Molecular Gels–Barriers, Advances, and Opportunities
Corresponding Author
Michael A. Rogers
Associate Professor and Tier II Canada Research Chair in Food Nanotechnology, University of Guelph, Guelph, Ontario, Canada
Search for more papers by this authorCorresponding Author
Michael A. Rogers
Associate Professor and Tier II Canada Research Chair in Food Nanotechnology, University of Guelph, Guelph, Ontario, Canada
Search for more papers by this authorMiguel Ângelo Parente Ribeiro Cerqueira
Search for more papers by this authorLorenzo Miguel Pastrana Castro
Search for more papers by this authorAbstract
Molecular gels are predominantly liquid systems, which self-recognize and assemble via microscopic separation, nucleation and crystal growth resulting in a continuous self-assembled fibrillar network (SAFiNs). The aggregation of molecular gelators into SAFiNs requires a meticulous balance between contrasting parameters of solubility and those controlling epitaxial growth. Self-assembly is programmed with the position and type of functional group (molecular synthons) that coordinate non-covalent interactions. Unfortunately, the complex interplay between gelator structure and concentration, solvent chemistry, and supersaturation on self-assembly continues to impede the rational design of molecular gels, and researchers still rely on serendipitous discovery. As the food industry pushes to create zero waste, molecular refinement will produce a steady supply of precursor molecules ideally suited for biorefinery, which has already proven successful in designing new oil structuring compounds.Patience and persistence are required because research is still needed to fill in numerous fundamental knowledge gaps before these technologies can be applied to the food supply chain.
References
- Abbott , S. ( 2020 ). Solubility, similarity, and compatibility: A general-purpose theory for the formulator . Current Opinion in Colloid & Interface Science 48 : 65 – 76 .
- Abraham , S. , Lan , Y. , Lam , R.S.H. , Grahame , D.A.S. , Kim , J.J.H. , Weiss , R.G. , and Rogers , M.A. ( 2012 ). Influence of positional isomers on the macroscale and nanoscale architectures of aggregates of racemic hydroxyoctadecanoic acids in their molecular gel, dispersion, and solid states . Langmuir 28 : 4955 – 4964 .
- AlHassawi , F. and Rogers , M.A. ( 2013 ). Ternary phase diagram of B-sitosterol, G-oryzanol and canola oil . Journal of the American Oil Chemists Society 90 : 1533 – 1540 .
- Basrur , V.R. , Guo , J. , Wang , C. , and Raghavan , S.R. ( 2013 ). Synergistic gelation of silica nanoparticles and a sorbitol-based molecular gelator to yield highly-conductive free-standing gel electrolytes veidhes . ACS Applied Materials & Interfaces 5 : 262 – 267 .
- Bonnet , J. , Suissa , G. , Raynal , M. , and Bouteiller , L. ( 2014 ). Organogel formation rationalized by Hansen solubility parameters: Dos and don'ts . Soft Matter 10 : 3154 – 3160 .
- Bonnet , J. , Suissa , G. , Raynal , M. , and Bouteiller , L. ( 2015 ). Organogel formation rationalized by Hansen solubility parameters: influence of gelator structure . Soft Matter 11 ( 11 ): 2308 – 2312 .
- Bot , A. and Agterof , W.G.M. ( 2006 ). Structuring of edible oils by mixtures of γ-Oryzanol with β- sitosterol or related phytosterols . Journal of the American Oil Chemical Society 83 : 513 – 521 .
- Bot , A. , den Adel , R. , and Roijers , E.C. ( 2008 ). Fibrils of gamma-Oryzanol plus beta-sitosterol in edible oil organogels . Journal of the American Oil Chemists Society 85 ( 12 ): 1127 – 1134 .
- Bot , A. , Gilbert , E.P. , Bouwman , W.G. , Sawalha , H. , den Adel , R. , Garamus , V.M. , Venema , P. , van der Linden , E. , and Flöter , E. ( 2012 ). Elucidation of density profile of self-assembled sitosterol + oryzanol tubules with small-angle neutron scattering . Faraday Discussion 158 : 223 – 238 .
- Buitimea-Cantúa , G.V. , Serna-Saldívar , S.O. , Pérez-Carrillo , E., Silva , T.J. , Barrera-Arellano , D. , and Buitimea-Cantúa , N.E. ( 2021 ). Effect of quality of carnauba wax (Copernica cerífera) on microstructure, textural, and rheological properties of soybean oil-based organogels . LWT 136 : 110267 .
