Chemical Structure and Occurrence of Natural Polyisoprenes
Part 2. Polyisoprenoids
Prof.Dr. Yasuyuki Tanaka,
Prof.Dr. Jitladda Tangpakdee Sakdapipanich,
Prof.Dr. Yasuyuki Tanaka
- [email protected]
- +662-4419003-1457 | Fax: +662-4411013
Mahidol University, Institute of Science and Technology for Research and Development, Salaya Campus, Nakornprathom, Thailand, 73170
Search for more papers by this authorProf.Dr. Jitladda Tangpakdee Sakdapipanich
- [email protected]
- +662-2461374-1604 | Fax: +662-247-7050
Mahidol University, Department of Chemistry, Faculty of Science, Rama VI Rd., Phayathai, Bangkok, Thailand, 10400
Search for more papers by this authorProf.Dr. Yasuyuki Tanaka,
Prof.Dr. Jitladda Tangpakdee Sakdapipanich,
Prof.Dr. Yasuyuki Tanaka
- [email protected]
- +662-4419003-1457 | Fax: +662-4411013
Mahidol University, Institute of Science and Technology for Research and Development, Salaya Campus, Nakornprathom, Thailand, 73170
Search for more papers by this authorProf.Dr. Jitladda Tangpakdee Sakdapipanich
- [email protected]
- +662-2461374-1604 | Fax: +662-247-7050
Mahidol University, Department of Chemistry, Faculty of Science, Rama VI Rd., Phayathai, Bangkok, Thailand, 10400
Search for more papers by this authorAbstract
- Historical Outline
- Rubber Production and Consumption
- Structure of Rubber
- Synthetic Rubber
- Outlook and Perspectives
- Rubber Production Technology
- Rubber Protein Allergy
- Purification of Natural Rubber
- Chemical Structure of Isoprene Units
- Geometric Isomerism of Isoprene Unit
- Structure of the Chain-Ends of Naturally Occurring Polyisoprenes
- Molecular Weight and Molecular Weight Distribution
- Occurrence of Polyisoprene in Living Organisms
- cis-Polyisoprene in Higher Plants
- trans-Polyisoprene in Other Higher Plants and Grasses
- cis-Polyisoprene in Mushrooms
- Natural Rubber from H. brasiliensis
- Production of Commercial Natural Rubber and Latex
- Composition of Natural Rubber
- Structure of both Chain Ends of Natural Rubber
- Initiating Terminal of the Rubber Molecule
- Terminating Chain End of Rubber Molecule
- Structural Change of Rubber Molecule in Rubber Tree
- Structure of Branch-Points and Gel
- Structure of trans-Polyisoprene from Higher Plants
- trans-Polyisoprene from Chicle
- trans-Polyisoprene from Gutta Percha and Balata
- trans-Polyisoprene from Eucommia ulmoides
- Other Natural Polyisoprenes
- Structure of cis-Polyisoprene from Fungi
- Structure of cis-Polyisoprene from Other Higher Plants
- cis-Polyisoprenes from Leaves from Goldenrod and Sunflower
- cis-Polyisoprene from Guayule
- Wild Rubbers Occurring as Latex
References
- Adams, R. P., Balandrin, M. F., Martineau, J. R. (1984) The showy milkweed, Asclepias speciosa: a potential new semi-arid land crop for energy and chemicals, Biomass 4, 81–104.
- Allen, P. W., Bristow, G. M. (1963) The gel phase in natural rubber, J. Appl. Polym. Sci. 7, 603–615.
- Anderson, R. F., Baker, T. I., Jayko, L. J., Benedict, R. G. (1961) Occurrence of polyisoprene in Lactarius species, Biochim. Biophys. Acta 50, 374–375.
- Angulo-Sanchez, J. L., Caballero-Mata, P. (1981) Long chain branching in natural Hevea rubber – Determination by gel permeation chromatography, Rubb. Chem. Technol. 54, 34–41.
- Archer, B. L., Audley, B. G. (1973) Rubber, gutta percha and chicle, in: Phytochemistry ( L. M. Miller, Ed.), Vol. 2, pp. 310–342. New York: Van Nostrand Reinhold Co.
- Archer, B. L., Audley, B. G. (1987) New aspects of rubber biosynthesis, Bot. J. Linnean Soc. 94, 181–196.
