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(Z)-5-tetradecen-1-ol, Potential female sex attractant



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(Z)-5-Tetradecen-1-ol, mw  212.37,   formula  C14H20O   CAS   40642-42-0

Odorant receptors, present on nasal sensory neurons, perceive volatile compounds and regulate animal behavior such as reproduction. The nature of the ligands interacting with these receptors is, however, largely unknown.
Keiichi Yoshikawa and colleagues, University of Tokyo, Japan, shed new light on this issue. The researchers demonstrated that, in mice, preputial gland cells generate and secrete into the urine the unsaturated aliphatic alcohol (Z)-5-tetradecen-1-ol (pictured). This compound is regulated by the male hormone testosterone and acts as a natural agonist of the mouse odorant receptor Olfr288, affecting attractiveness to female mice. The urine of males lacking (Z)-5-tetradecen-1-ol, in fact, failed to attract females.

(9Z)-9-Tetradecene-14-ol 40642-42-0

By identifying a novel receptor-ligand interaction in the mouse olfactory system, this study offers new insights into the complex chemistry regulating reproductive behavior.

  • An unsaturated aliphatic alcohol as a natural ligand for a mouse odorant receptor,
    K. Yoshikawa, H. Nakagawa, N. Mori, H. Watanabe, K. Touhara,
    Nature Chem. Biol. 2013.
    DOI: 10.1038/nchembio.1164
  • Ohloff, G. et al. 1977. Helv. Chim. Acta. 60:1161-1174.
  • Bestmann, H.J., Brosche, T., Koschatzky, K.H., Michaelis, K., Platz, H., Vostrowsky, O., and Knauf, W. 1980. Pheromone XXX. Identifizierung eines neuartigen pheromonkomplexes aus der graseule Scotia exclamationis. Tetrahedron Lett. 21:747-750.
    Kelkar, S.V., Reddy, G.B., and Kulkarni, G.H. 1989. Indian J. Chem. Sect. B. 28:980-981.
    Ohloff, G., Vial, C., Näf, F., and Pawlak, M. 1977. Stereoselective syntheses of the isomeric 5, 10-pentadecadienals. Helv. Chim. Acta. 60:1161-1174.
     (9Z)-9-Tetradecene-14-ol 40642-42-0



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DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, Dr T.V. Radhakrishnan and Dr B. K. Kulkarni, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 30 year tenure till date Dec 2017, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 50 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 19 lakh plus views on New Drug Approvals Blog in 216 countries...... , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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