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Artículos de revistas sobre el tema "12-Hydroxystearic acid"

Autor: Grafiati

Publicado: 8 de febrero de 2025

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1

Kuwahara, Tetsuro, Hiromasa Nagase, Tomohiro Endo, Haruhisa Ueda y Masayuki Nakagaki. "Crystal Structure of DL-12-Hydroxystearic Acid". Chemistry Letters 25, n.º 6 (junio de 1996): 435–36. http://dx.doi.org/10.1246/cl.1996.435.

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2

Lan, Yaqi y Michael A. Rogers. "12-Hydroxystearic acid SAFiNs in aliphatic diols – a molecular oddity". CrystEngComm 17, n.º 42 (2015): 8031–38. http://dx.doi.org/10.1039/c5ce00652j.

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3

Dari, Carolina, Fabrice Cousin, Clemence Le Coeur, Thomas Dubois, Thierry Benezech, Arnaud Saint-Jalmes y Anne-Laure Fameau. "Ultrastable and Responsive Foams Based on 10-Hydroxystearic Acid Soap for Spore Decontamination". Molecules 28, n.º 11 (24 de mayo de 2023): 4295. http://dx.doi.org/10.3390/molecules28114295.

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Currently, there is renewed interest in using fatty acid soaps as surfactants. Hydroxylated fatty acids are specific fatty acids with a hydroxyl group in the alkyl chain, giving rise to chirality and specific surfactant properties. The most famous hydroxylated fatty acid is 12-hydroxystearic acid (12-HSA), which is widely used in industry and comes from castor oil. A very similar and new hydroxylated fatty acid, 10-hydroxystearic acid (10-HSA), can be easily obtained from oleic acid by using microorganisms. Here, we studied for the first time the self-assembly and foaming properties of R-10-HSA soap in an aqueous solution. A multiscale approach was used by combining microscopy techniques, small-angle neutron scattering, wide-angle X-ray scattering, rheology experiments, and surface tension measurements as a function of temperature. The behavior of R-10-HSA was systematically compared with that of 12-HSA soap. Although multilamellar micron-sized tubes were observed for both R-10-HSA and 12-HSA, the structure of the self-assemblies at the nanoscale was different, which is probably due to the fact that the 12-HSA solutions were racemic mixtures, while the 10-HSA solutions were obtained from a pure R enantiomer. We also demonstrated that stable foams based on R-10-HSA soap can be used for cleaning applications, by studying spore removal on model surfaces in static conditions via foam imbibition.

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4

Fameau, Anne-Laure, Brnice Houinsou-Houssou, Bruno Novales, Laurence Navailles, Frdric Nallet y Jean-Paul Douliez. "12-Hydroxystearic acid lipid tubes under various experimental conditions". Journal of Colloid and Interface Science 341, n.º 1 (enero de 2010): 38–47. http://dx.doi.org/10.1016/j.jcis.2009.09.034.

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5

Kokotou, Maroula G., Christiana Mantzourani, Asimina Bourboula, Olga G. Mountanea y George Kokotos. "A Liquid Chromatography-High Resolution Mass Spectrometry (LC-HRMS) Method for the Determination of Free Hydroxy Fatty Acids in Cow and Goat Milk". Molecules 25, n.º 17 (29 de agosto de 2020): 3947. http://dx.doi.org/10.3390/molecules25173947.

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A liquid chromatography–high resolution mass spectrometry (LC-HRMS) method for the direct determination of various saturated hydroxy fatty acids (HFAs) in milk was developed for the first time. The method involves mild sample preparation conditions, avoids time-consuming derivatization procedures, and permits the simultaneous determination of 19 free HFAs in a single 10-min run. This method was validated and applied in 17 cow milk and 12 goat milk samples. This work revealed the existence of various previously unrecognized hydroxylated positional isomers of palmitic acid and stearic acid in both cow and goat milk, expanding our knowledge on the lipidome of milk. The most abundant free HFAs in cow milk were proven to be 7-hydroxystearic acid (7HSA) and 10-hydroxystearic acid (10HSA) (mean content values of 175.1 ± 3.4 µg/mL and 72.4 ± 6.1 µg/mL in fresh milk, respectively). The contents of 7HSA in cow milk seem to be substantially higher than those in goat milk.

