Dill apiol

DILL APIOLE Up to 60% in Indian dill seed oil and in varying amounts in other parts and other species of dill. In various small amounts in fennel and carrot seed oils. 

The principal conatitueDls ol the oil tv. rc loimd 10 be -phellandreoe, dill-apiol, and a lerpepe, which the auihora named crithmene, and which has the following characters -... 

Now then, A sowa is another story. Various reports show little to none dillapiole in the herb oil, but Baslas reports that one Indian herb oil contained 8.6% [27]. Dill seed oil is the bomb, though. It consistently displays dill apiole content from 20.7 - 66.8% [28,29]. Lucky you, because the seed oil is the most common. 

On account of the dill-apiole it contains, of which it forms an abundant source, the oil has strong physiological action, although it is not so active as oil of parsley, which contains apiole. The yield of oil from this plant has been studied by Borde, Bull. Sci. Pharmacol. 1909, 16, 132, via Chem. Centrulbl. 1909, 80, i, 1566) who collected the plants at different times with the following results ... 

For its (dill-apiole) isolation the portion boiling above 200° was separated into two fractions Chem. Centralbl. 1909, 80, ii, 1335) a dextro-rotatory fraction, boiling at 90-95°/13 mm, which constitutes 5 per cent of the original oil, and (Compt. rend. 1909,149, 215-17) an optically inactive fraction boiling at 157-158°/ 3 mm., specific gravity 1.175, representing 40 per cent of the original oil, and identified as 5 6-dimethoxy-3 4-methylene-dioxy-l-allyl benzene, or dill-apiole. 

Delepine Bull. Soc. Chem. 1918, 23 (iv), 24-35) states that the plant growing in different parts of France consistently contains the following characteristic substances dill-apiole, thymol methyl ether and crithmene. In some cases c/-pinene and a paraffin are also present. 

The Sardinian oil has been examined by Francesconi and Sernagiotto. (Atti. R. Acad. Lincei, Roma, 1913 (5), 22, i, 231-7 and 313-17, 382-6) It differs from the French oil the only constituents common to both being dill-apiole, p-cymene and crithmene, a new terpene. Crithmene has the formula shown above and appears to be delta,l, 7-4,8-menthadiene. It boils at 178-180°, specific gravity at 12°, 0.8679, nD 14806. Source Finnemore 1926... 

A botanically very similar fruit from Anethum sowa Roxb. ex Flem. is cultivated in Japan and India. The composition of the seed oil is very similar to the one of European oil, the carvone content is lower, and moreover the oil contains caryophyl-lene, apiol and dill apiol. The latter was reported to lack in European oil [93]. 

Indian Dili Seed Oil - contains up to 53% dill apiol (3,4-methyle-nedioxy-5,6-dimethoxy-alIylbenzene). Boiling point is 296° C with decomposition at normal pressure. Aspirator vacuum will distil it at about 170° C. Yields DMMDA-2, dosage about 50... 

C12H14O4, Mr 222.24. needles smelling mildly of parsley, mp. 30 °C, bp. 294 °C. A. is obtained from parsley oil. LDLq (mouse s.c.) 1000 mg/kg. For isolation of A. from Sassafras albidum see Lit. (see also dill apiol). A. has abortive and diuretic activities and exhibits a synergistic action with insecticides. Biosynthesis from cinnamoyl-CoA. 

The oil of ripe dill seeds consists mainly of (+)-limo-nene (up to 40%) and (+)-carvone (up to 60%). The so-called Indian dill oil distilled from the seeds of A. sowa contains carvone and limonene together with larger amounts of dill apiole. The organoleptic properties of both oils which are of less significance than the weed oil strongly resemble those of caraway oil. 

Apiolic Acid (2 -. d-Dimethoxy-Z 4-methyU ertedioxybenzoic add cf. Dill-apiolic Acid)... 

Dill-apiol (2 2-Dimetiioxy-4 5-melhylene-dioxy-l-allylbenzene. Apiol)... 

M644. ra 1-5278. Cr03 in AcOH— dill-apiolaldehyde diU-apiolic acid. Ale KOH - -> iso-dill-apiol, the corresponding propenyl analogue, m.p. 44°, b.p. 296° decomp. 

Dill weed oil is dominated by a-phellandrene, limonene, and carvone. Dill ether and the absence of dill apiol are further criteria for that oil. Dill seed oil contains mainly carvone and dihydro-carvone. Adulteration is done using phellandrenes, distilled limonene coming from orange terpenes, synthetic carvone, and dihydrocarvone. Detection is done by 2D enantiomeric separation. Lawrence (1996) reports the following ratios for dill seed oil (+)-limonene 98.4% (-)-limonene 1.6% (+)-carvone 98.7% (-)-carvone 1.3% (+)-trans-carveol 33.3% (-)-trans-carveol 66.7% and (+)-cti-carveol 100% (-)-cA-carveol 0%. The authors own ndings from biocultivated oil was (+)-carvone 98.4% (-)-carvone 1.6% (5)-(-)-a-pinene 4.0% (R)-(+)-a-pinene 96.0% (+)-limonene 95.4% (-)-limonene 4.6% (5)-(-)-p-phellandrene 0% (5)-(+) p-phellandrene 100% and (R)-(-)-a-phellandrene 100% (R)-(+)-a-phellandrene 0%. 

ILmonene dill apiol, and dill isoapiol. Pure dill oil is used to a considerable extent in pharmacy as a carminative. 

The principal constituents of the oil were found to be -phellandrene, dill-apiol and a terj)ene, which the authors named crithmene, and which has the following characters —... 

Piper aduncum (var. cordulatum) leaves 1.4-3.5 dill-apiole 21... 

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