Cold-pressed Florida (Valencia) orange oil contains a series of bases, the main one of which is 3-hexylpyridine at ca. 20 ppb. Smaller amounts of 3-heptyl-, 3-octyl-, and 5-hexyl-2-methylpyridine are also present, as are 3-(4-methylpentyl)- and 3-(4-methylhexyl)pyridine. There are traces of other, more generally known, pyridines. 3-Hexyl-, 3-heptyl-, and 3-octylpyridine and 5-hexyl-2-methylpyridine were also detected in Brazilian (Pera) orange oil. The flavor threshold concentration of 3-hexylpyridine in water is 0.28 ppb.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The Baeyer-Villiger reaction of bicyclo[3.1.1]heptanones yields the expected lactones, but with some difficulty. These lactones readily react with alcohols, including the ethanol present in commercial chloroform, to give the corresponding hydroxy esters. Pinocamphone and isopinocamphone exhibit conformational control in the Baeyer-Villiger reaction, the trans-isomer yielding mainly the expected lactone, the cis-isomer (isopinocamphone) yielding hydroxyisopinocamphone. The use of this pathway as a synthetic route to cyclobutane monoterpenoids is discussed.

Part 1 General and Analytical Chemistry of Flavours - synthesis of nature-identical flavour chemicals, F.Naf, R.Naf and G.Uhde chirality evaluation in flavour analysis, et al direct enantiomer separation of chiral volatiles from complex matrices by multidimensional gas chromatography, U.Hener et al chiral analysis in flavor and essential oil chemistry part a filberstone - the character impact compound of hazel nuts, M.Guntert et al chrial analysis in flavor and essential oil chemistry part b direct enantiomer resolution of ionone and damascone by inclusion gas chromatography, P.Werkhoff et al GLC enantiomer separation of alpha-substituted aliphatic acids via diastereomeric esterification with (R)-pantolactone, M.Barbeni et al resolution of chiral 2-methyl branched carboxylic acids and hydroxy carboxylic acids by lipase catalyzed trans-esterifications, K.H.Engel et al Craisins versus raisins - the flavor standpoint, D.Joulain and J.P.Fourniol o-amino-acetophenone, the foxy smelling component of labruscana grapes, T.E.Acree and E.H.Lavin the chemistry of sotolon - a key parameter for the study of a key component of flor sherry wines, B.Martin et al headspace gc-analysis of volatile sulfur and carbonyl compounds in chive and onion, H.Kallio et al volatile compounds in burley tobacco, I.Forsblom et al micro-dynamic headspace gas chromatography - study of changes in volatiles composition of black perigord truffles during ripening, T.Talou et al the changes in the volatile components of strawberries with maturation, O.Ito et al glucosides in vanilla beans and changes of their contents during maturation, K.Tokoro et al glycosidically bound aroma compounds in pineapple and peach C.T.Ho et al selected volatile components of some uncommon fruits, G.Macleod and J.M.Ames. Part 2 Reaction flavours, including Maillard reactions, oxidation and so on - processed flavors - scope and limitations, R.Tressl occurence and formation of roast-smelling odorants in wheat bread crust and popcorn, P.Schieberle biomometic synthesis of methoxpyrazines, G.P.Rizzi recent studies on the formation of meat-like aroma compounds, L.J.Farmer and D.S.Mottram part contents

ChemInformVolume 21, Issue 4 Reviews ChemInform Abstract: The Synthesis of Monoterpenes 1980-1986 A. F. THOMAS, A. F. THOMAS Edited by ApSimon, J. ;Wiley, New York, NY, USASearch for more papers by this authorY. BESSIERE, Y. BESSIERE Edited by ApSimon, J. ;Wiley, New York, NY, USASearch for more papers by this author A. F. THOMAS, A. F. THOMAS Edited by ApSimon, J. ;Wiley, New York, NY, USASearch for more papers by this authorY. BESSIERE, Y. BESSIERE Edited by ApSimon, J. ;Wiley, New York, NY, USASearch for more papers by this author First published: January 23, 1990 https://doi.org/10.1002/chin.199004343Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume21, Issue4January 23, 1990 RelatedInformation

