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Molecules (Basel, Switzerland) May 2020Crude glycerol (CHO) is a major by-product of biodiesel production from vegetable oils and animal fats. The increased biodiesel production in the last two decades has... (Review)
Review
Crude glycerol (CHO) is a major by-product of biodiesel production from vegetable oils and animal fats. The increased biodiesel production in the last two decades has forced glycerol production up and prices down. However, crude glycerol from biodiesel production is not of adequate purity for industrial uses, including food, cosmetics and pharmaceuticals. The purification process of crude glycerol to reach the quality standards required by industry is expensive and dificult. Novel uses for crude glycerol can reduce the price of biodiesel and make it an economical alternative to diesel. Moreover, novel uses may improve environmental impact, since crude glycerol disposal is expensive and dificult. Glycerol is a versatile molecule with many potential applications in fermentation processes and synthetic chemistry. It serves as a glucose substitute in microbial growth media and as a precursor in the synthesis of a number of commercial intermediates or fine chemicals. Chlorinated derivatives of glycerol are an important class of such chemicals. The main focus of this review is the conversion of glycerol to chlorinated derivatives, such as epichlorohydrin and chlorohydrins, and their further use in the synthesis of additional downstream products. Downstream products include non-cyclic compounds with allyl, nitrile, azide and other functional groups, as well as oxazolidinones and triazoles, which are cyclic compounds derived from ephichlorohydrin and chlorohydrins. The polymers and ionic liquids, which use glycerol as an initial building block, are highlighted, as well.
Topics: Chlorohydrins; Epichlorohydrin; Glycerol
PubMed: 32481583
DOI: 10.3390/molecules25112511 -
Macromolecular Rapid Communications Nov 2014Glycerol polymers are attracting increased attention due to the diversity of polymer compositions and architectures available. This article provides a brief... (Review)
Review
Glycerol polymers are attracting increased attention due to the diversity of polymer compositions and architectures available. This article provides a brief chronological review on the current status of these polymers along with representative examples of their use for biomedical applications. First, the underlying chemistry of glycerol that provides access to a range of monomers for subsequent polymerizations is described. Then, the various synthetic methodologies to prepare glycerol-based polymers including polyethers, polycarbonates, polyesters, and so forth are reviewed. Next, several biomedical applications where glycerol polymers are being investigated including carriers for drug delivery, sealants or coatings for tissue repair, and agents possessing antibacterial activity are described. Fourth, the growing market opportunity for the use of polymers in medicine is described. Finally, the findings are concluded and summarized, as well as the potential opportunities for continued research efforts are discussed.
Topics: Biomedical Research; Glycerol; Medicine; Polymerization; Polymers
PubMed: 25308354
DOI: 10.1002/marc.201400389 -
Molecules (Basel, Switzerland) Jul 2022Glycerol polyesters have recently become objects of interest in tissue engineering. Barely known so far is poly(glycerol itaconate) (PGItc), a biocompatible,...
Glycerol polyesters have recently become objects of interest in tissue engineering. Barely known so far is poly(glycerol itaconate) (PGItc), a biocompatible, biodegradable polyester. Due to the presence of a C=C electron-acceptor moiety, it is possible to post-modify the product by Michael additions to change the properties of PGItc. Thus, using PGItc as one of the elements of cellular scaffold crosslinked in situ for bone tissue regeneration seems to be a very attractive yet unexplored solution. This work aims to optimize the synthesis of PGItc to obtain derivatives with a double bond in the side chain with the highest conversion rates. The experiments were performed with itaconic anhydride and glycerol using mathematical planning of experiments according to the Box-Behnken plan without solvent and catalyst. The input variables of the process were the ratio of the OH/COOH, temperature, and reaction time. The optimised output variables were: the degree of esterification (ED), the degree of esterification calculated from the analysis of H NMR spectra (ED), and the degree of itaconic anhydride conversion-calculation based on C NMR spectra (%X). In each of statistical models, the significance of the changed synthesis parameters was determined. Optimal conditions are when OH/COOH ratio is equal to 1.5, temperature is 140 °C and time of reaction is 5 h. The higher OH/COOH ratio, temperature and longer the experiment time, the higher the value of the degree of esterification and the degree of anhydride conversion.