- Archer, B. L., Audley, B. G., McSweeney, G. P., Tang, C. H. (1969) Studies on the composition of latex serum and bottom fraction particles, J. Rubb. Res. Inst. Malaya 21, 560–569.
- Arnold, A. R., Evans, P. (1991) Role of fatty acids in antioxidation of deproteinized natural rubber, J. Natl. Rubb. Res. 6, 75–86.
- Audley, B. G., Archer, B. L. (1988) Biosynthesis of rubber, in: Natural Rubber Science and Technology ( A. D. Roberts, Ed.), pp. 35–62. London: Oxford University Press.
- Bloomfield, G. F. (1951) The rubber hydrocarbon in freshly tapped Hevea latex, J. Rubb. Res. Inst. Malaya 13, 737–749.
- Buchanan, R. A., Cull, I. M., Otey, F. H., Russel, C. R. (1976) Hydrocarbon and rubber producing crops: Evaluation of U.S. plant species, Rubber Div. ACS., 110th Meeting, San Francisco, Paper No. 40, 1–40.
- Buchanan, R. A., Swanson, C. L., Weisleder, D., Cull, I. M. (1979) Gutta-producing grasses, Phytochemistry 18, 1069–1071.
- Bunn, C. W. (1942) Molecular structure and rubber-like elasticity. I. The crystal structures of β-gutta percha, rubber and polychloroprene, Proc. Roy. Soc. A180, 40–66.
- Burfield, D. R. (1974) Epoxy groups responsible for crosslinking in natural rubber, Nature 249, 29–30.
- Burfield, D. R., Gan, S. N. (1975) Nonoxidative crosslinking reactions in natural rubber. I. Determination of crosslinking groups, Polymer 13, 2725–2734.
- Burger, K., Smit, H. P. (1999) How will the current crisis change global NR demand and supply of natural rubber patterns? International Rubber Marketing Conference 1999, Hatyai, Thailand, 19–55.
- Campos-Lopez, E., Angulo-Sanchez, J. L. (1976) Molecular weight characterization of natural guayule rubber by gel-permeation chromatography, J. Polym. Sci. Polym. Lett. Ed. 14, 649–652.
- Campos-Lopez, E., Neavez-Camacho, E., Ponce-Velez, M. A., Angulo-Sanchez, J. L. (1979) The rubber shrub, Chemtech, 9 (1) 50–57.
- Cornish, K., Backhaus, R. A. (1990) Rubber transferase activity in rubber particles of guayule, Phytochemistry 29, 3809–3813.
- Crafts, R. C., Davey, J. E., McSweeney, G. P., Stephens, I. S. (1990) Comparison of free fatty acid values with individually determined organic and inorganic acid concentrations in the extracts of Malaysian natural rubber, J. Natl. Rubb. Res. 5, 275–285.
- Eagle, F. A. (1981) Guayule, Rubb. Chem. Technol. 54, 662–684.
- Eng, A. H., Kawahara, S., Tanaka, Y. (1994a) Trans-isoprene units in natural rubber, Rubb. Chem. Technol. 67, 159–168.
- Eng, A. H., Ejiri, S., Kawahara, S., Tanaka, Y. (1994b) Structural characterization of natural rubber – Role of ester groups, J. Appl. Polym. Sci. Appl. Polym. Symp. 53, 5–14.
- Fuller, K. N. G., Fulton, W. S. (1990) The influence of molecular weight distribution and branching on the relaxation behaviour of uncrosslinked natural rubber, Polymer 31, 609–615.
- Gazeley, K. F., Gorton, A. D. T., Pendle, T. D. (1988) Latex concentrates: Properties and composition, in: Natural Rubber Science and Technology ( A. D. Roberts, Ed.), pp. 63–140. London: Oxford University Press.
- Gnecco, S., Pooley, A., Krause, M. (1997) Seasonal variation of polyisoprene contents in Euphorbia lactiflua latex, Bole. Soc. Chil. Quim. 42, 547–553.
- Gregg, E. C., Macey, J. H. (1973) The relationship of properties of synthetic polyisoprene and NR in the factory, Rubb. Chem. Technol. 46, 47–65.
- Hager, T., MacArthur, A., McIntyre, D., Seeger, R. (1979) Chemistry and structure of natural rubbers, Rubb. Chem. Technol. 52, 693–709.
