori MORITA, Akira HAYASHI

1980 Volume 29 Issue 11 Pages 849-854
Published: November 20, 1980
Released on J-STAGE: November 10, 2009

DOIhttps://doi.org/10.5650/jos1956.29.849

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The composition of conjugated lipids obtained from the viscera of sea squirts (Pyura michaelseni) was investigated. The sea squirts that belong to Prochordata on animal classification, are very unique marine animal in either evolutional or biological aspects. The conjugated lipids were extracted with chloroform-methanol (2 : 1, vol/vol) after simple lipids were extracted with acetone, and phosphatidyl ethanolamine (PE), phosphatidyl choline (PC), and sphingomyelin (SM) found as main phospholipids were separated and purified by silicic acid column chromatography, Iatrobeads column chromatography, DEAE-cellulose column chromatography, and preparative TLC. The purified phospholipids were identified by TLC, IR, analysis of their degradation products, and quantitative analysis of phosphorus and fatty acid ester.
The fatty acids composition of PE and PC were mainly composed of unsaturated acids (90%), in which polyunsaturated acids (C_{20 : 5}, C_{22 : 6}) were predominant. On the other hand, the fatty acids in SM contained hydroxy acids (h-FA) in addition to non-hydroxy acids (n-FA) (n-FA/h-FA, about 5/1) and both acids mainly composed of saturated acids, and main component of long chain bases was C₁₈-sphingadienine.
The facts that SM occurrs in a considerable amount and phosphonolipid is not found in sea squirts suggest the close relation between sea squirts and vertebrate.

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Glass Capillary Gas Chromatography of Fatty Acids from Lipids of Marine Organisms

Yutaka ITABASHI, Toru TAKAGI

1980 Volume 29 Issue 11 Pages 855-865
Published: November 20, 1980
Released on J-STAGE: November 10, 2009

DOIhttps://doi.org/10.5650/jos1956.29.855

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High resolution gas chromatography of fatty acid methyl esters derived from marine organism lipids was carried out on wall-coated open-tubular (WCOT) glass columns of different polarity.
The times required for the analysis were shortened with increasing polarity of the liquid phases, but the column efficiency decreased apparently.
Effective separations of positional isomers of monounsaturated and methylene-interrupted polyunsaturated fatty acids were obtained on SILAR-5CP column. The use of the column also made possible the separation of some non-methylene interrupted fatty acids. The equivalent chain lengths of 86 fatty acid methyl esters on SILAR-5CP have been presented.
Plots of carbon number vs. log relative retention time for methyl esters of normal saturated C₈C₂₂ fatty acids showed slightly positive or negative deviations from straight lines.
Peak area percentage of C_{22 : 6} methyl ester reduced with increasing retention time, but selection of appropriate conditions permitted fair agreement with weight percentage. Fatty acid compositions of sardine, pollack, copepod, seaweed and sea urchin have been presented as examples of the analysis.

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Evaluation of Denaturation Property of Surfactants onto Protein as Measured by Circular Dichroism

Kazuo OHBU, Nobuo JONA, Nobuyuki MIYAJIMA, Naoki MIZUSHIMA, Ichiro KAS ...

1980 Volume 29 Issue 11 Pages 866-871
Published: November 20, 1980
Released on J-STAGE: February 19, 2010

DOIhttps://doi.org/10.5650/jos1956.29.866

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The well known property of surfactants to denature proteins was systematically reexamined to elucidate the molecular aspects of denaturation associated with the chemical structure of surfactants. Bovine Serum Albumin (abbreviated as BSA) was used for specimen. The degree of denaturation of protein was estimated as the change of molar ellipticity of BSA as obtained from CD spectra at 220nm in 50mM sodium phosphate buffer at pH 7.0. The denaturation power of the commercially available surfactants were found to be in the order
LAS>SDS>DTMAC>AOS>AES>>Noionics≅Ampholytic
The ampholytic and nonionic surfactants hardly denatured BSA compared with those ionic surfactants. The effect of intramolecular electrical shielding is expected for ampholytic surfactant. The longer the oxyethylene chain of AES was, the less the BSA denaturation was. The AES with more than 6 oxyethylene chains does not cause any change in the CD spectrum of BSA. A remarkable effects was observed in inhibiting denaturation of BSA caused by anionic surfactants with the addition of cationic surfactant or amine oxide.

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Synthesis of 4-Nonanolide and 4-Undecanolide from Nitroalkane

Chikai KIMURA, Koichi MURAI

1980 Volume 29 Issue 11 Pages 872-873
Published: November 20, 1980
Released on J-STAGE: November 10, 2009

DOIhttps://doi.org/10.5650/jos1956.29.872

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4-Nonanolide (γ-nonalactone) and 4-undecanolide (γ-undecalactone), famous perfumes known as so-called Aldehyde C-18 and C-14, have been synthesized via lactonization of 4-hydroxy acid derived from 1-nitroalkane through the Michael addition to ethyl acrylate followed by the Nef reaction and reduction. Each step of the reaction sequence was found to proceed in fairly good yield, and thus this sequence prescribes a facile general synthetic method of γ-alkyl-γ-butyrolactone.

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