Ipsenol | CAS#35628-05-8 | monoterpene

MedKoo Cat#: 146316 | Name: Ipsenol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ipsenol is a naturally occurring monoterpene alcohol produced by certain bark beetle species, including Ips paraconfusus and Ips pini. It serves as an aggregation pheromone, attracting both male and female beetles to suitable breeding sites in host trees like pine. The biosynthesis of ipsenol involves the conversion of the monoterpene myrcene into ipsenol through a series of enzymatic steps, including oxidation and reduction reactions .

Chemical Structure

Ipsenol

CAS#35628-05-8

Theoretical Analysis

MedKoo Cat#: 146316

Name: Ipsenol

CAS#: 35628-05-8

Chemical Formula: C10H18O

Exact Mass: 154.1358

Molecular Weight: 154.25

Elemental Analysis: C, 77.87; H, 11.76; O, 10.37

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Ipsenol;

IUPAC/Chemical Name

(S)-2-methyl-6-methyleneoct-7-en-4-ol

InChi Key

RHAXCOKCIAVHPB-JTQLQIEISA-N

InChi Code

1S/C10H18O/c1-5-9(4)7-10(11)6-8(2)3/h5,8,10-11H,1,4,6-7H2,2-3H3/t10-/m0/s1

SMILES Code

CC(C)C[C@H](O)CC(=C)C=C

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 154.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Marco-Contelles J. The Synthesis of Ipsenol and Ipsdienol: A Review (1968-2020). Chem Rec. 2021 Apr;21(4):858-878. doi: 10.1002/tcr.202000160. Epub 2021 Feb 4. PMID: 33539044. 2: Miller DR, Asaro C. Ipsenol and ipsdienol attract Monochamus titillator (Coleoptera: Cerambycidae) and associated large pine woodborers in southeastern United States. J Econ Entomol. 2005 Dec;98(6):2033-40. doi: 10.1603/0022-0493-98.6.2033. PMID: 16539130. 3: Miller DR, Crowe CM, Dodds KJ, Galligan LD, de Groot P, Hoebeke ER, Mayfield AE 3rd, Poland TM, Raffa KF, Sweeney JD. Ipsenol, Ipsdienol, Ethanol, and α-Pinene: Trap Lure Blend for Cerambycidae and Buprestidae (Coleoptera) in Pine Forests of Eastern North America. J Econ Entomol. 2015 Aug;108(4):1837-51. doi: 10.1093/jee/tov126. Epub 2015 May 21. PMID: 26470326. 4: Miller DR, Borden JH, King GG, Slessor KN. Ipsenol: an aggregation pheromone forIps latidens (Leconte) (Coleoptera: Scolytidae). J Chem Ecol. 1991 Aug;17(8):1517-27. doi: 10.1007/BF00984685. PMID: 24257877. 5: Allison JD, McKenney JL, Miller DR, Gimmel ML. Role of ipsdienol, ipsenol, and cis-verbenol in chemical ecology of Ips avulsus, Ips calligraphus, and Ips grandicollis (Coleoptera: Curculionidae: Scolytinae). J Econ Entomol. 2012 Jun;105(3):923-9. doi: 10.1603/ec12078. PMID: 22812131. 6: Miller DR, Allison JD, Crowe CM, Dickinson DM, Eglitis A, Hofstetter RW, Munson AS, Poland TM, Reid LS, Steed BE, Sweeney JD. Pine Sawyers (Coleoptera: Cerambycidae) Attracted to α-Pinene, Monochamol, and Ipsenol in North America. J Econ Entomol. 2016 Apr 22;109(3):1205-1214. doi: 10.1093/jee/tow071. PMID: 27106224. 7: Miller DR, Asaro C, Berisford CW. Attraction of southern pine engravers and associated bark beetles (Coleoptera: Scolytidae) to ipsenol, ipsdienol, and lanierone in southeastern United States. J Econ Entomol. 2005 Dec;98(6):2058-66. doi: 10.1603/0022-0493-98.6.2058. PMID: 16539133. 8: Chen DF, Li YJ, Zhang QH, Zhang SF, Wang HB, Zhang Z, Zhao LL, Kong XB. Population divergence of aggregation pheromone responses in Ips subelongatus in northeastern China. Insect Sci. 2016 Oct;23(5):728-38. doi: 10.1111/1744-7917.12221. Epub 2015 May 19. PMID: 25783997. 