Solubility of Salicylic Acid as a Function of Dielectric Constant

Paruta, Anthony N.; Sciarrone, Bartley J.; Lordi, Nicholas G.

doi:10.1002/jps.2600531114

Cited by 77 publications

(40 citation statements)

References 1 publication

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“…Lower melting point temperatures and lower enthalpies of fusion, and hydrophobic effect were suggested as possible factors responsible for the observed phase separation. 7,16 Another possible explanation for this phase separation, might be a mechanism similar to salting out, as it has been reported for aqueous mixtures of 1-propanol, 2-propanol, 2-propanone, acetonitrile, 1,4-dioxane, and tetrahydrofuran in presence of alkali salts. 19,20 The experimental data reported in this study extends the available solubility databases 13,21 of drug/drug like molecules in monosolvent systems at different temperatures and binary solvent mixtures.…”

Section: ■ Results and Discussionmentioning

confidence: 79%

Solubility of 2-Hydroxybenzoic Acid in Water, 1-Propanol, 2-Propanol, and 2-Propanone at (298.2 to 338.2) K and Their Aqueous Binary Mixtures at 298.2 K

Fakhree¹,

Ahmadian²,

Panahi‐Azar³

et al. 2012

J. Chem. Eng. Data

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Solubility of 2-hydroxybenzoic acid (salicylic acid, with measured melting point of 432 K) in water, 1-propanol, 2-propanol, and 2-propanone was determined at (298.2 to 338.2) K and atmospheric pressure. Also, the solubility of salicylic acid in binary mixtures of 1-propanol (1) + water (2), 2-propanol (1) + water (2), and 2-propanone (1) + water (2) at 298.2 K and atmospheric pressure was investigated. Phase separation occurred in x 1 = 0.114, 0.167 of 1-propanol (1) + water (2) and x 1 = 0.171, 0.237 of 2-propanone (1) + water (2) mixtures. The van't Hoff and Grant equations were used to correlate the solubility of salicylic acid in monosolvents at different temperatures. The solubility values of salicylic acid in binary mixtures of solvents were calculated using the Jouyban−Acree model (J. Chem. Eng. Data 2009Data , 54, 1168Data −1170. The mean deviation was used as an error criterion. The overall mean deviation of correlated solubility data in monosolvents at different temperatures, and in mixed solvents at 298.2 K were 1.0 % and 8.3 %, respectively. ■ INTRODUCTION2-Hydroxybenzoic or salicylic acid, a phenolic acid compound, is a metabolite of salicin, one of the most ancient pain relievers extracted from the bark of willow (Figure 1). Salicylic acid, also an active metabolite of acetylsalicylic acid, shows antiinflammatory effects and is used in topical formulations as a chemical exfoliating agent. It is used in the organic synthesis of many other medicinal compounds including salicylates (its ester and salt derivatives) and acetylsalicylic acid (Aspirin). In recent years, it has been used in cocrystal synthesis of medicinal compounds with a desirable increase in solubility properties. Hence, solubility data of this compound might be of interest for chemists and formulator researchers in chemical, pharmaceutical, food, and cosmetic industries.There are a number of previously reported solubility data for salicylic acid in monosolvents and mixtures of solvents at different temperatures. Solubility data for salicylic acid in monosolvents at different temperatures were reported for water, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, 2-methyl-2-propanol, 1-pentanol, 1-octanol, dibutyl ether, ethylene glycol, propylene glycol, glycerin, acetone, ethyl acetate, butyl acetate, acetic acid, ethyl cellosolve, 1,4-dioxane, tetrahydrofuran, 2-propanone, 2-butanone, cyclohexanone, cyclohexanol, acetonitrile, chloroform, carbon tetrachloride, benzene, benzyl alcohol, and xylene.1−7 Salicylic acid solubility data in mixtures of solvents were reported for water and either methanol, ethanol, 1-propanol, 2-propanone, 2-ethoxyethanol, 1,4-dioxane, or polyethylene glycol 300; methanol and either benzene, 1,4-dioxane, chloroform, or ethyl acetate; ethanol and either benzene, 1,4-dioxane, chloroform, or ethyl acetate; 1-propanol and either benzene, 1,4-dioxane, chloroform, or ethyl acetate; 1-butanol and either benzene, 1,4-dioxane, chloroform, or ethyl acetate; ethylene glyco...

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Section: ■ Results and Discussionmentioning

confidence: 79%

Solubility of 2-Hydroxybenzoic Acid in Water, 1-Propanol, 2-Propanol, and 2-Propanone at (298.2 to 338.2) K and Their Aqueous Binary Mixtures at 298.2 K

Fakhree¹,

Ahmadian²,

Panahi‐Azar³

et al. 2012

J. Chem. Eng. Data

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show abstract

“…The solubility parameter of SAA dimer was actually lower, 22.1 MPa 1/2 23,24 , as the dimer was less available for hydrogen bonding, leading to a smaller difference in solubility parameters between drug and PSA and thus higher predicted saturation solubility. As neither of the calculated solubilities of monomeric and dimeric SAA using the Flory-Huggins equation were in agreement with the experimental results, it could be postulated that there was a mixture of monomer and dimer SAA in the DIA systems.…”

Section: Exploratory Stability Studiesmentioning

confidence: 97%

Development of a Predictive Model for the Long-Term Stability Assessment of Drug-In-Adhesive Transdermal Films Using Polar Pressure-Sensitive Adhesives as Carrier/Matrix

Chenevas-Paule

Wolff

Ashton

et al. 2017

Journal of Pharmaceutical Sciences

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“…The solubility parameter of SAA dimer was actually lower (22.1 MPa 1/2 34,35 ), as it was less available for hydrogen bonding, leading to a smaller difference in solubility parameters between drug and PSA and thus higher predicted saturation solubility. As neither of the calculated solubilities of monomeric and dimeric SAA using the Flory-Huggins equation were in agreement with the experimental results, it could be postulated that there was a mixture of monomer and dimer SAA in the DIA systems.…”

Section: Api -Silicone Psa Binary Systemsmentioning

confidence: 98%

Development of a Predictive Model for the Stabilizer Concentration Estimation in Microreservoir Transdermal Drug Delivery Systems Using Lipophilic Pressure-Sensitive Adhesives as Matrix/Carrier

Chenevas-Paule

Wolff

Ashton

et al. 2017

Journal of Pharmaceutical Sciences

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Solubility of Salicylic Acid as a Function of Dielectric Constant

Cited by 77 publications

References 1 publication

Solubility of 2-Hydroxybenzoic Acid in Water, 1-Propanol, 2-Propanol, and 2-Propanone at (298.2 to 338.2) K and Their Aqueous Binary Mixtures at 298.2 K

Solubility of 2-Hydroxybenzoic Acid in Water, 1-Propanol, 2-Propanol, and 2-Propanone at (298.2 to 338.2) K and Their Aqueous Binary Mixtures at 298.2 K

Development of a Predictive Model for the Long-Term Stability Assessment of Drug-In-Adhesive Transdermal Films Using Polar Pressure-Sensitive Adhesives as Carrier/Matrix

Development of a Predictive Model for the Stabilizer Concentration Estimation in Microreservoir Transdermal Drug Delivery Systems Using Lipophilic Pressure-Sensitive Adhesives as Matrix/Carrier

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