DOI: 10.1126/science.207.4436.1202. Phenolic Ethers in the Organic Polymer of the Murchison Meteorite

Phenolic Ethers in the Organic Polymer of the Murchison Meteorite

10.1126/science.207.4436.1202

Crossref journal-article

American Association for the Advancement of Science (AAAS)

Science (221)

Abstract

Seven phenolic acids and many nonphenolic organic acids, including large amounts of meta-hydroxy (3-hydroxy) benzoic acid and 3-hydroxy-1,5-benzenedicarboxylic acid, were obtained from the organic polymer of the Murchison C2 chondrite upon oxidation with alkaline cupric oxide. The phenolic acids apparently were derived from phenolic ethers in the polymer, which in turn probably were formed from carbon monoxide and hydrogen by catalytic Fischer-Tropsch type reactions in the solar nebula. In contrast, terrestrial polymers such as lignin, humic acid, and coal yield mainly para-hydroxy (4-hydroxy) benzene derivatives by the same oxidation procedure.

Bibliography

Hayatsu, R., Winans, R. E., Scott, R. G., McBeth, R. L., Moore, L. P., & Studier, M. H. (1980). Phenolic Ethers in the Organic Polymer of the Murchison Meteorite. Science, 207(4436), 1202â1204.

Authors 6

Ryoichi Hayatsu (first)
Randall E. Winans (additional)
Robert G. Scott (additional)
Robert L. McBeth (additional)
Leon P. Moore (additional)
Martin H. Studier (additional)

