Chemical composition of fragrant materials. IV. A new keto-alcohol, (-)-mintlactone, (+)-isomintlactone and minor components in peppermint oil.

Takahashi, Katsuhiro; Someya, Taichi; Muraki, Shigeru; Yoshida, Toshio

doi:10.1271/bbb1961.44.1535

Cited by 43 publications

(8 citation statements)

References 2 publications

(4 reference statements)

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“…One of the possible synthetic applications of these ethers could be the construction of α,β-unsaturated lactones, an important class of natural products. For example, the cyclic ether 1a could be transformed into isomintlactone, through dehydration followed by allylic oxidation . Nevertheless, the hydroxyl group of 1a proved to be very resistant to several dehydration conditions.…”

mentioning

confidence: 99%

Efficient Entry into Medium-Ring Keto-Lactones. The Ruthenium Tetraoxide-Promoted Oxidative Cleavage of β-Hydroxyethers

Ferraz

Longo

2003

Org. Lett.

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confidence: 99%

Efficient Entry into Medium-Ring Keto-Lactones. The Ruthenium Tetraoxide-Promoted Oxidative Cleavage of β-Hydroxyethers

Ferraz

Longo

2003

Org. Lett.

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“…Many minor components were detected, including the menthol isomers isomenthol ( 5 ) and neomenthol ( 6 ). The menthol concentration for the oil used in this study was rather higher than in some previously reported GC−MS analyses of peppermint oils from different sources. − The ES−MS of the crude derivatized peppermint oil, shown in Figure a, indicated ions at m / z 383, the molecular ion of derivatized menthol, but in this case the reaction byproduct at m / z 428 was the base peak in the spectrum. In addition, there were numerous peaks of much less abundance in the spectrum that could not be assigned with certainty.…”

Section: Resultsmentioning

confidence: 57%

Ferrocene-Based Electroactive Derivatizing Reagents for the Rapid Selective Screening of Alcohols and Phenols in Natural Product Mixtures Using Electrospray−Tandem Mass Spectrometry

2000

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The alcohols and phenols of oil of cloves, lemon oil, rose absolut, and oil of peppermint were derivatized with ferroceneoyl azide to generate their ferroceneoyl carbamates. These derivatives are selectively detected at the attomole level, in nanomolar concentrations by electrospray-tandem mass spectrometry (ES-MS/MS) without the need for sample cleanup. The ES-MS/MS analyses of the four essential oils revealed all the expected alcohols, and, in the case of lemon oil, it detected alpha-terpineol as a trace component that was not readily observed by GC-MS. The ES-MS/MS analyses complements the more conventional GC-MS analysis. The ES-MS method has the advantage of speed, selectivity, and sensitivity over GC-MS for detection of a targeted alcohol of a specific mass or structural type. The ES-MS method does not require a chromatographic separation of the components to accomplish its task. In contrast, GC-MS remains the preferred method for the determination of the total constituents of an oil. The ES-MS method may produce artifact ions, especially if the sample is wet and an excess of the ferroceneoyl azide is used; however, the artifacts did not interfere with the analyses.

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“…and neomenthol [5]. The menthol concentration for the oil used in this study was higher than in some previously reported GC/EI-MS analyses of peppermint oils from different sources (11,19,20). Derivatives of the known alcohols in peppermint oil each fragmenttoformtheproductionatmlz llO.Thus, t h e d z 110 precursor scan in Figure 5 shows as the base peak mlz 248 for derivatized menthol and its isomers.…”

Section: Es-ms/ms Analyses Of Each Oil Is Discussed In Turnmentioning

confidence: 67%

Selective Detection of Derivatized Alcohols and Phenols in Essential Oils by Electrospray-Tandem Mass Spectrometry

Quirke

Hsu

Berkel

2001

Journal of Essential Oil Research

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Primary and secondary alcohols of rose absolute, sandalwood oil and peppermint oil, together with the phenols of clove oil were selectively derivatized at ambient temperature using 1-methyl-2-fluoropyridinium tosylate. The alkyl N-methylpyridinium ether derivatives were selectively detected by electrospray-tandem mass spectrometry (ES-MS/MS) without the need for sample cleanup. ES-MUMS precursor ion and neutral loss spectra of the unpurified, derivatized oils revealed the expected compounds. The derivatization ES-MS/MS method provides a rapid, selective, and sensitive means for detection of primary and secondary alcohols and phenols in a complex mixture. It does not work for tertiary alcohols or geraniol. The derivatizations were successful at micromolar concentrations of the alcohols and detection levels approached the 100 amol level. No systematic study of intrasample reproducibilitywas carried out. The derivatization ES-MSfMS method might be used for the rapid screening of oils for selected alcohols or phenols either for quality control, or for the rapid assessment of a large number of extracts.

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Chemical composition of fragrant materials. IV. A new keto-alcohol, (-)-mintlactone, (+)-isomintlactone and minor components in peppermint oil.

Cited by 43 publications

References 2 publications

Efficient Entry into Medium-Ring Keto-Lactones. The Ruthenium Tetraoxide-Promoted Oxidative Cleavage of β-Hydroxyethers

Efficient Entry into Medium-Ring Keto-Lactones. The Ruthenium Tetraoxide-Promoted Oxidative Cleavage of β-Hydroxyethers

Ferrocene-Based Electroactive Derivatizing Reagents for the Rapid Selective Screening of Alcohols and Phenols in Natural Product Mixtures Using Electrospray−Tandem Mass Spectrometry

Selective Detection of Derivatized Alcohols and Phenols in Essential Oils by Electrospray-Tandem Mass Spectrometry

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