The existence of lignin in Sphagnum moss has been investigated. A vibratory ball milling technique gave a low yield (0·9 per cent) of a presumed lignin. This substance was low in methoxyl, aromatic hydrogen and ether oxygen. It gave an acetate containing 36·5 per cent COCH 3 and nitrobenzene oxidation of this acetate gave small amounts of p -hydroxybenzaldehyde, vanillin and syringaldehyde. Permanganate oxidation of the acetate gave p -hydroxybenzoic acid and traces of other acids. These properties show that the substance is basically a highly condensed CC linked polymer of methoxyl-free units with some methoxylated ether-linked units. This substance may therefore reasonably be classified as a lignin.

The existence of lignin in Sphagnum moss has been investigated. A vibratory ball milling technique gave a low yield (0·9 per cent) of a presumed lignin. This substance was low in methoxyl, aromatic hydrogen and ether oxygen. It gave an acetate containing 36·5 per cent COCH3 and nitrobenzene oxidation of this acetate gave small amounts of p-hydroxybenzaldehyde, vanillin and syringaldehyde. Permanganate oxidation of the acetate gave p-hydroxybenzoic acid and traces of other acids. These properties show that the substance is basically a highly condensed CC linked polymer of methoxyl-free units with some methoxylated ether-linked units. This substance may therefore reasonably be classified as a lignin.

Proton magnetic resonance estimations of the fraction of protons attached directly to aromatic nuclei in some lignin preparations from Pinus radiata and Eucalyptus regnans indicate that aromatic rings are present in the form of condensed structures. These results are in agreement with other data on condensed structures in lignins. Other features of p.m.r. spectra of the above materials are discussed.

A SAMPLE of methanol lignin from Eucalyptus regnans1, purified by counter-current distribution and possessing the empirical formula (on the basis of a C9 unit) of C9H8.1O2.70(OCH3)1.86, was examined by means of the high-resolution nuclear magnetic resonance technique. This lignin was shown to contain approximately equal numbers of guaiacyl and syringyl units and to have been methylated to the extent of 0.41 methoxyl groups per C9 unit1. The spectrum (Fig. 1) of an approximately 10 per cent solution in deuterochloroform was recorded on a Varian model A60 spectrometer operating at 60 Mc/s and was calibrated in parts per million from tetra-methyl silane as internal reference2. The feature centred at 6.62 p.p.m. can be attributed to protons linked directly to aromatic nuclei and that centred at 3.85 p.p.m. to protons in methoxyl groups. When recorded under the same conditions the spectrum of vanillin showed the methoxyl feature at 3.88 p.p.m. and that of syringaldehyde at 3.93 p.p.m. In the foregoing empirical formula, hydrogen present as methoxyl accounts for about 41 per cent of the total, whereas the feature at 4.98–3.45 p.p.m. equals 46 per cent of the total. The remaining features are most likely to be mainly associated with protons attached directly to oxygen (hydroxyl groups) or to carbon atoms bearing negative substituents. Protons resonating at corresponding frequencies may be found in the spectra of lignans3,4. There is a striking lack of features upfield from 2 p.p.m. where most aliphatic and alicyclic methyl, methylene and methine protons would be expected to occur5. In general, the proton magnetic resonance spectrum appears to be in agreement with the type of structure predicted by Freudenberg8.

Research Article| October 01 1961 Eugenol lignin: its chemical properties and significance DE BLAND DE BLAND Search for other works by this author on: This Site PubMed Google Scholar Biochem J (1961) 81 (1): 23–28. https://doi.org/10.1042/bj0810023 Views Icon Views Article contents Figures & tables Video Audio Supplementary Data Peer Review Share Icon Share Twitter LinkedIn Cite Icon Cite Get Permissions Citation DE BLAND; Eugenol lignin: its chemical properties and significance. Biochem J 1 October 1961; 81 (1): 23–28. doi: https://doi.org/10.1042/bj0810023 Download citation file: Ris (Zotero) Reference Manager EasyBib Bookends Mendeley Papers EndNote RefWorks BibTex toolbar search Search Dropdown Menu nav search search input Search input auto suggest search filter All ContentAll JournalsBiochemical Journal Search Advanced Search This content is only available as a PDF. © 1961 The Biochemical Society1961 Article PDF first page preview Close Modal You do not currently have access to this content.

Literatur (1) G. Jayme u. G. Hunger, Holz, Rohu. Werkstoff 13,212 (1955). (2) G. Jayme u. G. Hunger, Mh. Chemie 87, 8 (3) G. Jayme u. G. Hunger, Das Papier ir, 140 (195?)· (4) G. Jayme u. G. Hunger, Zellstoff u. Papier 6, 341 (195?)· (5) G. Jayme u. G. Hunger, Wbl. f. Papierfabrikation 85, 900 (195?)' « · (6) G. Jayme u. G. Hunger, Mikroskopie 13, 24 (1958). (7) G. Jayme u. G. Hunger, Fundamentals of Papermaking Fibres; Techn. Sect. of BP & BMA, Kenley 1958 S. 263 bis 271, ' r (8) G. Hunger u. G. Jayme, Naturwiss. 42, 209 (1955)·

The mixtures of aromatic aldehydes produced from 12 species of eucalypt woods and eight Australian gymnosperm woods by oxidation with nitrobenzene and alkali were separated by sublimation and the individual aldehydes identified. A paper partition chromatographic method for the separation of the aldehydes was used to confirm the results of the sublimation separation and to identify traces of aldehydes in some of the mixtures. The eucalypt woods all yielded vanillin, syringaldehyde, and traces of p-hydroxybenzaldehyde. The gymnosperm woods yielded mainly vanillin but traces of syringaldehyde were produced from some and traces of p-hydroxybenzaldehyde from most.