Alkyl Carbon Number Research Articles

Structure-antitumor activity relationship of purin-6-yl alkyl disulfides.

Antitumor activity and toxicity to host of newly synthesized disulfide derivatives of 6-mercaptopurine (6-MP) and 6-thioguanine (6-TG) were examined in murine ascites sarcoma-180 system (total packed cell volume method) by parenteral administration. The compounds tested were 6-alkyl disulfides (carbon number of alkyl group: 2, 3, 4, 5, 6, 7, 8, 10, and 14), 6-branched-alkyl disulfides (iso-propyl, sec-butyl, and tert-butyl), and 6-aralkyl disulfide (naphthyryl). Most disulfide derivatives of 6-MP and 6-TG showed higher antitumor activity (lower ED50) and higher toxicity to host (lower LD50) than parent compounds, but ratios of increase in activity and toxicity were different with each other. The compounds with higher chemotherapeutic index (LD50/ED50) than parent compounds were alpha-naphthyryl (8.7) disulfide in a series of 6-MP (7.5) derivatives; and sec-butyl (27), tert-butyl (24), octyl (23), decyl (26), and alpha-naphthyryl (28) disulfides in a series of 6-TG (14) derivatives. These 6-TG derivatives were promising for antitumor agents.

Solubility of various hydrocarbons in aqueous solutions of sodium p-cymenesulfonate and 1-butanol

Miscibilities of various hydrocarbons in systems containing n-butanol and aqueous solutions of sodium p-cymenesulfonate (sodium-2-methyl-5-isopropyl-benzenesulfonate) (2.5 moles/kg H/sub 2/O) have been determined at 25 C. The hydrocarbons included aliphatic hydrocarbons, cyclohexane, aromatic hydrocarbons, and various hydrocarbon mixtures. The amount of n-butanol required to achieve miscibility increases with increasing chain length of the aliphatic hydrocarbons and with an increasing number of alkyl carbons on the benzene ring of the aromatic hydrocarbons. The 2-phase region with cyclohexane is smaller than with n-hexane, and similar to that with butylbenzene. For mixtures of 2 hydrocarbons, the amount of n-butanol required seems to vary linearly with weight fraction of the hydrocarbon components.

Separation of Nonionic Surfactants in Aqueous Solutions by Reverse Osmosis Membrane Process

The removal of some polyoxyethylated nonionic surfactants in aqueous solution were studied by reverse osmosis process using cellulose acetate membrane.The results were as follows : 1) The permeability showed the high values when the carbon number of alkyl groups on the alkyl-phenyl ether and the alkyl ether surfactants was low, and as the carbon number of alkyl groups increases the permeability was tendencies to be lower.As the moles of ethylene oxide increases, the permeability comes to high, and the moles of ethylene oxide showed little difference in 20 to 40moles range.2) The rejection of the alkylphenyl ether and the alkyl amine surfactants were observed better than that of alkyl ether. The relation between the moles of ethylene oxide and the rejection of surfactants were little.

Miscibility relationships in systems containing various hydrocarbons, butylcarbitol, and aqueous solutions of sodium salicylate

A study has been made of misciblllty relatlonshlps in systems containing an aqueous solution of sodium salicylate, n-butylcarbitoi, and various hydrocarbons, lncludlng both n-alkanes and aikylbenzenes. At any fixed concentration of sodium salicylate, the minimum amount of n-butyicarbltoi required to produce mlscibillty at 1:l weight percent hydrocarbon-water mixtures increases nearly linearly wlth the number of alkyl carbon atoms in the hydrocarbon. In ail cases a considerably higher welght fraction of n-butyicarbitoi Is requlred to produce misclbillty In the systems containing the alkanes than in those containing aikyibenrenes with the same alkyl carbon number. When the n-butyicarbltoi is replaced by 1-butanol as the cosolvent, this order Is reversed and the misclbliity relationships are simllar to those observed In the hydrocarbon-1-butanol-aqueous sodium p-cymenesulfonate systems, where a higher weight fraction of cosoivent is usually needed to produce misclbllity with the aikylbenzenes than with the alkanes.

