(S)-Ipsdienol

(S)-Ipsdienol S-Ipsdienol.svg Ipsdienol-3D-spacefill.png Ipsdienol molecule (4S)-2-Methyl-6-methylideneocta-2,7-dien-4-ol (S)-(+)-Ipsdienol, 2-Methyl-6-methylene-2,7-octadiene-4-ol, Ipsdienol 35628-00-3 correct CAS 83332 609-154-9 correct FDA I0CK35047X 92301 1S/C10H16O/c1-5-9(4)7-10(11)6-8(2)3/h5-6,10-11H,1,4,7H2,2-3H3/t10-/m1/s1 NHMKYUHMPXBMFI-SNVBAGLBSA-N CC(=C[C@H](CC(=C)C=C)O)C 10 16 1 Colorless 09 Warning 400 273 391 501 87 (S)-Ipsdienol is a terpene alcohol. It is one of the major aggregation pheromones of the bark beetle. It was first identified from Ips confusus, in which it is believed to be a principle sex attractant.Silverstein Robert M. Rodin J. Otto Wood David L. Sex Attractants in Frass Produced by Male Ips confusus in Ponderosa Pine Science October 1966 154 3748 509–510 10.1126/science.154.3748.509 1720044 https://www.science.org/doi/abs/10.1126/science.154.3748.509 1966Sci...154..509S 80674108 subscription It is suggested that the compound plays a role in interspecies communication between Ips latidens and Ips ini, facilitating reductions in competition for breeding material and/or mating interference.Miller Daniel R. Borden John H. King G. G. S. Slessor Keith N. Ipsenol: an aggregation pheromone for Ips latidens (Leconte) (Coleoptera: Scolytidae) Journal of Chemical Ecology 1 August 1991 17 8 1517–1527 10.1007/BF00984685 24257877 22337300 Synthesis The compound has been synthesized from D-mannitol.Hanessian Stephen Total Synthesis of Natural Products: The 'Chiron' Approach 1983 Pergamon press 978-0-08-029247-2 63 Alternative syntheses were realized through the asymmetric isoprenylation of correspondent aldehyde (prenal) 10.1002/adsc.201900203 Enantioselective Isoprenylboration Reaction of Aldehydes Catalyzed by a Chiral Phosphoric Acid Advanced Synthesis & Catalysis 361 13 3074–3079 2019 Zhang Yu-Long He Bo-Jun Xie Yi-Wen Wang Yu-Hao Wang Yi-Long Shen Yong-Cun Huang Yi-Yong 133162412 and alcohol (prenol). 10.1039/C8CC09706B 30608076 6339811 Enantioselective iridium-catalyzed carbonyl isoprenylation via alcohol-mediated hydrogen transfer Chemical Communications 55 7 981–984 2019 Xiang Ming Luo Guoshun Wang Yuankai Krische Michael J. Chiral resolution of racemic precursor has been found10.1134/S1070428016050250 Improved synthesis of optically active ipsdienol Russian Journal of Organic Chemistry 52 5 757–758 2016 Kovalenko V. N. Prokhorevich K. N. 99770908 http://elib.bspu.by/handle/doc/1503410.1134/S1070428012090035 Stereoselective synthesis of (R)- and (S)-Ipsdienols, pheromone components of bark beetles of the Ips family Russian Journal of Organic Chemistry 48 9 1168–1172 2012 Kovalenko V. N. Matyushenkov E. A. 84179515 to provide both enantiomers of ipsdienol in high enantiomeric purity and in preparative scale. References Category:Monoterpenes Category:Insect pheromones Category:Secondary alcohols Category:Enols