Topics: Anhydrides; Esterification; Glycerol; Polyesters; Tissue Engineering
PubMed: 35889505
DOI: 10.3390/molecules27144627 -
Molecules (Basel, Switzerland) Dec 2020The acknowledgement that uncontrolled and excessive use of fossil resources has become a prime concern with regard to environmental deterioration, has shifted the... (Review)
Review
The acknowledgement that uncontrolled and excessive use of fossil resources has become a prime concern with regard to environmental deterioration, has shifted the orientation of economies towards the implementation of sustainable routes of production, through the valorization of biomass. Green chemistry plays a key role in this regard, defining the framework of processes that encompass eco-friendly methodologies, which aim at the development of highly efficient production of numerous bioderived chemicals, with minimum environmental aggravation. One of the major concerns of the chemical industry in establishing sustainable routes of production, is the replacement of fossil-derived, volatile solvents, with bio-based benign ones, with low vapor pressure, recyclability, low or no toxicity, availability and low cost. Glycerol is a natural substance, inexpensive and non-toxic, and it is a principal by-product of biodiesel industry resulting from the transesterification process. The ever-growing market of biodiesel has created a significant surplus of glycerol production, resulting in a concomitant drop of its price. Thus, glycerol has become a highly available, low-cost liquid, and over the past decade its use as an alternative solvent has been gaining unprecedented attention. This review summarizes the utilization of glycerol and glycerol-based deep eutectic mixtures as emerging solvents with outstanding prospect in bioactive polyphenol extraction.
Topics: Chemical Fractionation; Glycerol; Green Chemistry Technology; Hydrogen Bonding; Polyphenols; Solvents
PubMed: 33322032
DOI: 10.3390/molecules25245842 -
The Journal of Clinical Investigation Jan 1978A 70-yr-old mildly diabetic white male was discovered to have an elevated level of serum free glycerol in the range of 75 mg/dl and to excrete about 13 g of free...
A 70-yr-old mildly diabetic white male was discovered to have an elevated level of serum free glycerol in the range of 75 mg/dl and to excrete about 13 g of free glycerol in the urine per 24 h. During a 24-h fast the urine glycerol loss increased to 21.5 g per 24 h. Studies carried out in vitro using leukocytes prepared from the patient's blood which were incubated with [14C]glycerol demonstrated an almost complete absence of glycerol oxidation to 14CO2 and of glycerol phosphorylation, in contrast to control studies with leukocytes collected from normal subjects. Homogenates of the patient's leukocytes contained negligible activity of ATP:glycerol phosphotransferase (glycerokinase EC 2.7.1.30) as measured by a direct spectrophotometric method. Marked hyperglycerolemia has thus far been detected in one brother and in one son of the daughter of this patient. This evidence suggests an x-linked recessive inheritance pattern of the trait. There is a high prevalence of diabetes mellitus in this family.
Topics: Aged; Diabetes Mellitus; Glycerol; Glycerol Kinase; Humans; Leukocytes; Male; Pedigree
PubMed: 618910
DOI: 10.1172/JCI108914 -
Nature Metabolism Feb 2024Cellular senescence affects many physiological and pathological processes and is characterized by durable cell cycle arrest, an inflammatory secretory phenotype and...