- Callau , M. , Sow-Kébé , K. , Nicolas-Morgantini , L. , and Fameau , A.L. ( 2020 ). Effect of the ratio between behenyl alcohol and behenic acid on the oleogel properties . Journal of Colloid and Interface Science 560 : 874 – 884 .
- Capitani , D. , Segre , A.L. , Dreher , F., and Anzeigen , A. ( 1996 ). Multinuclear NMR investigation of phosphatidylcholine organogels . The Journal of Physical Chemistry 100 ( 37 ): 15211 – 15217 .
- Chapman , R. , Danial , M. , Koh , M.L., Jolliffe , K.A. , and Perrier , S. ( 2012 ). Design and properties of functional nanotubes from the self-assembly of cyclic peptide templates . Chemical Society Reviews 41 ( 18 ): 6023 – 6041 .
- Chen , L. , Corradini , M.G. , and Rogers , M.A. ( 2015 ). Self-assembly of 12-hydroxystearic acid molecular gels in mixed solvent systems rationalized using hansen solubility parameters . Colloid & Polymer Science 293 : 975 – 983 .
- Chivers , P.R.A. and Smith , D.K. ( 2019 ). Shaping and structuring supramolecular gels . Nature Reviews Materials 4 ( 7 ): 463 – 478 .
- Co , E. and Marangoni , A.G. ( 2013 ). The formation of a 12Hydroxystearic acid/vegetable oil organogel under shear and thermal fields . Journal of the American Oil Chemical Society 90 : 529 – 544 .
- Daniel , J. and Rajasekharan , R. ( 2003 ). Organogelation of plant oils and hydrocarbons by long-chain saturated FA, fatty alcohols, wax esters, and dicarboxylic acids . Journal of the American Oil Chemists' Society 80 ( 5 ): 417 – 421 .
- Dassanayake , L.S.K. , Kodali , D.R. , Ueno , S. , and Sato , K. ( 2009 ). Physical properties of rice bran wax in bulk and organogels . Journal of the American Oil Chemical Society 86 : 1163 – 1173 .
- De La Peña-Gil , A. , Toro-Vazques , J.F. , and Rogers , M.A. ( 2016 ). Simplifying hansen solubility parameters for complex edible fats and oils . Food Biophysics 11 : 283 – 291 .
-
den Adel , R.
,
Heussen , P.C.M.
, and
Bot , A.
(
2010
)
Effect of water on self-assembled tubules in β-sitosterol + γ-oryzanol-based organogels
.
Journal of Physics: Conference Series
,
247
,
012025
.
10.1088/1742-6596/247/1/012025 Google Scholar
- Dey , T. , Kim , D.A. , and Marangoni , A.G. ( 2011 ). Edible oleogels: Structure and health implications . In: Ethylcellulose oleogels (ed. A.G. and N. ), 295 – 311 . Urbana, IL : AOCS Press .
- Diehn , K.K. , Oh , H. , Hashemipour , R. , Weiss , R.G. , and Raghavan , S.R. ( 2014a ). Insights into organogelation and its kinetics from hansen solubility parameters. Toward a priori predictions of molecular gelation . Soft Matter 10 ( 15 ): 2632 – 2640 .
- Diehn , K.K. , Oh , H. , Hashemipour , R., Weiss , R.G. , and Raghavan , S.R ( 2014b ). The physical chemistry of molecular gels: Insights into self-assembly-based organogelation and its kinetics via hansen solubility parameters . Soft Matter 10 : 2632 – 2640 .
- Dong , L. , Lv , M. , Gao , X., Zhang , L. , Rogers , M. , Cao , Y. , and Lan , Y. ( 2020 ). In vitro gastrointestinal digestibility of phytosterol oleogels: Influence of self-assembled microstructures on emulsification efficiency and lipase activity . Food & Function 11 ( 11 ): 9503 – 9513 .
- Draper , E.R. and Adams , D.J. ( 2017 ). Low-molecular-weight gels: the state of the art . Chem 3 ( 3 ): 390 – 410 .
- Duval , F.P. , van Duynhoven , J.P.M. , and Bot , A. ( 2006 ). Practical implications of the phasecompositional assessment of lipid-based food products by time-domain NMR . Journal of the American Oil Chemists Society 83 : 905 – 912 .
- Engberg , O. , Kováčik , A. , Pullmannová , P., Juhasčik , M. , Opálka , L. , Huster , D. , and Vávrová , K. ( 2020 ). The sphingosine and acyl chains of ceramide [NS] show very different structure and dynamics that challenge our understanding of the skin barrier . Angewandte Chemie International Edition 59 ( 40 ): 17383 – 17387 .
