Lubricant and Bactericidal Properties of Calcium Salts of Fatty Acids: Effect of Degree of Unsaturation

Yamamoto, Yoshiaki; Kijima, Toshiki; Morikawa, T.; Nonomura, Yoshiaki

doi:10.5650/jos.ess15090

Cited by 14 publications

(15 citation statements)

References 27 publications

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“…Some previous studies showed that the n ‐stearic acid Ca salt has a lamellar crystalline structure (Garnier and Gregoire, ; Vold and Smith, ; Yamamoto et al, ). However, the structure of the alkyl chain changed the crystal structure: n ‐stearic acid Ca salt is in the lamellar crystalline state, while iso ‐stearic acid Ca salt is in the amorphous state.…”

Section: Resultsmentioning

confidence: 97%

“…Furthermore, the region of LC and W m decreases with the addition of metal ions. This is caused by the generation of hydrophobic solid particles when two carboxyl groups are bound to one metal ion (Yamamoto et al, , , ). Thus, solid particles are produced when the calcium content is high.…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, stearic acid zinc salt is used in cosmetics because of its soft texture and superior property of adhesion to the skin. In addition, some fatty‐acid Ca salts show selective bactericidal activity against Staphylococcus aureus and Propionibacterium acnes , which causes skin roughness and acne (Yamamoto et al, , , ).…”

Section: Introductionmentioning

confidence: 99%

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Phase Transitions of Branched Fatty‐Acid Calcium Salt/Water Systems

Yamamoto

Kakehashi

Aramaki

et al. 2018

J Surfact & Detergents

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Calcium (Ca) salts of fatty acids are powder materials, which exhibit lubricant, hydrophobic, and bactericidal properties. These physical and biological properties depend on the chemical structure of the alkyl chain of the fatty acids. In this study, the phase behavior of iso‐stearic acid Ca salt/water binary systems was studied, and the effect of the branched structure in the alkyl chain was analyzed. Herein, calcium chloride is added to the iso‐stearic acid aqueous solution. The state of the binary systems changed with the molar ratio (R) of [Ca2+]/[iso‐stearic acid]. Precipitation occurred when R was more than 0.05, whereas the mixture changed from a micelle phase (Wm) to an oil phase (O) through a liquid crystalline phase (LC) when R was less than 0.01. The polarized microscopy images and small‐angle X‐ray scattering profiles showed that the LC is in a lamellar liquid crystalline state. In addition, we evaluated the crystal structure of the precipitated material. These results showed that the iso‐stearic acid Ca salt was in the amorphous state. In contrast, the n‐stearic acid Ca salt formed only the Wm and gel phases. These findings suggest that the branched structure of fatty acids induces loose intermolecular packing of liquid crystalline structures.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

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Phase Transitions of Branched Fatty‐Acid Calcium Salt/Water Systems

Yamamoto

Kakehashi

Aramaki

et al. 2018

J Surfact & Detergents

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“…From then, many other studies have proven the bactericidal or bacteriostatic effect of several saturated and unsaturated fatty acids on Gram-positive and Gram-negative bacteria [20,30]. Nowadays, partially driven by the emergence of multidrug-resistant strains, the research on fatty acids and monoglycerides as potential antibacterial agents has gained new attention [30,31,32,33,34,35,36].…”

Section: Resultsmentioning

confidence: 99%

Intracellular Staphylococcus aureus Elicits the Production of Host Very Long-Chain Saturated Fatty Acids with Antimicrobial Activity

et al. 2019

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As a facultative intracellular pathogen, Staphylococcus aureus is able to invade and proliferate within many types of mammalian cells. Intracellular bacterial replication relies on host nutrient supplies and, therefore, cell metabolism is closely bound to intracellular infection. Here, we investigated how S. aureus invasion affects the host membrane-bound fatty acids. We quantified the relative levels of fatty acids and their labelling pattern after intracellular infection by gas chromatography-mass spectrometry (GC-MS). Interestingly, we observed that the levels of three host fatty acids—docosanoic, eicosanoic and palmitic acids—were significantly increased in response to intracellular S. aureus infection. Accordingly, labelling carbon distribution was also affected in infected cells, in comparison to the uninfected control. In addition, treatment of HeLa cells with these three fatty acids showed a cytoprotective role by directly reducing S. aureus growth.

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“… 31 Furthermore, the Ca salt of linoleic acid exhibits a stronger bactericidal activity than that of its stearic acid and oleic acid equivalents, demonstrating that the degree of unsaturation also affects the bactericidal activity. 32 …”

Section: Introductionmentioning

confidence: 99%

Selective Bactericidal Activity of Divalent Metal Salts of Lauric Acid

et al. 2017

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Bacteria play a crucial role in skin health. For example, Staphylococcus aureus and Propionibacterium acnes cause skin roughness and acne, whereas Staphylococcus epidermidis enhances innate barrier immunity. Therefore, controlling the bacterial flora is important in dermatology and cosmetic chemistry. In this study, the bactericidal activities of different metal salts of lauric acid were evaluated. The bactericidal behavior of the salts changed according to the type of metal ion. Specifically, the Mg-, Ca-, and Mn-containing salts effectively sterilized only S. aureus and P. acnes. Their Co, Ni, and Cu salts sterilized all bacteria, including S. epidermidis, whereas the Zn salt proved ineffective. The Cu salt displayed the strongest bactericidal activity. Spin-trapping, detected using electron spin resonance, showed that this salt catalyzed the generation of hydroxyl radicals, which can destroy bacterial cell membranes. These findings demonstrate that metal-ion selection is an important factor in the design of bactericidal agents for healthcare products.

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Lubricant and Bactericidal Properties of Calcium Salts of Fatty Acids: Effect of Degree of Unsaturation

Cited by 14 publications

References 27 publications

Phase Transitions of Branched Fatty‐Acid Calcium Salt/Water Systems

Phase Transitions of Branched Fatty‐Acid Calcium Salt/Water Systems

Intracellular Staphylococcus aureus Elicits the Production of Host Very Long-Chain Saturated Fatty Acids with Antimicrobial Activity

Selective Bactericidal Activity of Divalent Metal Salts of Lauric Acid

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