9: Blomquist GJ, Figueroa-Teran R, Aw M, Song M, Gorzalski A, Abbott NL, Chang E, Tittiger C. Pheromone production in bark beetles. Insect Biochem Mol Biol. 2010 Oct;40(10):699-712. doi: 10.1016/j.ibmb.2010.07.013. Epub 2010 Aug 19. PMID: 20727970. 10: Seybold SJ, Quilici DR, Tillman JA, Vanderwel D, Wood DL, Blomquist GJ. De novo biosynthesis of the aggregation pheromone components ipsenol and ipsdienol by the pine bark beetles Ips paraconfusus Lanier and Ips pini (Say) (Coleoptera: Scolytidae). Proc Natl Acad Sci U S A. 1995 Aug 29;92(18):8393-7. doi: 10.1073/pnas.92.18.8393. PMID: 11607576; PMCID: PMC41163. 11: Blomquist GJ, Tittiger C, MacLean M, Keeling CI. Cytochromes P450: terpene detoxification and pheromone production in bark beetles. Curr Opin Insect Sci. 2021 Feb;43:97-102. doi: 10.1016/j.cois.2020.11.010. Epub 2020 Dec 21. PMID: 33359166. 12: Kavallieratos NG, Boukouvala MC, Skourti A, Antonatos S, Petrakis PV, Papachristos DP, Papadoulis GT. Comparison of Three Attractants for the Effective Capture of Xylotrechus chinensis Adults in Multi-Funnel Traps. Insects. 2023 Jul 31;14(8):676. doi: 10.3390/insects14080676. PMID: 37623386; PMCID: PMC10455699. 13: Schlyter F, Birgersson G, Leufvén A. Inhibition of attraction to aggregation pheromone by verbenone and ipsenol : Density regulation mechanisms in bark beetleIps typographus. J Chem Ecol. 1989 Aug;15(8):2263-77. doi: 10.1007/BF01014114. PMID: 24272385. 14: Yuvaraj JK, Roberts RE, Sonntag Y, Hou XQ, Grosse-Wilde E, Machara A, Zhang DD, Hansson BS, Johanson U, Löfstedt C, Andersson MN. Putative ligand binding sites of two functionally characterized bark beetle odorant receptors. BMC Biol. 2021 Jan 26;19(1):16. doi: 10.1186/s12915-020-00946-6. PMID: 33499862; PMCID: PMC7836466. 15: Ikeda N, Arai I, Yamamoto H. Chiral allenylboronic esters as practical reagents for enantioselective carbon-carbon bond formation. Facile synthesis of (-)-ipsenol. J Am Chem Soc. 1986 Feb 1;108(3):483-6. doi: 10.1021/ja00263a020. PMID: 22175465. 16: Fang JX, Du HC, Shi X, Zhang SF, Liu F, Zhang Z, Zu PJ, Kong XB. Monoterpenoid signals and their transcriptional responses to feeding and juvenile hormone regulation in bark beetle Ips hauseri. J Exp Biol. 2021 May 1;224(9):jeb238030. doi: 10.1242/jeb.238030. Epub 2021 May 4. PMID: 33795419. 17: Seybold SJ, Tittiger C. Biochemistry and molecular biology of de novo isoprenoid pheromone production in the Scolytidae. Annu Rev Entomol. 2003;48:425-53. doi: 10.1146/annurev.ento.48.091801.112645. Epub 2002 Jun 4. PMID: 12460936. 18: Miller DR, Asaro C. Predators attracted to combination of bark beetle pheromones and host kairomones in pine forests of southeastern United States. Environ Entomol. 2023 Oct 16;52(5):787-794. doi: 10.1093/ee/nvad076. PMID: 37536266. 19: Shepherd WP, Sullivan BT, Goyer RA, Klepzig KD. Electrophysiological and olfactometer responses of two histerid predators to three pine bark beetle pheromones. J Chem Ecol. 2005 May;31(5):1101-10. doi: 10.1007/s10886-005-4250-4. PMID: 16124235. 20: Queffelec J, Gaudon JM, Miller DR, McKenney JL, Allison JD. Enantiospecific response of Ips avulsus (Coleoptera: Curculionidae: Scolytinae) to ipsdienol depends on semiochemical context. Environ Entomol. 2023 Dec 15;52(6):983-989. doi: 10.1093/ee/nvad090. PMID: 37788443.