Cyclizations of the C10 Fatty Acids from the Mandibulary Glands of the Honeybee Apis mellificaL.: Queen substance and royal jelly acid
✍ Scribed by Michel Barbier
- Publisher
- John Wiley and Sons
- Year
- 1981
- Tongue
- German
- Weight
- 324 KB
- Volume
- 64
- Category
- Article
- ISSN
- 0018-019X
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
Series of assays have been performed to cyclize the two main C~10~ aliphatic acids, (E)‐9‐oxo‐dec‐2‐enoic acid (3) (queen substance) and (E)‐10‐hydroxy‐dec‐2‐enoic acid (7) (royal jelly acid) produced by the mandibulary glands of the honeybee Apis mellifica L. Queen substance 3, resistant to thermocyclization, was cyclized by the action of polyphosphoric acid to the fulvene ketone 5. Triphenylphosphinediethyl azodicarboxylate treatment of royal jelly acid 7 mainly furnished the dilactide 6 together with a series of cyclic oligomers up to the pentamer. Attempts to favour the formation of the lactone 11 through other conditions failed, and thus the reaction does not seem suitable for the preparation of lactones using α, β‐unsaturated hydroxy acids.
Substances 3,7,12,13,14,15, were submitted to in vitro antibacterial as well as growth inhibition tests but all results were negative at the concentrations reported.