Parsley apiole

Beilstein Handbook Reference) 1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene 5-Allyl-4,7-dimethoxy-1,3-benzodioxol 5-Allyl-4,7-dimethoxy-1,3-benzodioxole AI3-14843 Apiol Apiole Apiole (parsley) Apioline Benzene. 1-allyl-2.5-dimethoxy-3,4-(methyl-enedioxy)- I. Benzodioxole, 4,7-dimethoxy-5- 2-propenyl)- BRN 0195747 EINECS 208-349-2 NSC 9070 Parsley apiol Parsley apiole Parsley camphor Petersiliencampher. Is synergistic with insecticides. Needles mp n 29.5° bp = 294°, bp35... 

Parsley Seed Oil - contains 0-80% parsley apiol (2-methoxy-3,4-methylene-dioxy-5-methoxy-allylbenzene). Its boiling point is 292 °C at normal pressure, and 179 C at 34 torr. It yields DMMDA, dosage about 75 mg. This oil may also contain 10-77% myristicin. 

The polarity of the compound is reduced if two neighbouring methoxyl groups in an aromatic ring are replaced by a methylenedioxy group (eugenol methyl ether hRf 22-safrole hRf 89 elemicin hi / 12-myristicin hRf 61 tetramethoxyallylbenzene hRf 12-parsley apiole hRf 45). 

APIOLE 23% of celery leaf oil, up to 30% in parsley leaf and seed oils, and in small amounts in cubeb, dill and fennel oils. 

Apiol, the principal constituent of oil of parsley, is an allyl-dimethoxy-... 

Parsley seed Petroselinum crispum (Mill.) Nym. ex A.W. Hill Myristicine (methoxy safrole) (25-50), apiole (dimethoxy safrole) (5-35), 2,3,4,5-tetrame-thoxy aUylbenzene (1-12)... 

SYNTHESIS Apiole, as the crystalline essential oil l-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene, is isolated directly from commercial Oil of Parsley, by... 

The essential oil that corresponds to DMMDA is, of course, apiole from the Oil of Parsley, which again ties together the spice world and the amphetamine world. And there is isoapiole, also a natural thing. This pair represents the ring-substitution pattern of one of the ten essential oils and DMMDA is one of the ten essential amphetamines. 

EXTENSIONS AND COMMENTARY This is pretty sparse information upon which to build a picture of biological activity. First, the synthesis was done by someone else and, as I have not been able to find where the notes are, this will be the one recipe in the footnote without explicit directions incorporated. The procedure used was exactly the same as that described for DMMDA, except that the starting material was dillapiole rather than apiole. The dillapiole was obtained by the careful fractionation of Oil of Dill (as opposed to the isolation of apiole from the careful fractionation of Oil of Parsley). Isomerization to isodillapiole, nitration with tetra-nitromethane to give 1 -(2,3-dimethoxy-4,5-methylenedioxyphenyl)-2-nitropropene, and its reduction with LAH in ether to give 2,3-dimethoxy-4,5-methylenedioxyamphetamine hydrochloride (DMMDA-2) proceeded in a precisely analogous manner to the preparation of DMMDA. 

The 2,5-dimethoxy-3,4-methylenedioxy pattern. The parent allyl benzene is apiole (with a final e ) or parsley camphor, and it is the major component of parsley seed oil. Its conjugated isomer is called isoapiole, and they are valuable as the chemical precurors to the amination product, DMMDA. Whereas both of these essential oils are white solids, there is a green oily liquid that... 

Among the leafy spices, 45 aroma volatiles of desert parsley have been identified, with the major constituents as myristicin, apiole, /3-phellandrene, p-mentha-1,3,8-triene and 4-isopropenyl-l-methylbenzene (MacLeod eta/., 1985). Among these, apiole in particular has a desirable parsley odour character. The leaf stems of celery show three main constituents of volatiles, e.g. 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%), P-selinene (16.3%), cis-ocimene (12.5%) and P-caryophyllene (10.5%) are some of the volatile oil constituents present in celery leaves from Nigeria (Ehiabhi et al., 2003). 

Extraction process 6 Extraction of Apiole from parsley (advanced process)... 

Apiole forms crystals with a melting point of 30 Celsius. Fresh apiole may be a semi-solid liquid. The compound can be distilled at 294 Celsius. Apiole is soluble in alcohol, benzene and chloroform, but insoluble in water. Apiole is a major constitute of parsley, and is responsible for the aroma and taste of parsley. 

This procedure is an advance procedure for the extraction of apiole from oil of parsley. This process utilizes vacuum distillation. 

Figure 013. Advanced setup for vacuum fractional distillation for the isolation of apiole from commercial oil of parsley.

Apiole (parsley) (= 4,7- Petroselinum hortense (seed, parsley oil) OD-R (parsley)... 

What did I say this thing came from Parsley Well, sure. But, I had no idea how varied the Apiole content can get in this species. And I was pleasantly surprised to find Apiole in other oils as well. Check it out ... 

It is interesting to note that Shaath also analyzed five other shipments of parsley seed oil and found apiole contents of 7.71 -10.56% but the origins of the shipments were not given. 

The following tables should tell you all that your brain ever need know about parsley oils and their apiole contents. (Yeesh Am I obsessed or what ) Table VI is a more recent study (1988) and is a good comparison to what is presented in Table V [6]. The geographical sources for the oils in Table VI were not given. Table VII shows the major component content from leaves of some of the more novel global parsley sources [7]. Finally, Porter did a comparative chemical composition study of the oils obtained from the leaves of the two major parsley types curly leaf and flat leaf [8]. These were taken from various commercial suppliers and the data can be seen in Table VIII. 

The most recent articles of note come from the compilations given in the excellent series Essential Oils by Brian M. Lawrence. He writes that Korean parsley is virtually devoid of apiole [2, vol. IV, p. 178-179]. Italian parsley was reported as having 5 % apiole content and that German parsley samples had an average content of around 2% [2, vol. V,p. 151-153]. 

Whew That s a lot of sources with the apiole content going all over the place. So why couldn 11 j ust have said that parsley had apiole in it and drop the subject there Well, you re gonna see later on in this book how this sourcing and knowledge will be indispensable in getting these products. 

Apiole Section you can see the consistent and humongous myristicin contents of various types of parsley oils (seeds, leaves and herbs), various types of parsley (curley and flat leaf) and various global origins. 

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