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6

Tamura, T. y M. Ichikawa. "Effect of lecithin on organogel formation of 12-hydroxystearic acid". Journal of the American Oil Chemists' Society 74, n.º 5 (mayo de 1997): 491–95. http://dx.doi.org/10.1007/s11746-997-0170-5.

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7

Takeno, Hiroyuki, Noriaki Kikuchi, Shingo Kondo y Toshiaki Dobashi. "Rheological and structural studies on gelation of 12-Hydroxystearic Acid Solution". Transactions of the Materials Research Society of Japan 32, n.º 3 (2007): 835–38. http://dx.doi.org/10.14723/tmrsj.32.835.

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8

Uehara, M., Y. Maki y T. Dobashi. "Preparation of 12-hydroxystearic acid microsphere containing oil-based contrast medium". Transactions of the Materials Research Society of Japan 36, n.º 3 (2011): 379–82. http://dx.doi.org/10.14723/tmrsj.36.379.

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9

Novoded, R. D., M. E. Krasnokutskaya, A. E. Mysak y S. M. Kisterskaya. "Phase transitions of calcium and lithium soaps of 12-hydroxystearic acid". Chemistry and Technology of Fuels and Oils 21, n.º 5 (mayo de 1985): 260–62. http://dx.doi.org/10.1007/bf00724256.

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10

Şahan, Nurten y Halime Paksoy. "Developing microencapsulated 12-hydroxystearic acid (HSA) for phase change material use". International Journal of Energy Research 42, n.º 10 (1 de mayo de 2018): 3351–60. http://dx.doi.org/10.1002/er.4090.

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11

Asaro, Fioretta, Carla Boga, Rita De Zorzi, Silvano Geremia, Lara Gigli, Patrizia Nitti y Sabrina Semeraro. "(R)-10-Hydroxystearic Acid: Crystals vs. Organogel". International Journal of Molecular Sciences 21, n.º 21 (30 de octubre de 2020): 8124. http://dx.doi.org/10.3390/ijms21218124.

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The chiral (R)-10-hydroxystearic acid ((R)-10-HSA) is a positional homologue of both (R)-12-HSA and (R)-9-HSA with the OH group in an intermediate position. While (R)-12-HSA is one of the best-known low-molecular-weight organogelators, (R)-9-HSA is not, but it forms crystals in several solvents. With the aim to gain information on the structural role of hydrogen-bonding interactions of the carbinol OH groups, we investigated the behavior of (R)-10-HSA in various solvents. This isomer displays an intermediate behavior between (R)-9 and (R)-12-HSA, producing a stable gel exclusively in paraffin oil, while it crystallizes in other organic solvents. Here, we report the X-ray structure of a single crystal of (R)-10-HSA as well as some structural information on its polymorphism, obtained through X-ray Powder Diffraction (XRPD) and Infrared Spectroscopy (IR). This case study provides new elements to elucidate the structural determinants of the microscopic architectures that lead to the formation of organogels of stearic acid derivatives.

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12

Zou, Jin, Denzil S. Frost y Lenore L. Dai. "Effects of gelator 12-hydroxystearic acid (12-HSA) on ionic liquid based Pickering emulsions". Colloids and Surfaces A: Physicochemical and Engineering Aspects 414 (noviembre de 2012): 477–85. http://dx.doi.org/10.1016/j.colsurfa.2012.08.001.

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13

Stan, Raluca, Nicoleta Chira, Cristina Ott, Cristina Todasca y Emile Perez. "Catanionic Organogelators Derived from D-Sorbitol and Natural Fatty Acids". Revista de Chimie 59, n.º 3 (9 de abril de 2008): 273–76. http://dx.doi.org/10.37358/rc.08.3.1747.

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Several catanionic organogelators derived from 1,3 :2,4-bis-O-(p-aminobenzylidene)-D-sorbitol (p-NH2-DBS) and hydroxy derivatives of natural fatty acids were synthesized, characterized and their gelation ability was evaluated. SEM observations of the xerogels formed by association of 1,3 :2,4-bis-O-(p-aminobenzylidene)-D-sorbitol and 12-hydroxystearic acid showed important modifications in the morphology and depend upon the nature of solvent as compared with the xerogels formed by each individual organogelator.

