Biotransformations of Turpentine Constituents : Oxygenation and Esterification
This thesis describes methods to obtain valueaddedcompounds 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 (...
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KTH, Kemi
2003
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ftkthstockholm:oai:DiVA.org:kth-3529 2024-06-23T07:46:29+00:00 Biotransformations of Turpentine Constituents : Oxygenation and Esterification Lindmark-Henriksson, Marica 2003 application/pdf http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-3529 eng eng KTH, Kemi Stockholm : Kemi Trita-IOK, 1100-7974 2003:76 http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-3529 urn:isbn:91-7283-476-5 info:eu-repo/semantics/openAccess 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 Doctoral thesis, comprehensive summary info:eu-repo/semantics/doctoralThesis text 2003 ftkthstockholm 2024-05-27T17:43:07Z This thesis describes methods to obtain valueaddedcompounds 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; ... Doctoral or Postdoctoral Thesis Antarc* Antarctica Royal Institute of Technology, Stockholm: KTHs Publication Database DiVA |
institution |
Open Polar |
collection |
Royal Institute of Technology, Stockholm: KTHs Publication Database DiVA |
op_collection_id |
ftkthstockholm |
language |
English |
topic |
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 |
spellingShingle |
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 Lindmark-Henriksson, Marica Biotransformations of Turpentine Constituents : Oxygenation and Esterification |
topic_facet |
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 |
description |
This thesis describes methods to obtain valueaddedcompounds 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; ... |
format |
Doctoral or Postdoctoral Thesis |
author |
Lindmark-Henriksson, Marica |
author_facet |
Lindmark-Henriksson, Marica |
author_sort |
Lindmark-Henriksson, Marica |
title |
Biotransformations of Turpentine Constituents : Oxygenation and Esterification |
title_short |
Biotransformations of Turpentine Constituents : Oxygenation and Esterification |
title_full |
Biotransformations of Turpentine Constituents : Oxygenation and Esterification |
title_fullStr |
Biotransformations of Turpentine Constituents : Oxygenation and Esterification |
title_full_unstemmed |
Biotransformations of Turpentine Constituents : Oxygenation and Esterification |
title_sort |
biotransformations of turpentine constituents : oxygenation and esterification |
publisher |
KTH, Kemi |
publishDate |
2003 |
url |
http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-3529 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
Trita-IOK, 1100-7974 2003:76 http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-3529 urn:isbn:91-7283-476-5 |
op_rights |
info:eu-repo/semantics/openAccess |
_version_ |
1802646311890059264 |