(S)-Ipsdienol

(S)-Ipsdienol
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Names
	Preferred IUPAC name (4S)-2-Methyl-6-methylideneocta-2,7-dien-4-ol
	Other names (S)-(+)-Ipsdienol, 2-Methyl-6-methylene-2,7-octadiene-4-ol, Ipsdienol
Identifiers
CAS Number	35628-00-3 Y;
3D model (JSmol)	Interactive image;
ChemSpider	83332;
ECHA InfoCard	100.128.974
EC Number	609-154-9;
PubChem CID	92301;
UNII	I0CK35047X Y;
CompTox Dashboard (EPA)	DTXSID50885627 ;
	InChI InChI=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 Key: NHMKYUHMPXBMFI-SNVBAGLBSA-N;
	SMILES CC(=C[C@H](CC(=C)C=C)O)C;
Properties
Chemical formula	C10H16O
Molar mass	152.237 g·mol−1
Appearance	Colorless
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H400
Precautionary statements	P273, P391, P501
Flash point	87 °C (189 °F; 360 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

(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.¹ 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.²

Synthesis

The compound has been synthesized from D-mannitol.³ Alternative syntheses were realized through the asymmetric isoprenylation of correspondent aldehyde (prenal)⁴ and alcohol (prenol).⁵ Chiral resolution of racemic precursor has been found⁶⁷ to provide both enantiomers of ipsdienol in high enantiomeric purity and in preparative scale.

References

Silverstein, Robert M.; Rodin, J. Otto; Wood, David L. (October 1966). "Sex Attractants in Frass Produced by Male Ips confusus in Ponderosa Pine". Science. 154 (3748): 509–510. Bibcode:1966Sci...154..509S. doi:10.1126/science.154.3748.509. JSTOR 1720044. S2CID 80674108.
Miller, Daniel R.; Borden, John H.; King, G. G. S.; Slessor, Keith N. (1 August 1991). "Ipsenol: an aggregation pheromone for Ips latidens (Leconte) (Coleoptera: Scolytidae)". Journal of Chemical Ecology. 17 (8): 1517–1527. doi:10.1007/BF00984685. PMID 24257877. S2CID 22337300.
Hanessian, Stephen (1983). Total Synthesis of Natural Products: The 'Chiron' Approach. Pergamon press. p. 63. ISBN 978-0-08-029247-2.
Zhang, Yu-Long; He, Bo-Jun; Xie, Yi-Wen; Wang, Yu-Hao; Wang, Yi-Long; Shen, Yong-Cun; Huang, Yi-Yong (2019). "Enantioselective Isoprenylboration Reaction of Aldehydes Catalyzed by a Chiral Phosphoric Acid". Advanced Synthesis & Catalysis. 361 (13): 3074–3079. doi:10.1002/adsc.201900203. S2CID 133162412.
Xiang, Ming; Luo, Guoshun; Wang, Yuankai; Krische, Michael J. (2019). "Enantioselective iridium-catalyzed carbonyl isoprenylation via alcohol-mediated hydrogen transfer". Chemical Communications. 55 (7): 981–984. doi:10.1039/C8CC09706B. PMC 6339811. PMID 30608076.
Kovalenko, V. N.; Prokhorevich, K. N. (2016). "Improved synthesis of optically active ipsdienol". Russian Journal of Organic Chemistry. 52 (5): 757–758. doi:10.1134/S1070428016050250. S2CID 99770908.
Kovalenko, V. N.; Matyushenkov, E. A. (2012). "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. doi:10.1134/S1070428012090035. S2CID 84179515.

[1] Silverstein, Robert M.; Rodin, J. Otto; Wood, David L. (October 1966). "Sex Attractants in Frass Produced by Male Ips confusus in Ponderosa Pine". Science. 154 (3748): 509–510. Bibcode:1966Sci...154..509S. doi:10.1126/science.154.3748.509. JSTOR 1720044. S2CID 80674108.

[2] Miller, Daniel R.; Borden, John H.; King, G. G. S.; Slessor, Keith N. (1 August 1991). "Ipsenol: an aggregation pheromone for Ips latidens (Leconte) (Coleoptera: Scolytidae)". Journal of Chemical Ecology. 17 (8): 1517–1527. doi:10.1007/BF00984685. PMID 24257877. S2CID 22337300.

[3] Hanessian, Stephen (1983). Total Synthesis of Natural Products: The 'Chiron' Approach. Pergamon press. p. 63. ISBN 978-0-08-029247-2.

[4] Zhang, Yu-Long; He, Bo-Jun; Xie, Yi-Wen; Wang, Yu-Hao; Wang, Yi-Long; Shen, Yong-Cun; Huang, Yi-Yong (2019). "Enantioselective Isoprenylboration Reaction of Aldehydes Catalyzed by a Chiral Phosphoric Acid". Advanced Synthesis & Catalysis. 361 (13): 3074–3079. doi:10.1002/adsc.201900203. S2CID 133162412.

[5] Xiang, Ming; Luo, Guoshun; Wang, Yuankai; Krische, Michael J. (2019). "Enantioselective iridium-catalyzed carbonyl isoprenylation via alcohol-mediated hydrogen transfer". Chemical Communications. 55 (7): 981–984. doi:10.1039/C8CC09706B. PMC 6339811. PMID 30608076.

[6] Kovalenko, V. N.; Prokhorevich, K. N. (2016). "Improved synthesis of optically active ipsdienol". Russian Journal of Organic Chemistry. 52 (5): 757–758. doi:10.1134/S1070428016050250. S2CID 99770908.

[7] Kovalenko, V. N.; Matyushenkov, E. A. (2012). "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. doi:10.1134/S1070428012090035. S2CID 84179515.

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