3- Decenoic acid

One of royal jelly acids (10-hydroxy-2-decenoic acid) (141) was prepared from the telomer of acetoacetate, 142 (128). The terminal double bond was converted to terminal alcohol by hydroboration. The internal double bond was reduced and then reintroduced at the conjugated position by the addition of phenylselenyl group, and its oxidative removal completed the synthesis ... 

Decenoic acid (143), easily prepared from the same telomer 142, was cyclized via acid chloride using A1C13 to give 2-pentyl-2-cyclopentenone (144). Michael addition of methyl malonate followed by removal of one ester group produced methyl dihydrojasmonate (145) (129) ... 

Virgin females of the furniture carpet beetle, Anthrenus flavipes, produce (Z)-3-decenoic acid as a sex pheromone 107 [207]. In contrast, the female-produced sex pheromone of the varied carpet beetle Anthrenus verbasci is a two component mixture of (Z)-5-undecenoic acid 108 and its (E)-isomer [208]. Recent investigations showed the presence of additional electrophysiologically active components, however, no behaviour tests have been carried out [209]. 

Recently, a patent described the use of Diplodia gossypina ATCC 10936 for the production of natural jasmonic acid [47]. With submerged cultures, up to 1.5 g L" jasmonic acid was obtained after 11 days of incubation the addition of 10-oxo-8-fra s-decenoic acid, a hormone stimulating mycelial growth, proved to be advantageous methyl jasmonate was obtained by autoclaving the... 

The gross structural features, presence of a tetramic acid and E-decenoyl side chain, could be inferred from NMR studies. Methanolysis (HCl/MeOH) of 47 and pentane extraction of the quenched reaction mixture gave two compounds that were determined to be the methyl esters of decenoic acid and N-(2-decenoyl)leucine. The nature of the 3-acyl tetramic acid was deduced from the identification of 48 and 49 in the aqueous portion of the methanolysis reaction mixture following treatment with trifluoroacetic acid anhydride. The unusual C-C bond fragmentation under acidic conditions, and the structure of the antibiotic was confirmed by synthesis of racemic 47 [86]. The configuration at the lone chiral centre was established as R by chiral GC. The carbon NMR spectrum of 47 indicated an equilibrium between three tautomers in which the A2-pyrrolin-4-one form is preferred (60%) and the two internal tautomers (50, 51) make equal contributions (20% each). 

A-4. Propose a series of synthetic steps to carry out the preparation of oleic acid [(Z)-9-octa-decenoic acid] from compound A. You may use any necessary organic or inorganic reagents. 

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). 

Hydroxy-(E)2-Decenoid acid 9-Hydroxy-(E)2-Decenoic acid... 

E,Z)-3,5-tetradecadienoic acid as a sex attractant (55). The sexual releaser emitted by females of the furniture carpet beetle, Anthrenus flavipes, has been identified as (Zj-3-decenoic acid (56). The (Z)-isomer is about 20X more active than the (E)-isomer. 

Sex Pheromones. Gary (137) demonstrated that (E)-9-oxo-2-decenoic acid, a mandibular gland product of the queen honey... 

HY-PHI 2102 INDUSTRENE 105 INDUSTRENE 205 INDUSTRENE 206 K 52 I ACIDE OLEIQUE (FRENCH) METAUPON NEOFAT 90-04 NEO-FAT 92-04 cis-A -OCTADECENOIC ACID ds-OCTADEC-9-ENOIC ACID cis-9-OCTA-DECENOIC ACID 9,10-OCTADECENOIC ACID PAMOLYN RED OIL TEGO-OLEIC 130 VOPCOLENE 27 WECOUNE OO WOCHEM No. 320... 

Iodolactonization of protected (Z)-9,10-dihydroxy-2,4,8-trimethyl-5-decenoic acid (4) under kinetic conditions affords exclusively the 5,6-tran.v-disubstituted lactone in 87% yield4. 

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... 

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