Alkylidene Phthalides and Dihydrophthalides from Celery

Gold, Harvey J.; Wilson, Charles W.

doi:10.1021/jo01039a026

Cited by 40 publications

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“…1) Gold and Wilson isolated celery volatiles by vacuum distillation and concluded that alkylidene (3a,4)-dihydrophthalides were the principal contributors to celery flavor. 2) In those early works, however, the phthalides could not be successfully separated by gas chromatography (GC) due to their instabilities in GC columns. In 1987, Uhlig separated 3-n-butylphthalide 1, sedanenolide (3-n-butyl-4,5-dihydrophthalide) 2, and sedanolide (3-n-butyl-3a,4,5,6-tetrahydrophthalide) 3 and/or 4 from eight cultivars of celery and three cultivars of celeriac by high performance liquid chromatography (HPLC).…”

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confidence: 99%

Potent Odorants Characterize the Aroma Quality of Leaves and Stalks in Raw and Boiled Celery

Kurobayashi¹,

Kouno²,

Fujita³

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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The raw and boiled odors of celery leaves and stalks were investigated. Among 12 compounds identified as potent odorants, 3-n-butylphthalide 1, sedanenolide 2, and trans- and cis-sedanolides 3, 4 were assessed to be most contributive to the overall odor of celery. These three phthalides, (3E,5Z)-1,3,5-undecatriene, myrcene, and (E)-2-nonenal were common to both raw and boiled materials. Two compounds, ((Z)-3-hexenal and (Z)-3-hexenol), were dominant in raw materials and four compounds, (2-methylbutanoic acid, sotolon, beta-damascenone, and beta-ionone), were dominant in boiled materials. Sensory evaluations were performed on natural celery odor and a series of reconstructed model aromas by assigning each intensity ratings for a set of seven odor qualities which aptly describe the odors of raw and boiled celery. According to the evaluation results, six common components contributed to the moderate odor of raw celery, two components dominant in raw materials enhanced the raw celery character, and four components dominant in boiled materials reduced the raw celery character and enhanced the boiled celery character. It was clarified that boiling-induced changes in celery odor were not affected by the amounts of phthalides, but by thermally generated compounds such as sotolon, beta-damascenone, and beta-ionone, which reduce the "green spicy" note.

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confidence: 99%

Potent Odorants Characterize the Aroma Quality of Leaves and Stalks in Raw and Boiled Celery

Kurobayashi¹,

Kouno²,

Fujita³

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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“…Alkylidenephtalides may occur as E-or as 2-isomers. Recently KNIGHT and PAITENDEN [2] stated that naturally occurring isobutylidenephtalide should be the E-isomer, and they expected isovalidenephtalidepresent in the essential oil of Apium graveolens L. [3] to be the E-isomer as well. This was based upon 'H-NMR data for the synthesized i~obut~lidenephtalides (Wirric synthesis) and the findings that both their s~nthesized E-isobutylidenephtalide and the naturally occurring compounds were liquid, whereas their synthesized 2-isomer was crystalline.…”

Section: Lntroductionmentioning

confidence: 99%

“…PLRKIN and GRICNAKD reactions) leadinglargely to the thermally rnore stable Z-isomers. RKKIN reactions for the synthesis of alkylidenephtalides were used many times [4][5][6][7][8]: the main reaction product obtained by GAHKIEL and MICHAEL [4] was a crystalline isopropylidenephtalide; BROMBERG [5] obtained liquid propylidenephtalide and liquid isobutylidenephtalide, though in the latter product a few crystals were forrned; ethylidenephtalide s~nthesized by G o r r~i~u [6] was a solid; but~lidene~htalide was found to be a solid by BERLINGOZZI and LUro [7]; MOWRY et al [8] re~orted that ethylidene~htalide was a solid, whereas propylidene-and hexylidenephtalide were liquids; GOLD and WILSON [3] reported that is~butylidene~htalide, which they synthesized, was a liquid. KARIYONE and SHIM~ZU [9] first synthesized free keto acids via GKIGNARU reactions.…”

Section: Lntroductionmentioning

confidence: 99%

Z-Butylidenephtalide in the Essential Oil from Roots of Levisticum officinale

Gijbels¹,

Scheffer²,

Svendsen³

1980

Planta Med

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“…Over the year's considerable efforts have been dedicated into the investigations of celery plants grown in other parts of the world especially in Asia using various analytical methods such as High-performance LiguidChromatography, HPLC and GC/MS [15,16], infrared (IR) and ultraviolet (UV) spectrophotometry [14,17] TLC [18]. However, surprisingly, despite the high promising therapeutic potentials of the pharmacological and pharmaceutical properties of the celery plants grown in Nigeria, to the best of our knowledge such level of works have been reported on celery plants cultivated in Nigeria.…”

Section: Introductionmentioning

confidence: 99%

TLC Analysis of Ethanol Extract of Fresh Leaves of Celery (Apium Graveolens L.) Grown In Jos, Nigeria

Mshelia¹,

Achuenu²,

Adelakun³

et al. 2022

IJRIAS

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Apium Graveolens L., is a member of the Apiaceaefamily. Apiaceae is a large family of mostly aromatic flowering plants whose leaf is commonly used as vegetables worldwide. The fresh leaves of Celery (Apium Graveolens L.) were crushed extracted with ethanol by Maceration and Fractionated with n-hexane and ethyl acetate. Thin Layer Chromatographic (TLC) analysis of the fractions of n-hexane and ethyl acetate were performed, important phytochemicals such as flavonoid, terpenoid and naturally occurring phhthalides were identified in the various fractions. The presence of flavonoid was revealed in n-hexane fraction with two spots whose R. f values are (0.82 and 0.58). Terpenoid presence was revealed in n-hexane fraction with two spots whose R f values are (0.79 and 0.61) and also based on their observed colour change under ultraviolet light probably due to reaction with (vanillin-H 2 SO 4 ) .Phthalide was observed in ethyl acetate fraction with four spots under UV/10% H 2 SO 4 with R f values of (0.97, 0.67, 0.51 and 0.41). The findings provided the evidence that Apium GraveolensL. is a potent source of some medicinally important phytochemicals and natural products which justifies its use as medicinal plant and food flavourings. This can be further investigated for the isolation and structural analyses of the biological active phytochemical components for medicinal application.

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Alkylidene Phthalides and Dihydrophthalides from Celery

Cited by 40 publications

References 0 publications

Potent Odorants Characterize the Aroma Quality of Leaves and Stalks in Raw and Boiled Celery

Potent Odorants Characterize the Aroma Quality of Leaves and Stalks in Raw and Boiled Celery

Z-Butylidenephtalide in the Essential Oil from Roots of Levisticum officinale

TLC Analysis of Ethanol Extract of Fresh Leaves of Celery (Apium Graveolens L.) Grown In Jos, Nigeria

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