Food Biophysics

, Volume 5, Issue 3, pp 193–202 | Cite as

Relationship Between Molecular Structure and Thermo-mechanical Properties of Candelilla Wax and Amides Derived from (R)-12-Hydroxystearic Acid as Gelators of Safflower Oil

  • Jorge F. Toro-Vazquez
  • Juan Morales-Rueda
  • V. Ajay Mallia
  • Richard G. Weiss
ORIGINAL ARTICLE

Abstract

In this research, we studied the relationship between the molecular structure of (R)-12-hydroxyoctadecanamide, (R)-N-propyl-12-hydroxyoctadecanamide, and (R)-N-octadecyl-12-hydroxyoctadecanamide and the thermo-mechanical properties of their 2% (wt/wt) organogels developed using safflower oil high in oleic acid (HOSFO) as the liquid phase. Candelilla wax (CW), a well-known edible gelling additive whose main component is hentriacontane, also was studied for comparative purposes. The results obtained show that the attractive interactions (i.e., hydrogen bonding and dipolar interactions) between amide groups and between hydroxyl groups present in the amides resulted in organogels with higher melting temperature, heat of melting, and crystallization parameters than those found in the CW organogel. The rheological parameters associated to the strength of the amide or CW-based gels developed in HOSFO (i.e., yield stress and elastic modulus) seem to be associated with the nature of amide groups (i.e., primary or secondary amide) and the increase in the length of the self-assembly molecular unit (i.e., L value determined by X-ray diffraction) and therefore to the extent of London dispersion forces along the hydrocarbon chain. The creep and recovery measurements allowed an evaluation among the internal structures of the different organogels and demonstrated that independent of the hydrogen bonding and dipolar interaction provided by the amide and the hydroxyl groups, the increase in the hydrocarbon chain length results in higher organogel resistance to deformation and higher instant recovery capacity. However, the stabilization of the self-assembly unit through polar groups (i.e., –CONH2 in HOA) reduces organogel elasticity but provides a higher extended recovery capacity. The results reported in this investigation showed some relationships between gelator structure and the thermo-mechanical properties of low-molecular-mass organic gelator amides. Our long-term objective is to understand the organogelation process to eventually develop trans-free vegetable oil-based food products with novel textures for the consumers.