- Fabri , D. , Guan , J. , and Cesàro , A. ( 1998 ). Crystallisation and melting behaviour of poly (3-hydroxybutyrate) in dilute solution: Towards an understanding of physical gels . Thermochimica Acta 321 ( 1 ): 3 – 16 .
- Flory , P.J. ( 1974 ). Introductory lecture . Faraday Discussions 57 : 7 – 18 .
- Gandolfo , F. , Bot , A. , and Floter , E. ( 2004 ). Structuring of edible oils by long-chain FA, fatty alcohols, and their mixtures . Journal of the American Oil Chemists' Society 81 : 1 – 6 .
- Gao , J. , Wu , S. , and Rogers , M.A. ( 2012 ). Harnessing Hansen solubility parameters to predict organogel formation . Journal of Materials Chemistry 22 : 12651 – 12658 .
- Goodrich , J.D. and Winter , W.T. ( 2007 ). Alpha-chitin nanocrystals prepared from shrimp shells and their specific surface area measurement . Biomacromolecules 8 ( 1 ): 252 – 257 .
- Grahame , D.A.S. , Olauson , C. , Lam , R.S.H., Pedersen , T. , Borondics , F. , Abraham , S. , Weiss , R.G. , and Rogers , M.A. ( 2011 ). Influence of chirality on the modes of self-assembly of 12-hydroxystearic acid in molecular gels of mineral oil . Soft Matter 7 : 7359 – 7365 .
- Grassi , S. , Carretti , E. , Dei , L. , Branham , C.W. , Kahr , B. , and Weiss , R.G. ( 2011 ). D-Sorbitol, a structurally simple, low molecular-mass gelator . New Journal of Chemistry 35 : 445 – 452 .
- Gronwald , O. and Shinkai , S. ( 2001a ). ‘Bifunctional’ sugar-integrated gelators for organic solvents and water—on the role of nitro-substituents in 1-O-methyl-4,6-O-(nitrobenzylidene)-monosaccharides for the improvement of gelation ability . Journal Chemical Society Perkin Trans 2 2001, 1933 – 1937 .
-
Gronwald , O.
and
Shinkai , S.
(
2001b
).
Sugar-integrated gelators of organic solvents
.
Chemistry – A European Journal
7
(
20
):
4328
–
4334
.
10.1002/1521-3765(20011015)7:20<4328::AID-CHEM4328>3.0.CO;2-S CAS PubMed Web of Science® Google Scholar
- E.A. Grulke (ed) ( 2005 ). Solubility Parameter Values , 4e . New York : John Wiley & Sonds .
- Gu , C.-H. , Li , H. , Gandhi , R.B. , and Raghavan , K. ( 2004 ). Grouping solvents by statistical analysis of solvent property parameters: implication to polymorph screening . International Journal of Pharmaceutics 283 : 117 – 125 .
- Guo , S. , Lv , M. , Chen , Y., Hou , T. , Zhang , Y. , Huang , Z. , Cao , Y. , Rogers , M. , and Lan , Y. ( 2020a ). Engineering water-induced ceramide/lecithin oleogels: Understanding the influence of water added upon pre-and post-nucleation . Food & Function 11 : 2048 – 2057 .
- Guo , S. , Song , M. , Gao , X., Dong , L. , Hou , T. , Lin , X. , Tan , W. , Cao , Y. , Rogers , M. , and Lan , Y. ( 2020b ). Assembly pattern of multicomponent supramolecular oleogel composed of ceramide and lecithin in sunflower oil: Self-assembly or self-sorting? Food & Function 11 ( 9 ): 7651 – 7660 .
- Hansen , C. and Smith , A.L. ( 2004 ). Using Hansen solubility parameters to correlate solubility of C60 fullerene in organic solvents and in polymers . Carbon 42 : 1591 – 1597 .
- Hughes , N.E. , Marangoni , A.G. , Wright , A.J. , Rogers , M. , and Rush , J. ( 2009 ). Potential food applications of edible oil organogels . Trends in Food Science & Technology 20 ( 10 ): 470 – 480 .
- Hwang , H.-S. , Singh , M. , Bakota , E.L., Winkler-Moser , J.K. , Kim , S. , and Liu , S.X ( 2013 ). Margarine from organogels of plant wax and soybean oil . Journal of the American Oil Chemists Society 90 : 1705 – 1712 .