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14

Yarova, Galina, William Lathrop, John Nip, John Bajor, Stacy S. Hawkins, Bivash R. Dasgupta, Kevin D. Hermanson y Andrew Mayes. "33261 Topically applied skin natural fatty acids and 12-hydroxystearic acid boosts barrier lipids". Journal of the American Academy of Dermatology 87, n.º 3 (septiembre de 2022): AB214. http://dx.doi.org/10.1016/j.jaad.2022.06.888.

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15

Farooq, M., A. Ramli, S. Gul y N. Muhammad. "The Study of Wear Behaviour of 12-hydroxystearic Acid in Vegetable Oils". Journal of Applied Sciences 11, n.º 8 (1 de abril de 2011): 1381–85. http://dx.doi.org/10.3923/jas.2011.1381.1385.

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16

Takeno, Hiroyuki, Akiko Maehara, Masami Kuchiishi, Kazuto Yoshiba, Hiroki Takeshita, Shingo Kondo, Toshiaki Dobashi, Mikihito Takenaka y Hirokazu Hasegawa. "Structural and Thermal Properties of Unpurified and Purified 12-Hydroxystearic Acid Solutions". Sen'i Gakkaishi 68, n.º 9 (2012): 248–52. http://dx.doi.org/10.2115/fiber.68.248.

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17

Rogers, Michael A. y Alejandro G. Marangoni. "Non-Isothermal Nucleation and Crystallization of 12-Hydroxystearic Acid in Vegetable Oils". Crystal Growth & Design 8, n.º 12 (3 de diciembre de 2008): 4596–601. http://dx.doi.org/10.1021/cg8008927.

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18

Ahn, WonSool y Joon-Man Lee. "Open-Cell Rigid Polyurethane Foam Using Lithium Salt of 12-Hydroxystearic acid as a Cell Opening Agent". Polymer Korea 42, n.º 6 (30 de noviembre de 2018): 919–24. http://dx.doi.org/10.7317/pk.2018.42.6.919.

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19

Yang, Hai-Kuan, Chen Zhang, Xiang-Ning He y Pin-You Wang. "Effects of alkyl chain lengths on 12-hydroxystearic acid derivatives based supramolecular organogels". Colloids and Surfaces A: Physicochemical and Engineering Aspects 616 (mayo de 2021): 126319. http://dx.doi.org/10.1016/j.colsurfa.2021.126319.

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20

Rong, Shaofeng, Xinhui Guan, Qianqian Li, Shimin Guan, Baoguo Cai y Shuo Zhang. "Biotransformation of 12-hydroxystearic acid to gamma-decalactone: Comparison of two separation systems". Journal of Microbiological Methods 178 (noviembre de 2020): 106041. http://dx.doi.org/10.1016/j.mimet.2020.106041.

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21

Rogers, Michael A. y Alejandro G. Marangoni. "Solvent-Modulated Nucleation and Crystallization Kinetics of 12-Hydroxystearic Acid: A Nonisothermal Approach†". Langmuir 25, n.º 15 (4 de agosto de 2009): 8556–66. http://dx.doi.org/10.1021/la8035665.

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22

Rogers, Michael A., Amanda J. Wright y Alejandro G. Marangoni. "Nanostructuring fiber morphology and solvent inclusions in 12-hydroxystearic acid / canola oil organogels". Current Opinion in Colloid & Interface Science 14, n.º 1 (febrero de 2009): 33–42. http://dx.doi.org/10.1016/j.cocis.2008.02.004.

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23

Delbecq, Frederic, Nobuhiro Kaneko, Hiroshi Endo y Takeshi Kawai. "Solvation effects with a photoresponsive two-component 12-hydroxystearic acid-azobenzene additive organogel". Journal of Colloid and Interface Science 384, n.º 1 (octubre de 2012): 94–98. http://dx.doi.org/10.1016/j.jcis.2012.06.045.

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24

Murakami, Yuya, Taisei Uchiyama y Atsushi Shono. "Correlation between Physical Properties of 12-Hydroxystearic Acid Organogels and Hansen Solubility Parameters". Gels 9, n.º 4 (7 de abril de 2023): 314. http://dx.doi.org/10.3390/gels9040314.