References 42 Referenced 65

ADLER, E, LIGNIN CHEMISTRY - PAST, PRESENT AND FUTURE, WOOD SCIENCE AND TECHNOLOGY 11: 169 (1977). (10.1007/BF00365615) / WOOD SCIENCE AND TECHNOLOGY (1977)
ANDERS, E, INTERSTELLAR-MOLECULES - ORIGIN BY CATALYTIC REACTIONS ON GRAIN SURFACES, ASTROPHYSICAL JOURNAL 192: L101 (1974). (10.1086/181601) / ASTROPHYSICAL JOURNAL (1974)
10.1126/science.182.4114.781
Asinger, F., Paraffins, Chemistry and Technology: CH2 (1968). / Paraffins, Chemistry and Technology (1968)
BANDURSKI, E.L., POLYMER-LIKE ORGANIC MATERIAL IN ORGUEIL METEORITE, GEOCHIMICA ET COSMOCHIMICA ACTA 40: 1397 (1976). (10.1016/0016-7037(76)90130-7) / GEOCHIMICA ET COSMOCHIMICA ACTA (1976)
Chang, H. M., Lignins: 433 (1971). / Lignins (1971)
Dryden, I. G. C., Chemistry of Coal Utilization: 272 (1963). / Chemistry of Coal Utilization (1963)
Emmett, P. H., Catalysis 7: CH1 (1958). / Catalysis (1958)
Emmett, P. H., Catalysis 6: CH2 (1958). / Catalysis (1958)
FRIEDMAN, L, OXIDATION OF ALKYLARENES WITH AQUEOUS SODIUM DICHROMATE . A USEFUL METHOD FOR PREPARING MONO- AND POLYAROMATIC CARBOXYLIC ACIDS, JOURNAL OF ORGANIC CHEMISTRY 30: 1453 (1965). (10.1021/jo01016a026) / JOURNAL OF ORGANIC CHEMISTRY (1965)
Fuchs L. H. Mineralogy mineral-chemistry and composition of the Murchison (C2) meteorite Smithsonian Contributions to the Earth Sciences 10 (1973). (10.5479/si.00810274.10.1)
FURY, L.A., SWAMPING CATALYST EFFECT .8. REARRANGEMENT OF METHYLATED AND BROMINATED PHENOLS, JOURNAL OF ORGANIC CHEMISTRY 30: 2301 (1965). (10.1021/jo01018a043) / JOURNAL OF ORGANIC CHEMISTRY (1965)
GRIFFITH, S.M., ALKALINE CUPRIC OXIDE OXIDATION OF HUMIC AND FULVIC ACIDS EXTRACTED FROM TROPICAL VOLCANIC SOILS, SOIL SCIENCE 122: 191 (1976). (10.1097/00010694-197610000-00003) / SOIL SCIENCE (1976)
Hayatsu, R., Advances in Chemistry 192: 133 (1981). (10.1021/ba-1981-0192.ch009) / Advances in Chemistry (1981)
HAYATSU, R, PREPRINTS OF PAPERS. AMERICAN CHEMICAL SOCIETY DIVISION OF FUEL CHEMISTRY 24: 110 (1979). / PREPRINTS OF PAPERS. AMERICAN CHEMICAL SOCIETY DIVISION OF FUEL CHEMISTRY (1979)
HAYATSU, R, TRAPPED ORGANIC-COMPOUNDS AND AROMATIC UNITS IN COALS, FUEL 57: 541 (1978). (10.1016/0016-2361(78)90039-X) / FUEL (1978)
HAYATSU, R, ORIGIN OF ORGANIC-MATTER IN EARLY SOLAR-SYSTEM .7. ORGANIC POLYMER IN CARBONACEOUS CHONDRITES, GEOCHIMICA ET COSMOCHIMICA ACTA 41: 1325 (1977). (10.1016/0016-7037(77)90076-X) / GEOCHIMICA ET COSMOCHIMICA ACTA (1977)
HAYATSU, R, LIGNIN-LIKE POLYMERS IN COALS, NATURE 278: 41 (1979). (10.1038/278041a0) / NATURE (1979)
HAYATSU, R, ORGANIC CHEM COAL: 108 (1978). / ORGANIC CHEM COAL (1978)
HAYATSU R UNPUBLISHED.
HAYES, J.M., ORGANIC CONSTITUENTS OF METEORITES - A REVIEW, GEOCHIMICA ET COSMOCHIMICA ACTA 31: 1395 (1967). (10.1016/0016-7037(67)90019-1) / GEOCHIMICA ET COSMOCHIMICA ACTA (1967)
HAYES, MHB, CHEM SOIL CONSTITUEN: 179 (1978). / CHEM SOIL CONSTITUEN (1978)
HEDGES, J.I., LAND-DERIVED ORGANIC-MATTER IN SURFACE SEDIMENTS FROM GULF OF MEXICO, GEOCHIMICA ET COSMOCHIMICA ACTA 40: 1019 (1976). (10.1016/0016-7037(76)90044-2) / GEOCHIMICA ET COSMOCHIMICA ACTA (1976)
HERBERT, W, ERDOEL UND KOHLE 9: 363 (1956). / ERDOEL UND KOHLE (1956)