Cellular senescence affects many physiological and pathological processes and is characterized by durable cell cycle arrest, an inflammatory secretory phenotype and metabolic reprogramming. Here, by using dynamic transcriptome and metabolome profiling in human fibroblasts with different subtypes of senescence, we show that a homoeostatic switch that results in glycerol-3-phosphate (G3P) and phosphoethanolamine (pEtN) accumulation links lipid metabolism to the senescence gene expression programme. Mechanistically, p53-dependent glycerol kinase activation and post-translational inactivation of phosphate cytidylyltransferase 2, ethanolamine regulate this metabolic switch, which promotes triglyceride accumulation in lipid droplets and induces the senescence gene expression programme. Conversely, G3P phosphatase and ethanolamine-phosphate phospho-lyase-based scavenging of G3P and pEtN acts in a senomorphic way by reducing G3P and pEtN accumulation. Collectively, our study ties G3P and pEtN accumulation to controlling lipid droplet biogenesis and phospholipid flux in senescent cells, providing a potential therapeutic avenue for targeting senescence and related pathophysiology.
Topics: Humans; Lipid Metabolism; Glycerol; Ethanolamines; Phosphates; Glycerophosphates
PubMed: 38409325
DOI: 10.1038/s42255-023-00972-y -
Microbial Cell Factories Nov 2017Today, biofuels represent a hot topic in the context of petroleum and adjacent products decrease. As biofuels production increase, so does the production of their major... (Review)
Review
Today, biofuels represent a hot topic in the context of petroleum and adjacent products decrease. As biofuels production increase, so does the production of their major byproduct, namely crude glycerol. The efficient usage of raw glycerol will concur to the biodiesel viability. As an inevitable waste of biodiesel manufacturing, glycerol is potentially an attractive substrate for the production of value-added products by fermentation processes, due to its large amounts, low cost and high degree of reduction. One of the most important usages of glycerol is its bioconversion through microbial fermentation to value-added materials like 1,3-propanediol and citric acid. There is a considerable industrial interest in 1,3-propanediol and citric acid production based on microbial fermentations, as it seems to be in competition with traditional technologies utilized for these products. In the present work, yields and concentrations of 1,3-propanediol and citric acid registered for different isolated strains are also described. Microbial bioconversion of glycerol represents a remarkable choice to add value to the biofuel production chain, allowing the biofuel industry to be more competitive. The current review presents certain ways for the bioconversion of crude glycerol into citric acid and 1,3-propanediol with high yields and concentrations achieved by using isolated microorganisms.
Topics: Bacteria; Biofuels; Biotechnology; Citric Acid; Fermentation; Glycerol; Industrial Microbiology; Propylene Glycols
PubMed: 29110678
DOI: 10.1186/s12934-017-0807-5 -
Physiological Reports Jan 2022Vaping is increasingly popular among the young and adult population. Vaping liquids contained in electronic cigarettes (e-cigarettes) are mainly composed of propylene...
Vaping is increasingly popular among the young and adult population. Vaping liquids contained in electronic cigarettes (e-cigarettes) are mainly composed of propylene glycol and glycerol, to which nicotine and flavors are added. Among several biological processes, glycerol is a metabolic substrate used for lipid synthesis in fed state as well as glucose synthesis in fasting state. We aimed to investigate the effects of glycerol e-cigarette aerosol exposure on the aspects of glycerol and glucose homeostasis. Adult and young male and female mice were exposed to e-cigarette aerosols with glycerol as vaping liquid using an established whole-body exposure system. Mice were exposed acutely (single 2-h exposure) or chronically (2 h/day, 5 days/week for 9 weeks). Circulating glycerol and glucose levels were assessed and glycerol as well as glucose tolerance tests were performed. The liver was also investigated to assess changes in the histology, lipid content, inflammation, and stress markers. Lung functions were also assessed as well as hepatic mRNA expression of genes controlling the circadian rhythm. Acute exposure to glycerol aerosols generated by an e-cigarette increased circulating glycerol levels in female mice. Increased hepatic triglyceride and phosphatidylcholine concentrations were observed in female mice with no increase in circulating alanine aminotransferase or evidence of inflammation, fibrosis, or endoplasmic reticulum stress. Chronic exposure to glycerol e-cigarette aerosols mildly impacted glucose tolerance test in young female and male mice. Fasting glycerol, glucose, and insulin remained unchanged. Increased pulmonary resistance was observed in young male mice. Taken together, this study shows that the glycerol contained in vaping liquids can affect the liver as well as the aspects of glucose and glycerol homeostasis. Additional work is required to translate these observations to humans and determine the biological and potential pathological impacts of these findings.
