Queen substance

The telomer 137, obtained by the reaction of butadiene with malonate, is a suitable compound for the syntheses of naturally occurring dodecanoic acid derivatives, such as queen substance (I38)[l 7], one of the royal jelly acids (139)[I18], and pellitorine fl40)[ll9]. 

Quaternary ammonium compounds biocidal activity mechanism, 1, 401 toxicity, 1, 124 Quaternization heterocyclic compounds reviews, 1, 73 ( )-Quebrach amine synthesis, 1, 490 Queen substance synthesis, 1, 439 4, 777 Quercetin occurrence, 3, 878 pentamethyl ether photolysis, 3, 696 photooxidation, 3, 695 Quercetrin hydrolysis, 3, 878 Quinacetol sulfate as fungicide, 2, 514 Quinacridone, 2,9-dimethyl-, 1, 336 Quinacridone pigments, 1, 335-336 Quinacrine... 

Gengva l Examp Ig Queen substance C 5) is a hormone produced by a queen bee to prevent the worker bees ovaries maturing and to train them to serve her. 

In one synthesis of the queen substance of honey bees (9) (cf p ) the double bond is derived from an... 

Queen substance (140) was synthesized from the same telomer 137 (127). The PdCl2-catalyzed oxidation of the terminal double bond produced the methyl ketone. Reduction of the internal double bond was followed by partial hydrolysis and the displacement of the carboxyl group with phenylselenyl group, which was removed to produce queen substance (140) ... 

Interest in the vitamin B12 catalyzed light assisted electrolysis directed to the preparation of fine chemicals has been well illustrated in the synthesis of some natural products. One typical example is the synthesis of the Queen substance of Apis mellifera which involves two efficient electrochemical C,C-bond-forming steps by addition to conjugated double and triple bonds (Scheme 4) [63]. 

Scheme 4. Synthesis of the Queen substance of Apis melHfera...

Hi) Carboxylic acids and derivatives. The haloform reaction on thienyl methyl ketones leads to thiophenecarboxylic acids, which can be treated with Raney nickel to produce the open-chain acids. This method has been used for the five-carbon homologation of carboxylic acids and to produce dicarboxylic acids (Scheme 51). Long-chain carboxylic acids may also be prepared by using dicarboxylic acid derivatives for the acylation of thiophenes (Scheme 52). In the synthesis of Queen substance, the precursor (213) has been generated by Raney nickel desulfurization of the appropriate thiophene-2-acetic acid derivative (79T329). 

Callow R. K. and Johnson N. C. (1960) The chemical constitution and synthesis of queen substance of honeybees (Apis mellifera L.). Bee World 41, 152-153. 

The best understood of the sexual pheromones of social insects is the queen substance of honeybees. Interestingly, the queen substance used for queen control inside the nest is also the substance used by virgin queens to attract drones for mating. Callow and Johnston (1960) and Barbier and Lederer (1960) identified 9-keto-2(E)-decenoic acid ([E]-9-oxodec-2-enoic acid) (9-ODA) as major components of the queen mandibular glands. 9-Hydroxy-2(E)-decenoic acid is also present (Callow et al., 1964) and together both attract drones. Additional components of the queen retinue pheromone have recently been identified (Keeling et al., 2003). 

Queen Substance. The queens of many hymenopterous species release primer pheromones in the colonial milieu and these compounds strongly influence the reproductive or endocrine systems of the workers. Butler et al. (139) identified ( )-9-oxo-2-decenoic as the compound that inhibits both ovarian development in workers (140) and queen cell construction (141). The queen substance of the Oriental hornet has been identified as 6-hexadecalactone (XXXVII) (142). 

One of the reported syntheses of ( )-9-oxodec-2-enoic acid 392, the queen substance of the honey bee Apis mellifera, uses two ylide reactions 222). Starting from pimelic acid 385 the resonance-stabilized ylide 386 is prepared by alkylation of methylene-triphenylphosphorane 209 and the former hydrolyzed to 7-oxooctanoic acid 387. Reduction of the corresponding thiol ester 389 and olefination of the resulting aldehyde 390 with phosphorane 67 gives the ( )-2-unsaturated ester 391. The latter was hydrolyzed to pheromone 392 222) (Scheme 69). 

Queen substance (secreted by the queen bee to prevent development of other queens)... 

Attraction of worker bees to queens in the hive is also due to a mixture of volatile acids (containing queen substance ) extracted from queen mandibular glands attractivity is lost by chromatography and can be recovered by remixing fractions 33). 

Primer pheromones, which cause long-term behavioral changes, are harder to isolate and identify. One example, however, is the queen substance produced by queen honeybees. All the eggs in a colony are laid by one queen bee. If she is removed from the hive or dies, the worker bees are activated by the absence of the queen substance and begin to feed royal jelly to bee larvae to raise a new queen. The queen substance also prevents the development... 

The chemical information channel is especially vital for social insects. The nearly ideal social order in a beehive is perpetuated as long as the honeybee s queen maintains the ability to produce a very simple aliphatic compound, ( )-9-oxo-2-decenoic acid 20 ( queen substance ).This multipurpose compound... 

Eiter used the reagent (methyl ester) in one of the more practicable syntheses of queen substance isolated from royal jelly. 

A similar approach was applied in the study of the silkmoth bombykol pheromone receptor (Sakurai et al. 2004 Nakagawa et al. 2005), a receptor for honeybee queen substance p-oxo-2-decenoic acid (Wanner et al. 2007), and a ligand repertoire for Anopheles ORs (Lu et al. 2007). In these cases, however, coexpression of Ga15 was not necessary, but expression of one member of the Or83b family was absolutely necessary. The molecular mechanisms for signal transduction are discussed in Sect. 4. 

Vosshall LB et al (2000) An olfactory sensory map in the fly brain. Cell 102 147-159 Wanner KW et al (2007) A honeybee odorant receptor for the queen substance 9-oxo-2-decenoic acid. Proc Natl Acad Sci USA 104 14383-14388 Wetzel CH et al (2001) Functional expression and characterization of a Drosophila odorant receptor in a heterologous cell system. Proc Natl Acad Sci USA 98 9377-9380 Wicher D et al (2008) Drosophila odorant receptors are both ligand-gated and cyclic-nucleotide-activated cation channels. Nature 452 1007-1011 Wilson RI et al (2004) Transformation of olfactory representations in the Drosophila antennal lobe. Science 303 366-370... 

The consecutive addition of alkyl halide to activated olefins by photoelectrocatalysis (PEC) of hydroxocobalamin hydrochloride allows the construction of extended carbon chains as shown for the synthesis of pheromone queen substance 9. The mild conditions of the B12/PEC reaction are suited for the addition of primary alkyl halides 10 containing a potential leaving group. This is illustrated in the synthesis of endo- and exo-brevicomin (11) (Scheme 4). 

Zur Herstellung von, Royal jelly acid" und Queen substance" iiber Malonsaure-diester und 3-Oxo-butansaure-ester-Synthesen s. K. Yokoiu. K Matsubara, Nippon Kagaku Kaishi 1978,1415 C. A. 90, 22266 (1979). 

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