Solubility of toluene in aqueous solutions of various benzenecarboxylates with or without 1-butanol

Miscibility relationships in systems containing short alkyl-side-chain sodium benzenecarboxylats, toluene, and water without (three-component systems) or with (four-component systems) 1-butanol were studied at 55 and 25/sup 0/C, respectively. The results are compared with corresponding sulfonates. The benzenecarboxylates included those of benzene, 2,4-dimethylbenzene, 2,4,6-trimethylbenzene, and tert-butylbenzene. The solubility of toluene in aqueous solutions of the carboxylates increases with the number of alkyl carbons N/sub AC/ attached to the benzene ring and generally with carboxylate concentration (up to ca. 3 mole/kg of H/sub 2/O); it is somewhat higher in the carboxylate solutions than in the corresponding sulfonate solutions. Four-component systems were treated as pseudoternary systems by maintaining a constant carboxylate to water ratio (2 mole/kg of water). Boundaries between one and two phases are fairly symmetrical. The amount of 1-butanol (cosolvent) required to produce miscibility decreases with increasing number of alkyl carbons on the carboxylate. These systems required somewhat less 1-butanol to produce miscibility than the corresponding sulfonate systems. 4 figures, 3 tables.

Miscibility in systems containing aqueous solutions of various alkylbenzenesulfonates, toluene and, n-butanol

Miscibility relationships in four-component systems containing sodium alkylbenzenesulfonates, toluene, n-butanol, and water were studied at 25°C in the hope of clarifying the complex systems used in the “micellar flood” enhanced oil recovery process. Phase boundary curves for the pseudo three-component systems (constant sulfonate/water ratios, 2.5 moles sulfonate per kg water) were determined. The sulfonates included those of benzene, toluene, xylene, ethylbenzene, isopropylbenzene, mesitylene, cymene, methyl- t-butylbenzene, and diisopropylbenzene, in all of which the alkyl substituents are smaller than in the usual surfactants. The phase boundary curves have similar and fairly symmetrical shapes. The amount of n-butanol (cosolvent) required to produce miscibility decreases with increasing number of alkyl carbons on the benzene ring of the sulfonates and seems relatively independent of the isomeric structure. The sodium salt of diisopropylbenzenesulfonate gives the lowest phase boundary curve (least n-butanol required for miscibility) among the nine sulfonates studied.

Analytical studies of maridomycin I. High-performance liquid chromatography of maridomycins and some other macrolide antibiotics

Maridomycins and their acyl derivatives (9-propionyl, 2′-propionyl and 9,2′-dipropionyl maridomycins) were separated quantitatively into six components by high-performance liquid chromatography using a Corasil I column (200 cm × 2 mm I.D.) with a mixed sovent (upper layer of n-hexane, diisopropyl ether, ethanol and water) as the eluent. A linear relationship was found between the logarithm of the capacity factors (k′) and the logarithm of the alkyl carbon numbers in the acyl group at position 4′'. This relationship led to the discovery of a new component of maridomycin (3-propionyl-4′'-n-butyryl analogue) in a crude sample. A similar relationship was found on chromatographic separation of some other macrolide antibiotics such as leucomycin, carbomycin A and B groups, under similar conditions.

Gel filtration of solubilized systems. II. Studies on the complexes of sodium lauryl sulfate and alkyl paraben by the gel filtration on Bio Gel P-4 (author's transl)

The presence of complexes of monomer sodium lauryl sulfate (SLS) and alkylparaben (methyl-, ethyl-, and butyl-parabens) can be observed by gel filtration on Bio-Gel P-4. Stability constants for the complex formation from monomer SLS and respective alkyl parabens in aqueous SLS solutions below critical micelle concentration (s) (cmc) were estimated from the elution curves of SLS and alkylparabens obtained by the tail analysis on Bio-Gel P-4. It was found that stability constants increased as the carbon number of alkyl group for alkylparabens increased. It was observed that stability constants for the complex formation in SLS micellar solutions solubilizing alkylparabens were nearly equal to those in the SLS solution below cmc. However, the partition ratio of respective alkylparabens between the aqueous and SLS micellar phases, found by considering a complex formation in the solubilized system, was approximately equal to the apparent partition ratio obtained without considering the complex formation, because concentration of the complexes was negligibly low compared with those of free alkylparabens in the aqueous phase.