- Jadhav , R.S. , Vemula , P.K. , Kumar , R. , Raghavan , S.R. , and John , G. ( 2010 ). Sugar-derived phase-selective molecular gelators as model solidifiers for oil spills . Angewandte Chemie 49 : 7695 – 7698 .
- Jang , A. , Bae , W. , Hwang , H.S., Lee , H.G. , and Lee , S. ( 2015 ). Evaluation of canola oil oleogels with candelilla wax as an alternative to shortening in baked goods . Food Chemistry 187 : 525 – 529 .
- Jiang , Q. , Du , L. , Li , S., Liu , Y. , and Meng , Z. ( 2021 ). Polysaccharide-stabilized aqueous foams to fabricate highly oil-absorbing cryogels: Application and formation process for preparation of edible oleogels . Food Hydrocolloids 120 : 106901 .
- Jiang , Q. , Li , P. , Ji , M. , Du , L. , Li , S. , Liu , Y. , and Meng , Z. ( 2022 ). Synergetic effects of water-soluble polysaccharides for intensifying performances of oleogels fabricated by oil-absorbing cryogels . Food Chemistry 372 : 131357 .
- John , G. , Vijai Shankar , B. , Jadhav , S.R. , and Vemula , P.K. ( 2010 ). Biorefinery: a design tool for molecular gelators . Langmuir 26 ( 23 ): 17843 – 17851 .
- John , G. , Zhu , G. , Li , J. , and Dordick , J.S. ( 2006 ). Enzymatically derived sugar-containing self-assembled organogels with nanostructured morphologies . Angewandte Chemie International Edition 45 ( 29 ): 4772 – 4775 .
- Kaszynska , J. , Lapinski , A. , Bielejewski , M., Luboradzki , R. , and Tritt-Goc , J. ( 2012 ). On the relation between the solvent parameters and the physical properties of methyl-4,6-O-benzylidene-α-d-glucopyranoside organogels . Tetrahedron 68 : 3803 – 3810 .
- Lam , R. , Quaroni , L. , Pederson , T. , and Rogers , M.A. ( 2010 ). A molecular insight into the nature of crystallographic mismatches in self-assembled fibrillar networks under non-isothermal crystallization conditions . Soft Matter 6 : 404 – 408 .
- Lam , R. , Rogers , M.A. , and Marangoni , A.G. ( 2009 ). Thermo-mechanical method for the determination of the fractal dimension of fat crystal networks . Journal of Thermal Analysis and Calorimetry 98 ( 1 ): 7 – 12 .
- Lan , Y. , Corradini , M.G. , Liu , X., May , T.E. , Borondics , F. , Weiss , R.G. , and Rogers , M.A. ( 2014a ). Comparing and correlating solubility parameters governing the self-assembly of molecular gels using 1, 3:2,4-dibenzylidenesorbitol as the gelator . Langmuir 30 ( 47 ): 14128 – 14142 .
- Lan , Y. , Corradini , M.G. , and Rogers , M.A. ( 2014b ). Do molecular gelators cluster in hansen space? Crystal Growth & Design 14 : 4811 – 4818 .
- Lan , Y. , Corradini , M.G. , Weiss , R.G., Raghavan , S.R. , and Rogers , M.A. ( 2015 ). To gel or not to gel: Correlating molecular gelation with solvent parameters . Chemical Society Reviews 44 : 6035 – 6058 .
- Lan , Y. , Lv , M. , Guo , S., Nasr , P. , Ladizhansky , V. , Vaz , R. , Corradini , M.G. , Hou , T. , Ghazani , S.M. , Marnangoni , A. , and Rogers , M.A. ( 2019 ). Molecular motifs encoding self-assembly of peptide fibers into molecular gels . Soft Matter 15 ( 45 ): 9205 – 9214 .
- Laredo , T. , Barbut , S. , and Marangoni , A.G. ( 2011 ). Molecular interactions of polymer oleogelation . Soft Matter 7 ( 6 ): 2734 – 2743 .
- Li , J. , Fan , K. , Guan , X., Yu , Y. , and Song , J. ( 2014 ). Self-assembly mechanism of 1, 3:2,4-di(3,4-dichlorobenzylidene)-d-sorbitoland control of the supramolecular chirality . Langmuir 30 ( 44 ): 13422 – 13429 .
- Li , J.L. and Liu , X.Y. ( 2010 ). Architecture of supramolecular soft functional materials: From understanding to micro-/nanoscale engineering . Advanced Functional Materials 20 : 3196 – 3216 .
