| Glycolic acid (or hydroxyacetic acid; chemical formula HOCH2CO2H) is a colorless, odorless and hygroscopic crystalline solid, highly soluble in water. It is used in various skin-care products. Glycolic acid is widespread in nature. A glycolate (sometimes spelled "glycollate") is a salt or ester of glycolic acid.
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| InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5) |
| AEMRFAOFKBGASW-UHFFFAOYSA-N |
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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keratolytic drug
A drug that softens, separates, and causes desquamation of the cornified epithelium or horny layer of skin. Keratolytic drugs are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases.
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View more via ChEBI Ontology
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2-Hydroxyacetic acid
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ChemIDplus
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2-Hydroxyethanoic acid
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NIST Chemistry WebBook
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α-hydroxyacetic acid
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NIST Chemistry WebBook
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alpha-Hydroxyacetic acid
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HMDB
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Glycolic acid
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KEGG COMPOUND
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GLYCOLIC ACID
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PDBeChem
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Glycollic acid
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ChemIDplus
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HOCH2COOH
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NIST Chemistry WebBook
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Hydroxyacetic acid
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KEGG COMPOUND
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Hydroxyethanoic acid
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ChemIDplus
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1209322
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Reaxys Registry Number
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Reaxys
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79-14-1
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CAS Registry Number
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KEGG COMPOUND
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79-14-1
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CAS Registry Number
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NIST Chemistry WebBook
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79-14-1
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CAS Registry Number
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ChemIDplus
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Kar HK, Gupta L, Chauhan A (2012)
A comparative study on efficacy of high and low fluence Q-switched Nd:YAG laser and glycolic acid peel in melasma.
Indian journal of dermatology, venereology and leprology 78, 165-171 [PubMed:22421647]
[show Abstract]
BackgroundMelasma is acquired symmetric hypermelanosis characterized by light-to-deep brown pigmentation over cheeks, forehead, upper lip, and nose. Treatment of this condition is difficult and associated with high recurrence rates. With the advent of newer therapies, there is interest in the use of glycolic acid peels and Q-switched Nd:YAG laser (QSNYL) in high and low fluence for this disorder.AimsTo compare the therapeutic efficacy of low fluence QSNYL, high fluence QSNYL, and glycolic acid peel in melasma in three study groups of 25 patients each.MethodsSeventy-five Indian patients diagnosed as melasma were included. These patients were randomly divided in three groups (Group A = 25 patients of melasma treated with low-fluence QSNYL at weekly intervals, Group B = 25 patients of melasma treated with glycolic acid peel at 2 weeks intervals, Group C = 25 patients of melasma treated with high-fluence QSNYL at 2 weeks intervals). Study period and follow-up period was of 12 weeks each. Out of the 75 patients included, 21 patients in Group A, 19 patients in Group B, and 20 patients in Group C completed the study. Response to treatment was assessed using melasma area and severity index score.ResultsSignificant improvement was recorded in all the three groups. The improvement was statistically highly significant in Group A as compared to Group C (P<0.005), significant in Group A as compared to Group B (P<0.05), and also in Group B when compared to Group C (P<0.05). Low-fluence QSNYL was associated with least side effects.ConclusionsThis study shows the efficacy of low-fluence QSNYL and glycolic acid peel in melasma. These could be an effective treatment options compared to conventional methods for the treatment of melasma. | Kumari S, Singh RP (2012)
Glycolic acid-g-chitosan-gold nanoflower nanocomposite scaffolds for drug delivery and tissue engineering.
International journal of biological macromolecules 50, 878-883 [PubMed:22044748]
[show Abstract]
This paper reports a simple novel method for the synthesis of flower like gold nanoparticle (three dimensional branched nanoparticle) with >30 tips, under controlled temperature condition. Formation of flower like Au nanoparticle was confirmed by scanning electron microscopy (SEM) and transmission electron microscopy (TEM). Next step of this paper reveals the potential use of novel hybrids of chitosan-g-glycolic acid and gold nanoflower (AuNF) in controlled drug delivery and tissue engineering applications. The drug loaded novel nanohybrid scaffold is prepared by freeze drying of grafted polymer solution. Grafting of glycolic acid to the chitosan and incorporation of drug were evaluated by Fourier transform infrared spectroscopy (FTIR). The nanohybrid scaffolds were found to be stable towards the pH of the medium. The cell viability study shows that prepared nanohybrid scaffolds are biocompatible. Gold nanoflowers were found to control the drug release rate in the buffer solution (pH 7.4). Therefore, for the glycolic acid grafted chitosan based system, gold nanoflowers are the viable additive for drug delivery. | Sobhi RM, Sobhi AM (2012)
A single-blinded comparative study between the use of glycolic acid 70% peel and the use of topical nanosome vitamin C iontophoresis in the treatment of melasma.