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The Hansen solubility parameter (HSP) is a useful index for reasoning the gelation behavior of low-molecular-weight gelators (LMWGs). However, the conventional HSP-based methods only “classify” solvents that can and cannot form gels and require many trials to achieve this. For engineering purposes, quantitative estimation of gel properties using the HSP is highly desired. In this study, we measured critical gelation concentrations based on three distinct definitions, mechanical strength, and light transmittance of organogels prepared with 12-hydroxystearic acid (12HSA) and correlated them with the HSP of solvents. The results demonstrated that the mechanical strength, in particular, strongly correlated with the distance of 12HSA and solvent in the HSP space. Additionally, the results indicated that the constant volume-based concentration should be used when comparing the properties of organogels to a different solvent. These findings are helpful in efficiently determining the gelation sphere of new LMWGs in HSP space and contribute to designing organogels with tunable physical properties.

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25

Duaa Razzaq Jaafer y Masar Basim Mohsin Mohamed. "Curcumin-Loaded Organogel for The Topical Skin Disorder Based on 12 Hydroxystearic Acid". Iraqi Journal of Pharmaceutical Sciences( P-ISSN 1683 - 3597 E-ISSN 2521 - 3512) 33, n.º 3 (15 de septiembre de 2024): 171–86. http://dx.doi.org/10.31351/vol33iss3pp171-186.

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Curcumin (CUR) possesses various pharmacological properties, including antibacterial and improving injury healing. This work aimed to formulate curcumin organogel using 12 hydroxy stearic acid as gelator with tween 80 as surfactant and PEG 400 as co surfactant to improve the CUR permeation through the skin. The CUR organogels were prepared using different 12HSA concentrations with solvents sesame oil (SO), and orange oil (OO), in addition to T80 and P400 and evaluated for their saturated solubility, tabletop rheology, oil binding capacity, pH, spreadability, in vitro release, antibacterial activity, oscillatory rheology study, skin irritation, histological examination and ex- with in- vivo permeation study across rat abdominal skin. Results: The important results that distinguished organogels were the spreadability and in vitro release studies. The 4SO, 2OO, 2T80, and 10P400 organogels presented successful gelation and represented the lowest 12HSA concentration in each solvent that approached the current aim’s study by being more spreadable with higher CUR released. At the same time, the 2T80 and 10P400 gave zones of inhibition to 4 bacterial strains and good viscoelasticity by exhibiting large flow point values in the frequency sweep study compared with 4SO and 2OO. In vivo study affirmed the CUR permeation by studying the fluorescent images of 2T80 and 10P400, and the ex vivo permeation study for 10P400 proved the CUR permeation through rat’s skinOur results indicated the potential of 10P400 and 2T80 organogel to improve the topical therapeutic efficacy of CUR.

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26

Hoang, Son A., Khanh D. Pham, Nhung H. Nguyen, Ha T. Tran, Ngoc Hoang y Chi M. Phan. "Synthesis of a Grease Thickener from Cashew Nut Shell Liquor". Molecules 28, n.º 22 (16 de noviembre de 2023): 7624. http://dx.doi.org/10.3390/molecules28227624.

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Thickener, also known as a gelling agent, is a critical component of lubricating greases. The most critical property of thickener, temperature resistance, is determined by the molecular structure of the compounds. Currently, all high-temperature-resistant thickeners are based on 12-hydroxystearic acid, which is exclusively produced from castor oil. Since castor oil is also an important reagent for other processes, finding a sustainable alternative to 12-hydroxystearic acid has significant economic implications. This study synthesises an alternative thickener from abundant agricultural waste, cashew nut shell liquor (CNSL). The synthesis and separation procedure contains three steps: (i) forming and separating calcium anacardate by precipitation, (ii) forming and separating anacardic acid (iii) forming lithium anacardate. The obtained lithium anacardate can be used as a thickener for lubricating grease. It was found that the recovery of anacardic acid was around 80%. The optimal reaction temperature and time conditions for lithium anacardate were 100 °C and 1 h, respectively. The method provides an economical alternative to castor and other vegetable oils. The procedure presents a simple pathway to produce the precursor for the lubricating grease from agricultural waste. The first reaction step can be combined with the existing distillation of cashew nut shell processing. An effective application can promote CNSL to a sustainable feedstock for green chemistry. The process can also be combined with recycled lithium from the spent batteries to improve the sustainability of the battery industry.

