Myristicin 193

Thus far myristicin (4-allyl-6-methoxy-l,2-methylenedihydroxy benzene),1) C11H1203, has been found only in the oils of nutmeg and mace, also in French parsley oil. It is characterized by the following constants:

B. p. 171 to 173° (40 mm.); d 20o/20o 1,1437; nD20o1,54032; nD45.5o1,52927;2)

B. p. 149,5° (15 mm.); d19o1,1425.8)

Even in a freezing mixture myristicin does not congeal. With bromine it yields dibrommyristicindibromide,

C6Br2(C3H5Br2)(OCH3)(02CH2), m. p. 130°, upon oxidation myristicinic aldehyde and myristicinic acid (see below).

When boiled with alcoholic potassa, or when treated with sodium, the allyl group is rearranged to the propenyl group and the myristicin thereby changed to solid isomyristicin for which Power and Salway1) record the following constants:

1) This is not to be confounded with the "myristicin" of John and Mulder, a stearoptene that occasionally crystallizes out of old oils and which consists of myristinic acid as shown by Fluckiger [Pharmaceutical Journ. III 5 (1874), 136].

2) Power and Salway, )ourn. chem. Soc. 91 (1907), 2054.

3) Thorns, Berl. Berichte 36 (1903), 3447.

M. p. 44°; b. p. 166° (18 mm.); nD45.5o1,56551.1)

Characteristic derivatives are the dibromide, m. p. 109°, and the dibromIsomyristicin dibromide, m. p. 156°. Like myristicin, Isomyristicin yields myristicinic aldehyde, m. p. 130° and myris-ticinic acid, m. p. 210°, upon oxidation with permanganate.

With nitrous acid both phenol ethers yield addition products from which a series of derivatives can be obtained.

The isomeric apiols C6HC3H5(02CH2)(OCH3)2 are derivatives of an unsaturated, tetratomic phenol. With reference to their occurrence they are designated apiol, dillapiol, also allyltetramethoxy benzene.