Solubility of Alkyl Benzoates I: Effect of Some Alkyl p-Hydroxybenzoates (Parabens) on the Solubility of Benzyl p-Hydroxybenzoate

Shihab, F.; Sheffield, William; Sprowls, Joseph B.; Nematollahi, Jay

doi:10.1002/jps.2600591106

Cited by 13 publications

(3 citation statements)

References 2 publications

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“…The solubility of methyl paraben was highest in TC, followed by the two PEGs ( P > 0.05), DMI ( P < 0.05), butanol, heptanol and, finally, IPM ( P < 0.05). The data are in line with the values reported in the literature for butanol and PEG , respectively. They are also consistent with the solubility of methyl paraben in TC, DMI and IPM determined at 32°C .…”

Section: Resultssupporting

confidence: 91%

The role of vehicle interactions on permeation of an active through model membranes and human skin

Oliveira

Hadgraft

Lane

2012

Intern J of Cosmetic Sci

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Previous work from this group has focused on the molecular mechanism of alcohol interaction with model membranes, by conducting thermodynamic and kinetic analyses of alcohol uptake, membrane partitioning and transport studies of a model compound (i.e. methyl paraben) in silicone membranes. In this article, similar membrane transport and partitioning studies were conducted in silicone membranes to further extend the proposed model of alcohol interactions with silicone membranes to include other vehicles more commonly used in dermal formulations, that is, isopropyl myristate (IPM), dimethyl isosorbide (DMI), polyethylene glycol (PEG) 200, PEG 400 and Transcutol P® (TC). More importantly, membrane partitioning studies were conducted using human SC to evaluate the application of the proposed model of solvent-enhanced permeation in simple model membranes for the more complex biological tissue. The findings support a model of vehicle interactions with model membranes and skin where high solvent uptake promotes drug partitioning (i.e. K) by enabling the solute to exist within the solvent fraction/solvent-rich areas inside the membrane or skin in a concentration equivalent to that in the bulk solvent/vehicle. High solvent sorption may also ultimately impact on the membrane diffusional characteristics, and thus the diffusion coefficient of the solute across the membrane. The implications for skin transport are that increased partitioning of a drug into the SC may be achieved by (i) selecting vehicles that are highly taken up by the skin and also (ii) by having a relatively high concentration (i.e. molar fraction) of the drug in the vehicle. It follows that, in cases where significant co-transport of the solvent into and across the skin may occur, its depletion from the formulation and ultimately from the skin may lead to drug crystallization, thus affecting dermal absorption.

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Section: Resultssupporting

confidence: 91%

The role of vehicle interactions on permeation of an active through model membranes and human skin

Oliveira

Hadgraft

Lane

2012

Intern J of Cosmetic Sci

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“…It can, however, be explained by the solubilizing action of PEG. For example, 20% PEG-400 is known to solubilize drugs and cosmetics that have low water solubility − and to interact with surfactants. , Thus, the PEG polymer molecules are excluding the protein and at the same time PEG is solubilizing, or increasing the aqueous solubility of, the short-chain amphipathic inhibitors. The net effect is that the inhibitor-binding equilibrium is shifted and less inhibitor is bound at the active site of the enzyme.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structure−Activity Relationships, and the Effect of Polyethylene Glycol on Inhibitors of Phosphatidylinositol-Specific Phospholipase C fromBacillus cereus

et al. 1996

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Substrate analog inhibitors of Bacillus cereus phosphatidylinositol-specific phospholipase C (PI-PLC) were synthesized and screened for their suitability to map the active site region of the enzyme by protein crystallography. Analogs of the natural substrate phosphatidylinositol (PI) were designed to examine the importance of the lipid portion and the inositol phosphate head group for binding to the enzyme. The synthetic compounds contained pentyl, hexyl, or hexanoyl and octyl lipid chains at the sn-1 and sn-2 positions of the glycerol backbone and phosphonoinositol, phosphonic acid, methyl phosphonate, phosphatidic acid, or methyl phosphate at the sn-3 position. The most hydrophobic compound, dioctyl methyl phosphate 14, was also the best inhibitor with an IC50 of 12 microM. In a series of dihexyl lipids, compounds with phosphonoinositol head groups inhibited more strongly than those that do not contain inositol but are otherwise identical. Compound 29, a short-chain lipid with a phosphonoinositol head group, was found to be a competitive inhibitor and the most potent in this series with an IC50 of 18 microM (Ki = 14 microM). Analogs with dihexyl chains were better inhibitors than those with dihexanoyl chains, presumably because the ether-linked lipids are more hydrophobic than the ester-linked lipids. No appreciable difference in inhibition was found between a phosphonoinositol lipid and the corresponding difluorophosphonoinositol lipid. Inositols and inositol derivatives that do not contain lipid moieties show IC50s about 3 orders of magnitude above those of the short-chain lipids. In this group, glucosaminyl(alpha 1-->6)-D-myo-inositol inhibited more strongly than myo-inositol, which in turn is a better inhibitor than inositol phosphate. The addition of polyethylene glycol (PEG-600) resulted in a marked decrease in inhibition by the short-chain lipids, but had little effect on the water-soluble head group analogs. This is accounted for in terms of solubilization of the amphipathic inhibitors by PEG. Since PEG is required in the crystallization, these data indicate that the best strategy for obtaining enzyme inhibitor complexes is to start by cocrystallizing PI-PLC with the head group analogs. The next step is to synthetically add the shortest possible hydrophobic moieties to the analogs and cocrystallize these with the enzyme. This strategy may be applicable to other lipolytic enzymes.

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“…Figure 5 Solubility of BP in various solvents from 1.0˚C to 50.0˚C [56] Parabens are soluble in organic solvents [50,57] (ethyl acetate, propanol, acetone, methanol, acetonitrile and ethanol) but insoluble in water [58][59]. Solubility of parabens in these solvents increases with increasing temperature, shown in Figure . At low temperature, e.g.…”

Section: Solubility Analysismentioning

confidence: 99%

Review on Life Cycle of Parabens: Synthesis, Degradation, Characterization and Safety Analysis

Yang

Zhang

2018

COC

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In this review, we show the life cycle of parabens, commonly used preservatives that exist in nature and commercial products. Typical synthetic methods to produce parabens, and a set of complimentary characterization techniques to monitor the composition of parabens are also highlighted. These includes solid state analysis using Scanning Electron Microscope (SEM), Differential Scanning Calorimetry (DSC) and X-Ray Diffraction (XRD), in-situ monitoring of crystallization process using Focused Beam Reflectance Measurement (FBRM), Particle Vision Measurement (PVM), quantitative detection via High Performance Liquid Chromatography (HPLC), and Gas Chromatography (GC). An improved understanding of the overall physical, biophysical and chemical properties of parabens and their life cycle, summarized in this article, are vital for the safety control and extensive applications of relevant products in food, cosmetic and pharmaceutical industries.

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Solubility of Alkyl Benzoates I: Effect of Some Alkyl p-Hydroxybenzoates (Parabens) on the Solubility of Benzyl p-Hydroxybenzoate

Cited by 13 publications

References 2 publications

The role of vehicle interactions on permeation of an active through model membranes and human skin

The role of vehicle interactions on permeation of an active through model membranes and human skin

Synthesis, Structure−Activity Relationships, and the Effect of Polyethylene Glycol on Inhibitors of Phosphatidylinositol-Specific Phospholipase C fromBacillus cereus

Review on Life Cycle of Parabens: Synthesis, Degradation, Characterization and Safety Analysis

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