Suggested Production of a Guaiacyl Benzofuran Derivative from Softwood via Lignocresol
Lignocresol was isolated from softwood with p-cresol using sulfuric acid and phase separation. An alkaline treatment of the lignocresol, followed by acidification, selectively yielded a guaiacyl coumaran, G1, in the acid-soluble fraction. With further alkaline treatment of G1 in 0.5 M of NaOH soluti...
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| Format: | Article |
| Language: | English |
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North Carolina State University
2016-07-01
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| Series: | BioResources |
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| Online Access: | http://ojs.cnr.ncsu.edu/index.php/BioRes/article/view/BioRes_11_3_6932_Nonaka_Guaiacyl_Benzofuran_Derivative_Softwood |
| _version_ | 1818511031072194560 |
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| author | Hiroshi Nonaka; Ryota Yamamoto Hirotaka Katsuzaki Masamitsu Funaoka |
| author_facet | Hiroshi Nonaka; Ryota Yamamoto Hirotaka Katsuzaki Masamitsu Funaoka |
| author_sort | Hiroshi Nonaka; |
| collection | DOAJ |
| description | Lignocresol was isolated from softwood with p-cresol using sulfuric acid and phase separation. An alkaline treatment of the lignocresol, followed by acidification, selectively yielded a guaiacyl coumaran, G1, in the acid-soluble fraction. With further alkaline treatment of G1 in 0.5 M of NaOH solution at 170 °C for 60 min, it was strongly suggested that a guaiacyl benzofuran derivative, G2, was obtained by the elimination of formaldehyde, based on analytical data of the reaction mixture. The process is very unique and well-designed based on the reactivity of Cα-ethers, or Cα-OH, Cβ-aryl-ethers, and Cγ-OH of lignin, although condensation reactions via formaldehyde occurred in parallel to give condensed products with a diarylmethane structure. Because these phenolic dimers, G1 and G2, were recovered from the guaiacyl unit linked with the neighboring guaiacyl units via two Beta-aryl-ether bonds, they are promising lignin-derived chemicals that are obtainable in a high yield. |
| first_indexed | 2024-12-10T23:27:59Z |
| format | Article |
| id | doaj.art-5c2ca39c8e564c3396e4decc417e00a8 |
| institution | Directory Open Access Journal |
| issn | 1930-2126 1930-2126 |
| language | English |
| last_indexed | 2024-12-10T23:27:59Z |
| publishDate | 2016-07-01 |
| publisher | North Carolina State University |
| record_format | Article |
| series | BioResources |
| spelling | doaj.art-5c2ca39c8e564c3396e4decc417e00a82022-12-22T01:29:30ZengNorth Carolina State UniversityBioResources1930-21261930-21262016-07-011136932693910.15376/biores.11.3.6932-6939Suggested Production of a Guaiacyl Benzofuran Derivative from Softwood via LignocresolHiroshi Nonaka;0Ryota Yamamoto1Hirotaka Katsuzaki2Masamitsu Funaoka3Graduate School of Bioresources, Mie University; JapanGraduate School of Bioresources, Mie University; JapanGraduate School of Bioresources, Mie University; JapanGraduate School of Bioresources, Mie University; JapanLignocresol was isolated from softwood with p-cresol using sulfuric acid and phase separation. An alkaline treatment of the lignocresol, followed by acidification, selectively yielded a guaiacyl coumaran, G1, in the acid-soluble fraction. With further alkaline treatment of G1 in 0.5 M of NaOH solution at 170 °C for 60 min, it was strongly suggested that a guaiacyl benzofuran derivative, G2, was obtained by the elimination of formaldehyde, based on analytical data of the reaction mixture. The process is very unique and well-designed based on the reactivity of Cα-ethers, or Cα-OH, Cβ-aryl-ethers, and Cγ-OH of lignin, although condensation reactions via formaldehyde occurred in parallel to give condensed products with a diarylmethane structure. Because these phenolic dimers, G1 and G2, were recovered from the guaiacyl unit linked with the neighboring guaiacyl units via two Beta-aryl-ether bonds, they are promising lignin-derived chemicals that are obtainable in a high yield.http://ojs.cnr.ncsu.edu/index.php/BioRes/article/view/BioRes_11_3_6932_Nonaka_Guaiacyl_Benzofuran_Derivative_SoftwoodLignocresolLigninPhenolic dimerGuaiacylBenzofuran |
| spellingShingle | Hiroshi Nonaka; Ryota Yamamoto Hirotaka Katsuzaki Masamitsu Funaoka Suggested Production of a Guaiacyl Benzofuran Derivative from Softwood via Lignocresol BioResources Lignocresol Lignin Phenolic dimer Guaiacyl Benzofuran |
| title | Suggested Production of a Guaiacyl Benzofuran Derivative from Softwood via Lignocresol |
| title_full | Suggested Production of a Guaiacyl Benzofuran Derivative from Softwood via Lignocresol |
| title_fullStr | Suggested Production of a Guaiacyl Benzofuran Derivative from Softwood via Lignocresol |
| title_full_unstemmed | Suggested Production of a Guaiacyl Benzofuran Derivative from Softwood via Lignocresol |
| title_short | Suggested Production of a Guaiacyl Benzofuran Derivative from Softwood via Lignocresol |
| title_sort | suggested production of a guaiacyl benzofuran derivative from softwood via lignocresol |
| topic | Lignocresol Lignin Phenolic dimer Guaiacyl Benzofuran |
| url | http://ojs.cnr.ncsu.edu/index.php/BioRes/article/view/BioRes_11_3_6932_Nonaka_Guaiacyl_Benzofuran_Derivative_Softwood |
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