11- Dodecynoic acid

Finally, since fatty acid hydroxylations at the o), 00-1, 00-2, 00-3, and co-4 positions also occur in plants and bacteria °, acetylenic fatty acids have also been employed to examine whether these hydroxylases are mechanistically similar to their mammalian counterparts and/or to identify the role of specific plant and bacterial P450 enzymes °. Thus, midchain and terminal acetylenes such as 10-dodecynoic acid have been used as probes of plant lauric acid oo-hydroxylases . Similarly, 17-ODYA has been shown to inactivate P450g, 3 (CYP108), an enzyme that hydroxylates fatty acids at positions other than the terminal (oo) carbon, through a heme alkylation mechanism . 

The (fl)-(-)-enantiomers of (z)- and (E)-14-methy1 -8-hexadecen-1-ol, pheromones of Tvogod Tma, have been obtained by coelectrolysis of ()-(-)-4-methy1hexanoic acid (45) and 12- tetrahydro-2-pyranyl-oxy)-4-dodecynoic acid (46) followed by stereospecific hydrogenation of (47). ... 

---