Keywords

Organogels Hydroxystearic acid Candelilla wax Thixotropy Creep and compliance 

References

  1. 1.
    D.J. Abdallah, R.G. Weiss, n-Alkanes gel n-alkanes (and many other organic liquids). Langmuir. 16, 352–355 (2000). doi:10.1021/1a990795r CrossRefGoogle Scholar
  2. 2.
    E. Ostuni, P. Kamaras, R.G. Weiss, Novel X-ray method for in situ determination of gelator strand structure: polymorphism of cholesteryl anthraquinone-2-carboxylate. Angew. Chem. Int. Ed Engl. 35, 1324–1326 (1996). doi:10.1002/anie.199613241 CrossRefGoogle Scholar
  3. 3.
    A. Bot, G.M. Agterof, Structuring of edible oils by mixtures of γ-oryzanol with β-sitosterol or related phytosterols. J. Am. Oil Chem. Soc. 83, 513–521 (2006). doi:10.1007/s11746-006-1234-7 CrossRefGoogle Scholar
  4. 4.
    R. Kumar, O.P. Katare, Lecithin organogels as a potential phospholipid-structured system for topical drug delivery: a review. AAPS PharmSciTech. 6, E298–E310 (2005). doi:10.1208/pt060240 CrossRefGoogle Scholar
  5. 5.
    S. Murdan, G. Gregoriadis, A.T. Florence, Novel sorbitan monostearate organogels. J. Phar. Sci. 88, 608–614 (2000). doi:10.1021/js980342r CrossRefGoogle Scholar
  6. 6.
    D.J. Abdallah, L. Lu, R.G. Weiss, Thermoreversible organogels from alkane gelators with one heteroatom. Chem. Mater. 11, 2907–2911 (1999). doi:10.1021/cm9902826 CrossRefGoogle Scholar
  7. 7.
    H. Takeno, T. Mochizuki, K. Yoshiba, S. Kondo, T. Dobashi, Self-assembling structures and sol–gel transition of optically active and racemic 12-hydroxystearic acids in organic solvents. Progr. Colloid. Polym. Sci. 136, 47–54 (2009). doi:10.1007/2882_2009_7 Google Scholar
  8. 8.
    V.A. Mallia, M. George, D.L. Blair, R.G. Weiss, Robust organogels from nitrogen-containing derivatives of (R)-12-hydroxystearic acid as gelators: comparisons with gels from stearic acid derivatives. Langmuir. 25, 8615–8625 (2009). doi:10.1021/la8042439 CrossRefGoogle Scholar
  9. 9.
    P. Terech, R.G. Weiss, Low molecular mass gelators of organic liquids and the properties of their gels. Chem. Rev. 97, 3133–3159 (1997). doi:10.1021/cr9700282 CrossRefGoogle Scholar
  10. 10.
    R.G. Weiss, P. Terech, Molecular Gels: Materials with Self-Assembled Fibrillar Networks (Springer, Dordrecht, 2006), pp. 449–551Google Scholar
  11. 11.
    J.F. Toro-Vazquez, J.A. Morales-Rueda, E. Dibildox-Alvarado, M.A. Charó-Alonso, M. Alonzo-Macías, M.M. González-Chávez, Development of organogels with candelilla wax and safflower oil with high triolein content. J. Am. Oil Chem. Soc. 84, 989–1000 (2007). doi:10.1007/s11746-007-1139-0 CrossRefGoogle Scholar
  12. 12.
    J.A. Morales-Rueda, E. Dibildox-Alvarado, M. Charó-Alonso, R.G. Weiss, J.F. Toro-Vazquez, Thermo-mechanical properties of candelilla wax and dotriacontane organogels in safflower oil. Europ. J. Lipid. Sci. Technol. 111, 207–215 (2009). doi:10.1002/ejlt.200810174 CrossRefGoogle Scholar
  13. 13.
    J.A. Morales-Rueda, E. Dibildox-Alvarado, M.A. Charó-Alonso, J.F. Toro-Vazquez, Rheological properties of candelilla wax and dotriacontane organogels measured with a true-gap system. J. Am. Oil Chem. Soc. 86, 765–772 (2009). doi:10.1007/s11746-009-1414-3 CrossRefGoogle Scholar
  14. 14.
    M. Dolz, M.J. Hernández, J. Delegido, Creep and recovery experimental investigation of low oil content food emulsions. Food Hydrocolloids. 22, 421–427 (2008). doi:10.1016/j.foodhyd.2006.12.011 CrossRefGoogle Scholar
  15. 15.
    D.J. Abdallah, S.A. Sirchio, R.G. Weiss, Hexatriacontane organogels. The first determination of the conformation and molecular packing of a low-molecular-mass organogelator in its gelled state. Langmuir. 16, 7558–7561 (2000). doi:10.1021/la000730k CrossRefGoogle Scholar
  16. 16.
    J.F. Steffe, Rheological Methods in Food Process Engineering, 2nd edn. (Freeman, East Lansing, 1996), pp. 304–310Google Scholar
  17. 17.
    The AOCS Lipid Library. Anandamide, oleamide and other simple fatty amides structure, occurrence, biology and analysis. http://lipidlibrary.aocs.org/Lipids/amides/index.htm
  18. 18.
    J. Joseph, B. Niggemann, K.S. Zaenker, F. Entschladen, Anandamide is an endogenous inhibitor for the migration of tumor cells and T lymphocytes. Cancer Immunol. Immunother. 53, 723–728 (2004). doi:10.1007/s00262-004-0509-9 CrossRefGoogle Scholar
  19. 19.
    S. Huitrón-Reséndiz, L. Gombart, B.F. Cravatt, S.J. Henriksen, Effect of oleamide on sleep and its relationship to blood pressure, body temperature, and locomotor activity in rats. Exp. Neurol. 72, 235–243 (2001). doi:10.1006/exnr.2001.7792 CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Jorge F. Toro-Vazquez
    • 1
    • 3
  • Juan Morales-Rueda
    • 1
  • V. Ajay Mallia
    • 2
  • Richard G. Weiss
    • 2
  1. 1.Facultad de Ciencias Químicas-CIEPUniversidad Autónoma de San Luis PotosíSan Luis PotosíMéxico
  2. 2.Department of ChemistryGeorgetown UniversityWashingtonUSA
  3. 3.Facultad de Ciencias Químicas-CIEPZona UniversitariaSan Luis PotosíMéxico

Personalised recommendations