- Hurley, P. E. (1981) History of natural rubber, J. Macromol. Sci.-Chem. A15, 1279–1287.
- Hayman, E., Yokoyama, H., Schuster, R. (1982) Carbon-13 nuclear magnetic resonance determination of rubber in guayule (Parthenium argentatum), J. Agric. Food Chem. 30, 399–401.
- Hemming, F. W. (1983) Biosynthesis of dolichols and related compounds, in: Biosynthesis of Isoprenoid Compounds ( J. W. Porter and S. L. Spurgeon, Eds.), Vol. 2, pp. 305–354. New York: John Wiley Press.
- Ibata, K., Mizuno, M., Takigawa, T., Tanaka, Y. (1983) Long-chain betulaprenol-type polyprenols from the leaves of Gingko biloba, Biochem. J. 213, 305–311.
- Jacob, J. L., d'Auzac, J., Prevot, J. C. (1993) The composition of natural latex from Hevea brasiliensis, Clin. Rev. Allergy 11, 325–337.
- Kadir, A. A. S. A. (1994) Advances in natural rubber production, Rubb. Chem. Technol. 67, 537–548.
- Kawahara, S., Nishiyama, N., Kakubo, T., Tanaka, Y. (1996) Original of characteristic properties of natural rubber – Synergistic effect of fatty acids on crystallization of cis-1,4-polyisoprene: I. Saturated and unsaturated fatty acids, Rubb. Chem. Technol. 69, 600–607.
- Kawahara, S., Kakubo, T., Sakdapipanich, J. T., Isono, Y., Tanaka, Y. (2000) Characterization of fatty acids linked to natural rubber – Role of linked fatty acids in crystallization of the rubber, Polymer 41, 7483–7488.
- Kishore, K., Pandey, H. K. (1986) Spectral studies on plant rubbers, Prog. Polym. Sci. 12, 155–178.
- Kurihara, K., Kato, K., Takei, Y., Shichiji, S. (1962) Studies on rubber productive microorganisms (Part 1), Rep. Ferment. Res. Inst. Chiba, Jpn. 22, 61–68.
- Kurihara, K., Kato, K., Takei, Y., Shichiji, S. (1963) Studies on rubber productive microorganisms. 2. On screening of rubber productive Basidomycetes (2), Rep. Ferment. Res. Inst. Chiba, Jpn. 24, 25–31.
- Kurihara, K., Kato, K., Takei, Y., Shichiji, S. (1964) Studies on rubber productive microorganisms. 3. On screening of rubber productive Basidomycetes (3), Rep. Ferment. Res. Inst. Chiba, Jpn. 25, 33–36.
- Loyen, G. (2000) Prospective for natural rubber in the early 21st century, Rubb. Int. Mag. 2 (13), 73–82.
- Lynen, F. (1969) Biochemical problems of rubber synthesis, J. Rubb. Res. Inst. Malaya 21, 389–406.
- Lynen, F., Henning, U. (1960) The biological pathway to natural rubber, Angew. Chem. 72, 820–829.
- Madhavan, S., Greenblatt, G. A., Foster, M. A., Benedict, C. R. (1989) Stimulation of isopentenyl pyrophosphate incorporation into polyisoprene in extracts from guayule plants (Parthenium argentatum Gray) by low temperature and 2-(3,4-dichlorophenoxy)triethylamine, Plant Physiol. 89, 506–511.
- Mooibroek, H., Cornish, K. (2000) Alternative sources of natural rubber, Appl. Microbiol. Biotechnol. 53, 355–365.
- Moyle, A. E. (1942) Bibliography and collected abstracts on rubber producing plants, Texas Agric. Exp. Sta. Circ., 99.
- Muller, E. (2000) Current rubber industries situation in Thailand, Rubb. Int. Mag. 2 (14), 71–78.
- Nair, S. (1987) Characterisation of natural rubber for greater consistency, Proceedings, International Rubber Conference 1987, P. 2A/1–10, PRI, London.
- Nakade, S., Kuga, A., Hayashi, M., Tanaka, Y. (1997) Highly purified natural rubber. IV. Preparation and characterization of gloves and condoms, J. Natl. Rubb. Res. 12, 33–42.
