Chemical Composition of Aerosols from the E-Cigarette Vaping of Natural and Synthetic Cannabinoids.

Vaping cannabinoids in electronic (e)-cigarette devices is rapidly increasing in popularity, particularly among adolescents, although the chemistry affecting the composition of the vape aerosol is not well understood. This work investigates the formation of aerosol mass, bioactive hydroxyquinones, and harmful or potentially harmful carbonyls from the e-cigarette vaping of natural and synthetic cannabinoids e-liquids in propylene glycol and vegetable glycerin (PG/VG) solvent at a 50 mg/mL concentration in a commercial fourth-generation vaping device. The following cannabinoids were studied: cannabidiol (CBD), 8,9-dihydrocannabidiol (H2CBD), 1,2,8,9-tetrahydrocannabidiol (H4CBD), cannabigerol (CBG), and cannabidiolic acid (CBDA).

Industrial Routes from Sugars and Biomass to CMF and Other 5-(Halomethyl)furfurals.

The synthesis of 5-(halomethyl)furfurals (XMFs, X=F, Cl, Br, I), including 5-(chloromethyl)furfural (CMF), 5-(bromomethyl)furfural (BMF), 5-(iodomethyl)furfural (IMF), and 5-(fluoromethyl)furfural (FMF), from biomass represents a pivotal advancement in renewable chemistry and engineering. Harnessing waste biomass as a raw material offers a sustainable alternative to fossil-based resources, mitigating environmental degradation and addressing pressing energy needs. CMF and BMF, characterized by their enhanced stability over the hydroxyl analog, 5-(hydroxymethyl)furfural (HMF), exhibit promise as renewable building blocks for scale-up and commercialization.

Pseudocannabinoid H4CBD improves glucose response during advanced metabolic syndrome in OLETF rats independent of increase in insulin signaling proteins.

Cannabidiol (CBD) use has grown exponentially more popular in the last two decades, particularly among older adults (>55 yr), though very little is known about the effects of CBD use during age-associated metabolic dysfunction. In addition, synthetic analogues of CBD have generated great interest because they can offer a chemically pure product, which is free of plant-associated contaminants. To assess the effects of a synthetic analogue of CBD (H4CBD) on advanced metabolic dysfunction, a cohort of 41-wk-old Otsuka Long-Evans Tokushima Fatty (OLETF) rats were administered 200 mg H4CBD/kg by oral gavage for 4 wk.

Electrochemical Incorporation of Electrophiles into the Biomass-Derived Platform Molecule 5-(Chloromethyl)furfural.

The 5-(chloromethyl)furfural (CMF) derivative ethyl 5-(chloromethyl)furan-2-carboxylate undergoes two-electron electrochemical reduction in a simple, undivided cell to give the corresponding furylogous enolate anion, which can either be quenched with carbon dioxide to give a 5-(carboxymethyl)furan-2-carboxylate or with hydrogen ion to give a 5-methylfuran-2-carboxylate, thereby expanding the derivative scope of CMF as a biobased platform molecule.

Cannabidiol Does Not Impair Anabolic Signaling Following Eccentric Contractions in Rats.

Cannabidiol (CBD) has proven clinical benefits in the treatment of seizures, inflammation, and pain. The recent legalization of CBD in many countries has caused increased interest in the drug as an over-the-counter treatment for athletes looking to improve recovery. However, no data on the effects of CBD on the adaptive response to exercise in muscle are available.

Anion Exchange Doping: Tuning Equilibrium to Increase Doping Efficiency in Semiconducting Polymers.

High electron affinity (EA) molecules p-type dope low ionization energy (IE) polymers, resulting in an equilibrium doping level based on the energetic driving force (IE-EA), reorganization energy, and dopant concentration. Anion exchange doping (AED) is a process whereby the dopant anion is exchanged with a stable ion from an electrolyte. We show that the AED level can be predicted using an isotherm equilibrium model.

Effects of Methyl Branching on the Properties and Performance of Furandioate-Adipate Copolyesters of Bio-Based Secondary Diols.

