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Glycolic acid(CAS No. 79-14-1)

Glycolic acid C2H4O3 (cas 79-14-1) Molecular Structure

79-14-1 Structure

Identification and Related Records

Glycolic acid
【CAS Registry number】
Hydroxyacetic acid
Glycolic acid solution
glycollic acid
Hydroxyethanoic acid
【Molecular Formula】
C2H4O3 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【MOL File】

Chemical and Physical Properties

Light yellow to amber liquid
【Melting Point】
【Boiling Point】
【Refractive Index】
n20/D 1.424
【Flash Point】
128.7 °C
H2O: 0.1 g/mL, clear
Colorless, translucent solid
Solid glycolic acid forms colorless, monoclinic, prismatic crystals.
Orthorhombic needles from water; leaves from diethyl ether
Stable. Incompatible with bases, oxidizing agents and reducing agents.
【Spectral properties】
IR: 6254 (Coblentz Society Spectral Collection)
1H NMR: 6411 (Sadtler Research Laboratories Spectral Collection)
MASS: 381 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
【Computed Properties】
Molecular Weight:76.05136 [g/mol]
Molecular Formula:C2H4O3
H-Bond Donor:2
H-Bond Acceptor:3
Rotatable Bond Count:1
Exact Mass:76.016044
MonoIsotopic Mass:76.016044
Topological Polar Surface Area:57.5
Heavy Atom Count:5
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Donor Count:1
Feature 3D Anion Count:1
Effective Rotor Count:1
Conformer Sampling RMSD:0.4
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】

Moderately toxic by ingestion. A severe eye irritant. A skin and mucous membrane irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety Information of Glycolic acid (CAS NO.79-14-1):
Hazard Codes: CCorrosive
Risk Statements: 34-22???
R34: Causes burns.?
R22: Harmful if swallowed.
Safety Statements: 26-36/37/39-45-23
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S23: Do not breathe vapour.
RIDADR: UN 3265 8/PG 3
WGK Germany: 1
RTECS: MC5250000
HazardClass: 8
PackingGroup: II

【PackingGroup 】
【Skin, Eye, and Respiratory Irritations】
Skin contact may cause severe skin irritation with discomfort or rash. Higher or prolonged exposure may cause skin burns or ulceration. Eye contact may cause eye corrosion with corneal or conjunctival ulceration. Permanent eye damage can occur. /70% Glycolic acid/
Toxicity results indicate that glycolic acid (70%) causes effects that are typical of a strong acid, such as dermal and eye irritation; however, concentrations of
Mild irritant to skin, mucous membranes.
It produces very severe burns of skin or eye in 70% technical solution.
A mini-cumulative irritation patch assay was performed on a variety of cosmetic formulations containing glycolic acid. Approximately 0.2 mL of the material was applied undiluted to the back under an occlusive patch for 4 consecutive days. The patches were removed approximately 24 hr after each application. Irritation was scored 5 hr after removal of the fourth patch. The sites were not scored daily; however, if a score of 2/4 (moderate erythema) was observed following immediate removal of any patch, no further patching was done and the score was recorded under that patch application and as the final score. The results of the mini-cumulative irritation patch assays using glycolic acid ... /ranged from essentially nonirritating to severely irritating depending on glycolic acid concentration and product pH/.
【Cleanup Methods】
Sweep up, place in a bag and hold for waste disposal. Ventilate area and wash spill site after material pickup is complete. /99% Glycolic acid/
Neutralize spills with lime or soda ash. /70% Glycolic acid/
UN 3265 8/PG 3
【Fire Fighting Procedures】
FIREFIGHTING. Protective Equipment: Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes. /99% Glycolic acid/
EXTINGUISHING MEDIA. Water spray. Carbon dioxide, dry chemical powder, or appropriate foam. /99% Glycolic acid/
Available commercially as either a 57% (Hoechst) or a 70% (Du Pont) aqueous solution
CLOROX PATCH: Active Ingredient 1.5% Glycolic acid.
X-MEN: Active Ingredients 3.070% Glycolic acid, 0.180% Alkyl dimethyl benzyl ammonium chloride (50%C14, 40%C12, 10%C16), 0.081% Didecyl dimethyl ammonium chloride, 0.135% Octyl decyl dimethyl ammonium chloride & 0.054% Dioctyl dimethyl ammonium chloride.
SHOW: Active Ingredient 11.185% Glycolic acid.
DUPONT GLYCLEAN AM: Active Ingredient 70% Glycolic acid.
DUPONT BOWL CLEANER: Active Ingredient 9.5% Glycolic acid.
DUPONT KLEANIT: Active Ingredient 5% Glycolic acid.
【Exposure Standards and Regulations】
Hydroxyacetic acid is an indirect food additive for use as a component of adhesives.
【Reactivities and Incompatibilities】
Contact with active metals may produce flammable hydrogen gas (solid).
【Other Preventative Measures】
When chemicals containing glycolic acid are used on a daily basis, protection for the skin and eyes is advised to prevent localized irritation. Child-proof packaging is available to prevent children from ingesting these products. Overall, the evidence indicates there is minimal risk of adverse health effects from glycolic acid during the normal use of commercially available cleaning products.
Wear self-contained breathing apparatus, rubber boots, and heavy rubber gloves. In case of leak or spill, evacuate area. /99% Glycolic acid/
Do not breathe dust. Do not get in eyes, on skin, on clothing. Avoid prolonged or repeated exposure. /99% Glycolic acid/
Avoid breathing mist. Do not get in eyes, on skin, or on clothing. Wash thoroughly after handling. /70% Glycolic acid/
Wash contaminated clothing before reuse. Discard contaminated shoes. Wash thoroughly after handling. /99% Glycolic acid/
If in eyes: Hold eye open and rinse slowly and gently with water for 15-20 minutes. Remove contace lenses, if present, after the first 5 minutes, then continue rinsing. Call a poison control center or doctor for treatment advice. If swallowed: Call poison control center or doctor immediately for treatment advice. Have person sip a glass of water if able to swallow. Do not induce vomiting unless told to do so by the poison control center or doctor... If inhaled: Move person to fresh air. ... /5% Glycolic acid/
Causes substantial but temporary eye injury. Do not get in eyes or on clothing. WWear protective eyewear (such as goggles). Wash thoroughly with soap and water after handling. Remove contaminated clothing and wash clothing before reuse... Do not use with chlorine bleach or any other chemical product. /5% Glycolic acid/
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: When working with strong solutions of acids or bases or other caustic or corrosive materials, always wear a full face mask. When working with caustic or corrosive gases or vapors, a full face mask will not protect the eyes or prevent inhaling the material. A full face respirator is required.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
【Protective Equipment and Clothing】
ENGINEERING CONTROLS. Safety shower and eye bath. Use only in a chemical fume hood. /99% Glycolic acid/
PERSONAL PROTECTIVE EQUIPMENT. Respiratory: Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or SIAL - 124737 type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. /99% Glycolic acid/
Hand: Compatible chemical-resistant gloves. Eye: Chemical safety goggles. /99% Glycolic acid/
Engineering Controls: Use sufficient ventilation to keep employee exposure below recommended limits. Personal Protective Equipment: Chemical splash goggles and rubber gloves. Wear a butyl rubber acid suit and NIOSH permissible respiratory protection if there is a reasonable possibility for exposure. /70% Glycolic acid/

