Solubility properties octanol-water partition coefficients

The toxicological or cumulative effect of illicit drugs on the ecosystems has not been studied yet. Moreover, their fate and transport in the environment is to a big extent still unknown. Due to their physical-chemical properties (octanol-water partition coefficient, solubility, etc.) some of them, such as cannabinoids, are likely to bioaccumulate in organisms or concentrate in sediments whereas the rest, much more polar compounds, will tend to stay in aqueous environmental matrices. However, continuous exposure of aquatic organisms to low aquatic concentrations of these substances, some of them still biologically active (e.g., cocaine (CO), morphine (MOR) and MDMA) may cause undesirable effects on the biota. 

The use of data concerning the physicochemical properties of chemicals (e.g., stability, solubility, pH, octanol-water partition coefficient, and protein binding). 

De Maagd, P.G.-J., ten Hulscher, T.E.M., Van den Heuvel, H., Opperhuizen, A., Sijm, D.T.H.M. (1998) Physicochemical properties of polycyclic aromatic hydrocarbons aqueous solubilities, n-octanol/water partition coefficients, and Henry s law constants. Environ. Toxicol. Chem. 17, 252-257. 

Figure 1.1.1 Examples of property estimation techniques (Sw = water solubility Kow = octanol-water partition coefficient). Chlorobenzene is the query compound. F are fragment or atom constants / is a property-property or a structure-property relationship.

Generic chemical class data are often relevant to assessing potential toxicity and should be a part of any evaluation. The relevant information includes structure-activity relationships and physical-chemical properties, such as melting point, boiling point, solubility, and octanol-water partition coefficient. Physical-chemical properties affect an agent s absorption, tissue distribution, biotransformation, and degradation in the body. 

Input of physico-chemical properties of the pesticide realize a more precise prediction of indoor behavior, and the necessary data are easily available properties, such as molecular weight, vapor pressure, water solubility and octanol/water partition coefficient. 

In addition to GC properties, Kurz [4] has investigated HPLC retention of 106 PCDE congeners. Retention indexes (RI) were measured on three reversed phase columns having phenyl, cyanopropyl, and octadecyl phases. Like HRGC retention, HPLC retention of PCDEs depends on the structure. LC data of PCDEs have been used to determine water solubility and octanol-water partition coefficients [66]. 

A further OECD Council Decision in 1991 focused on HPV chemicals. These decisions prompted the development of a minimum hazard data set to describe an HPV chemical - the Screening Information Data Set, or SIDS. This includes physicochemical properties (melting point, boiling point, vapor pressure, water solubility, and octanol-water partition coefficient) environmental fate (stability in water, photodegradation, biodegradation, and an estimate of distribution/transport in the environment) environmental effects (acute toxicity to aquatic vertebrates, invertebrates, and plants) and human health effects (acute toxicity, repeated-dose toxicity, toxicity to the gene and the chromosome, and reproductive and developmental toxicity). 

A polarity ranking is not possible based only on dielectric constant and dipole moment because they do not take into account H-bonding thus, polarity series are often constructed empirically, using such factors as the solvent strength parameter obtained from the observed ability of various solvents to elute solutes from aluminum oxide absorbent. However, for environmental chemicals, a numerical index for polarity does not exist only the consequences of polarity, as reflected in measureable properties such as water solubility and octanol-water partition coefficient, are available for fate predictions. 

Numerous relationships exist among the structural characteristics, physicochemical properties, and/or biological qualities of classes of related compounds. Simple examples include bivariate correlations between physicochemical properties such as aqueous solubility and octanol-water partition coefficients (Jtow) and correlations between equilibrium constants of related sets of compounds. Perhaps the best-known attribute relationships to chemists are the correlations between reaction rate constants and equilibrium constants for related reactions commonly known as linear free-energy relationships or LFERs. The LFER concept also leads to the broader concepts of property-activity and structure-activity relationships (PARs and SARs), which seek to predict the environmental fate of related compounds or their bioactivity (bioaccumulation, biodegradation, toxicity) based on correlations with physicochemical properties or structural features of the compounds. Table 1 summarizes the types of attribute relationships that have been used in chemical fate studies and defines some important terms used in these relationships. 

Table 2.2 summarizes the physicochemical properties (solubility [S], octanol/water partition coefficient [log Kow], Henry s law constant, and vapor pressure) of several explosives. As evident in Table 2.2, the volatility of most explosives is relatively low, so that with the exception of NG, when released into the environment these chemicals do not generally migrate to the atmosphere [139], The compounds can be... 

