DOI: 10.1126/science.172.3987.1044. Odor Incongruity and Chirality

10.1126/science.172.3987.1044

Crossref journal-article

American Association for the Advancement of Science (AAAS)

Science (221)

Abstract

The enantiomers R -(-)- and S -(+)-carvone are the organoleptic constituents in oil of spearmint and caraway, respectively. Their odor distinctiveness has been unambiguously demonstrated by chemical interconversion, independent synthesis, and resolution. Odor differences between other chiral isomers were also firmly established.

Bibliography

Friedman, L., & Miller, J. G. (1971). Odor Incongruity and Chirality. Science, 172(3987), 1044â1046.

Authors 2

Lester Friedman (first)
John G. Miller (additional)

References 28 Referenced 174

MERCK INDEX: 757 (1968). / MERCK INDEX (1968)
MERCK INDEX: 761 (1968). / MERCK INDEX (1968)
AMOORE, J.E., CHEMISTRY PHYSIOLOGY: CH5 (1965). / CHEMISTRY PHYSIOLOGY (1965)
AMOORE J.E. MOLECULAR BASIS ODOR (1970).
AMOORE, J.E., MOLECULAR BASIS ODOR: 164 (1970). / MOLECULAR BASIS ODOR (1970)
BORDENCA, C, L-CARVONE FROM D-LIMONENE, INDUSTRIAL AND ENGINEERING CHEMISTRY 43: 1196 (1951). (10.1021/ie50497a055) / INDUSTRIAL AND ENGINEERING CHEMISTRY (1951)
COFFEN, D.L., FRANGOMERIC AND ANCHIMERIC PROCESSES IN PREPARATION AND REACTIONS OF ALPHA-BETA-EPOXY KETONES, JOURNAL OF ORGANIC CHEMISTRY 36: 390 (1971). (10.1021/jo00802a006) / JOURNAL OF ORGANIC CHEMISTRY (1971)
DOLL, W, PHARMAZIE 4: 224 (1949). / PHARMAZIE (1949)
DRAVNIEKS, A, FLAVOR CHEMISTRY: CH2 (1966). / FLAVOR CHEMISTRY (1966)
GUILLOT, M, *PHYSIOLOGIE DES SENSATIONS - ANOSMIES PARTIELLES ET ODEURS FONDAMENTALES, COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES 226: 1307 (1948). / COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES (1948)
HENKIN, R.I., LIFE SCI 5: 1031 (1966). (10.1016/0024-3205(66)90009-9) / LIFE SCI (1966)
HONWAD, V.K., TERPENOIDS .84. HYDRAZINE REDUCTION OF ALPHA,BETA-EPOXY KETONES FROM CARVONE AND AR-TURMERONE AND CONVERSION OF (-) CARVONE TO ITS ENANTIOMER, INDIAN JOURNAL OF CHEMISTRY 5: 234 (1967). / INDIAN JOURNAL OF CHEMISTRY (1967)
KAPP, R, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 65: 2061 (1943). (10.1021/ja01251a008) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (1943)
KATSUHARA, J, EPOXIDATION OF ALPHA,BETA-UNSATURATED TERPENE KETONES, BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 42: 2391 (1969). (10.1246/bcsj.42.2391) / BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN (1969)
KLEIN, E, DER STEREOCHEMISCHE VERLAUF DER ALKALISCHEN EPOXYDATION VON ALPHA,BETA-UNGESATTIGTEN CARBONYLVERBINDUNGEN DER CYCLISCHEN MONOTERPENREIHE, TETRAHEDRON 19: 1091 (1963). (10.1016/S0040-4020(01)99364-0) / TETRAHEDRON (1963)
MCCARTNEY W OLFACTION ODOURS (1968). (10.1007/978-3-642-87699-8)
MONCRIEFF R.W. CHEMICAL SENSES (1967).
MONCRIEFF, R.W., INT PERFUMER 1: 19 (1951). / INT PERFUMER (1951)
NAVES, Y.R., MOL STRUCTURE ORGANO: 38 (1957). / MOL STRUCTURE ORGANO (1957)
RODERICK, W.R., CURRENT IDEAS ON CHEMICAL BASIS OF OLFACTION, JOURNAL OF CHEMICAL EDUCATION 43: 510 (1966). (10.1021/ed043p510) / JOURNAL OF CHEMICAL EDUCATION (1966)
RODERICK, W.R., CORRECTIONS, JOURNAL OF CHEMICAL EDUCATION 44: 37 (1967). (10.1021/ed044p37) / JOURNAL OF CHEMICAL EDUCATION (1967)
RUSSELL, G.F., ODOR DIFFERENCES BETWEEN ENANTIOMERIC ISOMERS, SCIENCE 172: 1043 (1971). (10.1126/science.172.3987.1043) / SCIENCE (1971)
SCHENCK, G.O., JUSTUS LIEBIGS ANNALEN DER CHEMIE 674: 93 (1964). (10.1002/jlac.19646740111) / JUSTUS LIEBIGS ANNALEN DER CHEMIE (1964)
THEIMER, E.T., ODOR AND OPTICAL ACTIVITY, JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS 22: 15 (1971). / JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS (1971)
WAEDA, T, KOGYO KAGAKU ZASSHI 64: 2080 (1961). (10.1246/nikkashi1898.64.11_2080) / KOGYO KAGAKU ZASSHI (1961)
WHARTON, P.S., HYDRAZINE REDUCTION OF ALPHA,BETA-EPOXY KETONES TO ALLYLIC ALCOHOLS, JOURNAL OF ORGANIC CHEMISTRY 26: 3615 (1961). (10.1021/jo01067a117) / JOURNAL OF ORGANIC CHEMISTRY (1961)
Wright, R. H., Nature 198:782 (1963). / Nature (1963)
Wright R. H. The Science of Smell (1964).

Dates

Type	When
Created	18 years, 10 months ago (Oct. 5, 2006, 9:17 a.m.)
Deposited	1 year, 7 months ago (Jan. 11, 2024, 9:58 a.m.)
Indexed	1 day, 18 hours ago (Sept. 3, 2025, 5:58 a.m.)
Issued	54 years, 3 months ago (June 4, 1971)
Published	54 years, 3 months ago (June 4, 1971)
Published Print	54 years, 3 months ago (June 4, 1971)

Funders 0

None

BibTeX

@article{Friedman_1971, title={Odor Incongruity and Chirality}, volume={172}, ISSN={1095-9203}, url={http://dx.doi.org/10.1126/science.172.3987.1044}, DOI={10.1126/science.172.3987.1044}, number={3987}, journal={Science}, publisher={American Association for the Advancement of Science (AAAS)}, author={Friedman, Lester and Miller, John G.}, year={1971}, month=jun, pages={1044–1046} }

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