Chemical characterization of polymerized products formed in the reactions of matairesinol and pinoresinol with the stable radical 2,2-diphenyl-1-picrylhydrazyl

Annika I. Smeds (Corresponding Author), Patrik C. Eklund, Evanthia Monogioudi, Stefan M. Willför

Research output: Contribution to journalArticleScientificpeer-review

27 Citations (Scopus)

Abstract

Polymerization reactions of the lignans matairesinol and pinoresinol with the stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) were studied. The reactions were rapid and almost quantitative. The molecular weight distribution (MWD) of the formed lignan dimers and polymers was determined by high-performance size-exclusion chromatography (HPSEC) combined with evaporative light-scattering detection (ELSD), and the compounds were characterized by HPLC-MS, pyrolysis-GC/MS, NMR, MALDI-ToF-MS, and GC-MS of the monomeric and dimeric units formed by KMnO4 oxidation. The yield of high-MW polymers is higher for pinoresinol (69%) than for matairesinol (43%). According to the HPSEC-ELSD analyses, the MWD is also broader for the pinoresinol polymers. The latter seem to consist mainly of hepta-hexacontalignans (MW 2.5–21.4 kDa), whereas the matairesinol polymers are mainly penta-pentadecalignans (MW 1.8–5.3 kDa). The polymers seem to contain mainly unmodified lignan units linked by 5-5′ bonds.
Original languageEnglish
Pages (from-to)283-294
JournalHolzforschung
Volume66
Issue number3
DOIs
Publication statusPublished - 2012
MoE publication typeA1 Journal article-refereed

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Polymers
Lignans
Size exclusion chromatography
Molecular weight distribution
Light scattering
Dimers
Pyrolysis
Polymerization
Nuclear magnetic resonance
2,2-diphenyl-1-picrylhydrazyl
matairesinol
pinoresinol
Oxidation

Keywords

  • 2,2-diphenyl-1-picrylhydrazyl (DPPH)
  • evaporative light-scattering detection (ELSD)
  • high-performance size exclusion chromatography (HPSEC)
  • KMnO4 oxidation
  • lignan polymers
  • lignans
  • MALDI-ToF-MS
  • matairesinol
  • pinoresinol
  • pyrolysis-GC/MS (Py-GC/MS

Cite this

Smeds, Annika I. ; Eklund, Patrik C. ; Monogioudi, Evanthia ; Willför, Stefan M. / Chemical characterization of polymerized products formed in the reactions of matairesinol and pinoresinol with the stable radical 2,2-diphenyl-1-picrylhydrazyl. In: Holzforschung. 2012 ; Vol. 66, No. 3. pp. 283-294.
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abstract = "Polymerization reactions of the lignans matairesinol and pinoresinol with the stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) were studied. The reactions were rapid and almost quantitative. The molecular weight distribution (MWD) of the formed lignan dimers and polymers was determined by high-performance size-exclusion chromatography (HPSEC) combined with evaporative light-scattering detection (ELSD), and the compounds were characterized by HPLC-MS, pyrolysis-GC/MS, NMR, MALDI-ToF-MS, and GC-MS of the monomeric and dimeric units formed by KMnO4 oxidation. The yield of high-MW polymers is higher for pinoresinol (69{\%}) than for matairesinol (43{\%}). According to the HPSEC-ELSD analyses, the MWD is also broader for the pinoresinol polymers. The latter seem to consist mainly of hepta-hexacontalignans (MW 2.5–21.4 kDa), whereas the matairesinol polymers are mainly penta-pentadecalignans (MW 1.8–5.3 kDa). The polymers seem to contain mainly unmodified lignan units linked by 5-5′ bonds.",
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pages = "283--294",
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Chemical characterization of polymerized products formed in the reactions of matairesinol and pinoresinol with the stable radical 2,2-diphenyl-1-picrylhydrazyl. / Smeds, Annika I. (Corresponding Author); Eklund, Patrik C.; Monogioudi, Evanthia; Willför, Stefan M.

In: Holzforschung, Vol. 66, No. 3, 2012, p. 283-294.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Chemical characterization of polymerized products formed in the reactions of matairesinol and pinoresinol with the stable radical 2,2-diphenyl-1-picrylhydrazyl

AU - Smeds, Annika I.

AU - Eklund, Patrik C.

AU - Monogioudi, Evanthia

AU - Willför, Stefan M.

PY - 2012

Y1 - 2012

N2 - Polymerization reactions of the lignans matairesinol and pinoresinol with the stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) were studied. The reactions were rapid and almost quantitative. The molecular weight distribution (MWD) of the formed lignan dimers and polymers was determined by high-performance size-exclusion chromatography (HPSEC) combined with evaporative light-scattering detection (ELSD), and the compounds were characterized by HPLC-MS, pyrolysis-GC/MS, NMR, MALDI-ToF-MS, and GC-MS of the monomeric and dimeric units formed by KMnO4 oxidation. The yield of high-MW polymers is higher for pinoresinol (69%) than for matairesinol (43%). According to the HPSEC-ELSD analyses, the MWD is also broader for the pinoresinol polymers. The latter seem to consist mainly of hepta-hexacontalignans (MW 2.5–21.4 kDa), whereas the matairesinol polymers are mainly penta-pentadecalignans (MW 1.8–5.3 kDa). The polymers seem to contain mainly unmodified lignan units linked by 5-5′ bonds.

AB - Polymerization reactions of the lignans matairesinol and pinoresinol with the stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) were studied. The reactions were rapid and almost quantitative. The molecular weight distribution (MWD) of the formed lignan dimers and polymers was determined by high-performance size-exclusion chromatography (HPSEC) combined with evaporative light-scattering detection (ELSD), and the compounds were characterized by HPLC-MS, pyrolysis-GC/MS, NMR, MALDI-ToF-MS, and GC-MS of the monomeric and dimeric units formed by KMnO4 oxidation. The yield of high-MW polymers is higher for pinoresinol (69%) than for matairesinol (43%). According to the HPSEC-ELSD analyses, the MWD is also broader for the pinoresinol polymers. The latter seem to consist mainly of hepta-hexacontalignans (MW 2.5–21.4 kDa), whereas the matairesinol polymers are mainly penta-pentadecalignans (MW 1.8–5.3 kDa). The polymers seem to contain mainly unmodified lignan units linked by 5-5′ bonds.

KW - 2,2-diphenyl-1-picrylhydrazyl (DPPH)

KW - evaporative light-scattering detection (ELSD)

KW - high-performance size exclusion chromatography (HPSEC)

KW - KMnO4 oxidation

KW - lignan polymers

KW - lignans

KW - MALDI-ToF-MS

KW - matairesinol

KW - pinoresinol

KW - pyrolysis-GC/MS (Py-GC/MS

U2 - 10.1515/hf.2011.151

DO - 10.1515/hf.2011.151

M3 - Article

VL - 66

SP - 283

EP - 294

JO - Holzforschung

JF - Holzforschung

SN - 0018-3830

IS - 3

ER -