lightningscientific
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Isolongifolenone: A Novel Sesquiterpene Repellent of Ticks and Mosquitoes
Just a few months ago the Journal of Medical Entomology published an article on Isolongifolenone. According to the article, it's more effective at
repelling mosquitoes than DEET is and it can be synthed from Terpentine oil on a large scale.
"Isolongifolenone is a natural product that was found
in Humiria balsamifera St. (Aubl.) Hill (Humiriaceae),
a plantcommonlyfound in South America(Da
Silva et al. 2004). Isolongifolenone is odorless and
some of its derivatives have a characteristic woody
smell (Hall 1973, Pickenhagen and Schatkowski 2002,
De Bruyn et al. 2003). Therefore, derivatives of isolongifolenone
have been widely used as fragrances in
cosmetics, perfumes, space sprays, detergents, deodorants,
fabrics, Þbers, and paper products (Curtis et
al. 1971, 1972, 1978, Pickenhagen and Schatkowski
2004). In addition, (Ð)-isolongifolenone inhibits tyrosinase
that is a multifunctional copper-containing
enzyme for melanin biosynthesis in plants and animals
(Choudhary et al. 2003). Also, hydrogenated (Ð)-
isolongifolenone has been used as a bridged core to
prepare a chiral ligand for the estrogen receptor that
could be useful in regulating fertility, preventing, and
treating breast cancer, and for menopausal hormone
replacement (Muthyala et al. 2003).
The previous methods of obtaining isolongifolenone
from turpentine oil (Ranganathan et al. 1970,
Pickenhagen and Schatkowski 2004) were inefÞcient
(Dauben et al. 1969, Lala and Hall 1970, Mihelich and
Eickhoff 1983, McQuillin and Wood 1997) and produced
many unwanted by-products (Prahlad et al.
1964, Shieh et al. 1978, Foricher et al. 1991, Pickenhagen
and Schatkowski 2004). We developed a facile
and efÞcient method (Wang and Zhang 2008, Zhang
et al. 2008) to synthesize isolongifolenone from isolon-
This article reports the results of research only. Mention of trade
names or commercial products in this article is solely for the purpose
of providing speciÞc information and does not imply recommendation
or endorsement by the U.S. Department of Agriculture or the U.S.
Department of Defense for it use.
1 USDAÐARS, Invasive Insect Biocontrol and Behavior Laboratory,
Beltsville Agricultural Research Center-West, Beltsville, MD 20705.
2 Corresponding author, e-mail: aijun.zhang@ars.usda.gov.
3 College of Chemical Engineering, Nanjing Forestry University,
Nanjing, Jiangsu 210037, China.
4 USDAÐARS, Animal Parasitic Diseases Laboratory, Beltsville Agricultural
Research Center-East, Beltsville, MD 20705.
5 U.S. Army Medical Department Center & School, Academy of
Health Sciences, Department of Preventive Health Services, Medical
Zoology Branch, Fort Sam Houston, TX 78234.
gifolene, which is commercially available as a feedstock
in kilogram to ton quantities.
Given the widespread need for naturally occurring
and environmentally benign repellents, our laboratories
have sought to discover new natural chemicals to
fulÞll this need. This report shows the effectiveness of
()-isolongifolenone in deterring feeding of two species
of mosquitoes and repelling two species of ticks of
medical importance....()-Isolongifolenone was prepared as
the major product from ()-isolongifolene (Sigma, St.
Louis, MO). The preparation, using tert-butyl hydroperoxide
as an oxidant, chromium hexacarbonyl as
the catalyst, and acetonitrile and benzene as the solvent,
yielded 90% product with high purity (99%)
in a reaction time of 2 h (Wang and Zhang 2008,
Zhang et al. 2008)."
J. Med. Entomol. 46(1): 100Ð106 (2009)
This is pretty fascinating stuff. I can attach the article if anybody is interested. I would like to make some of this up and test it out, but they
don't go into details of the synthesis.
Does anybody have access to this article?
Wang, S., and A. Zhang. 2008. Facile and effecient synthesis
of isolongifolenone. Org. Prep. Proced. Int. 40: 405Ð410
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Nicodem
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It is made by oxidation of isolongifolene (which is way too expensive), see patents:
US7378557
EP1178105
WO2009012091
EP198351
There are some total syntheses of the above isolongifolene in the literature as well, but I guess those are not particularly interesting to the
members here.
I do not have access to the digital version of OPPI journal.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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matei
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Org. Prep. Proc. Int., 2008, 40, 405
Attachment: 908781055.pdf (513kB)
This file has been downloaded 761 times
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lightningscientific
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Thank you matei for the article. Aldrich wants 97.70 for 1 ml of (− -Isolongifolene. Forget that. I wonder if manganese ammonium alum could oxidize this.... more later.
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donlaszlow
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Or how about silver or copper-oxide? 
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