Journal of cosmetic dermatology 11, 65-71 [PubMed:22360337]
[show Abstract]
Background Melasma is a common pigmentary disorder. Despite the availability of a wide range of skin-lightening treatments, melasma of skin remains a therapeutic challenge.Objective The aim of this study was to evaluate the efficacy and safety of nanosome vitamin C iontophoresis and to compare the therapeutic effects of nanosome vitamin C iontophoresis vs. glycolic acid peel 70% in the treatment of melasma in Egyptian women.Methods This study included 14 patients of melasma with skin type IV-V taken for a right-left comparison study of six sessions. Glycolic acid 70% peel was applied on the right side, whereas nanosome vitamin C was applied by iontophoresis on the other side. The results are evaluated using the melasma area and severity index score and with photographs at baseline and after six sessions. Also the photographs were evaluated by two single-blinded physicians before and after sessions.Results Both sides were improved, but the side treated with nanosome vitamin C showed better results. Side effects were few and transient.Conclusion We concluded that nanosome vitamin C is a new, safe and effective, easy and painless method in the treatment of melasma. | Rigobello-Masini M, Penteado JC, Tiba M, Masini JC (2012)
Study of photorespiration in marine microalgae through the determination of glycolic acid using hydrophilic interaction liquid chromatography.
Journal of separation science 35, 20-28 [PubMed:22128110]
[show Abstract]
Determination of organic acids in intracellular extracts and in the cultivation media of marine microalgae aid investigations about metabolic routes related to assimilation of atmospheric carbon by these organisms, which are known by their role in the carbon dioxide sink. The separation of these acids was investigated by hydrophilic interaction liquid chromatography (HILIC) using isocratic elution with a mobile phase composed of 70:30 v/v acetonitrile/20 mmol/L ammonium acetate buffer (pH 6.8) and detection at 220 nm. HILIC allowed the determinations of glycolic acid, the most important metabolite for the evaluation of the photorespiration process in algae, to be made with better selectivity than that achieved by reversed phase liquid chromatography, but with less detectability. The concentration of glycolic acid was determined in the cultivation media and in intracellular extracts of the algae Tetraselmis gracilis and Phaeodactylum tricornutum submitted to different conditions of aeration: (i) without forced aeration, (ii) aeration with atmospheric air, and (iii) bubbling with N(2). The concentration of glycolic acid had a higher increase as the cultures were aerated with nitrogen, showing higher photorespiratory flux than that occurring in the cultures aerated with atmospheric air. | Takenaka Y, Hayashi N, Takeda M, Ashikaga S, Kawashima M (2012)
Glycolic acid chemical peeling improves inflammatory acne eruptions through its inhibitory and bactericidal effects on Propionibacterium acnes.
The Journal of dermatology 39, 350-354 [PubMed:21950544]
[show Abstract]
Glycolic acid chemical peeling is effective for treating comedones, and some clinical data show that it also improves inflammatory eruptions. The purpose of this study was to identify the mechanism of glycolic acid chemical peeling to improve inflammatory acne. To assess growth inhibitory and bactericidal effects of glycolic acid on Propionibacterium acnes in vitro, we used an agar diffusion method and a time-kill method. To reveal bactericidal effects in vivo, we established an agar-attached method which correlated well with the ordinary swab-wash method, and we used the agar-attached method to compare the numbers of propionibacteria on the cheek treated with glycolic acid chemical peeling. Our results show that 30% glycolic acid (at pH 1.5, 3.5 and 5.5) formed growth inhibitory circles in the agar diffusion method, but the diameters of those circles were smaller than with 1% nadifloxacin lotion or 1% clindamycin gel. In the time-kill method, 30% glycolic acid (at pH 1.5 and 3.5) or 1% nadifloxacin lotion reduced the number of P. acnes to less than 100 CFU/mL within 5 min. In contrast, in 30% glycolic acid (at pH 5.5) or in 1% clindamycin gel, P. acnes survived for more than 4 h. Chemical peeling with 35% glycolic acid (at pH 1.2) decreased the number of propionibacteria on the cheeks of patients compared with untreated controls (P < 0.01). Our results demonstrate that glycolic acid has moderate growth inhibitory and bactericidal effects on P. acnes, and that chemical peeling with glycolic acid works on inflammatory acne via those effects. | Carney EW, Tornesi B, Markham DA, Rasoulpour RJ, Moore N (2008)
Species-specificity of ethylene glycol-induced developmental toxicity: toxicokinetic and whole embryo culture studies in the rabbit.
