C. Myristicin
Chemical Structure 4-(Methoxy)-6-(2-propenyl)-1, 3-benzodioxole.
Occurrence The aromatic ether is extracted from nutmeg, mace, French parsley, carrots and dill oils.
The botanical sources of myristicin are as follows: Anethum graveolens L. (Apiaciae) (Dil, Dill Seed, Garden Dill); Daucus Carota subsp. Sativus (Hoffm.) Arcang [Apiaceae] (Cultivated carrot,
Queen Anne’s Lace (Wild)); Myristica fragrans Houtt. [Myristaceae] (Mace, Nutmeg); Petroselinum crispum (Mill) Nym. [Apiaceae] (Parsley); Piper nigrum L. [Piperaceae] (Black Pepper); Sassafras albidum (Nutt.) Nees [Lauraceae] (Sassafras).
Isolation The rich source of volatile oil containing myristicin is subjected to fractional distillation under reduced pressure when the latter is collected as a colourless oily liquid.
Characteristic Features It is an oily liquid having a characteristic aromatic odour. It does not congeal at low-temperature.
Myristicin on being treated with either metallic sodium or boiled with alcoholic KOH undergoes isomerism to yield isomyristicin as given below:
i.e., the allyl group in the former gets converted to the propenyl group in the latter.
It has the following physical parameters:
bp40 173°C; n20D 1.54032; d2020 1.1437.
Identification
1. On oxidation with KMnO4 it gives rise to two products, namely:
(a) Myristicin aldehyde (mp 130°C); and
(b) Myristinic acid (mp 208-210°C).
2. On interaction with bromine it yields the corresponding dibromoderivative having mp 130°C.
Uses It is used as a flavouring agent in food products and confectioneries.
