Skip to main content
SpringerLink
Log in

Preparation and Characterization of 4-Methoxy Cinnamoyl Glycerol

  • Original Paper
  • Published:
Journal of the American Oil Chemists' Society

Abstract

Glycerol was reacted with 4-methoxy cinnamic acid to prepare the corresponding 4-methoxy cinnamoyl glycerol. The reaction proceeded in toluene under reflux conditions with p-toluenesulfonic acid catalyst. Reaction of equimolar amounts of reactants produced the monoester in 20% yield after 2 h. The product was isolated and characterized by FTIR, mass spectrometry, and NMR techniques. Results of mass spectrometry and NMR experiments showed that the ester linkage formed between the carboxylic acid and the primary hydroxyl of glycerol. The ester displayed strong absorbance between 250 and 350 nm and shows potential as a UV filter in formulations where hydrophilic compounds are advantageous.

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

Similar content being viewed by others

References

  1. Klein K (1995) Encyclopedia of UV absorbers for sunscreen products. Cosmet Toilet 7:47–58

    Google Scholar 

  2. Steinberg DC (1996) Sunscreen encyclopedia regulatory update. Cosmet Toilet 111:77–86

    CAS  Google Scholar 

  3. Freitas ZMF, Machado GM, Dellamora-Oritz GM, Santos EP, Goncalves JCS (2000) Evaluation of phototoxicity of different sunscreens: 1,2,3-propanetriol-1,3-dipalmitoyl-2-p-methoxycinnamoyl and 1,2,3-propanetriol-1,3-dioctanoyl-2-p-methoxycinnamoyl. STP Pharm Sci 10:239–242

    CAS  Google Scholar 

  4. Freitas ZMF, Goncalves JCS, Santos EP, Verganini A (2001) Glyceridic esters of p-methoxycinnamic acid. A new sunscreen of the cinnamate class. Int J Cosmet Sci 23:147–152

    Article  CAS  Google Scholar 

  5. Compton D, Laszlo JA, Berhow MA (2000) Synthesis of ferulate esters. J Am Oil Chem Soc 77:513–519

    Article  CAS  Google Scholar 

  6. Alvarez-Roman R, Barre G, Guy RH, Fessi H (2001) Biodegradable polymer nanocapsules containing a sunscreen agent: preparation and photoprotection. Eur J Pharm Biopharm 52:191–195

    Article  CAS  Google Scholar 

  7. Benson HA (2000) Assessment and clinical implications of absorption of sunscreens across skin. Am J Clin Dermatol 1:217–224

    Article  CAS  Google Scholar 

  8. Janjua NR, Mogensen B, Andersson AM, Petersen JH, Henriksen M, Skakkebaek NE, Wulf HC (2004) Systemic absorption of the sunscreens benzophenone-2, octyl-methoxycinnamate, and 3-(4-methyl-benzylidene) camphor after whole-body topical application and reproductive hormone levels in humans. J Invest Dermatol 123:57–61

    Article  CAS  Google Scholar 

  9. Gervasio GC (1996) Glycerine. In: Hui YH (ed) Bailey’s industrial oil and fat products. Wiley, New York, pp 63–71

    Google Scholar 

  10. Batovska DI, Kishimoto T, Bankova VS, Kamenarska ZG, Ubukata M (2005) Synthesis of some phenylpropenoid monoglycerides via the Mitsunobu protocol. Molecules 10:552–558

    Article  CAS  Google Scholar 

  11. Nohynek GJ, Schaefer H (2001) Benefit and risk of organic ultraviolet filters. Regul Toxicol Pharmacol 33:285–299

    Article  CAS  Google Scholar 

  12. Chatelain E, Gabard B, Surber C (2003) Skin penetration and sun protection factor of five UV filters: effect of the vehicle. Skin Phamacol Appl Skin Physiol 16:28–35

    Article  CAS  Google Scholar 

  13. Holser, RA (2007) Kinetics of cinnamoyl glycerol formation. J Am Oil Chem Soc (in press). doi:10.1007/S11746-007-1189-3

  14. Myher JJ, Marai L, Kuksis A (1974) Identification of monoacyl- and monoalkylglycerols by gas–liquid chromatography–mass spectrometry using polar siloxane liquid phases. J Lipid Res 15:586–592

    CAS  Google Scholar 

  15. Graca J, Pereira H (2000) Suberin structure in potato periderm: glycerol, long-chain monomers, and glyceryl and feruloyl dimers. J Agric Food Chem 48:5476–5483

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to Gregory P. Wylie, University of Georgia, Department of Chemistry for performing the NMR experiments.

Author information

Authors and Affiliations

  1. Richard Russell Agricultural Research Center, Agricultural Research Service, United States Department of Agriculture, 950 College Station Road, Athens, GA, 30605, USA

    R. A. Holser, T. R. Mitchell & D. Himmelsbach

  2. National Center for Agriculture Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 North University Street, Peoria, IL, 61604, USA

    R. E. Harry-O’kuru, S. F. Vaughn & E. Walter

Authors
  1. R. A. Holser
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. R. Mitchell
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. E. Harry-O’kuru
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. F. Vaughn
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. E. Walter
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. D. Himmelsbach
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. A. Holser.

Additional information

Disclaimer

The use of trade, firm, or corporation names in this publication is for the information and convenience of the reader. Such use does not constitute an official endorsement or approval by the United States Department of Agriculture or the Agricultural Research Service of any product or service to the exclusion of others that may be suitable.

About this article

Cite this article

Holser, R.A., Mitchell, T.R., Harry-O’kuru, R.E. et al. Preparation and Characterization of 4-Methoxy Cinnamoyl Glycerol. J Am Oil Chem Soc 85, 347–351 (2008). https://doi.org/10.1007/s11746-008-1197-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-008-1197-y

Keywords

Search

Navigation