- Nishiyama, N., Kawahara, S., Kakubo, T., Eng, A. H., Tanaka, Y. (1996) Original of characteristic properties of natural rubber – Synergistic effect of fatty acids on crystallization of cis-14,-polyisoprene: II. Mixed and esterified fatty acids in natural rubber, Rubb. Chem. Technol. 69, 608–614.
- Nyburg, S. C. (1954) Statistical structure for crystallized rubber, Acta Crystallogr. 7, 385–392.
- Ohya, N., Takizawa, J., Kawahara, S., Tanaka, Y. (1998) Molecular weight distribution of polyisoprene from Lactarius volemus, Phytochemistry 48, 781–786.
- Paterson-Jones, J. C. (1983) The polyisoprene content of some South Africa plants, Biomass 3, 225–234.
- Pendle, T. D., Swinyard, P. E. (1991) The particle size of natural rubber latex concentrates by photon correlation spectroscopy, J. Natl. Rubb. Res. 6, 1–11.
- Ratti, N., Sidhu, O. P., Behl, H. M. (1995) Quantification of polyisoprenes from some promising euphorbs, Bioresource Technol. 52, 231–235.
-
Sakaki, T.,
Hioki, Y.,
Kojima, M.,
Kuga, A.,
Tanaka, Y.
(1996)
Highly purified natural rubber. I. Preparation of anionic latex and its physical properties,
Nippon Gomu Kyokashi 69,
553–556.
10.2324/gomu.69.553 Google Scholar
- Sakdapipanich, J. T., Tanaka, Y., Jacob, J. L., d'Auzac, J. (1999a) Characterization of Hevea brasiliensis rubber from virgin trees: a possible role of cis-polyisoprene in unexploited tree, Rubb. Chem. Technol. 72, 299–307.
- Sakdapipanich, J. T., Kowitteerawut, T., Suchiva, K., Tanaka, Y. (1999b) Long-chain branching and mechanism controlling molecular weight in Hevea rubber, Rubb. Chem. Technol. 72, 712–720.
- Schlesinger, W., Leeper, H. M. (1951) Chicle, cis- and trans-polyisoprene from a single plant species, Ind. Eng. Chem. 43, 398–403.
- Schloman, W. W., Wyzgoski, F., McIntyre, D., Cornish, K., Siler, D. J. (1996) Characterization and performance testing of guayule latex, Rubb. Chem. Technol. 69, 215–222.
- Sekhar, B. C. (1960) Degradation and crosslinking of polyisoprene in Hevea brasiliensis latex during processing and storage, J. Polym. Sci. 48, 133–137.
- Sekhar, B. C. (2000) Rubber in the new millennium, Rubber Asia 2, 34–36.
- Sentheshanmuganathan, S. (1975) Some aspects of lipids chemistry of natural rubber, Proceedings International Rubber Conference 1975, 457–469.
- Stewart, W. D., Wachtel, W. L., Shipman, J. J., Yanko, J. A. (1955) Synthesis of rubber by fungi, Science 122, 1271–1272.
- Stipanovic, R. D., O'Brien, D. H., Rogers, C. E., Hanlon, K. D. (1980) Natural rubber from Sunflower, J. Agric. Food Chem. 28, 1322–1323.
- Stipanovic, R. D., Seiler, G. R., Rogers, C. E. (1982) Natural rubber from Sunflower, 2 J. Agric. Food Chem. 30, 611–613.
- Subramaniam, A. (1980) Molecular Weight and Molecular Weight Distribution of Natural Rubber, RRIM Technical Bulletin, No. 4, Rubber Research Institute of Malaysia.
- Tanaka, Y. (1989a) Structure and biosynthesis mechanism of natural polyisoprene, Prog. Polym. Sci. 14, 339–371.
- Tanaka, Y. (1989b) Structural characterization of naturally occurring cis- and trans-polyisoprene by 13C-NMR spectroscopy, J. Appl. Polym. Sci. Appl. Polym. Symp. 44, 1–9.
- Tanaka, Y., Eng, A. H. (1994) Liquid natural rubber from Lactarius mushroom, Polymer News 19, 136–140.
- Tanaka, Y., Takagi, M. (1979) Structural characterization of ficaprenol-11 by 13C nuclear magnetic resonance, Biochem. J. 183, 163–165.
- Tanaka, Y., Tangpakdee, J. (1997) Structural control and origin of characteristic properties in natural rubber, Curr. Polym. Res., 12–15.
