Skip to main content
SpringerLink
Log in

Use of cyclodextrins as a cosmetic delivery system for fragrance materials: Linalool and benzyl acetate

  • Published:
AAPS PharmSciTech Aims and scope Submit manuscript

Abstract

The aim of this study was to increase the stability and water solubility of fragrance materials, to provide controlled release of these compounds, and to convert these substances from liquid to powder form by preparing their inclusion complexes with cyclodextrins (CDs). For this purpose, linalool and benzyl acetate were chosen as the fragrance materials. The use of β-cyclodextrin (βCD) and 2-hydroxypropyl-β-cyclodextrin (2-HPβCD) for increasing the solubility of these 2 fragrance materials was studied. Linalool and benzyl acetate gave a B-type diagram with βCD, whereas they gave an AL-type diagram with 2-HPβCD. Therefore, complexes of fragrance materials with 2-HPβCD at 1:1 and 1:2 molar ratios (guest:host) were prepared. The formation of inclusion complexes was confirmed using proton nuclear magnetic resonance (1H-NMR) spectroscopy and circular dichroism spectroscopy. The results of the solubility studies showed that preparing the inclusion complex with 2-HPβCD at a 1:1 molar ratio increased the solubility of linalool 5.9-fold and that of benzyl acetate 4.2-fold, whereas the complexes at a 1:2 molar ratio increased the solubility 6.4- and 4.5-fold for linalool and benzyl acetate, respectively. The stability and in vitro release studies were performed on the gel formulations prepared using uncomplexed fragrance materials or inclusion complexes of fragrance materials at a 1:1 molar ratio. It was observed that the volatility of both fragrance materials was decreased by preparing the inclusion complexes with 2-HPβCD. Also, in vitro release data indicated that controlled release of fragrances could be possible if inclusion complexes were prepared.

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

Similar content being viewed by others

References

  1. Healy LL. Gelled emollient systems for controlled fragrance release and enhanced product performance.Cosmet Toilet. 2002;117:47–54.

    CAS  Google Scholar 

  2. Matsuda H, Ito K, Fujiwara Y, et al. Complexation of various fragrance materials with 2-hydroxypropyl-β-cyclodextrin.Chem Pharm Bull (Tokyo). 1991;39:827–830.

    CAS  Google Scholar 

  3. Tanaka M, Matsuda H, Sumiyoshi H, et al. 2-Hydroxypropylated cyclodextrins as a sustained release carrier for fragrance materials.Chem Pharm Bull (Tokyo). 1996;44:416–420.

    CAS  Google Scholar 

  4. Amann M, Dressnandt G. Solving problems with cyclodextrins in cosmetics.Cosmet Toilet. 1993;108:90–95.

    CAS  Google Scholar 

  5. Loftsson T. Cyclodextrins in skin delivery.Cosmet Toilet. 2000;115:59–66.

    CAS  Google Scholar 

  6. Del Valle EMM. Cyclodextrins and their uses: a review.Process Biochem. 2004;39:1033–1046.

    Article  Google Scholar 

  7. Motwani M, Zatz JL. Applications of cyclodextrins in skin products.Cosmet Toilet. 1997;112:39–47.

    CAS  Google Scholar 

  8. Loftsson T, Másson M. Cyclodextrins in topical drug formulations: theory and practice.Int J Pharm. 2001;225:15–30.

    Article  PubMed  CAS  Google Scholar 

  9. Másson M, Loftsson T, Másson G, Stefánsson E. Cyclodextrins as permeation enhancers: some theoretical evaluations and in vitro testing.J Control Release. 1999;59:107–118.

    Article  PubMed  Google Scholar 

  10. Loftsson T, Ólafsdóttir BJ, Bodor N. The effects of cyclodextrins on transdermal delivery of drugs.Eur J Pharm Biopharm. 1991;37:30–33.

    CAS  Google Scholar 

  11. Rogers K. Controlled release technology and delivery systems.Cosmet Toilet. 1999;114:53–60.

    Google Scholar 

  12. Buschmann HJ, Schollmeyer E. Applications of cyclodextrins in cosmetic products: a review.J Cosmet Sci. 2002;53:185–191.

    PubMed  CAS  Google Scholar 

  13. Duchene D, Wouessıdjewe D. Physicochemical characteristics and pharmaceutical uses of cyclodextrin derivatives, Part I.Pharm Technol. 1990;14:26–34.