- Lim , J. , Hwang , H.S. , and Lee , S. ( 2016 ). Oil-structuring characterization of natural waxes in canola oil oleogels: Rheological, thermal, and oxidative properties . Applied Biological Chemistry 60 : 17 – 22 .
-
Lipowitz , A.
(
1841
).
Versuche und Resultate über die Löslichkeit der Harnsäure
.
Justus Liebigs Annalen der Chemie
38
(
3
):
348
–
355
.
10.1002/jlac.18410380314 Google Scholar
- Liu , X. , Fei , J. , Wang , A., Cui , W. , Zhu , P. , and Li , J. ( 2017 ). Transformation of dipeptide-based organogels into chiral crystals by cryogenic treatment . Angewandte Chemie International Edition 56 ( 10 ): 2660 – 2663 .
- Liu , X.Y. and Sawant , P.D. ( 2001 ). Formation kinetics of fractal nanofiber networks in organogels . Applied Physics Letters 19 : 3518 – 3520 .
- Liu , X.Y. and Sawant , P.D. ( 2002 ). Determination of the fractal characteristic of nanofiber-network formation in supramolecular materials . CHEMPHYSCHEM 4 : 374 – 377 .
- Luboradzki , R. , Gronwald , O. , Ikeda , A. , and Shinkai , S. ( 2000 ). Sugar-integrated “supergelators” which can form organogels with 0.03–0.05% [g mL−1] . Chemistry Letters 29 ( 10 ): 1148 – 1149 .
- Manchinella , S. and Govindaraju , T. ( 2017 ). Molecular self-assembly of cyclic dipeptide derivatives and their applications . ChemPlusChem 82 : 88 – 106 .
- Mandu , C.C. , Barrera-Arellano , D. , Santana , M.H.A. , and Fernandes , G.D. ( 2020 ). Waxes used as structuring agents for food organogels: A review . Grasas y Aceites 71 ( 1 ): e344 .
- Marangoni , A.G. , Idziak , S.H.J. , Vega , C., Batte , Heidi , Ollivon , M. , Jantzi , P.S. , and Rush , J.W.E. ( 2007 ). Encapsulation-stucturing of edible oil attenuates acute elevation of blood lipids and insulin in humans . Soft Matter 3 ( 2 ): 183 – 187 .
- Murdan , S. , Gregoriadis , G. , and Florence , A.T. ( 1999 ). Novel sorbitan monostearate organogels . Journal of Pharmaceutical Sciences 88 ( 6 ): 608 – 614 .
- Na , N. , Mu , X. , Liu , Q. , Wen , J. , Wang , F. , and Ouyang , J. ( 2013 ). Self-assembly of diphenylalanine peptides into microtubes with “turn on” fluorescence using an aggregation-induced emission molecule . Chemical Communications 49 ( 86 ): 10076 .
- Nasr , P. , Corradini , M.G. , Hill , J., Read , S.T. , Rosendahl , S.M. , Weiss , R.G. , Auzanneau , F.I. , and Rogers , M.A. ( 2020 ). Hansen solubility parameters clarify the role of the primary and secondary hydroxyl groups on the remarkable self-assembly of 1:3,2:4-dibenzylidene sorbitol . The Journal of Physical Chemistry C 124 ( 48 ): 26455 – 26466 .
- Nguyen , V. , Zhu , R. , Jenkins , K. , and Yang , R. ( 2016 ). Self-assembly of diphenylalanine peptide with controlled polarization for power generation . Nature Communiations 7 : 13566 .
- Nikiforidis , C.V. and Scholten , E. ( 2015 ). Polymer organogelation with chitin and chitin nanocrystals . RSC Advances 5 ( 47 ): 37789 – 37799 .
- Ojijo , N.K.O. , Neeman , I. , Eger , S. , and Shimoni , E. ( 2004 ). Effects of monoglyceride content, cooling rate and shear on the rheological properties of olive oil/monoglyceride gel networks . Journal of the Science of Food and Agriculture 84 ( 12 ): 1585 – 1593 .
- Okesola , B.O. , Vieira , V.M.P. , Cornwell , D.J., Whitelaw , N.K. , and Smith , D.K. ( 2015 ). 1,3:2,4-Dibenzylidene-D-sorbitol (DBS) and its derivatives – efficient, versatile and industrially relevant low-molecular-weight gelators with over 100 years of history and a bright future . Soft Matter 11 : 4768 – 4787 .
