Cyclopinolenic acids: Synthesis, derivatives and thermal properties

Anneli Hase, Maija Ala-Peijari, S. Kaltia, J. Matikainen, Tapio Hase

Research output: Contribution to journalArticleScientificpeer-review

7 Citations (Scopus)

Abstract

The two isomeric cyclopinolenic acids (CP-1 and CP-2), components of distilled tall oil, have been synthesized by means of an intramolecular Diels-Alder reaction of isomers of 5,10,12-octadecatrienoic esters, themselves synthesized in a stereocontrolled manner. The 5 cis, 10 trans, 12 trans isomer cyclizes at 200°C to a 1:3 mixture of esters of CP-1 and CP-2. At 200°C, the 5 cis, 10 trans, 12c is isomer is unreactive, but at 240°C it gives the same CP-1 + CP-2 ester mixture, presumably by way of prior isomerization to the 5 cis, 10 trans, 12 trans isomer. A subambient thermal study of CP-1 and CP-2 and their derivatives shows that the compounds, excluding CP-1, lack crystalline structures or melting points, and display glass transitions only, below −80°C for esters and below −50°C for the carboxylic acids.
Original languageEnglish
Pages (from-to)1027-1031
Number of pages5
JournalJournal of the American Oil Chemists' Society
Volume69
Issue number10
DOIs
Publication statusPublished - 1992
MoE publication typeA1 Journal article-refereed

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Isomers
Esters
Thermodynamic properties
Derivatives
Acids
Tall oil
Isomerization
Carboxylic Acids
Carboxylic acids
Melting point
Glass transition
Display devices
Crystalline materials

Cite this

Hase, Anneli ; Ala-Peijari, Maija ; Kaltia, S. ; Matikainen, J. ; Hase, Tapio. / Cyclopinolenic acids : Synthesis, derivatives and thermal properties. In: Journal of the American Oil Chemists' Society. 1992 ; Vol. 69, No. 10. pp. 1027-1031.
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title = "Cyclopinolenic acids: Synthesis, derivatives and thermal properties",
abstract = "The two isomeric cyclopinolenic acids (CP-1 and CP-2), components of distilled tall oil, have been synthesized by means of an intramolecular Diels-Alder reaction of isomers of 5,10,12-octadecatrienoic esters, themselves synthesized in a stereocontrolled manner. The 5 cis, 10 trans, 12 trans isomer cyclizes at 200°C to a 1:3 mixture of esters of CP-1 and CP-2. At 200°C, the 5 cis, 10 trans, 12c is isomer is unreactive, but at 240°C it gives the same CP-1 + CP-2 ester mixture, presumably by way of prior isomerization to the 5 cis, 10 trans, 12 trans isomer. A subambient thermal study of CP-1 and CP-2 and their derivatives shows that the compounds, excluding CP-1, lack crystalline structures or melting points, and display glass transitions only, below −80°C for esters and below −50°C for the carboxylic acids.",
author = "Anneli Hase and Maija Ala-Peijari and S. Kaltia and J. Matikainen and Tapio Hase",
year = "1992",
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Hase, A, Ala-Peijari, M, Kaltia, S, Matikainen, J & Hase, T 1992, 'Cyclopinolenic acids: Synthesis, derivatives and thermal properties', Journal of the American Oil Chemists' Society, vol. 69, no. 10, pp. 1027-1031. https://doi.org/10.1007/BF02541071

Cyclopinolenic acids : Synthesis, derivatives and thermal properties. / Hase, Anneli; Ala-Peijari, Maija; Kaltia, S.; Matikainen, J.; Hase, Tapio.

In: Journal of the American Oil Chemists' Society, Vol. 69, No. 10, 1992, p. 1027-1031.

Research output: Contribution to journalArticleScientificpeer-review

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T2 - Synthesis, derivatives and thermal properties

AU - Hase, Anneli

AU - Ala-Peijari, Maija

AU - Kaltia, S.

AU - Matikainen, J.

AU - Hase, Tapio

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N2 - The two isomeric cyclopinolenic acids (CP-1 and CP-2), components of distilled tall oil, have been synthesized by means of an intramolecular Diels-Alder reaction of isomers of 5,10,12-octadecatrienoic esters, themselves synthesized in a stereocontrolled manner. The 5 cis, 10 trans, 12 trans isomer cyclizes at 200°C to a 1:3 mixture of esters of CP-1 and CP-2. At 200°C, the 5 cis, 10 trans, 12c is isomer is unreactive, but at 240°C it gives the same CP-1 + CP-2 ester mixture, presumably by way of prior isomerization to the 5 cis, 10 trans, 12 trans isomer. A subambient thermal study of CP-1 and CP-2 and their derivatives shows that the compounds, excluding CP-1, lack crystalline structures or melting points, and display glass transitions only, below −80°C for esters and below −50°C for the carboxylic acids.

AB - The two isomeric cyclopinolenic acids (CP-1 and CP-2), components of distilled tall oil, have been synthesized by means of an intramolecular Diels-Alder reaction of isomers of 5,10,12-octadecatrienoic esters, themselves synthesized in a stereocontrolled manner. The 5 cis, 10 trans, 12 trans isomer cyclizes at 200°C to a 1:3 mixture of esters of CP-1 and CP-2. At 200°C, the 5 cis, 10 trans, 12c is isomer is unreactive, but at 240°C it gives the same CP-1 + CP-2 ester mixture, presumably by way of prior isomerization to the 5 cis, 10 trans, 12 trans isomer. A subambient thermal study of CP-1 and CP-2 and their derivatives shows that the compounds, excluding CP-1, lack crystalline structures or melting points, and display glass transitions only, below −80°C for esters and below −50°C for the carboxylic acids.

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