What it is

Ajoene is a sulphur-containing compound derived from allicin.

In an oil maceration process of garlic bulb, a mixture of other organosulfur compounds was formed. In general, oil-macerated garlic products contained primarily vinyldithiins as well as some dialk(en)yl sulphides, mainly diallyl trisulfide and ajoene (Table 1). Ajoene is typically not found in steam-distilled garlic but only in oil-macerated garlic. An important structural feature of ajoene is that the central double bond is capable of existing in E or Z forms. It was found that Z-Ajoene is the dominant isomer in fresh preparations of oil-macerated garlic. Gradually, Z-isomer will be converted to the E-isomer and it was thought that E-ajoene is more stable during storage. The E/Z ratio and yield depend on the polarity of the solvent system, the reaction condition during processing and cultivar (Lawson et al, 1990).

Compounds
Oil-macerated products
µg/g
%
Diallyl disulfide
34 ± 17
3.9
Diallyl trisulfide
65 ± 16
7.5
Methyl allyl trisulfide
58 ± 19
6.7
2-Vinyl-4H-1/3-dithiin
435 ± 69
50.4
2-Vinyl-4H-1/2-dithiin
167 ± 28
19.4
E-Ajoene
68 ± 28
7.9
Z-Ajoene
36 ± 16
4.2
Total sulphides
845 ± 98
100.0