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; Patrik C. Eklund; Evanthia Monogioudi; Stefan M. Willför

doi:10.1515/hf.2011.151

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

VTT Technical Research Centre of Finland

Research output: Contribution to journal › Article › Scientific › peer-review

30 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 language	English
Pages (from-to)	283-294
Journal	Holzforschung
Volume	66
Issue number	3
DOIs	https://doi.org/10.1515/hf.2011.151
Publication status	Published - 2012
MoE publication type	A1 Journal article-refereed

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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@article{4cd2519cb5f44a67a49aedf6ea061e8d,

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

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.",

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",

author = "Smeds, {Annika I.} and Eklund, {Patrik C.} and Evanthia Monogioudi and Willf{\"o}r, {Stefan M.}",

year = "2012",

doi = "10.1515/hf.2011.151",

language = "English",

volume = "66",

pages = "283--294",

journal = "Holzforschung",

issn = "0018-3830",

publisher = "De Gruyter",

number = "3",

}

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 -