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27

Lam, Ricky Sze Ho y Michael A. Rogers. "Activation Energy of Crystallization for Trihydroxystearin, Stearic Acid, and 12-Hydroxystearic Acid under Nonisothermal Cooling Conditions". Crystal Growth & Design 11, n.º 8 (3 de agosto de 2011): 3593–99. http://dx.doi.org/10.1021/cg200553t.

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28

Lin, Hui-Chi, Chih-Hung Wang, Jyun-Kai Wang y Sheng-Feng Tsai. "Fast Response and Spontaneous Alignment in Liquid Crystals Doped with 12-Hydroxystearic Acid Gelators". Materials 11, n.º 5 (7 de mayo de 2018): 745. http://dx.doi.org/10.3390/ma11050745.

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29

Bois, A. G., J. F. Baret, V. S. Kulkarni, I. Panaiotov y M. Ivanova. "Relaxations of surface pressure and surface potential in 12-hydroxystearic acid alkyl ester monolayers". Langmuir 4, n.º 6 (noviembre de 1988): 1358–62. http://dx.doi.org/10.1021/la00084a027.

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30

Viklund, Fredrik y Karl Hult. "Enzymatic synthesis of surfactants based on polyethylene glycol and stearic or 12-hydroxystearic acid". Journal of Molecular Catalysis B: Enzymatic 27, n.º 2-3 (febrero de 2004): 51–53. http://dx.doi.org/10.1016/j.molcatb.2003.09.006.

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31

Gordon, Ryan, Spencer T. Stober y Cameron F. Abrams. "Aggregation of 12-Hydroxystearic Acid and Its Lithium Salt in Hexane: Molecular Dynamics Simulations". Journal of Physical Chemistry B 120, n.º 29 (19 de julio de 2016): 7164–73. http://dx.doi.org/10.1021/acs.jpcb.6b04193.

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32

Eloundou, Jean Pascal, Emmanuel Girard-Reydet, Jean-Fran�ois G�rard y Jean-Pierre Pascault. "Calorimetric and rheological studies of 12-hydroxystearic acid / digycidyl ether of bisphenol A blends". Polymer Bulletin 53, n.º 5-6 (10 de febrero de 2005): 367–75. http://dx.doi.org/10.1007/s00289-005-0345-x.

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33

Alvarez-Mitre, Flor M., V. Ajay Mallia, Richard G. Weiss, Miriam A. Charó-Alonso y Jorge F. Toro-Vazquez. "Self-assembly in vegetable oils of ionic gelators derived from (R)-12-hydroxystearic acid". Food Structure 13 (julio de 2017): 56–69. http://dx.doi.org/10.1016/j.foostr.2016.07.003.

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34

Rogers, Michael A., Amanda J. Wright y Alejandro G. Marangoni. "Crystalline stability of self-assembled fibrillar networks of 12-hydroxystearic acid in edible oils". Food Research International 41, n.º 10 (diciembre de 2008): 1026–34. http://dx.doi.org/10.1016/j.foodres.2008.07.012.

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35

Ishchuk, Yu L., L. N. Dugina, M. E. Krasnokutskaya y B. A. Godun. "Influence of composition of technical 12-hydroxystearic acid on properties of anhydrous calcium greases". Chemistry and Technology of Fuels and Oils 22, n.º 8 (agosto de 1986): 402–5. http://dx.doi.org/10.1007/bf01130493.

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36

Razaq, Duaa, Masar Basim Mohsin Mohamed y Lina A. Dahabiyeh. "Formulation and Characterization of Curcumin 12-Hydroxystearic Acid in Triacetin Organogel for Topical Administration". Al Mustansiriyah Journal of Pharmaceutical Sciences 24, n.º 2 (8 de abril de 2024): 190–204. http://dx.doi.org/10.32947/ajps.v24i2.1011.

