Skip to main content
SpringerLink
Log in

Preparation and characterization of inclusion complexes containing fixolide, a synthetic musk fragrance and cyclodextrins

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

AHTN (7-Acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene), commercially known as fixolide or tonalide, is a synthetic fragrance widely used in replace of natural musk odor which is more expensive. It is a popular fragrance material added in the manufacturing of personal care and household products, such as perfumes, soaps, shampoos, detergents, and fabric softeners. AHTN is semivolatile and is degraded under light exposure and high temperature. This work focuses on the complexation of AHTN with cyclodextrins in the effort to stabilize the fragrance material. AHTN was complexed with β-cyclodextrin, methyl (MβCD), and hydroxypropyl (HPβCD) derivatives in the mole ratio 1:1, 1:2, and 1:3 guest:host, and the complexes formed by physical mixing, co-precipitation, kneading, and freeze-drying were analyzed by DSC and FTIR. Percent AHTN included in the complex was also determined by hexane extraction and GC analysis. It was found that no inclusion complex was formed in the physical mixture. When co-precipitation method was performed, only βCD could form inclusion complex with AHTN, while the other two derivatives could not. Using 1:2 AHTN:βCD, no free AHTN was left in the complex as evidenced by DSC and FTIR spectrum. In kneading and freeze-drying methods, complexes could be formed with all CDs tested. However, co-precipitation method with 1:2 AHTN:βCD and kneading method with 1:2 AHTN:MβCD provided the highest complex yield with highest amount of AHTN included in the complex. AHTN in the complex form was more stable against high temperature and UV exposure than its free form.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig 5

Similar content being viewed by others

References

  1. Bender, H.: Production, characterization and application of cyclodextrins. Adv. Biotech. Proc. 6, 31–71 (1986)

    CAS  Google Scholar 

  2. Szejtli, J: Cyclodextrin Technology, Chapters 1 and 5. Kluwer Academic Publishers (1988)

  3. Szente, L., Szejtli, J.: Highly soluble cyclodextrin derivatives: chemistry, properties, and trends in development. Adv. Drug Del. Rev. 36, 17–28 (1999)

    Article  CAS  Google Scholar 

  4. Peck, A.M, Hornbuckle, K.C.: Synthetic musk fragrances in Lake Michigan. Environ. Sci. Technol. 38, 367–372 (2004)

    Article  CAS  Google Scholar 

  5. Rimkus, G.G.: Polycyclic musk fragrances in the aquatic environment. Toxicol. Lett. 111, 37–56 (1999)

    Article  CAS  Google Scholar 

  6. Giordano, F., Novak, C., Moyano, J.R.: Thermal analysis of cyclodextrins and their inclusion compounds. Thermochim. Acta. 380, 123–151 (2001)

    Article  CAS  Google Scholar 

  7. Mura, P., Faucci, M.T., Parrini, P.L., Furlanetto, S., Pinzauti, S.: Influence of the preparation method on the physicochemical properties of ketoprofen–cyclodextrin binary systems. Int. J. Pharm. 179, 117–128 (1998)

    Article  Google Scholar 

  8. Hara, K., Mikuni, K., Hara, K., Hashimoto, H.: Effects of cyclodextrins on deodoration of “Aging Odor”. J. Inclusion Phenom. Macro. Chem. 44, 241–245 (2002)

    Article  CAS  Google Scholar 

  9. Reineccius, T.A, Reineccius, G.A., Peppard, T.L.: Utilization of β-cyclodextrin for improved flavor retention in thermally processed foods. J. Food Sci. 69(1), 58–62 (2004)

    Article  Google Scholar 

  10. Saikosin, R., Tipaporn, L., Pongsawasdi, P.: Formation of inclusion complexes between cyclodextrins and carbaryl and characterization of the complexes. J. Inclusion Phenom. Macro. Chem. 44, 191–196 (2002)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The financial support from Rachadapiseksompote Fund, 90 years CU Fellowship and the support to Starch and Cyclodextrin Research Unit of Chulalongkorn University is appreciated.

Author information

Authors and Affiliations

  1. M.Sc Program in Biotechnology, Chulalongkorn University, Bangkok, 10330, Thailand

    Putcharin Chittiteeranon

  2. Starch and Cyclodextrin Research Unit, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand

    Suganya Soontaros & Piamsook Pongsawasdi

Authors
  1. Putcharin Chittiteeranon
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Suganya Soontaros
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Piamsook Pongsawasdi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Piamsook Pongsawasdi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chittiteeranon, P., Soontaros, S. & Pongsawasdi, P. Preparation and characterization of inclusion complexes containing fixolide, a synthetic musk fragrance and cyclodextrins. J Incl Phenom Macrocycl Chem 57, 69–73 (2007). https://doi.org/10.1007/s10847-006-9219-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-006-9219-6

Keywords

Search

Navigation