Estimation of Optimal Salinity and Solubilization Parameters for Alkylorthoxylene Sulfonate Mixtures

Abstract Economic constraints are such that it is unlikely a pure surfactant will be used for major enhanced oil recovery projects. However, it is possible to manufacture at competitive prices classes of syntheic and natural petroleum sulfonates that have fairly narrow molecular-weight distributions. Under some reservoir conditions, one of these narrow-distribution sulfonates may serve quite well as the basic component of a surfactant flood, however, in many instances a mixture of two or more of these may be required. Since evaluation of a significant subset of "all possible combinations" is a formidable undertaking screening techniques must be established that can reduce the number of laboratory core floods required. It is well known that interfacial tension plays a dominant role in surfactant flooding. It has recently been shown that minimal interfacial tensions occur at optimal salinity, Cphi, where the solubilization parameters VO/Vs and Vw/Vs are equal. Additionally, it has been shown that interracial tensions are inversely proportional to the magnitude of the solubilization parameters. This paper demonstrates that optimal salinity and solubilization parameters for any mixture of orthoxylene sulfonates can be estimated by summation of mole-fraction-weighted component properties. Those properties, which could not be properties. Those properties, which could not be measured directly, were obtained by least-squares regression on mixture data. Moreover, for surfactants of known carbon number distributions, equations that are linear in mole fractions of components and logarithmic in alkyl carbon number were found to be excellent estimators of both Cphi and solubilization parameters evaluated at Cphi. parameters evaluated at Cphi. Optimal salinity and associated solubilization parameters were measured using constant weight parameters were measured using constant weight fractions of alcohol cosolvents and mixtures of seven products with narrow molecular weight distributions. The average alkyl carbon number of these products varied from about 8 to 19. Alkyl chain lengths of individual surfactant chemical species ranged from 6 to 24 carbon atoms. Introduction Optimal salinity and the amounts of oil and water contained in a microemulsion have been shown to play important roles in obtaining low interfacial tensions and high oil recoveries. Since economics of enhanced oil recovery projects demand use of inexpensive surfactants, broad-distribution products likely will be chosen. Knowledge of how to estimate optimal salinity and oil-water contents of microemulsions prepared from such products would reduce time involved in laboratory screening procedures. This paper presents a method for procedures. This paper presents a method for obtaining such estimates that should prove useful for all types of surfactant mixtures that involve homologous series. The basic concept used is that a given property of a mixture of components (Yi) is related to the sum of products of mole fraction of components in the mixture (Xij) and the "mixing value" of the property in question for that component (Y'j). In property in question for that component (Y'j). In other words, (1) This approach is similar, for example, to the pseudocritical method used by Kay to calculate pseudocritical method used by Kay to calculate gas deviation factors at high pressures. The properties of interest in this paper are optimal properties of interest in this paper are optimal salinity and solubilization parameters, Vo/Vs, and Vw/Vs, at optimal salinity. Two separate approaches were developed that depended on the degree of detail of the available surfactant-composition data. In the first approach, only average molecular weights of several surfactant products were assumed known. Optimal salinity and products were assumed known. Optimal salinity and solubilization parameters could be measured for some, but not all, of the products. Regression on mixture data was used to estimate these quantities for the remainder of the products. Those properties, either measured experimentally or estimated from mixture data, are referred to as surfactant product contributions since they can be used as mixing values of the property in question in Eq. 1 or Eq. 2. SPEJ P. 193

Effects of Phthalate Esters on the Respiration of Rat Liver Mitochondria

The effects of phthalate esters on the oxidation of succinate, glutamate, beta-hydroxybutyrate and NADH by rat liver mitochondria were examined and it was found that di-n-butyl phthalate (DBP) strongly inhibited the succinate oxidation by intact and sonicated rat mitochondria, but did not inhibit the State 4 respiration with NAD-linked substrates such as glutamate and beta-hydroxybutyrate. However, oxygen uptake accelerated by the presence of ADP and substrate (State 3) was inhibited and the rate of oxygen uptake decreased to that without ADP (State 4). It was concluded that phthalate esters were electron and energy transport inhibitors but not uncouplers. Phthalate esters also inhibited NADH oxidation by sonicated mitochondria. The degree of inhibition depended on the carbon number of alkyl groups of phthalate esters, and DBP was the most potent inhibitor of respiration. The activity of purified beef liver glutamate dehydrogenase [EC 1.4.1.3] was slightly inhibited by phthalate esters.