    CAS  Google Scholar 

  14. Çelebi N, Kışlal Ö, Tarımcı N. The effect of β-cyclodextrin and penetration additives on the release of naproxen from ointment bases.Pharmazie. 1993;48:914–917.

    Google Scholar 

  15. Anadolu RY, Sen T, Tarımcı N, Birol A, Erdem C. Improved efficacy and tolerability of retinoic acid in acne vulgaris: a new topical formulation with cyclodextrin complex.J Eur Acad Dermatol Venereol. 2004;18:416–421.

    Article  PubMed  CAS  Google Scholar 

  16. Matsuda H, Ito K, Taki A, Uejima O, inventors. Shiseido Company Ltd., assignee. Cosmetic composition containing inclusion product with hydroxyalkylated cyclodextrin. US patent 5 447 920. September 5, 1995.

  17. Higuchi T, Connors KA. Phase-solubility techniques.Adv Anal Chem Instrum. 1965;4:117–210.

    CAS  Google Scholar 

  18. Ajısaka N, Hara K, Mikuni K, Hara K, Hashimoto H. Effects of branched cyclodextrins on the solubility and stability of terpenes.Biosci Biotechnol Biochem. 2000;64:731–734.

    Article  PubMed  Google Scholar 

  19. Lu CS, Hu CJ, Yu Y, Meng QJ. The inclusion compounds of β-cyclodextrin with 4-substituted benzoic acid and benzaldehyde drugs studied by proton nuclear magnetic resonance spectroscopy.Chem Pharm Bull (Tokyo). 2000;48:56–59.

    CAS  Google Scholar 

  20. Choi HS, Knevel AM, Chang C. Molecular complexation: β-cyclodextrin and benzaldehyde inclusion complex.Pharm Res. 1992;9:690–693.

    Article  PubMed  CAS  Google Scholar 

  21. Anguıano-Igea S, Otero-Espınar FJ, Vıla-Jato JL, Blanco-Mendez J. Interaction of clofibrate with cyclodextrin in solution: phase solubility1H NMR and molecular modelling studies.Eur J Pharm Sci. 1997;5:215–221.

    Article  Google Scholar 

  22. Frank SG. Inclusion compounds.J Pharm Sci. 1975;64:1585–1604.

    Article  PubMed  CAS  Google Scholar 

  23. Szejtli J.Cyclodextrin Technology. Dordrecht, The Netherlands: Kluwer Academic Publishers; 1988.

    Google Scholar 

  24. Bekers O, Uıjtendaal EV, Beıjnen JH, Bult A, Underberg WJM. Cyclodextrins in the pharmaceutical field.Drug Dev Ind Pharm. 1991;17:1503–1549.

    Article  CAS  Google Scholar 

  25. Duchene D, Wouessidjewe D, Poelman MC. Dermal uses of cyclodextrins and derivatives. In: Duchêne D, ed.New Trends in Cyclodextrins and Derivatives. Paris, France: Editions de Sante; 1991:302.

    Google Scholar 

  26. Frömming KH, Szejtli J.Cyclodextrins in Pharmacy. Dordrecht, The Netherlands: Kluwer Academic Publishers; 1994.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Pharmaceutical Technology, Ankara University, Faculty of Pharmacy, 06100, Ankara, Turkey

    Ulya Numanoğlu, Tangül Şen & Nilüfer Tarimci

  2. Department of Pharmacognosy, Ankara University, Faculty of Pharmacy, 06100, Ankara, Turkey

    Murat Kartal

  3. Department of Biopharmaceutical Sciences, University of Illinois at Chicago, 60612, Chicago, IL

    Otilia M. Y. Koo & Hayat Önyüksel

Authors
  1. Ulya Numanoğlu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tangül Şen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nilüfer Tarimci
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Murat Kartal
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Otilia M. Y. Koo
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Hayat Önyüksel
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nilüfer Tarimci.

Additional information

Published: October 19, 2007

Rights and permissions

Reprints and permissions

About this article

Cite this article

Numanoğlu, U., Şen, T., Tarimci, N. et al. Use of cyclodextrins as a cosmetic delivery system for fragrance materials: Linalool and benzyl acetate. AAPS PharmSciTech 8, 85 (2007). https://doi.org/10.1208/pt0804085

Download citation

  • Received:

  • Revised:

  • Accepted:

  • DOI: https://doi.org/10.1208/pt0804085

Keywords

Search

Navigation