Topics: Animals; Electronic Nicotine Delivery Systems; Female; Glycerol; Homeostasis; Liver; Male; Mice; Vaping
PubMed: 35075822
DOI: 10.14814/phy2.15146 -
Biochimica Et Biophysica Acta.... Apr 2019For its fundamental relevance, transport of water and glycerol across the erythrocyte membrane has long been investigated before and after the discovery of aquaporins...
For its fundamental relevance, transport of water and glycerol across the erythrocyte membrane has long been investigated before and after the discovery of aquaporins (AQPs), the membrane proteins responsible for water and glycerol transport. AQP1 is abundantly expressed in the human erythrocyte for maintaining its hydrohomeostasis where AQP3 is also expressed (at a level ~30-folds lower than AQP1) facilitating glycerol transport. This research is focused on two of the remaining questions: How permeable is AQP3 to water? What is the glycerol-AQP3 affinity under near-physiological conditions? Through atomistic modelling and large-scale simulations, we found that AQP3 is two to three times more permeable to water than AQP1 and that the glycerol-AQP3 affinity is approximately 500/M. Using these computed values along with the data from the latest literature on AQP1 and on erythrocyte proteomics, we estimated the water and glycerol transport rates across the membrane of an entire erythrocyte. We used these rates to predict the time courses of erythrocyte swelling-shrinking in response to inward and outward osmotic gradients. Experimentally, we monitored the time course of human erythrocytes when subject to an osmotic or glycerol gradient with light scattering in a stopped-flow spectrometer. We observed close agreement between the experimentally measured and the computationally predicted time courses of erythrocytes, which corroborated our computational conclusions on the AQP3 water-permeability and the glycerol-AQP3 affinity.
Topics: Aquaporin 3; Cell Membrane Permeability; Erythrocyte Membrane; Glycerol; Humans
PubMed: 30659792
DOI: 10.1016/j.bbamem.2019.01.008 -
Journal of Chromatography. B,... Nov 2009A high-performance liquid chromatographic method that accurately measures glycerol and myo-inositol from plasma and tissue is described. The method incorporates a...
A high-performance liquid chromatographic method that accurately measures glycerol and myo-inositol from plasma and tissue is described. The method incorporates a pre-column derivatization reaction using aqueous extracts with benzoyl chloride as a modifying agent. The benzoylated derivatives are isolated by HPLC using reversed-phase gradient chromatography and quantified via absorbance detection at 231 nm. The benzoylated derivatives of glycerol and myo-inositol are well resolved from other known carbohydrates, internal standard and other contaminants encountered within samples and during incubation. The benzoylation of these analytes reach a maximum between 3.5 and 6 h of incubation and are stable for at least 24 days at 4 degrees C. The limit of quantization (LOQ) of glycerol was equal to 2.5 nmol/ml plasma and 6.4 nmol/g tissue and the LOQ of myo-inositol was 1.8 nmol/ml plasma and 3.6 nmol/g tissue. Incubation of known standards and samples with benzoyl chloride at 40 degrees C for 4 h showed fully benzoylated products as determined by mass spectral analysis. Calibration curves were linear between 2.7 and 174 nmol for glycerol and 1.4-89 nmol for myo-inositol. Comparison of tissue and plasma concentrations of glycerol and myo-inositol found using this method are in good agreement with other reported values using other techniques.
Topics: Animals; Chromatography, High Pressure Liquid; Glycerol; In Vitro Techniques; Inositol; Male; Rats; Rats, Sprague-Dawley; Reproducibility of Results
PubMed: 19783233
DOI: 10.1016/j.jchromb.2009.09.015