Research Progress on Synthesis and Application of p-Menthane-3,8-diol

doi:A

Abstract

Abstract: p-Menthane-3, 8-diol (PMD) is a bioactive compound, which is first found in essential oil of leaves of Eucalyptus citriodora and often used as an active composition for perfume, insecticide, and medicine. It is usually synthesized by chemical or biological approaches instead of the direct isolation from the E. citriodora oil. PMD can be synthesized from citronellal through a prins reaction and a hydration, or be transformed from citronellal through a Solanum aviculare suspension culture. It can also be produced from menthol with an oxidation, or synthesized from 2-butenal by a long step reactions with reagents such as MeLi, NaClO2, etc. PMD can be used as repellent, coolant, pharmaceutical, cosmetics, and coatings.

Key words: p-Menthane-3, 8-diol, synthetic process, application

CLC Number:

R284.2

HE Li-zhi, ZHAO Zhen-dong, BI Liang-wu, WANG Peng. Research Progress on Synthesis and Application of p-Menthane-3,8-diol[J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2012, 23(8): 1147-.

References

1 Barasa SS,Ndiege IO,Lwande W,et al.Repellent activities of stereoisomers of p-menthane-3,8-diols against Anopheles gambiae (Diptera:Culicidae).J Med Entomol,39(2002),pp.736–741.
2 Sikinami Y, Hata K,Yasuhara M.Controlled release insect pest repellent.US 5017377.
3 Nishimura H,Kaku K,Nakamura T,et al. Isolation of isopulegol hydrate.Agric Biol Chem,1982,46(1):319-320.
4 Tian YH(田玉红),et al.Extraction and determination of volatile construction in leaves of Eucalyptus citriodora.Chin J Chromatogr(色谱),2005, 23(6): 651-654.
5 Curtis CF,Lines JD,Biolin L,et al.Appropriate Technology in Vector Control: CRC Press, Boca Raton,Florida,1990, 75-92.
6 Zimmerman HE,English J Jr.Stereoisomerism of isopulegol hydrates and some analogous 1,3-diols.J Am Chem Soc, 1953, 75: 2367.
7 Clark BC Jr,Chamblee TS,Iacobucci GA.Rate enhancement in the cyclization of citronellal.J Org Chem,1984, 49:4557-4559.
8 Yuasa Y,Tsuruta H,Yuasa Y.A practical and efficient synthesis of p-menthane-3,8-diols. Org Proc Res Dev,2000,4 (3):159–161.
9 Vaněk T,et al.Biotransformation of citronellal by Solanum aviculare suspension cultures: preparation of p-menthane-3,8-diols and determination of their absolute configurations. J Nat Prod, 2003, 66 (9): 1239–1241.
10 Hong BC,et al.Enantioselective organocatalytic [3+3] cycloaddition of α,β-unsaturated aldehydes and application to the asymmetric synthesis of (–)-isopulegol hydrate and (–)-cubebaol.Org. Lett, 2006,8(11):2217-2220.
11 Maki S,Konno K,Takayama H.Selective oxidation of terminal isopropyl groups to tertiary alcohols by electrochemical methodology. Tetrahedron Lett,1997,38(40):7067-7070.
12 Atta-ur-Rahman,et al.Fungal transformation of (1R,2S,5R)-(–)-menthol by Cephalosporium aphidicola.J Nat Prod, 1998, 61(11):1340-1342.
13 Asakawa Y,et al.Preparation of biologically active substances and animal and microbial metabolites from menthols,cineoles and kauranes.Phytochemistry:1988,27(12):3861-3869.
14 Lusiak D,Antoni S.Method for manufacturing 3,8-p-menthandiol.PL 163209,1994-2-28.
15 Strickman D.PMD (p-Menthàne-3,8-diol) and Quwenling.Insect Repellents:Principles, Methods,and Uses:2007,(20): 347~351.
16 Nishimura H,Kaku K,Nakamura T.Allelopathic substances,(±)-p-Menthane-3,8-diols isolated from Eucalyptus citriodora.Agric Biol Chem.,1982,46:319
17 Nishimura H, Kobayashi K, Unno T, et al. Repellent for Injurious Organism. JP60199804, 1985-10-09.
18 Lett BD, Kraus HS. PCT Int. Appl. Insect Repellent. WO9202136, 1992-02-20.
19 Moore SJ,Lenglet A,Hill N.Plant-based insect repellents.In: M. Debboun, S. Frances and D. Strickman, Editors, Insect Repellents: Principles, Methods, and Uses, CRC Press, Boca Raton,2007,3-29.
20 Scott P.Carroll,Jenella Loye.PMD,a registered botanical mosquito repellent with deet-like efficacy.J Am Mosq Control Assoc, 2006,22(3):507-514.
21 Lin XY(林翔云).Plant oil’s repellent for creatures.Chin J Hyg Insect & Equip(中华卫生杀虫药械).2009,15(5): 430~431.
22 Shiroyama K,Sawano K,Ohta H.Cool feeling composition,US6328982,2001-12-11.
23 Leffingwell JC.Cool without menthol & cooler than menthol and cooling compounds as insect repellents, Reprinted from Handbook of cosmetic science and technology,3rd ed.,Andre′ O.Barel,Marc Paye,Howard I.Maibach,Eds., Informa Healthcare (Pub.),New York,2009.
24 Douglas Clark P.(保罗?道格拉斯?克拉克).The antivirus composition containing p-menthane-3,8-diol(含有3,8-松油二醇的抗病毒组合物). CN 200580015067.1,2007-05-02.
25 Hattori R,Fukuma T.Hair growth stimulants.US 6194468,2001-2-27.
26 Johansson R.Mathias.(乔纳森 R?马泰尔斯).The composition of innocuity coatings, its method of application and usage in against bioadhesives(无毒涂料组合物、其使用方法和被保护不附着生物附着物的物品).CN01813653.2, 2003-9-24.

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