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Background: Curcumin (CUR) and its derivatives have shown a wide variety of biological activities, such as anti-oxidant, anti-inflammatory, anti-tumor, antimicrobial and antiparasitic effects as well as for the treatment of skin diseases. Due to its physico-chemical limitations such as low aqueous solubility and low bioavailability, we developed curcumin organogel as a topical delivery system to overcome those limitations. The12-hydroxystearic acid (12-HSA) is well known as a low-molecular-weight organogelators (LMOGs) capable of gelling an organic liquid phase. Different concentrations of (12-HSA) in triacetin with 50 mg CUR were gelled and applied for various examinations: tabletop rheology, oil binding capacity, pH measurement, spreadability, in vitro drug release, antibacterial activity and oscillatory rheology studies. The results revealed that the organogels transition temperatures from solid to liquid were greater than the normal body temperature, this helped the organogels keep their shape; they had good spreadability,and the organogels pH levels were within the safe range for the skin . In vitro release data showed that 4% 12HSA+5%CUR +TA (4TA) gave us 100% release after 6 hours. The selected 4TA illustrated good viscoelastic properties in the amplitude sweep test and a frequency-independent as seen in the frequency sweep test. CUR has good antibacterial action against Staphylococcus aureus; Streptococcus pyrogen, Proteus mirabilis, and Escherichia coli, which prevail at the site of wound injury as this pointed out that 4TA organogel can be used for topical wound healing.

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37

Almeida, Maëva, Daniel Dudzinski, Catherine Amiel, Jean-Michel Guigner, Sylvain Prévost, Clémence Le Coeur y Fabrice Cousin. "Aqueous Binary Mixtures of Stearic Acid and Its Hydroxylated Counterpart 12-Hydroxystearic Acid: Cascade of Morphological Transitions at Room Temperature". Molecules 28, n.º 11 (25 de mayo de 2023): 4336. http://dx.doi.org/10.3390/molecules28114336.

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Here, we describe the behavior of mixtures of stearic acid (SA) and its hydroxylated counterpart 12-hydroxystearic acid (12-HSA) in aqueous mixtures at room temperature as a function of the 12-HSA/SA mole ratio R. The morphologies of the self-assembled aggregates are obtained through a multi-structural approach that combines confocal and cryo-TEM microscopies with small-angle neutron scattering (SANS) and wide-angle X-ray scattering (WAXS) measurements, coupled with rheology measurements. Fatty acids are solubilized by an excess of ethanolamine counterions, so that their heads are negatively charged. A clear trend towards partitioning between the two types of fatty acids is observed, presumably driven by the favorable formation of a H-bond network between hydroxyl OH function on the 12th carbon. For all R, the self-assembled structures are locally lamellar, with bilayers composed of crystallized and strongly interdigitated fatty acids. At high R, multilamellar tubes are formed. The doping via a low amount of SA molecules slightly modifies the dimensions of the tubes and decreases the bilayer rigidity. The solutions have a gel-like behavior. At intermediate R, tubes coexist in solution with helical ribbons. At low R, local partitioning also occurs, and the architecture of the self-assemblies associates the two morphologies of the pure fatty acids systems: they are faceted objects with planar domains enriched in SA molecules, capped with curved domains enriched in 12-HSA molecules. The rigidity of the bilayers is strongly increased, as well their storage modulus. The solutions remain, however, viscous fluids in this regime.

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38

Waskar, Morris y Xuelan Gu. "33255 Handwash formulations containing 12-hydroxystearic acid provide long-lasting protection against bacteria in vivo". Journal of the American Academy of Dermatology 87, n.º 3 (septiembre de 2022): AB63. http://dx.doi.org/10.1016/j.jaad.2022.06.286.

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39

Waskar, Morris, Xuelan Gu, Meenakshi Swaminathan, Carol Vincent, Rimpa Ghosh, Chandraprabha Doraiswamy y Amitabha Majumdar. "33255 Handwash formulations containing 12-hydroxystearic acid provide long-lasting protection against bacteria in vivo". Journal of the American Academy of Dermatology 87, n.º 3 (septiembre de 2022): AB170. http://dx.doi.org/10.1016/j.jaad.2022.06.713.

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40

Sakai, H. y J. Umemura. "Molecular Orientation in Langmuir Films of 12-Hydroxystearic Acid Studied by Infrared External-Reflection Spectroscopy". Langmuir 14, n.º 21 (octubre de 1998): 6249–55. http://dx.doi.org/10.1021/la971016e.

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41

Lee, Chan Woo, Yoshiharu Kimura y Jin Do Chung. "Enzymatic formation of 13,26-Dihexyl-1,14-dioxacyclohexacosane-2,15-dione via Oligomerization of 12-Hydroxystearic acid". Macromolecular Research 17, n.º 11 (noviembre de 2009): 919–25. http://dx.doi.org/10.1007/bf03218636.