Indeed, OCPs, once released into the environment, are distributed into various environmental compartments (e.g., water, soil, and biota) as a result of complex physical, chemical, and biological processes. In order to perform appropriate exposure and risk assessment analyses, multimedia models of pollutant partitioning in the environment have been developed. Properties which are at the base of such a partitioning are water solubility (WS), octanol-water partition coefficient (Ko ), soil adsorption (K ), and bioconcentration factors (BCFs) in aquatic organisms, following these four equilibriums ... 

It is obvious that the nature of the toxicological effects, the persistence, and more generally the environmental behavior of the pesticides depend on their physicochemical properties (e.g. water solubility, 1-octanol/water partition coefficient (logP), vapor pressure) [4-9]. 

As can be seen in Table 18.1, a number of groups of chemical compounds are employed for crop protection, and the properties of which differ widely. The environmental fate of pesticides can be predicted from some major physicochemical parameters including water solubility, the octanol-water partition coefficient dissociation constant... 

Two approaches to quantify/fQ, i.e., to establish a quantitative relationship between the structural features of a compoimd and its properties, are described in this section quantitative structure-property relationships (QSPR) and linear free energy relationships (LFER) cf. Section 3.4.2.2). The LFER approach is important for historical reasons because it contributed the first attempt to predict the property of a compound from an analysis of its structure. LFERs can be established only for congeneric series of compounds, i.e., sets of compounds that share the same skeleton and only have variations in the substituents attached to this skeleton. As examples of a QSPR approach, currently available methods for the prediction of the octanol/water partition coefficient, log P, and of aqueous solubility, log S, of organic compoimds are described in Section 10.1.4 and Section 10.15, respectively. 

The following physico-chemical properties of the analyte(s) are important in method development considerations vapor pressure, ultraviolet (UV) absorption spectrum, solubility in water and in solvents, dissociation constant(s), n-octanol/water partition coefficient, stability vs hydrolysis and possible thermal, photo- or chemical degradation. These valuable data enable the analytical chemist to develop the most promising analytical approach, drawing from the literature and from his or her experience with related analytical problems, as exemplified below. Gas chromatography (GC) methods, for example, require a measurable vapor pressure and a certain thermal stability as the analytes move as vaporized molecules within the mobile phase. On the other hand, compounds that have a high vapor pressure will require careful extract concentration by evaporation of volatile solvents. 

The order of the mobilities of alachlor, butylate, and metolachlor in columns of various soils was metolachlor > alachlor > butylate. This correlates directly with the water solubilities and inversely to the adsorption coefficients and octanol/water partition coefficients of these compounds. Diffusion of these compounds in soil thin-layers was as follows butylate > alachlor > metolachlor, which correlates directly with the vapor pressures of these compounds. Significant soil properties affecting diffusion appeared to be bulk density and temperature. Soil moisture is also probably important, but its effect on the diffusion of these compounds was not determined. 

Many groups have discussed the correlation between solubility and molecular properties [14-19], and the octanol/water partition coefficient, the molecular volume and surface area, the boiling point and charge distribution in the molecules are well-documented molecular descriptors that correlate strongly with experimental solubility. 

Absorption, in general, is treated as a physicochemical transport process based on computations of logP (the octanol/water partition coefficient) and solubility governed by factors such as polar surface area on the molecule. It is conceivable that SNPs in drug transporter genes will affect the pharmacokinetic properties of compounds and, therefore, these may have to be taken into consideration in the design process. 

There is a continuing effort to extend the long-established concept of quantitative-structure-activity-relationships (QSARs) to quantitative-structure-property relationships (QSPRs) to compute all relevant environmental physical-chemical properties (such as aqueous solubility, vapor pressure, octanol-water partition coefficient, Henry s law constant, bioconcentration factor (BCF), sorption coefficient and environmental reaction rate constants from molecular structure). 

Kamlet, M. J., Doherty, R. M., Carr, P. W., Mackay, D., Abraham, M. H., Taft, R. W. (1988) Linear solvation energy relationships. 44. Parameter estimation rules that allow accurate prediction of octanol/water partition coefficients and other solubility and toxicity properties of polychlorinated biphenyls and polycyclic aromatic hydrocarbons. Environ. Sci. Technol. 22, 503-509. 

Wame, M., St. J., Connell, D. W., Hawker, D. W. (1990) Prediction of aqueous solubility and the octanol-water partition coefficient for lipophilic organic compounds using molecular descriptors and physicochemical properties. Chemosphere 16, 109-116. 

Laskowski [1] has thoroughly reviewed the physico-chemical properties of the SPs, and these are summarized briefly below. SPs are typically of low water solubility (in the low microgram per liter range) and are highly nonpolar (logarithmic octanol water partition coefficients of around 6-7), indicating potential for bioaccumulation. Fish bioconcentration factors (BCF) of several hundred to several thousand are reported however metabolism limits the amount of bioaccumulation,... 

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