Birth defects research. Part B, Developmental and reproductive toxicology 83, 573-581 [PubMed:19025792]
[show Abstract]
High-dose gavage exposure to ethylene glycol (EG) is teratogenic in rats, but not rabbits. To investigate the reason for this species difference, toxicokinetic and whole embryo culture (WEC) studies were conducted in gestation day 9 New Zealand White rabbits, and the data compared to very similar data previously generated in pregnant rats. In the toxicokinetic study, maximal levels of unchanged EG in rabbits were comparable to those reported for rats. However, maximal levels of EG's teratogenic metabolite, glycolic acid (GA), in rabbit maternal blood and embryo were only 46% and 10% of the respective levels in rats. The toxicokinetic profile suggested that the lower GA levels in rabbits were due to a slower rate of maternal metabolism of EG to GA, slow uptake of GA into the yolk sac cavity fluid which surrounds the embryo, and negligible transfer via the visceral yolk sac (VYS) placenta. In the WEC study, exposure of rabbit conceptuses to high concentrations (< or = 12.5 mM) of GA was without effect, which contrasts with reported effects in rat WEC at > or = 3 mM. Overall, these data implicate toxicokinetics as an important factor underlying the species difference, although intrinsic insensitivity of the rabbit embryo might also be involved. Integration of these findings with published human data suggest that the rabbit is the more relevant model for human EG exposure, based on the negligible role of the rabbit VYS in placental transfer (humans lack a VYS) and similar rates of EG metabolism and extraembryonic fluid turnover. | Corley RA, McMartin KE (2005)
Incorporation of therapeutic interventions in physiologically based pharmacokinetic modeling of human clinical case reports of accidental or intentional overdosing with ethylene glycol.
Toxicological sciences : an official journal of the Society of Toxicology 85, 491-501 [PubMed:15716481]
[show Abstract]
Although occupational uses of the high production volume (HPV) chemical ethylene glycol (EG) have not been associated with adverse effects, there are case reports where humans have either intentionally or accidentally ingested large quantities of EG, primarily from antifreeze. The acute toxicity of EG can proceed through three stages, each associated with a different metabolite: central nervous system depression (ethylene glycol), cardiopulmonary effects associated with metabolic acidosis (glycolic acid), and ultimately renal toxicity (oxalic acid), depending on the total amounts consumed and the effectiveness of therapeutic interventions. A physiologically based pharmacokinetic (PBPK) model developed in a companion paper (Corley et al., 2005). Development of a physiologically based pharmacokinetic model for ethylene glycol and its metabolite, glycolic acid, in rats and humans. Toxicol. Sci., in press 2005) was refined in this study to include clinically relevant treatment regimens for EG poisoning such as hemodialysis or metabolic inhibition with either ethanol or fomepizole. Such modifications enabled the model to describe data from several human case reports, confirming the ability of the previous model to describe the pharmacokinetics of EG and its metabolite, glycolic acid, in humans across a broad range of doses and multiple exposure routes. By integrating the case report data sets with controlled studies in this PBPK model, it was demonstrated that fomepizole, if administered early enough in a clinical situation, can be more effective than ethanol or hemodialysis in preventing the metabolism of EG to more toxic metabolites. Hemodialysis remains an important option, however, if treatment is instituted after a significant amount of EG is metabolized or if renal toxicity has occurred. | Corley RA, Bartels MJ, Carney EW, Weitz KK, Soelberg JJ, Gies RA, Thrall KD (2005)
Development of a physiologically based pharmacokinetic model for ethylene glycol and its metabolite, glycolic Acid, in rats and humans.
