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Biotransformations of Turpentine Constituents: Oxygenation and Esterification
KTH, Superseded Departments, Chemistry.
2003 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

This thesis describes methods to obtain value–addedcompounds from TMP-turpentine obtained from the spruce, Piceaabies. The methodology focuses on biotransformations using twoapproaches: an oxygenation approach (i.e. oxygenation ofterpene hydrocarbons by cell cultures) and an esterificationapproach (i.e. lipase-catalysed transesterification of vinylacetate with terpene alcohols, and a further fractionation ofthe TMP-turpentine).

The main constituents of the turpentine, a-pinene, b-pineneand limonene, were subjected to a P. abies suspension culture.Allylic oxidation formed the major products for α-pineneand β-pinene, which were further oxidised to theirrespective aldehyde or ketone. One of the minor products froma-pinene, cis-verbenol, was not only transformed into verbenonebut also isomerised to trans-verbenol. Limonene gavelimonene-(1,2)-epoxide as the major product.

Fractionation of monoterpenes is accomplished throughphysical separation methods, chromatography and distillation,and lipase-catalysed transesterification of vinyl acetate withterpene alcohols. The esters of myrtenol and trans-pinocarveolwere separated from the more slowly reacting alcohols such asborneol and carveol by use of a combination of the Mucor mieheilipase and Candida antarctica lipase A as catalysts.Furthermore, the non-reacting tertiary terpene alcohols wereseparated from the reacting alcohols in a single step byCandida antarctica lipase A.

Lipase-catalysed (Candida antarctica lipase B andPseudomonas cepacia lipase) transesterification of vinylacetate with sterically hindered secondary alcoholsunexpectedly yielded hemiacetals or hemiacetal esters. Thereaction conditions required to obtain these side products havebeen studied.

Keywords:Picea abies, Pinaceae, Essential oilscomposition; Terpene alcohol; Hemiacetal; Hemiacetal ester,TMP-turpentine; Monoterpene; α-Pinene; β-Pinene;Limonene; Verbenol; Pinocarveol; Borneol; Myrtenol; Suspensioncell culture; Biotransformation; Lipase-catalysed; Oxidation;Allylic oxidation; Transesterification; Autoxidation;Separation.

Place, publisher, year, edition, pages
Stockholm: Kemi , 2003. , xii, 67 p.
Trita-IOK, ISSN 1100-7974 ; 2003:76
Keyword [en]
Picea abies, Pinaceae, Essential oils composition, Terpene alcohol, Hemiacetal, Hemiacetal ester, TMP-turpentine, Monoterpene, alpha-pinene, beta-pinene, Limonene, Verbenol, Pinocarveol, Borneol, Myrtenol, Suspension cell culture, Biotransformation,
URN: urn:nbn:se:kth:diva-3529ISBN: 91-7283-476-5OAI: diva2:9344
Public defence
NR 20140805Available from: 2003-05-16 Created: 2003-05-16Bibliographically approved

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