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42

Co, Edmund y Alejandro G. Marangoni. "The Formation of a 12-Hydroxystearic Acid/Vegetable Oil Organogel Under Shear and Thermal Fields". Journal of the American Oil Chemists' Society 90, n.º 4 (3 de enero de 2013): 529–44. http://dx.doi.org/10.1007/s11746-012-2196-6.

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43

Tantishaiyakul, Vimon, Passaporn Ouiyangkul, Makawan Wajasat, Tasana Pawisat, Namon Hirun y Tanatchaporn Sangfai. "A Supramolecular Gel Based on 12-Hydroxystearic Acid/Virgin Coconut Oil for Injectable Drug Delivery". European Journal of Lipid Science and Technology 120, n.º 10 (16 de agosto de 2018): 1800178. http://dx.doi.org/10.1002/ejlt.201800178.

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44

Takeno, Hiroyuki y Mai Kozuka. "Effects of Cooling Rates on Self-Assembling Structures of 12-Hydroxystearic Acid in an Ionic Liquid". Advances in Materials Science and Engineering 2017 (2017): 1–8. http://dx.doi.org/10.1155/2017/4762379.

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We investigated effects of cooling rates on self-assembling structures and mechanical and electrochemical properties of 12-hydroxystearic acid (12-HSA) in an ionic liquid (IL), 1-allyl-3-butylimidazolium bis(trifluoromethanesulfonyl) imide ([ABIm][TFSI]). The mixture of 12-HSA with [ABIm][TFSI] had an upper critical solution temperature (UCST) above the sol-gel transition temperature, and the microstructure of the ionogel was significantly affected by cooling rates, where it was prepared. The twisted self-assembling structure was formed during a slow cooling process at a rate of 0.4°C/min, whereas spherical domains caused by the liquid-liquid phase separation and radiate fibrous structure were observed for the quenched gel. The real-time small-angle X-ray scattering (SAXS) measurements for the ionogel during a slow cooling process at a rate of 0.4°C/min presented three different (001) peaks arising from long spacings of 46.5, 42.4, and 39.7 Å, which were also observed for SAXS curves of a neat 12-HSA. These results suggest that three polymorphic forms of 12-HSA are formed in the IL. The polymorphic form significantly affected the mechanical properties of the ionogel, whereas it did not affect the ionic conductivity. The ionic conductivity of the ionogel was close to that of a neat [ABIm][TFSI] irrespective of the polymorphic forms of 12-HSA.

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45

Almeida, Maëva, Daniel Dudzinski, Bastien Rousseau, Catherine Amiel, Sylvain Prévost, Fabrice Cousin y Clémence Le Coeur. "Aqueous Binary Mixtures of Stearic Acid and Its Hydroxylated Counterpart 12-Hydroxystearic Acid: Fine Tuning of the Lamellar/Micelle Threshold Temperature Transition and of the Micelle Shape". Molecules 28, n.º 17 (29 de agosto de 2023): 6317. http://dx.doi.org/10.3390/molecules28176317.

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This study examines the structures of soft surfactant-based biomaterials which can be tuned by temperature. More precisely, investigated here is the behavior of stearic acid (SA) and 12-hydroxystearic acid (12-HSA) aqueous mixtures as a function of temperature and the 12-HSA/SA molar ratio (R). Whatever R is, the system exhibits a morphological transition at a given threshold temperature, from multilamellar self-assemblies at low temperature to small micelles at high temperature, as shown by a combination of transmittance measurements, Wide Angle X-ray diffraction (WAXS), small angle neutron scattering (SANS), and differential scanning calorimetry (DSC) experiments. The precise determination of the threshold temperature, which ranges between 20 °C and 50 °C depending on R, allows for the construction of the whole phase diagram of the system as a function of R. At high temperature, the micelles that are formed are oblate for pure SA solutions (R = 0) and prolate for pure 12-HSA solutions (R = 1). In the case of mixtures, there is a progressive continuous transition from oblate to prolate shapes when increasing R, with micelles that are almost purely spherical for R = 0.33.

