Enantiomeric synthesis of 9-hydroxy-(E)-2-decenoic acid, a queen honeybee pheromone

1983 ◽  
Vol 61 (6) ◽  
pp. 1166-1168 ◽  
Author(s):  
Ali A. Kandil ◽  
Keith N. Slessor
Keyword(s):  
Mandibular Gland ◽  
Decenoic Acid ◽  
Queen Honeybee ◽  
Important Constituent

S-(+)-, R-(−)-, and (±)-9-hydroxy-(E)-2-decenoic acid have been synthesized by organocuprate-catalyzed opening of S-(−)-, R-(+)-, and racemic methyl oxiranes. This acid, of unknown chirality, is an important constituent of the honeybee queen's mandibular gland.

INTRA-NEST TRANSMISSION OF AROMATIC HONEY BEE QUEEN MANDIBULAR GLAND PHEROMONE COMPONENTS: MOVEMENT AS A UNIT

1992 ◽  
Vol 124 (5) ◽  
pp. 917-934 ◽  
Author(s):  
Ken Naumann ◽  
Mark L. Winston ◽  
Keith N. Slessor ◽  
Glenn D. Prestwich ◽  
Bachir Latli
Keyword(s):  
Honey Bee ◽  
Mandibular Gland ◽  
Queen Pheromone ◽  
The Body ◽  
Decenoic Acid ◽  
Pheromone Components ◽  
Aromatic Components ◽  
Honey Bee Queen ◽  
Pheromone Complex ◽  
Queen Mandibular Gland Pheromone

AbstractThe intra-nest transmission of two aromatic components of honey bee queen mandibular gland pheromone, 4-hydroxy-3-hydroxyphenylethanol (HVA) and methyl p-hydroxybenzoate (HOB), is quantitatively described. After being secreted onto the body surface of the queen, the greatest quantities of HVA and HOB are removed by workers in the queen’s retinue, especially those contacting the queen with their mouthparts. Other workers acquire pheromone components via direct contact with retinue bees or with other workers that have already acquired queen pheromone. HVA and HOB can also reach workers through queen or worker "footprints," although the relatively little material deposited onto the comb wax becomes less available with time, presumably because of diffusion into the wax. Pheromone material is removed from circulation by being internalized into workers, the queen, and the wax. Rates of HVA and HOB transfer between different entities within the nest are described in terms of pseudo first-order rate constants. The intra-nest transfer of these two components, both qualitatively and quantitatively, is similar to that described earlier for the most abundant queen mandibular gland pheromone component, 9-keto-2-(E)-decenoic acid (9-ODA; Naumann et al. 1991). Thus, the queen mandibular gland pheromone complex is transferred through the nest as a unit rather than as individual components moving at different rates.

New approach to the synthesis of 9-oxo-2E-decenoic acid, a multifunctional pheromone of queen honeybee, from the telomer of butadiene and water

2011 ◽  
Vol 47 (5) ◽  
pp. 789-791 ◽  
Author(s):  
G. Yu. Ishmuratov ◽  
V. A. Vydrina ◽  
G. V. Nasibullina ◽  
M. P. Yakovleva ◽  
R. R. Muslukhov ◽  
...  
Keyword(s):  
Decenoic Acid ◽  
New Approach ◽  
Queen Honeybee

Synthetic pheromones to attract honeybee (Apis mellifera) swarms

1981 ◽  
Vol 97 (2) ◽  
pp. 427-431 ◽  
Author(s):  
J. B. Free ◽  
J. A. Pickett ◽  
A. W. Ferguson ◽  
M. C. Smith
Keyword(s):  
Apis Mellifera ◽  
Mandibular Gland ◽  
Natural Conditions ◽  
Decenoic Acid ◽  
Synthetic Pheromone ◽  
Pheromone Components ◽  
Practical Implications

SummaryLures containing the synthetic pheromone components (E)- and (Z)-citrals, geraniol and nerolic and geranic acids made new hives, not previously occupied by honeybee colonies, more attractive to caged honeybee swarms than unbaited hives (20 out of 20 tests). The lure also made old hives, previously occupied by colonies, more attractive to caged swarms (19 out of 20 tests) and to swarms in natural conditions (12 occupied compared with none without the lure). Adding (E)-9-oxo-2-decenoic acid (part of the queen's mandibular gland pheromone) to the lure increased its attractiveness to caged swarms (20 out of 20 tests). Practical implications in beekeeping are discussed.

Observations On the Transmission of Queen Substances in the Honey Bee Colony By the Attendants of the Queen

Behaviour ◽  
1972 ◽  
Vol 41 (1-2) ◽  
pp. 105-128 ◽  
Author(s):  
H.H.W. Velthuis
Keyword(s):  
Mandibular Gland ◽  
The Body ◽  
Second Phase ◽  
Final Phase ◽  
Mandibular Glands ◽  
Decenoic Acid ◽  
Food Exchange ◽  
Bee Colony ◽  
Behaviour Type ◽  
Worker Bee

AbstractThe material produced in the mandibular glands of queen honey bees can be transported by her attendants and causes an inhibition of oogenesis in the workers who cannot make a direct contact with the queen. It seems that the only substance involved in this procedure is 9-oxo-decenoic acid from the queen's mandibular glands. A worker bee from a queenless group of workers shows a variety of behaviour types when it encounters a queen. This consists of avoidance and aggression, offering food, feeding and retinue behaviour and finally negligence. Although most changes of one behaviour type into another occur randomly, the overall pattern can be divided into an initial phase in which avoidance and aggression are frequently observed, a second phase characterized by feeding and retinue behaviour and a final phase in which negligence of the queen dominates. When back in her group of workers this bee functions as substitute queen by attracting the attention of the others, which show principally the same behaviour types to her. This attractiveness of the substitute queen is due to mandibular gland substances from the queen, adhering to the bee's body. Food exchange between the substitute queen and her attendants is mainly directed to the substitute queen. Feeding by the substitute queen is almost always related to the occurrence of aggression towards her. This is opposite to what might be expected when food exchange would be the mechanism by which information about the presence of the queen is distributed among the colony members. When a queen is deprived of her mandibular glands she evokes the same behaviour types in an encountered bee, but the frequency of negligence is higher, whereas feeding and retinue occur less frequently. When back in her group of workers this bee hardly functions as substitute queen, since she is almost treated as an arbitrary bee. Both the attractiveness of the returned worker and the direction of food exchange indicate that sensory perception by means of the antennae of 9-oxo-decenoic acid on the body of the queen or the substitute queen plays a major part in the "queenright" behaviour of the bees.

scholarly journals Responses of Queenright and Queenless Workers of Apis Cerana to 9-keto-2(E)-decenoic Acid, a Pheromonal Constituent of the Mandibular Gland

2010 ◽  
Vol 36 (9) ◽  
pp. 966-968 ◽  
Author(s):  
Ken Tan ◽  
Zheng-Wei Wang ◽  
Hua Li ◽  
Ming-Xian Yang ◽  
Christian W. W. Pirk ◽  
...  
Keyword(s):  
Apis Cerana ◽  
Mandibular Gland ◽  
Decenoic Acid
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