Right-rotatory cholesteric liquid crystals: Derivatives of Δ8(14)-cholestanol

A new series of cholesteric liquid crystals which are derivatives of Δ8(14)-cholestanol has been synthesized. Although some of the compounds are monotropic and others enantiotropic, on the average, they are liquid crystalline about 30°C lower than the cholesteryl equivalents. Their effective pitches, as measured by the method of mixtures, are all smaller than those of the equivalent cholesteryl compounds. A note-worthy feature is that they are all strongly right handed, and from extrapolation of a plot of pitch vs number of alkyl carbons for the esters, it is expected that they will remain right handed up to C16 chain length. Heretofore, only a few individual right-handed cholesteric liquid crystals have been known.

The interaction of thorium-Eriochrome Cyanine R complex with quaternary ammonium salts

The interaction of thorium-Eriochrome Cyanine R (ECR) complex with quaternary ammonium salts has been studied. Cetyltrimethyl ammonium chloride, dodecyltrimethyl ammonium bromide, decyltrimethyl ammonium bromide, and octyltrimethyl ammonium bromide were used as the quaternary ammonium salts. A shift of absorption maximum to a longer wavelength and an increase in the absorbance of thorium-ECR complex were observed by addition of each quaternary ammonium salt. But absorption spectra of thorium-ECR complex in aqueous solutions of the quaternary ammonium salts were varied considerably with difference of carbon number of alkyl group of the quaternary ammonium salts. Under the optimum concentration of the quaternary ammonium salts, the molar absortivity at the absorption maximum of thorium-ECR complex were 1.07 × 105 at 584 nm for cetyltrimethyl ammonium bromide, 1.13 × 105 at 599 nm for dodecyltrimethyl ammonium bromide, 1.0 × 105 at 600 nm for decyltrimethyl ammonium bromide, 1.59 × 105 at 604 nm for octyltrimethyl ammonium bromide and 4.0 × 104 at 530 nm for no addition. The composition of thorium-ECR complex measured by the continuous variation method was estimated to be thorium: ECR=1:2 in each case. Absorption spectrum of the thorium-ECR complex was not so changed by addition of heptyltrimethyl ammonium bromide.

Preparation and properties of sodium alkyl sulfoacetates

AbstractThe preparation and properties for a homologous series of sodium salts of alkyl sulfoacetates, containing 10, 12, 14 and 16 carbon atoms are described. The sodium salts of alkyl sulfoacetates were prepared from monochloroacetic acid, sodium sulfite and corresponding higher alcohol. The Krafft point, c.m.c. value, surface tension, solubilizing power, emulsifying power, foaming power, and calcium ion stability and resistance to acid hydrolysis were measured as the properties of these compounds. The c.m.c. values at 40 C obtained by electrical conductivity were related to the alkyl carbon number (N) of the compounds by log c.m.c.=4.852–0.301 N. Solubilizing power, emulsifying power and foaming power increased with the number of carbon atoms of alkyl chain in the surfactant. But the calcium ion stability and resistance to the acid hydrolysis decreased with an increase in the length of the hydrophobic portion.

STUDIES ON NAPHTHALENEALKYLAMINES FOR MEDICAL PURPOSE. I. SYNTHESES AND PHARMACOLOGICAL ACTIONS OF 2-NAPHTHALENEALKYLAMINES

Syntheses of 2-naphthalenealkylamine derivatives, whose carbon number (n) of the alkyl group was varied from n=0-7 and n=10 (IIIa-XIa), and their N, N-dimethyl derivatives (IIIb-XIb) as well as their methiodide (IIIc-XIc) were carried out in order to examine their pharmacological activities.Anti-acetylcholine activities and anti-histamine activities were tested according to the Magnus method. Both activities showed a tendency to strengthen as the carbon number of alkyl group increased. However, the anti-acetylcholine activities of primary amine, whose n is 10, was observed to be a little lower than that of the amine of n=7. As to the anti-histamine activities, dimethylamino derivative of n=2 was found to be the strongest, that of 3 and 4 were weaker and it became stronger as the carbon number increased. The activities of methiodide of n=1 was a little stronger than that of n=2 in both activities.As to the blood pressure activities of primary amines, n=0 showed depression and n=1-4 showed, after a little depression, a rise type, whose degree was observed to be the maximum with n=2 and later weakened to a depress type. Dimethyl compounds were depressive andmethiodide showed usually a continuous rise, after the depression.