Furandioate-adipate copolyesters are an emerging class of bio-based biodegradable polymers with great potential to replace fossil-derived terephthalic acid-based copolyesters such as poly(butylene adipate--terephthalate) (PBAT). Furandioate-adipate polyesters have almost exclusively been prepared with conventional primary (1°) alcohol diols, while secondary (2°) alcohol diol monomers have largely been overlooked until now, despite preliminary observations that using methyl-branched diols increases the of the resultant polyesters. Little is known of what impact the use of 2° alcohol diols has on other properties such as material strength, hydrophobicity, and rate of enzymatic hydrolysis-all key parameters for performance and end-of-life.

Diversification of the Renewable Furanic Platform via 5-(Chloromethyl)furfural-Based Carbon Nucleophiles.

Biobased 5-(chloromethyl)furoate and 5-methylfuroate esters can be deprotonated to function as furylogous lithium enolates, and the former can also undergo zinc insertion to access Reformatsky-type chemistry. Carbon nucleophilicity represents hitherto little-explored reactivity in these key carbohydrate-derived platform molecules, expanding their synthetic utility and potentially opening up new sustainable product markets (e. g.

In Silico Design of Cylindrophanes: The Role of Functional Groups in a Fluoride Selective Host.

Molecular recognition is the key driver in the formation of supramolecular complexes, enabling the selective encapsulation of specific guests. Here, we explore the delicate balance between different energetic terms in the formation of an efficient host for fluoride anions based on a cylindrophane structure, which can be achieved by the incorporation of ligand sites into a cyanuric acid based cyclophane framework, resulting a close proximity between the ammonium hydrogens and the anion. This study describes the character and contribution of different energetic and repulsive terms that favor the efficient inclusion of fluoride.

Across the Board: Mark Mascal on the Challenges of Lignin Biorefining.

In this series of articles, the board members of ChemSusChem discuss recent research articles that they consider of exceptional quality and importance for sustainability. This entry features Prof. M.

Butenolide Derivatives of Biobased Furans: Sustainable Synthetic Dyes.

The dye and pigment manufacturing industry is one of the most polluting in the world. Each year, over one million tons of petrochemical colorants are produced globally, the synthesis of which generates a large amount of waste. Naturally occurring, plant-based dyes, on the other hand, are resource intensive to produce (land, water, energy), and are generally less effective as colorants.

Synthetic, non-intoxicating 8,9-dihydrocannabidiol for the mitigation of seizures.

There can be a fine line between therapeutic intervention and substance abuse, and this point is clearly exemplified in herbal cannabis and its products. Therapies involving cannabis have been the treatment of last resort for some cases of refractory epilepsy, and this has been among the strongest medical justifications for legalization of marijuana. In order to circumvent the narcotic effects of Δ-tetrahydrocannabinol (THC), many studies have concentrated on its less intoxicating isomer cannabidiol (CBD).

High-mobility, trap-free charge transport in conjugated polymer diodes.

Charge transport in conjugated polymer semiconductors has traditionally been thought to be limited to a low-mobility regime by pronounced energetic disorder. Much progress has recently been made in advancing carrier mobilities in field-effect transistors through developing low-disorder conjugated polymers. However, in diodes these polymers have to date not shown much improved mobilities, presumably reflecting the fact that in diodes lower carrier concentrations are available to fill up residual tail states in the density of states.

A Zwitterionic, 10 π Aromatic Hemisphere.

A new concept in anionic 10 π aromaticity is described by the embedding of a compensating charge within an aromatic cyclononatetraenide ring by the symmetric superposition of an alkyl ammonium bridge. This is accomplished by the methylation of azatriquinacene to give a quaternary ammonium salt, followed by oxidation to the tetraene and final deprotonation. The resulting zwitterion is a stable [9]annulene with strong aromaticity as shown by its degree of C-C bond equalization and a nucleus-independent chemical shift value lower than that of benzene.

New bio-based monomers: tuneable polyester properties using branched diols from biomass.

A family of monomers, including 2,5-hexandiol, 2,7-octandiol, 2,5-furandicarboxylic acid (FDCA), terephthalic acid (TA), and branched-chain adipic and pimelic acid derivatives, all find a common derivation in the biomass-derived platform molecule 5-(chloromethyl)furfural (CMF). The diol monomers, previously little known to polymer chemistry, have been combined with FDCA and TA derivatives to produce a range of novel polyesters. It is shown that the use of secondary diols leads to polymers with higher glass transition temperatures (T) than those prepared from their primary diol equivalents.

