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.
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Kandil et al. (1983) studied this question.
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