4-Dihydrophthalide

Fig. 102. Separation of some phthalides from coumarin. Layer silica gel GF254 detection fluorescence quenching in short wave UV light [258]. 1 phthalide 2 coumarin 3 isobutylidene-3a, 4-dihydrophthalide 4 phenylphthalide 5 butyl-phthalide 6 benzalphthalide 7 ligustilide blue fluorescence in 365 nm light 8 butylidene phthalide. G mixture 1—8...

The main constituent of the leaf oil is a-terpinyl acetate, while the main constituent and odor-determining component of the root oil is ligustilide [4431-01-0] (3-butylidene-4,5-dihydrophthalide) [609-612a]. 

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). 

The three main constituents of volatiles from leaf stems of a local cv. from Libya were apiole (about 23%), 3-butylphthalide (about 22%) and sedanolide (about 24%). The last two possess a strong characteristic celery aroma (MacLeod et al., 1988). Limonene (40.5%), /l-selinene (16.3%), c/s-ocimene (12.5%) and /l-caryophyllene (10.5%) were the major volatile oil constituents of celery leaves collected from Nigeria (Ehiabhi et al., 2003). Analysis of celery leaf oil from Cuba revealed 28 compounds, representing about 94% of the oil. Limonene (18.3%), j3-caryophyllene (13.5%) and 3-butyl-4,5-dihydrophthalide (32.1%) were the major constituents (Pino et al., 1997). 

PROP The constituents include d-a-terpineol, butyl dihydrophthalides, butyl tetrahydrophthalides, coumarin, aldehydes, acetic acid, and isovaleric acid. From steam distillation of fresh root of Ijevisticum officinale L. Koch syn. Angelica levisticum, Baillon (Fam. Vmbelliferae). Yellow to green to brown liquid strong odor and taste. D ... 

Although not isolated, a trienyl-lactone intermediate (397) has been assumed to be responsible for the formation of frans-1,2-dihydrophthalide (396) (together with tricyclic compound 395) in the photolysis... 

A new electroreductive method for the synthesis of tetrahydro-phthalide-iso-quinolines is also known If isoquinolinium methiodide is used in the reaction the 1,2-dihydrophthalide isoquinoline is obtained... 

Butyl-4,5- dihydrophthalide) 166733-97-7 L. wallichii Meum athamanticum Petroseimum crispum, P. crispum var. tuberosum, P. sativum 65, 97-100]... 

The cause of the typical smell of fresh parsley Petroselinum hortense) is p-mentha-l,3,8-triene (Figure 8.9). As in other vegetables of the Apiaceae family, important substances of root parsley and leaf parsley are phthalides. The main phthalides are sedanenolide, (E)-Hgustilide and butylphthahde, while (Z)- and (E)-butyhdene-phthahde, (Z)-ligustilide, (Z)-sedanolide and 3-butyl-5,6-dihydrophthalide are present in smaller amounts. Other important components of leaf parsley are linalool, P-dtroneUol, methyl... 

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... 

Levisticum officinale 3-Butylidene-4,5-dihydrophthalide (ligustilide), other phthalides, a-terpinyl acetate, a-terpineol. 

Macrocyclic lactones such as ambrettolide (= 7-hexadecen-l,16-olide) (19), 15-pen-tadecanolide (20), hexadecanolide (21), and so on, as well as coumarin (22), dihydro-coumarin (23), bergaptene (24) nepetalactones (25) phthalides such as 3-butylphthahde (26), sedanolide (27), (Z)-ligustilide (28), 3-butyhdene-4,5-dihydrophthalide (29), and... 

The phthalides are the odoriferous principles and consist mostly of 3-u-butyl phthalide, sedanenolide(3- -butyl-4,5-dihydrophthalide),... 

---