Volatiles from Oranges. 1. Hydrocarbons. Identified by Infrared, Nuclear Magnetic Resonance, and Mass Spectra

Teranishi, Roy; Schultz, Thomas; McFadden, W. H.; Lundin, Robert E.; Black, D. R.

doi:10.1111/j.1365-2621.1963.tb00240.x

Cited by 27 publications

(13 citation statements)

References 8 publications

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“…The composition of the nonaqueous essence products was investigated by combined capillary GLC and fast-scan mass spectrometry (McFadden et al, 1962;Teranishi et al, 1963aTeranishi et al, , 1964. The effluent from the column was introduced directly into the ionization chamber of a Bendix time-of-flight mass spectrometer.…”

Section: Discussionmentioning

confidence: 99%

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Volatiles from Oranges. II. Constituents of the Juice Identified by Mass Spectra

Schultz

Teranishi

McFadden

et al. 1964

Journal of Food Science

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SUMMARY Volatiles from California Valencia orange juice low in peel oil were removed under vacuum in a Kontro evaporator. The organic constituents were extracted with ether and examined by capillary gas‐liquid chromatography and mass spectrometry in combination. Constituents of relatively high water solubility were found mainly in the first condensers of the essence recovery system, whereas sesquiterpenoids were more prominent in a downstream colder condenser. The major esters of the juice were found to be ethyl 3‐hydroxy‐hexanoate (a new orange volatile) and ethyl acetate. Nine other previously unreported orange volatiles were identified, and the presence of seven others, previously identified only tentatively, was confirmed.

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Section: Discussionmentioning

confidence: 99%

“…Paper I of this series (Teranishi et al, 1963b) deals with identification of the hydrocarbons isolated from orange oils by infrared (IR), NMR, and mass spectra. Peel oil is important because it is incorporated with the juice in normal juicing operations and the oil is a major contributor to the flavor.…”

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confidence: 99%

Volatiles from Oranges. II. Constituents of the Juice Identified by Mass Spectra

Schultz

Teranishi

McFadden

et al. 1964

Journal of Food Science

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“…Indeed, other than in recent reports by Teranishi et al (1963) and Kov6ts (1963), the literature does not indicate its identification in any of the essential oils (Guenther, 1947a;Gildemeister, 1929;Ikeda et al, 1962) ; yet, in accordance with the classically accepted definition of "terpenes" (Haagen-Smit, 1948)) there is no reason not to consider it as a member of this class of compounds.…”

Section: Recent Investigationsmentioning

confidence: 63%

“…However, specific details of this identification were not given. A later, more comprehensive study on orange volatiles (Teranishi et al, 1963) indicates the presence of a compound CloH1? that was tentatively assigned the structure of p,a-dimethylstyrene based on mass spectroscopic fragmentation pattern and gas chromatographic retention time.…”

Section: Recent Investigationsmentioning

confidence: 98%

The Mechanism of Formation of p,α‐Dimethylstyrene in the Essential Oil of Distilled Lime (Citrus Aurantifolia)

Loori¹,

Cover²

1964

Journal of Food Science

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SUMMARY The terpene p,α‐dimethylstyrene was isolated and identified in the essential oil of distilled Mexican lime (Citrus aurantifolia, Swingle) but could not be demonstrated in oil expressed from Citrus aurantifolia. Experimental evidence is presented supporting a nonbiogenetic mechanism of formation of p,α‐dimethylstyrene in distilled lime oil from the acid‐catalyzed cyclization of citral. The mechanism involves novel reactions of citral and its reaction products that are not consistent with the classically accepted acid‐catalyzed reactions of citral and seem to provide an explanation for the appearance of p,α‐dimethylstyrene in other citral‐containing essential oils of the Rutaceae citrus plants.

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“…There are numerous papers on grapefruit and orange oil constituents (2-7, 13-17, 33,34,36,38,39,40).…”

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Advances in Fruit Flavor Chemistry

Teranishi

1969

Flavor Chemistry

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Advances in separation, physical measurement equipment, and manipulation techniques have overcome some of the difficulties encountered in fruit flavor research. Capacity of high resolution gas chromatography columns has been increased. Gas chromatography and mass spectrometry have been combined to give information with submicrogram quantities. Sample sizes required for proton magnetic resonance studies have been reduced to submilligram quantities. A flavor component of Bartlett pears has been identified. Most of the volatile constituents of mandarin peel oil and lime oil have been identified.The constituent mainly responsible for grapefruit aroma has been identified as nootkatone. The chief bitter principle of grapefruit, naringin, has been changed to an intensely sweet compound, a chalcone.The quantities that one deals with in aroma chemistry research vary greatly: in one phase of the research, tens of tons of fruit are extracted and concentrated for the volatile constituents; in another, as little as tenths of nanograms are separated and detected in the vapor from a single fruit. This is indeed a staggering ratio, comparable to the ratio of the earth's diameter to that of an atoml Because the concentration of the compounds responsible for the desirable aroma of fruits is small, even though we start with large amounts of raw material, only very small amounts of pure material are isolated. Thus, assignment of chemical structure is difficult, and the degree of certainty of the assignment decreases with decreasing amount of material isolated and purified. However, advances in gas chromatographic separations and in physical measurement equipment and techniques are now being applied in the field of fruit flavor chemistry, and the impact of obtaining more information with much less material than previously necessary is just now being felt.

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Volatiles from Oranges. 1. Hydrocarbons. Identified by Infrared, Nuclear Magnetic Resonance, and Mass Spectra

Cited by 27 publications

References 8 publications

Volatiles from Oranges. II. Constituents of the Juice Identified by Mass Spectra

Volatiles from Oranges. II. Constituents of the Juice Identified by Mass Spectra

The Mechanism of Formation of p,α‐Dimethylstyrene in the Essential Oil of Distilled Lime (Citrus Aurantifolia)

Advances in Fruit Flavor Chemistry

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