Toxicological sciences : an official journal of the Society of Toxicology 85, 476-490 [PubMed:15716482]
[show Abstract]
An extensive database on the toxicity and modes of action of ethylene glycol (EG) has been developed over the past several decades. Although renal toxicity has long been recognized as a potential outcome, in recent years developmental toxicity, an effect observed only in rats and mice, has become the subject of extensive research and regulatory reviews to establish guidelines for human exposures. The developmental toxicity of EG has been attributed to the intermediate metabolite, glycolic acid (GA), which can become a major metabolite when EG is administered to rats and mice at high doses and dose rates. Therefore, a physiologically based pharmacokinetic (PBPK) model was developed to integrate the extensive mode of action and pharmacokinetic data on EG and GA for use in developmental risk assessments. The resulting PBPK model includes inhalation, oral, dermal, intravenous, and subcutaneous routes of administration. Metabolism of EG and GA were described in the liver with elimination via the kidneys. Metabolic rate constants and partition coefficients for EG and GA were estimated from in vitro studies. Other biochemical constants were optimized from appropriate in vivo pharmacokinetic studies. Several controlled rat and human metabolism studies were used to validate the resulting PBPK model. When internal dose surrogates were compared in rats and humans over a broad range of exposures, it was concluded that humans are unlikely to achieve blood levels of GA that have been associated with developmental toxicity in rats following occupational or environmental exposures. | Carney EW, Scialli AR, Watson RE, DeSesso JM (2004)
Mechanisms regulating toxicant disposition to the embryo during early pregnancy: an interspecies comparison.
Birth defects research. Part C, Embryo today : reviews 72, 345-360 [PubMed:15662707]
[show Abstract]
The dose of toxicant reaching the embryo is a critical determinant of developmental toxicity, and is likely to be a key factor responsible for interspecies variability in response to many test agents. This review compares the mechanisms regulating disposition of toxicants from the maternal circulation to the embryo during organogenesis in humans and the two species used predominantly in regulatory developmental toxicity testing, rats and rabbits. These three species utilize fundamentally different strategies for maternal-embryonic exchange during early pregnancy. Early postimplantation rat embryos rely on the inverted visceral yolk sac placenta, which is in intimate contact with the uterine epithelium and is equipped with an extensive repertoire of transport mechanisms, such as pinocytosis, endocytosis, and specific transporter proteins. Also, the rat yolk sac completely surrounds the embryo, such that the fluid-filled exocoelom survives through most of the period of organogenesis, and can concentrate compounds such as certain weak acids due to pH differences between maternal blood and exocelomic fluid. The early postimplantation rabbit conceptus differs from the rat in that the yolk sac is not closely apposed to the uterus during early organogenesis and does not completely enclose the embryo until relatively later in development (approximately GD13). This suggests that the early rabbit yolk sac might be a relatively inefficient transporter, a conclusion supported by limited data with ethylene glycol and one of its predominant metabolites, glycolic acid, given to GD9 rabbits. In humans, maternal-embryo exchange is thought to occur via the chorioallantoic placenta, although it has recently been conjectured that a supplemental route of transfer could occur via absorption into the yolk sac. Knowledge of the mechanisms underlying species-specific embryonic disposition, factored together with other pharmacokinetic characteristics of the test compound and knowledge of critical periods of susceptibility, can be used on a case-by-case basis to make more accurate extrapolations of test animal data to the human. | Woo MY, Greenway DC, Nadler SP, Cardinal P (2003)
Artifactual elevation of lactate in ethylene glycol poisoning.
The Journal of emergency medicine 25, 289-293 [PubMed:14585457]
[show Abstract]
The diagnosis of ethylene glycol poisoning is based on nonspecific clinical symptoms and signs and indirect and direct laboratory measurement. Few institutions have timely access to direct measurement of ethylene glycol. As a result, diagnosis sometimes can be delayed and therapy initiated late. We present two cases of ethylene glycol poisoning. These cases demonstrate the need to recognize the false elevation of lactate in some chemistry analyzers due to the interference of glycolic acid, a metabolite of ethylene glycol. Using the "lactate gap" in comparing the measurement of lactate with two commonly used chemical analyzers aids in differentiating ethylene glycol poisoning from lactic acidosis. | Couch LH, Howard PC (2002)
Quantification of glycolic acid in cosmetic products using reversed phase high performance liquid chromatography.
International journal of cosmetic science 24, 89-95 [PubMed:18498500]
[show Abstract]
Many cosmetics contain keratolytic hydroxy acids to correct the effects of photoageing on human skin. Although methods exist for quantifying the alpha-hydroxy acid, glycolic acid in aqueous media, accurate methods for quantification in mixed hydrophobic and aqueous cosmetic creams and lotions are lacking. Glycolic acid was extracted from cosmetics using aqueous tetrahydrofuran (THF), separated with strong-anion exchange cartridges, and quantified by high performance liquid chromatography (HPLC) with UV-VIS detection without the paired-ion reagents. In a recovery experiment, the mean accuracy of the method was 100.6%. The dynamic range of the method allows for the detection of glycolic acid at concentrations used in over-the-counter cosmetics. |
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