Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 283-294 |
| Journal | Holzforschung |
| Volume | 66 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - 2012 |
| MoE publication type | A1 Journal article-refereed |
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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
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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 journal › Article › Scientific › peer-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 -