- Tanaka, Y., Sato, Y., Kageyu, A. (1983) Structure and biosynthesis mechanism of natural cis-polyisoprene from Goldenrod, Rubb. Chem. Technol. 56, 299–303.
- Tanaka, Y., Sato, H., Tomita, T. (1987) Determination of arrangement of isoprene units in pig liver dolichol by 13C-NMR spectroscopy, Biochem. J. 243, 481–485.
- Tanaka, Y., Nunogaki, K., Kageyu, A., Mori, M., Sato, Y. (1988) Structure and biosynthesis mechanism of trans-polyisoprene from chicle, J. Natl. Rubb. Res. 3, 177–183.
- Tanaka, Y., Mori, M., Ute, K., Hatada, K. (1990a) Structure and biosynthesis mechanism of rubber from fungi, Rubb. Chem. Technol. 63, 1–7.
- Tanaka, Y., Mori, M., Takei, A., Boochathum, P. (1990b) Structural characterization of naturally occurring trans-polyisoprenes, J. Natl. Rubb. Res. 5, 241–245.
- Tanaka, Y., Mori, M., Takei, A. (1992) Structure and biosynthesis mechanism of rubber from Lactarius mushroom, J. Appl. Polym. Sci. Appl. Polym. Symp. 50, 43–50.
- Tanaka, Y., Eng, A. H., Ohya, N., Tangpakdee, J., Kawahara, S., Wititsuwannakul, R. (1996) Initiation of rubber biosynthesis in Hevea brasiliensis: characterization of initiating species by structural analysis, Phytochemistry 41, 1501–1505.
- Tanaka, Y., Kawahara, S., Tangpakdee, J. (1997) Structural characterization of natural rubber, Kautsch. Gummi Kunstst. 50, 6–11.
- Tangpakdee, J., Tanaka, Y. (1997) Purification of natural rubber, J. Natl. Rubb. Res. 12, 112–119.
- Tangpakdee, J., Tanaka, Y. (1998a) Long-chain polyprenols and rubber in young leaves of Hevea brasiliensis, Phytochemistry 48, 447–450.
- Tangpakdee, J., Tanaka, Y. (1998b) Why rubber tree produce polyisoprene – A possible role of natural rubber in the Hevea tree, J. Rubb. Res. 1, 77–83.
- Tangpakdee, J., Tanaka, Y. (1998c) Branching in natural rubber, J. Natl. Rubb. Res. 1, 14–21.
- Tangpakdee, J., Tanaka, Y. (1998d) Characterization of sol and gel in Hevea natural rubber, Rubb. Chem. Technol. 70, 707–713.
- Tangpakdee, J., Tanaka, Y., Wititsuwannakul, R., Chareonthiphakorn, N. (1996) Possible mechanisms controlling molecular weight of rubbers in Hevea brasiliensis, Phytochemistry 42, 353–355.
- Tangpakdee, J., Tanaka, Y., Ogura, K., Koyama, T., Wititsuwannakul, R., Wititsuwannakul, D. (1997a) Rubber formation by fresh bottom fraction of Hevea latex, Phytochemistry 45, 269–274.
- Tangpakdee, J., Tanaka, Y., Ogura, K., Koyama, T., Wititsuwannakul, R., Chareonthiphakorn, N. (1997b) Structure of in vitro rubber from fresh bottom fraction of Hevea latex, Phytochemistry 45, 275–281.
- Tangpakdee, J., Tanaka, Y., Shiba, K., Kawahara, S., Sakurai, K., Suzuki, Y. (1997c) Structure and biosynthesis of trans-polyisoprene from Eucommia ulmoides, Phytochemistry 45, 75–80.
- Tomoda, M., Gonda, R., Shimizu, N., Kanari, M. (1990) A reticuloendothelial system-activating glycan from the barks of Eucommia ulmoides, Phytochemistry 29, 3091–3094.
- Trautmann, I. A., Visser, J. H., Spies, H. S. C. (1991) Detection of rubber in cultured material of Parthenium argentatum Gray guayule), Plant Sci. 73, 97–102.
- Vanderbilt, B., Ukkelberg, H. (1977) On rubber plants (1), Chemtech, 693–694.
-
Verhaar, G.
(1959)
Natural rubber as a colloidal system,
Rubb. Chem. Technol. 32,
1627–1659.
10.5254/1.3542496 Google Scholar
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