KAPLAN, I.R., ORGANIC COMPOUNDS IN STONY METEORITES, GEOCHIMICA ET COSMOCHIMICA ACTA 27: 805 (1963). (10.1016/0016-7037(63)90045-0) / GEOCHIMICA ET COSMOCHIMICA ACTA (1963)
KVENVOLDEN, K, EVIDENCE FOR EXTRATERRESTRIAL AMINO-ACIDS AND HYDROCARBONS IN MURCHISON METEORITE, NATURE 228: 923 (1970). (10.1038/228923a0) / NATURE (1970)
KVENVOLDEN K.A. GEOCHEMISTRY ORIGIN (1974).
LAWLESS, J.G., NATURE 251: 40 (1974). (10.1038/251040a0) / NATURE (1974)
LEMMON, R.M., CHEMICAL EVOLUTION, CHEMICAL REVIEWS 70: 95 (1970). (10.1021/cr60263a003) / CHEMICAL REVIEWS (1970)
MEISSNER, H.P., ISOMERIZATION OF THE CRESOLS BY ALUMINUM CHLORIDE, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 74: 1000 (1952). (10.1021/ja01124a038) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (1952)
PELTZER, E.T., ALPHA-HYDROXYCARBOXYLIC ACIDS IN MURCHISON METEORITE, NATURE 272: 443 (1978). (10.1038/272443a0) / NATURE (1978)
PICHLER, H, COMPOSITION OF HYDROCARBONS PREPARED FROM CARBON MONOXIDE AND HYDROGEN UNDER DIFFERENT PREPARATIVE CONDITIONS, BRENNSTOFF-CHEMIE 49: 344 (1968). / BRENNSTOFF-CHEMIE (1968)
PICHLER, H, RECENT RESULTS IN SYNTHESIS OF HYDROCARBONS FROM CO AND H2, CHEMIE INGENIEUR TECHNIK 42: 1162 (1970). (10.1002/cite.330421808) / CHEMIE INGENIEUR TECHNIK (1970)
10.1038/277102a0
STUDIER, M.H., ANAL METHODS COAL CO 2: 43 (1978). / ANAL METHODS COAL CO (1978)
STUDIER, M.H., ORIGIN OF ORGANIC MATTER IN EARLY SOLAR SYSTEM .I. HYDROCARBONS, GEOCHIMICA ET COSMOCHIMICA ACTA 32: 151 (1968). (10.1016/S0016-7037(68)80002-X) / GEOCHIMICA ET COSMOCHIMICA ACTA (1968)
STUDIER, M.H., ORIGIN OF ORGANIC-MATTER IN EARLY SOLAR SYSTEM .5. FURTHER STUDIES OF METEORITIC HYDROCARBONS AND A DISCUSSION OF THEIR ORIGIN, GEOCHIMICA ET COSMOCHIMICA ACTA 36: 189 (1972). (10.1016/0016-7037(72)90006-3) / GEOCHIMICA ET COSMOCHIMICA ACTA (1972)
TANABE K SOLID ACIDS BASES (1970). (10.1016/B978-0-12-683250-1.50005-5)
THENG BKG CHEM CLAY ORGANIC RE (1974).
THOMAS, C.L., CHEMISTRY OF CRACKING CATALYSTS, INDUSTRIAL AND ENGINEERING CHEMISTRY 41: 2564 (1949). (10.1021/ie50479a042) / INDUSTRIAL AND ENGINEERING CHEMISTRY (1949)
VANVELDEN, W, GEOCHIM COSMOCHIM AC 41: 961 (1977). (10.1016/0016-7037(77)90155-7) / GEOCHIM COSMOCHIM AC (1977)
YUEN, G.U., MONOCARBOXYLIC ACIDS IN MURRAY AND MURCHISON CARBONACEOUS METEORITES, NATURE 246: 301 (1973). (10.1038/246301a0) / NATURE (1973)

Dates

Type	When
Created	18 years, 10 months ago (Oct. 5, 2006, 1:45 p.m.)
Deposited	1 year, 7 months ago (Jan. 11, 2024, 9:23 p.m.)
Indexed	1 month, 2 weeks ago (July 9, 2025, 6:58 p.m.)
Issued	45 years, 5 months ago (March 14, 1980)
Published	45 years, 5 months ago (March 14, 1980)
Published Print	45 years, 5 months ago (March 14, 1980)

Funders 0

None

BibTeX

@article{Hayatsu_1980, title={Phenolic Ethers in the Organic Polymer of the Murchison Meteorite}, volume={207}, ISSN={1095-9203}, url={http://dx.doi.org/10.1126/science.207.4436.1202}, DOI={10.1126/science.207.4436.1202}, number={4436}, journal={Science}, publisher={American Association for the Advancement of Science (AAAS)}, author={Hayatsu, Ryoichi and Winans, Randall E. and Scott, Robert G. and McBeth, Robert L. and Moore, Leon P. and Studier, Martin H.}, year={1980}, month=mar, pages={1202–1204} }

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