Phthalide, celery

The lactones are the intramolecular esters of the corresponding hydroxy fatty acids. They contribute to the aroma of butter and various fruits. 15-Pentadeca-nolide is responsible for the musk-like odor of angelica root oil. Of the naturally occurring bicyclic lactones, phthalides are responsible for the odor of celery root oil, and coumarin for woodruff. 

The cartridge was flushed with hexane followed by dichloromethane plus 0.5% methanol to desorb the celery aroma components (phthalides). 

Fischer et al. (1991) have applied a highspeed counter-current chromatography with an Ito multi-layer coil separator-extractor to perform efficient separations of aromarelevant constituents, such as phthalides, from celery and parsley roots. 

The volatiles also showed variation between genotypes. The concentration of terpenes and phthalides, the key volatile components, found in various cultivars of both celery and celeriac varied over a wide range (Van et al., 1990). Eleven flavour compounds were identified in cv. Black Celery of Trevi, 17 compounds in cv. D Elne and 21 compounds in cv. Verde Pascal. The main constituent of these cultivars was limonene. Twenty-one compounds were identified in cv. Dorato d Asti. The main constituent was y-terpinene. The cv. Black Celery of Trevi had a very low amount of y-terpinene compared with other varieties (Tirillini et al., 2004). 

GC-MS analysis to study the content and composition of extracts of celery revealed the presence of terpenoids, sesquiterpenoids and phthalides in the essential oils and extracts obtained with organic solvents from two celery cultivars (Wolski et al., 2004). The composition of the essential oil obtained from the fruits of three A. graveolens var. dulce cultivars, i.e. Helios, Orient and Zefir, showed that the main components of the essential oil were isoprenoids, including monoterpenes and sesquiterpenes. Essential oil content ranged from 2.5 to 3.0%. The percentage... 

The celery x parsley hybrid inherited all the terpenoids from celery and heptanol from parsley, while synthesizing new compounds of its own. The content of these new compounds was higher than that of the main celery components, limonene and myrcene (Madjarova et al., 1979). The volatile components of celery consisted of monoterpene hydrocarbons (46.0%) and phthalides (42.3%). The major components were limonene and 3-butyl-4,5-dihydrophthalide (or sedanenolide). Celery volatiles contained higher concentrations of y-lerpinene and a-pinene. A celery-like odour was associated during GC elution with each of the 16 phthalides reported (MacLeod and Ames, 1989). 

Celery is used both as a vegetable and a spice. It has several medicinal uses. It is believed to cure most urinary disorders. It has diuretic properties. It is also commonly used to relieve pain. Limonene is the major volatile compound in both leaf and seed oil. Phthalides, myrcene, pinene, etc., are also present. Higher nitrogen inhibited limonene... 

Group 11 is the home for mint lactone (Flavis 10.036, FEMA 3764) and various phthalides, which are well known from the flavour chemistry of celery. 

Zheng G-Q, Kenney PM, Zhang J, et al. 1993. Chemoprevention of benzo[a]pyrene-induced forestomach cancer in mice by natural phthalides from celery seed oil. Nutr Cancer 19 77-86. 

Kosaka M, Sekiguchi S, Naito J, Uemura M, Kuwahara S, Watanabe M, Harada N, Hiroi K (2005) Synthesis of enantiopure phthalides including 3-butylphthalide, a fragrance component of celery oil, and determination of their absolute configurations. Chirality 17 218-232... 

Recently, ketone hydroacylation has been extended to the asymmetric synthesis of phthalides (Scheme 2.45) [91]. Since the ketoaldehyde substrates lack an ether O, decarbonylation was found to be a major competing pathway when noncounterion effect was observed, with N03 being optimal. This methodology was applied to a short synthesis of (S)-(-)-3-n-butylphthalide, an extract of celery [91]. 

Another group of lactones is that of the phthalides which occur in oil of lovage and celery oil for example and are responsible for the odour. Mitsuhashi and co-workers [170] carried out orientation tests of purity... 

The essential oil of celery, for example, contains 3-butyl-phthalide (63), 3-butyl-hexahydro-phthalide (64) as well as sedanolide (65) (705). The latter two lactones (64) and (65) have the characteristic odor and flavor of celery (705). Reports on the occurrence and importance of this class of aroma compounds are to be found in specialized review articles (795, 354). 

Cassie P-Mentha-8-thiol-3-one Celery 3-Propylidene phthalide... 

Isomeric phthalides have an odour reminiscent of celery or acid protein hydrolysates, but the key component of protein hydrolysates is maggi lactone, known as abhexon. Phthalides occur... 

The typical components of the aroma of celery (Apium grave-olens var. rapaceum, Apiaceae) and celeriac (A. g. var. duke) are numerous dihydrophthalides, tetrahydrophthalides, hexahydroph-thalides and phthalides. The main odour-active compound is... 

Phthalides have been reported to have sedative activities on mice (see celery). 

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