Electrochemical Coupling of Biomass-Derived Acids: New C Platforms for Renewable Polymers and Fuels.

Electrolysis of biomass-derived carbonyl compounds is an alternative to condensation chemistry for supplying products with chain length >C for biofuels and renewable materials production. Kolbe coupling of biomass-derived levulinic acid is used to obtain 2,7-octanedione, a new platform molecule only two low process-intensity steps removed from raw biomass. Hydrogenation to 2,7-octanediol provides a chiral secondary diol largely unknown to polymer chemistry, whereas intramolecular aldol condensation followed by hydrogenation yields branched cycloalkanes suitable for use as high-octane, cellulosic gasoline.

Crystal structure determination as part of an undergraduate laboratory experiment: 1',3',3'-tri-methyl-spiro-[chromene-2,2'-indoline] and 1',3',3'-trimethyl-4-[()-(1,3,3-tri-methyl-indolin-2-yl-idene)meth-yl]spiro-[chroman-2,2'-indoline].

The crystal structures of the title compounds, CHNO and CHNO, were determined as part of an experiment in an undergraduate teaching laboratory that demonstrates the relationship between mol-ecular structure and function. 1',3',3'-Tri-methyl-spiro-[chromene-2,2'-indoline] is both a photoswitch and thermochromic mol-ecule. Students synthesized it and a bis-indoline adduct and compared the crystallographically determined structures to computed gas-phase models.

Processed Lignin as a Byproduct of the Generation of 5-(Chloromethyl)furfural from Biomass: A Promising New Mesoporous Material.

The lignin by-product of the conversion of lignocellulosic biomass to 5-(chloromethyl)furfural (CMF) has been characterised by thermogravimetric analysis, N2 physisorption porosimetry, attenuated internal reflectance IR spectroscopy, elemental analysis and solid-state NMR spectroscopy. The lignin (LCMF) has a moderate level of mesoporosity before thermal treatment and a surface area of 63 m(2)  g(-1) , which increases dramatically on pyrolysis at temperatures above 400 °C. An assessment of the functionality and textural properties of the material was achieved by analysing LCMF treated thermally over a range of pyrolysis temperatures.

5-(Chloromethyl)furfural is the New HMF: Functionally Equivalent But More Practical in Terms of its Production From Biomass.

5-(Chloromethyl)furfural (CMF) is a disruptive innovation in the biorefinery. Chemically, it is at least as versatile as the well-known HMF but, unlike HMF, it is accessible in high yield directly from cellulosic biomass due to its lipophilicity and stability under acidic conditions, which facilitate isolation. It has a rich derivative chemistry that includes biofuels, renewable polymers, specialty chemicals, and value-added agrochemical and pharmaceutical products.

Efficient, chemical-catalytic approach to the production of 3-hydroxypropanoic acid by oxidation of biomass-derived levulinic acid with hydrogen peroxide.

3-Hydroxypropanoic acid (HPA), a precursor to acrylic acid, can be produced in high yield by oxidation of the biomass-derived platform chemical levulinic acid. While treatment of levulinic acid with H2 O2 under acidic conditions gives predominantly succinic acid, a remarkable reversal of selectivity is observed under basic conditions, leading either directly to HPA or, under modified conditions, initially to 3-(hydroperoxy)propanoic acid, which can be quantitatively hydrogenated to HPA.

Novel pathways to 2,5-dimethylfuran via biomass-derived 5-(chloromethyl)furfural.

2,5-Dimethylfuran (DMF) is one of the most actively pursued biomass-derived chemicals due to the fact that it can serve both as a biofuel and an intermediate for drop-in terephthalate polymers. DMF can be accessed via catalytic hydrogenation of 5-(hydroxymethyl)furfural (HMF), but the difficult accessibility of HMF from cellulosic biomass is a major impediment to the commercial development of such a process. Alternatively, 5-(chloromethyl)furfural (CMF) is freely accessible in high yield directly from raw biomass and is shown here to be efficiently reduced to DMF under mild conditions via simple derivatives (aldimine, acetal).