David Rutolo - Academia.edu (original) (raw)

Papers by David Rutolo

Chemical Communications (London), 1967

Journal of Functional Biomaterials, Oct 4, 2019

Organic Preparations and Procedures, 1969

Journal of the American Chemical Society, 1969

Hydrolysis of methyl dimethylsulfonium acetate p-toluenesulfonate (1) at constant pH is shown to ... more Hydrolysis of methyl dimethylsulfonium acetate p-toluenesulfonate (1) at constant pH is shown to be first order in hydroxide ion and first order in ester in the range of pH 7 to 8.5. The entropy of activation is +17 & 2.3 eu. Evidence is presented which suggests that the unusual value for AS* involves a sulfonium hydroxide intimate ion pair. n an earlier paper' we reported that cationic electro-I static catalysis to ester hydrolysis was very small in the system schematically illustrated by C& \-S-CHZ +I ' O R for which a sulfonium sulfur atom was potentially capable of serving as an internal electrophilic catalyst during ester hydrolysis. That observation has been reinforced and generalized by the extensive data of Bruice2 using other systems. In our earlier report we observed unusually large positive entropies of activation and suggested that the intervention of a ketene intermediate, the decomposition of which was monomolecular and rate controlling, could account for such an observation. The purpose of the present work was to test that suggestion. Results and Discussion A simple a-sulfonium ester capable of facile ylide formation was required for this study. Methyl dimethylsulfonium acetate p-toluenesulfonate (l), shown in Scheme I, satisfied that requirement. Hydrolysis of

Tetrahedron Letters, 1973

La presente invention concerne des systemes d'administration transmuqueuse et transdermique c... more La presente invention concerne des systemes d'administration transmuqueuse et transdermique comprenant : au moins un agent tensioactif non ionique ; au moins un polyol ; et au moins un agent actif ; et eventuellement comprenant en outre au moins une huile. Dans des modes de realisation particuliers, le systeme d'administration a une taille moyenne de particule d'environ 5 nm a environ 200 nm.

Chemischer Informationsdienst. Organische Chemie

Journal of Clinical Oncology

TPS12127 Background: Cannabinoid molecules derived from Cannabis sativa L. have been posited to a... more TPS12127 Background: Cannabinoid molecules derived from Cannabis sativa L. have been posited to ameliorate conditions, including pain, chemotherapy induced nausea and multiple sclerosis associated spasticity. The clinical use of cannabinoids refers to a wide variety of formulations and extracts that may contain different active ingredients and adulterants as well as inter batch variability. Novel matrix formulations (e.g., water-soluble nanoparticles) for cannabis delivery may add further efficacy and tolerability to standard routes of administration (e.g., oral / gastrointestinal, inhaled, sublingual). This is further emphasized by the dysbiotic effects on the intestinal microbiome reported for oral formulations of medicinal cannabis, and which resulted in reduced efficacy. Similar results have been reported for other psychotropic compounds, such as alcohol and nicotine. Therapeutic use of cannabinoid formulations may be mode of delivery dependent in order to achieve safe, tolerabl...

Journal of Functional Biomaterials

Coenzyme Q10 (CoQ10) has a central role in the generation of cellular bioenergy and its regulatio... more Coenzyme Q10 (CoQ10) has a central role in the generation of cellular bioenergy and its regulation. The hydrophobicity exhibited by the CoQ10 molecule leads to reports of poor absorption profiles, therefore, the optimization of formulations and modes of delivery is an ever-evolving therapeutic goal. The aim of this study was to investigate different CoQ10 formulations. The article summarizes the findings from an Australian comparative study involving adults administered CoQ10 through different oral delivery platforms. A total of 11 participants (six males and five females) voluntarily participated in a comparative clinical study of three different CoQ10 formulations across a six-week period, completing 198 person-hours of cumulative contribution equivalent to n = 33 participation. All of the eligible participants (n = 11) administered the three formulations blinded from who the commercial supplier of the formulation was and from what the chemical form of the CoQ10 was that was being...

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Journal of functional biomaterials, Jan 21, 2018

The administration of biological compounds that optimize health benefits is an ever-evolving ther... more The administration of biological compounds that optimize health benefits is an ever-evolving therapeutic goal. Pharmaceutical and other adjunctive biological compounds have been administered via many different routes in order to produce a systemic pharmacological effect. The article summarizes the findings from an Australian comparative study in adults administered vitamin B through different oral delivery platforms. A total of 16 subjects (9 males, 7 females) voluntarily partook in a comparative clinical study of five different vitamin B formulations across a six-month period, completing 474 person-hours of cumulative contribution, that was equivalent to an = 60 participation. A nanoparticle delivered vitamin B through a NanoCelle platform was observed to be significantly ( < 0.05) better absorbed than all other dose equivalent platforms (i.e., tablets, emulsions, or liposomes) from baseline to 1, 3, and 6 h of the study period. The nanoparticle platform delivered vitamin B demo...

J Org Chem, 1978

Communications 189-191 "C). On refluxing 11 and 12 in acetic anhydride and sodium acetate for 0.5... more Communications 189-191 "C). On refluxing 11 and 12 in acetic anhydride and sodium acetate for 0.5 h, respectively, we readily obtained the same dehydrated product 13 (pale yellow crystals, mp 164-166 "C). The product 13 was further converted to 14 (orange crystals, mp 113-115 "C) by treating with hydrochloric acid in chloroform. The main photoproduct 11 was quantitatively oxidized to 15 (mp 135-136 "C) by chromic acid oxidation in acetic acid. In a similar manner, 13 was oxidized to 15 (50%). The structure of 11 was confirmed by X-ray diffraction. The stereochemistry of 12 is assigned on the basis of its lH NMR spectra compared with that of 11: partial IH NMR (6) of 11, 4.1-4.4 (m, 2 H, two methine), 3.78 (m, 2 H, NCH,); 12,4.92 (m, 1 H, HCOMe), 3.74 and 3.50 (twodd, 2 H, NCHz), 2.76 (d, 1 H, HCPh). On irradiation of 10 in methanol, the presence of a triplet quencher (penta-1,3-diene, 1 mol/L) did not significantly affect the rate of formation of the photoproducts, analogous to the case of photolysis of N-(dibenzylami-nomethy1)phthalimide. le Irradiation of N-(4-methyl-3-pentenyl)phthalimide (16) in methanol gave the corresponding isomers 17/18 = 1:l (84%). These intramolecular photocyclizations of phthalimides may be reasonably explained by a mechanism involving initial one-electron t r a n~f e r .~ Thus, for example, in the photocyclization of 1, the primary photoprocess may be one-electron transfer from the double bond (1-19 in Scheme I) followed by polar addition of methanol to give a diradical (19-20)j which cyclizes to produce 2a and 3a.'j Scheme I The reaction pattern of the photocyclization of N-alkenylphthalimide described above seems to be novel in the widely studied photochemistry of carbonyl compounds with olefins. The scope, limitation, and detailed mechanism of this reaction are under investigation.