- Pal , A. , Abraham , S. , Rogers , M.A., Dey , J. , and Weiss , R.G. ( 2013 ). Comparison of dipolar, H-bonding, and dispersive interactions on gelation efficiency of positional isomers of keto and hydroxy substituted octadecanoic acids . Langmuir 29 : 6467 – 6475 .
- Panagiotopoulou , E. , Moschakis , T. , and Katsanidis , E. ( 2016 ). Sunflower oil organogels and organogel-in-water emulsions (part II): Implementation in frankfurter sausages . Lwt – Food Science and Technology 73 : 351 – 356 .
- Parween , S. , Misra , A. , Ramakumar , S. , and Chauhan , V.S. ( 2014 ). Self-assembled dipeptide nanotubes constituted by flexible β-phenylalanine and conformationally constrained α,β-dehydrophenylalanine residues as drug delivery system . Journal of Materials Chemistry B 2 ( 20 ): 3096 .
- Patel , A.R. , Schatteman , D. , Lesaffer , A. , and Dewettinck , K. ( 2013 ). A foam-templated approach for fabricating organogels using a water-soluble polymer . RSC Advances 3 ( 45 ): 22900 – 22903 .
- Pommella , A. , Mathonnat , M. , and In , M. ( 2020 ). Texturing edible oil with crystals of phenolic compounds: Platelets versus rods . Journal of Food Engineering 283 : 110039 .
- Raynal , M. and Bouteiller , L. ( 2011 ). Organogel formation rationalized by hansen solubility parameters . Chemical Communication 47 : 8271 – 8273 .
- Rogers , M.A. ( 2018 ). Hansen solubility parameters as a tool in the quest for new edible oleogels . Journal of the American Oil Chemists' Society 95 ( 4 ): 393 – 405 .
- Rogers , M.A. , Abraham , S. , Bodondics , F. , and Weiss , R.G. ( 2012a ). Influence of the hydroxyl position in racemic hydroxyoctadecanoic acids on the crystallization kinetics and activation energies of gels and dispersions in mineral oil . Crystal Growth & Design 12 : 5497 – 5504 .
- Rogers , M.A. , Abraham , S. , Bodondics , F. , and Weiss , R.G. ( 2012b ). Positional isomers of hydroxyoctadecanoic acid molecular gels and dispersions influence crystallization kinetics and activation energies . Crystal Growth & Design 12 : 5497 – 5504 .
- Rogers , M.A. , Feng , Q. , Ladizhansky , V. , Good , D.B. , Smith , A.K. , Corridini , M. , Grahame , D.A.S. , Bryska , B.C. , Jadhav , P.D. , Sammynaiken , S. , Lim , L.T. , Guild , B. , Shim , Y.Y. , Burnett , P.G. , and Reaney , M.J.T. ( 2016a ). Self-assembled supramolecular fibrillar networks comprised of a cyclic peptide–LOB3 . RCS Advances 6 : 40765 – 40776 .
- Rogers , M.A. , Feng , Q. , Ladizhansky , V., Good , D.B. , Smith , A.K. , Corridini , M. , Grahame , D.A.S. , Bryska , B.C. , Jadhav , P.D. , Sammynaiken , S. , Lim , L.T. , Guild , B. , Shim , Y.Y. , Burnett , P.G. , and Reaney , M.J.T. ( 2016b ). Self-assembled fibrillar networks comprised of a naturally-occurring cyclic peptide—LOB3 . RSC Advances 6 ( 47 ): 40765 – 40776 .
- Rogers , M.A. and Marangoni , A.G. ( 2009 ). Solvent-modulated nucleation and crystallization kinetics of 12-hydroxystearic acid: A nonisothermal approach . Langmuir 25 : 8556 – 8566 .
- Rogers , M.A. and Marangoni , A.G. ( 2016 ). Kinetics of 12-hydroxyoctadecanoic acid SAFiN crystallization rationalized using hansen solubility parameters . Langmuir 32 ( 48 ): 12833 – 12841 .
-
Rogers , M.A.
,
Strober , T.
,
Bot , A.,
Toro-Vazquez , J.F.
,
Stortz , T.
, and
Marangoni , A.G.
(
2014
).
Edible oleogels in molecular gastronomy
.
International Journal of Gastronomy and Food Science
2
(
1
):
22
–
31
.
10.1016/j.ijgfs.2014.05.001 Google Scholar
- Rogers , M.A. and Weiss , R.G. ( 2015 ). Alkane-based molecular gelators and the structures and properties of their gels . New Journal of Chemistry 39 : 785 – 799 .