ChemInformVolume 21, Issue 47 Reviews ChemInform Abstract: The Use of Monoterpenes to Synthesize Complex Cyclic Structures A. F. THOMAS, Res. Lab., Firmenich SA, 1211 Geneva 8, SwitzerlandSearch for more papers by this author A. F. THOMAS, Res. Lab., Firmenich SA, 1211 Geneva 8, SwitzerlandSearch for more papers by this author First published: November 20, 1990 https://doi.org/10.1002/chin.199047318Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume21, Issue47November 20, 1990 RelatedInformation

2,5-Dimethyl-4-hydroxy-3-(2 H )furanone β-glucoside has been isolated from strawberry juice and synthesized. Both the natural and synthetic material exist as a mixture of diastereoisomers.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNew synthesis from .beta.-pinene of tetracyclo[6.2.1.101,606,10]undecanes, an unusual ring systemAlan F. Thomas and Florence ReyCite this: J. Org. Chem. 1989, 54, 14, 3504–3507Publication Date (Print):July 1, 1989Publication History Published online1 May 2002Published inissue 1 July 1989https://doi.org/10.1021/jo00275a050RIGHTS & PERMISSIONSArticle Views144Altmetric-Citations3LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (1 MB) Get e-Alerts Get e-Alerts

AbstractThe Wharton rearrangement of 2,3‐epoxytricyclo[7.1.1.02,7]undecan‐3‐one, a sterically hindered system, which should have led to an allyl alcohol with the OH group at a bridgehead, gave instead the allylically rearranged alcohol. The desired hydroxy compound was prepared by the Barton modification of the Wharton rearrangement: borohydride reduction to the epoxy alcohols, reaction with N, N′‐thiocarbonylbisimidazole, and treatment with Bu3SnH. The bridgehead alcohol (and other 2‐oxygenated tricyclo[7.1.1.02,7]undecanes) readily rearranged under acidic or thermal conditions.

Ozonolysis of α-terpineol (1) then steam distillation in presence of acid gives the known 4-isopropylidenecyclopentenyl methyl ketone (4). This is oxidized in air to 4-(1-hydroperoxy-1-methylethyl)-1,3-cydopentadienyl methyl ketone (10), a compound frequently reacting as if it were one of the elusive dimethylfulvene epoxides. It is converted by silica gel to two dimers (12, 13) of 2-acetyl-6,6-dimethylfulvene epoxide (19). Catalytic reduction of the dimers occurs mostly by exo addition of hydrogen to the conjugated double bond, and thermolysis of the dimers yields 4-acetyl-6,6-dimethylcyclohexa-2, 4-dienone (20). With triphenylphosphine the hydroperoxide (10) yields two [6 + 4] dimers of 2-acetyl-6,6-dimethylfulvene (26). This is the first reported isolation of [6 + 4] dimers of a fulvene. The hydroperoxide (10) adds diazomethane to give an unstable pyrazoline (28); this pyrazoline loses nitrogen to yield a single isomer XXX. 5-acetyl-3' ,3'-dimethylbicyclo[3.1.0] hex-3-ene-2-spiro-2'-oxirane (29). Catalytic hydrogenation of the latter involves ring opening of the epoxide.

The Conversion of alkyl-substituted 4-hydroxybut-2-ynones to 2,5-dialkyl-3[2H]-furanones via 2,5-dialkyl-3-methoxyfurans is described.

AbstractThree diols, 2‐methylidene‐1,3‐propanediol, 2‐methyl‐1,3‐propanediol and 1,3‐butanediol, esterified on one hydroxyl group with isobutyric acid and on the other with angelic acid1), have been isolated from Anthemis nobilis oil (Roman camomile) and synthesized. The presence of homologous esters is very probable.