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46

Tamura, Takamitsu, Takashi Suetake, Toshinaga Ohkubo y Kazuo Ohbu. "Effect of alkali metal ions on gel formation in the 12-hydroxystearic acid/soybean oil system". Journal of the American Oil Chemists' Society 71, n.º 8 (agosto de 1994): 857–61. http://dx.doi.org/10.1007/bf02540462.

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47

Fameau, Anne-Laure y Michael A. Rogers. "The curious case of 12-hydroxystearic acid — the Dr. Jekyll & Mr. Hyde of molecular gelators". Current Opinion in Colloid & Interface Science 45 (febrero de 2020): 68–82. http://dx.doi.org/10.1016/j.cocis.2019.12.006.

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48

Mallia, V. Ajay y Richard G. Weiss. "Self-assembled fibrillar networks and molecular gels employing 12-hydroxystearic acid and its isomers and derivatives". Journal of Physical Organic Chemistry 27, n.º 4 (18 de septiembre de 2013): 310–15. http://dx.doi.org/10.1002/poc.3193.

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49

Asaro, Fioretta, Carla Boga, Nicola Demitri, Rita De Zorzi, Sara Drioli, Lara Gigli, Gabriele Micheletti, Patrizia Nitti y Ennio Zangrando. "X-Ray Crystal Structures and Organogelator Properties of (R)-9-Hydroxystearic Acid". Molecules 24, n.º 15 (6 de agosto de 2019): 2854. http://dx.doi.org/10.3390/molecules24152854.

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(R)-9-hydroxystearic acid, (R)-9-HSA, is a chiral nonracemic hydroxyacid of natural origin possessing interesting properties as an antiproliferative agent against different cancer types. Considering its potential application for medical and pharmaceutical purposes, the structures and rheological properties of (R)-9-HSA were investigated. Oscillatory rheology measurements reveal that (R)-9-HSA gels only paraffin oil, with less efficiency and thermal stability than its positional isomer (R)-12-HSA. Conversely, (R)-9-HSA affords crystals from methanol, acetonitrile, and carbon tetrachloride. The single crystal structures obtained both at 293 K and 100 K show non-centrosymmetric twisted carboxylic acid dimers linked at the midchain OHs into long, unidirectional chains of hydrogen bonds, owing to head-tail ordering of the molecules. Synchrotron X-ray powder diffraction experiments, performed on the solids obtained from different solvents, show the occurrence of polymorphism in paraffin oil and through thermal treatment of the solid from methanol.

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50

Granata, Alessandro, Françoise Sauriol y Arthur S. Perlin. "Acid-catalysed transformation of oleic acid, and 12-hydroxystearic acid, into γ-octadecanolactone. Evidence for the occurrence of a novel side reaction". Canadian Journal of Chemistry 72, n.º 7 (1 de julio de 1994): 1684–90. http://dx.doi.org/10.1139/v94-212.

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γ-Octadecanolactone is produced in the reaction between oleic acid (cis-9-octadecenoic acid) and concentrated sulfuric acid at 80 °C. To account for its formation, two types of mechanism have been considered. Both begin with protonation at C-9/C-10 to give a carbocation, following which the positive charge is transmitted to C-4, where nucleophilic attack by the carboxyl group is facilitated. One of them invokes a "zipperlike" succession of 1,2-shifts of intervening methylenic protons, whereas the other amounts to a stepwise migration of the alkene function along the carbon chain. Results obtained through the use of deuterated sulfuric acid to catalyse formation of the lactone allow for the existence of both types. However, each is characteristic of a different region of the C18 structure. Of the total isotope incorporated (individual molecules contained from zero to nine atoms of deuterium), >85% had been distributed relatively uniformly over the chain segment from C-7 to C-17, according to 2H nuclear magnetic resonance spectra recorded in the presence of the shift reagent Yb(fod)3, and 13C nuclear magnetic resonance data. This evidence is consistent with the occurrence of a side reaction that creates many protonation sites over that specific region of the lactone's precursors. By contrast, as very little of the isotope had reached the proximity of the lactone ring, the latter is more likely to have been formed via the 1,2 shift type of mechanism. These events can also be initiated at other sites, as shown by the preparation of γ-octadecanolactone, and a comparably deuterated form of it, from 12-hydroxystearic acid. Reactions of these three stearic acid derivatives with HI, HBr, and HCl are described, by way of comparison.

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