- Rogers , M.A. , Wright , A.J. , and Marangoni , A.G. ( 2008 ). Crystalline stability of self-assembled fibrillar networks of 12-hydroxystearic acid in edible oils . Food Research International 41 ( 10 ): 1026 – 1034 .
- Rogers , M.A. , Wright , A.J. , and Marangoni , A.G. ( 2009a ). Nanostructuring fiber morphology and solvent inclusions in 12-hydroxystearic acid/canola oil organogels (vol 14, pg 33, 2009) . Current Opinion in Colloid & Interface Science 14 ( 3 ): 223-223 .
- Rogers , M.A. , Wright , A.J. , and Marangoni , A.G. ( 2009b ). Oil organogels: the fat of the future? Soft Matter 5 ( 8 ): 1594 – 1596 .
- Rosa Nunes , D. , Raynal , M. , Isare , B., Albouy , P.A. , and Bouteiller , L. ( 2018 ). Organogel formation rationalized by Hansen solubility parameters: improved methodology . Soft Matter 14 ( 23 ): 4805 – 4809 .
- Sawalha , H. , Margry , G. , den Adel , R., Venema , P. , Bot , A. , Flöter , E. , and van der Linden , E. ( 2013 ). The influence of the type of oil phase on the self-assembly process of γ-oryzanol + β-sitosterol tubules in organogel systems . European Journal of Lipid Science and Technology 115 : 295 – 300 .
- Scholten , E. ( 2019 ). Edible oleogels: How suitable are proteins as a structurant? Current Opinion in Food Science 27 : 36 – 42 .
- Schurtenberger , P. , Scartazzini , R. , Magid , L.J., Leser , M.E. , and Luisi , P.L. ( 1990 ). Structural and dynamic properties of polymer-like reverse micelles . The Journal of Physical Chemistry 94 ( 9 ): 3695 – 3701 .
- Shaikh , H. , Rho , J.Y. , Macdougall , L.J. , Gurnani , P. , Lunn , A.M. , Yang , J. , Husband , S. , Mansfield , E.D.H. , Peltier , R. , and Perrier , S. ( 2018 ). Hydrogel and organogel formation by hierarchical self-assembly of cyclic peptides nanotubes . Chemistry – A European Journal 24 ( 71 ): 19066 – 19074 .
- Shakeel , A. , Farooq , U. , Gabriele , D., Marangoni , A.G. , and Lupi , F.R. ( 2021 ). Bigels and multi-component organogels: An overview from rheological perspective . Food Hydrocolloids 111 : 106190 .
- Shchipunov , Y.A. and Shumilina , E.V. ( 1995 ). Lecithin bridging by hydrogen bonds in the organogel . Materials Science and Engineering: C 3 ( 1 ): 43 – 50 .
- Shen , H. , Niu , L. , Fan , K., Li , J. , Guan , X. , Song , J. ( 2014 ). Application of solubility parameters in 1, 3:2,4-bis(3,4-dimethylbenzylidene) sorbitolorganogel in binary organic mixtures . Langmuir 30 : 9176 – 9182 .
- Silva , P.M. , Martins , A.J. , Fasolin , L.H. , and Vicente , A.A. ( 2021 ). Modulation and characterization of wax-based olive oil organogels in view of their application in the food industry . Gels 7 ( 1 ): 12 .
- Singh , A. , Auzanneau , F. I. , Corradini , M.G. , Grover , G. , Weiss , R.G. , and Rogers , M.A. ( 2017 ). Molecular nuances governing the self-assembly of 1,3:2,4-dibenzylidene-d-sorbitol . Langmuir 33 ( 41 ): 10907 – 10916 .
- Song , J. , Sun , H. , Sun , S. , and Feng , R. ( 2013 ). Synthesis and gel properties of sorbitol derivative gelators . Transactions of Tianjin University 19 ( 5 ): 319 – 325 .
- Suzuki , M. and Hanabusa , K. ( 2010 ). Polymer organogelators that make supramolecular organogels through physical cross-linking and self-assembly . Chemical Society Reviews 39 ( 2 ): 455 – 463 .
- Tamura , T. and Ichikawa , M. ( 1997 ). Effect of lecithin on organogel formation of 12-hydroxystearic acid . Journal of the American Oil Chemists Society 74 ( 5 ): 491 – 495 .
- Toro-Vazquez , J.F. , Morales-Rueda , J. , Mallia , V.A. , and Weiss , R.G. ( 2010 ). Relationship between molecular structure and thermo-mechanical properties of candelilla wax and amides derived from (R)-12-hydroxystearic acid as gelators of safflower oil . Food Biophysics 5 ( 3 ): 193 – 202 .
