The Extraction and Infrared Identification of <i>Gamma</i>-Hydroxybutyric Acid (GHB) from Aqueous Solutions

Chappell, J.S.; Meyn, Ashleigh W.; Ngim, Kenley K.

doi:10.1520/jfs2003175

Cited by 35 publications

(36 citation statements)

References 18 publications

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“…Chappell et al . also reported that the use of n ‐hexane as the extraction solvent gave low recoveries of γ ‐hydroxy butyric acid during a liquid–liquid extraction, further supporting the idea of polar oxylipins and their minimal role in determining CSH.…”

Section: Resultsmentioning

confidence: 81%

Flocculation, cell surface hydrophobicity and 3-OH oxylipins in the SMA strain ofSaccharomyces pastorianus

2015

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Three-hydroxy-oxylipins (3-OH oxylipins) have been previously detected in brewing yeast production strains at flocculation onset. In this work, the SMA strain of Saccharomyces pastorianus was characterized during growth in a miniature fermentation assay by measuring flocculation and cell surface hydrophobicity (CSH). Proportions of 3-OH oxylipin were also measured concurrently during growth in the miniature fermentation assay and a defined 3-OH oxylipin extraction protocol using ethyl acetate is presented along with a novel derivatization and gas chromatography-mass spectrometry (GC-MS) detection approach. When the SMA strain was grown in the assay, near maximal CSH and flocculation levels were achieved by a 36 h fermentation time. Under the same culture conditions, the oxylipin 3-OH decanoic acid (3-OH 10:0) was identified. This oxylipin could not be detected early in the fermentation, but elevated relative levels of 3-OH 10:0 were reached by 36 h, coinciding with increased CSH levels. It was previously presumed that the formation of 3-OH oxylipins at flocculation onset might increase the CSH. However, results from this study suggest that 3-OH 10:0 may not contribute to cell wall hydrophobicity. The flocculation behaviour of the SMA strain was also monitored in the presence of 3-OH 10:0, but exposure to this oxylipin did not impact the sedimentation of this yeast, suggesting that 3-OH oxylipins may not act as mediators of quorum sensing in this strain.

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Section: Resultsmentioning

confidence: 81%

Flocculation, cell surface hydrophobicity and 3-OH oxylipins in the SMA strain ofSaccharomyces pastorianus

2015

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“…The chemistry of GHB in aqueous solution is conditioned by a double equilibrium. On one hand, the cyclization reaction to yield the lactone (GBL) and, on the other, the acid/base equilibrium in which the carboxylic acid form is dissociated into the ionic form with a pK a = 4.6 [21]. The conversion speed into lactone is a relatively slow process in moderately acidic media and it requires a time frame of hours at pH ≥ 2 [22].…”

Section: Methodsmentioning

confidence: 99%

Electrochemical behaviour of gamma hydroxybutyric acid at a platinum electrode in acidic medium

Jiménez‐Pérez

Sevilla

Pineda

et al. 2013

Electrochimica Acta

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Abstract.Gamma Hydroxybutyric Acid (GHB), when studied in a platinum electrode using cyclic voltammetry, presented three oxidation peaks in acid solutions that correspond to the oxidation of the alcohol group to the corresponding aldehyde and carboxylic acid (succinic acid). An anodic scan of GHB yielded two characteristic waves, which indicates an oxidation process dependent on the chemical environment on the surface of the electrode. The cathodic scan presented an inverted oxidation peak with an onset partially overlapping with the tail of the cathodic peak for the reduction of the platinum oxide formed initially during the anodic scan. This inverted peak can be observed at a potential close to +0.2V (vs Ag/AgCl at pH 2) and separated 0.4 and 0.8 V from the two other oxidation peaks obtained during the anodic scan and in such conditions that the surface is particularly activated to favour this electrochemical process. The response obtained in the electronic current for the different peaks when GHB concentration and scan rate were changed allows inferring that these are the result of a potential dependent mechanism.

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“…This general appearance is consistent with that expected for PB, which has the stronger intermolecular and intramolecular hydrogen bonds due to the higher contents of carboxylic and hydroxyl groups. After reaction, the characteristic bond at 968 cm −1 ascribed to trimethyl quaternary ammonium diminished and a prominent feature at 1593 cm −1 attributed to the presence of the carbonyl‐stretching mode appeared . Also, bands at 1300–1500 got more intense which was attributed to the in‐plane deformation of the carboxyl hydrogen and stretching of the carbon–oxygen bond in the carboxyl group.…”

Section: Resultsmentioning

confidence: 67%

Efficient and green aqueous−solid system for transphosphatidylation to produce phosphatidylhydroxybutyrate: Potential drugs for central nervous system's diseases

Wang

et al. 2018

Biotechnology Progress

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The synthesis of nonnatural phospholipid, phosphatidylhydroxybutyrate (PB), was firstly introduced by phospholipase D (PLD)‐mediated transphosphatidylation of phosphatidylcholine (PC) with sodium γ‐hydroxybutyrate (NaGHB) in the aqueous–solid system. Nanoscale silicon dioxide (NSD) was employed as a carrier to provide an “artificial interphase” between PC and PLD. Special attention has been paid to the effect of the PC coverage on the surface area of hybrids of NSD‐PC, the PC loading and the yield of PB. Results indicated that the highest PC loading of 98.3% and the highest PB yield of 97.3% were achieved. In addition, the free PLD in the aqueous–solid system showed the greater stability and pH tolerance than that in the traditional liquid–liquid system. The operational stability of free PLD solution was investigated. The yield of PB remained 70.7% after being used for five batches. The authors provide a new idea for drug design and the potential source of PB for medical experiments. PB is a potential drug and may have the excellent performance in the treatment of central nervous system's diseases. © 2018 American Institute of Chemical Engineers Biotechnol. Prog., 35: e2726, 2019

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The Extraction and Infrared Identification of Gamma-Hydroxybutyric Acid (GHB) from Aqueous Solutions

Cited by 35 publications

References 18 publications

Flocculation, cell surface hydrophobicity and 3-OH oxylipins in the SMA strain ofSaccharomyces pastorianus

Flocculation, cell surface hydrophobicity and 3-OH oxylipins in the SMA strain ofSaccharomyces pastorianus

Electrochemical behaviour of gamma hydroxybutyric acid at a platinum electrode in acidic medium

Efficient and green aqueous−solid system for transphosphatidylation to produce phosphatidylhydroxybutyrate: Potential drugs for central nervous system's diseases

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