The Synthesis of Monoterpenes, 1971—1979 Alan F. Thomas, Alan F. Thomas Research Laboratory, Firmenich SA, Geneva, SwitzerlandSearch for more papers by this authorYvonne Bessiere, Yvonne Bessiere Research Laboratory, Firmenich SA, Geneva, SwitzerlandSearch for more papers by this author Alan F. Thomas, Alan F. Thomas Research Laboratory, Firmenich SA, Geneva, SwitzerlandSearch for more papers by this authorYvonne Bessiere, Yvonne Bessiere Research Laboratory, Firmenich SA, Geneva, SwitzerlandSearch for more papers by this author Book Editor(s):John ApSimon, John ApSimon Deparment of Chemistry, Carlten University, OttawaSearch for more papers by this author First published: 01 January 1981 https://doi.org/10.1002/9780470129678.ch5Citations: 5Book Series:Total Synthesis of Natural Products AboutPDFPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShareShare a linkShare onFacebookTwitterLinked InRedditWechat Summary This chapter contains sections titled: Introduction Terpene Synthesis from Isoprene 6-Methyl-5-hepten-2-one 2,6-Dimethyloctane Derivatives Substances Related to Chrysanthemic Acid Cyclobitane Monoterpenes Cyclopentane Monoterpenes The p-Menthanes The o-Menthenes The m-Menthenes The Tetramethylcyclohexanes The Dimethylethylcyclohexanes The Cycloheptanes Bicyclo[3.2.0]heptanes Bicyclo[3.1.0]hexanes, the Thujanes Bicyclo[3.1.1]heptanes Bicyclo[4.1.0]heptanes Furan Monoterpenoids Pyran Monoterpenoids Citing Literature Total Synthesis of Natural Products, Volume 4 RelatedInformation

AbstractDie NMR‐Untersuchung des deuterierten Tricyclons (Ia) bestätigt die cis‐Konfiguration der Starnmverbindung (Ib).

AbstractThe synthesis of 2‐methyl‐6‐(4′‐methylphenyl)‐l‐hepten‐3‐one (1) and 2‐methyl‐6‐(4′‐methylphenyl)‐3‐heptanone (2), constituents of the oil of Cinnamomum cassia, is described.

AbstractPatchoulol (1) forms 2,2,6,8‐tetramethylbicyclo [5.3.1]undec‐7‐en‐3‐one (5) with lead tetraacetate. This ketone undergoes acid‐catalyzed cyclization to 2,6,6,10‐tetramethyltricyclo [5.3.1.01,5]undec‐9‐en‐5‐ol (10), and is reduced to 2 stereoisomeric alcohols with lithium aluminium hydride. One of these alcohols 8 is readily dehydrated with cyclization to 2,6,6,10‐tetramethyltricyclo [5.3.1.01,5]undec‐9‐ene (12) and a double bond isomer 13, longer treatment with acid resulting in a Wagner‐Meerwein rearrangement to a mixture of two 1,3,7,7‐tetramethyltricyclo [6.2.1.02,6]‐undecenes (19 and 20), isomeric with β‐patchoulene (23). The other alcohol 7 with p‐toluenesulfonic acid forms the cyclic ether, 1,3,7,7‐tetramethyl‐11‐oxatricyclo‐[4.4.1.12,8]dodecane (15).

Patschulialkohol (I) ‐ die wichtigste Geruchskomponente des Öls von Pogostemon cablin ‐ liefert bei der Umsetzung mit Bleitetraacetat das Decalon (IIa), das Acetal (IIb) und das Bicycloundecenon (III).

Abstract(+)‐β‐Eudesmol (7), (+)‐10‐epi‐elemol (8), (−)‐(Z)‐dihydrofarnesol (3), and an alcohol believed to be a guai‐9‐en‐11‐ol (4) have been isolated from Galbanum resin. Together with (‐)‐β‐dihydroagarofuran (1) and epi‐ligulyl oxide (13) (reported naturally occurring for the first time), 10‐elemol (8) and 10‐epi‐junenol (2) involve the enantiomeric stereochemistry at C (10) compared with β‐eudesmol 7, and guaiol 5, the major sesquiterpene alcohol of Galbanum.