- Vauthey , S. , Santoso , S. , Gong , H., Watson , N. , and Zhang , S. ( 2002 ). Molecular self-assembly of surfactant-like peptides to form nanotubes and nanovesicles . Proceedings of the National Academy of Sciences 99 ( 8 ): 5355 – 5360 .
- Wang , R.Y. , Wang , P. , Li , J.L., Yuan , B. , Liu , Y , Li , L. , and Liu , X.Y. ( 2013 ). From kinetic-structure analysis to engineering crystalline fiber networks in soft materials . Physical Chemistry Chemical Physics 15 ( 9 ): 3313 – 3319 .
- Wei , F. , Lu , M. , Li , J. , Xiao , J. , Rogers , M.A. , Cao , Y. , and Lan , Y. ( 2022 ). Construction of foam-templated oleogels based on rice bran protein . Food Hydrocolloids 124 : 107245 .
- Weiss , R.G. ( 2014 ). The past, present, and future of molecular gels. What is the status of the field, and where is it going? Journal of the American Chemcial Society 136 : 7519 – 7530 .
-
Weiss , R.G.
and
Terech , P.
(
2006
).
Introduction
. In:
Molecular Gels: Materials with Self-Assembled Fibrillar Networks
(ed.
R.G. Weiss
and
P. Terech
),
1
–
13
.
Dordrecht The Netherlands
:
Springer
.
10.1007/1-4020-3689-2_1 Google Scholar
- Wilder , E.A. , Spontak , R.J. , and Hall , C.K. ( 2003 ). The molecular structure and intermolecular interactions of 1, 3:2,4-dibenzylidene-D-sorbitol . Molecular Physics 101 : 3017 – 3027 .
- Wright , A.J. and Marangoni , A.G. ( 2006 ). Formation, structure, and rheological properties of ricinelaidic acid-vegetable oil organogels . Journal of the American Oil Chemists' Society 83 ( 6 ): 497 – 503 .
- Wu , S. , Gao , J. , Emge , T. , and Rogers , M.A. ( 2013 ). Solvent induced polymorphic nanoscale transitions for 12-hydroxyoctadecanoic acid molecular gels . Crystal Growth & Design 13 : 1360 – 1366 .
- Xue , P. , Xu , Q. , Gong , P., Quan , C. , Ren , A. , Zhang , Y. , and Lu , R. ( 2013 ). Fibrous film of a two-component organogel as a sensor to detect and discriminate organic amines . Chemical Communications 49 ( 52 ): 5838 – 5840 .
- Yamasaki , S. , Ohashi , Y. , Tsutsumi , H. , and Tsujii , K. ( 1995 ). The aggregated higher-structure of 1, 3:2,4-di-O-benzylidene-D-sorbitolin organic gels . Bulletin of the Chemical Society Japan 68 : 146 – 151 .
- Yan , N. , Xu , Z. , Diehn , K.K., Raghavan , S.R. , Fang , Y. , and Weiss , R.G. ( 2013 ). How do liquid mixtures solubilize insoluble gelators? Self-assembly properties of pyrenyl-linker-glucono gelators in tetrahydrofuran-water mixtures . Journal of the American Chemical Society 135 : 8989 – 8999 .
- Yan , X. , Cui , Y. , He , Q., Wang , K. , and Li , J. ( 2008 ). Organogels based on self-assembly of diphenylalanine peptide and their application to immobilize quantum dots . Chemistry of Materials 20 ( 4 ): 1522 – 1526 .
- Zetzl , A.K. , Marangoni , A.G. , and Barbut , S. ( 2012 ). Mechanical properties of ethylcellulose oleogels and their potential for saturated fat reduction in frankfurters . Food & Function 3 : 327 – 337 .
- Zheng , W. , Kollmeyer , J. , Symolon , H., Momin , A. , Munter , E. , Wang , E. , Kelly , S. , Allegood , J.C. , Liu , Y. , Peng , Q. , Ramaraju , H. , Sullards, M.C ., Cabot , M. , and Merrill Jr. , A.H. ( 2006 ). Ceramides and other bioactive sphingolipid backbones in health and disease: Lipidomic analysis, metabolism and roles in membrane structure, dynamics, signaling and autophagy . Biochimica et Biophysica Acta (BBA) – Biomembranes 1758 ( 12 ): 1864 – 1884 .