?Glycolic acid , its CAS NO. is 79-14-1, the synonyms are 2-Hydroxyacetic acid ; Acetic acid, hydroxy- ; EPA Pesticide Chemical Code 000101 ; Glycollic acid ; Hydroxyacetic acid ; Hydroxyethanoic acid ; Kyselina glykolova ; Kyselina hydroxyoctova .

【Octanol/Water Partition Coefficient】
log Kow = -1.11

Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
If Glyclean (TM) AN is spilled and not recovered, or is recovered as a waste for treatment or disposal, the CERCLA Reportable Quantity is 100 lbs. (Release of an unlisted Hazardous Waste Characteristic of Corrosivity). /70% Glycolic acid)
Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations. /99% Glycolic acid/
Do not contaminate water, food, or feed by ... disposal. ... Do not re-use empty container. Wrap empty bottle and put in trash or recycle. /5% Glycolic acid/

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Under high pressure, 30.4-91.2 MPa (300-900 atm), formaldehyde reacts with carbon monoxide and water in the presence of an acidic catalyst to form hydroxyacetic acid. Reaction temperature depends on the acid in use: 160-200 deg C for sulfuric, hydrochloric, or phosphoric acid; 20-60 deg C for hydrofluoric acid
Hydrolysis of glyconitrile with an acid (eg phosphite or sulfite) at 100-150 deg C
Water hydrolysis of trichloroethylene under pressure at 150 deg C; treating glycine with nitric acid; oxidation of hexoses, isoamyl benzoate, and 5-oxodigluconic acid
Hydroxyacetic acid is produced commercially in the United States (Du Pont) by treating formaldehyde or trioxymethylene with carbon monoxide and water in the presence of acid catalysts at >30 MPa.
Glycolic acid is usually produced by hydrolysis of molten monochloroacetic acid with 50% aqueous sodium hydroxide at 90-130 deg C. The resulting glycolic acid solution has a concentration of about 60% and contains 12-14% sodium chloride. The salt may be removed by evaporative concentration, followed by extraction of the acid with acetone. Attempts have also been made to conduct the hydrolysis with acid catalysts at 150-200 deg C with water or steam under pressure. In this case, the byproduct is hydrogen chloride, rather than sodium chloride, which can be removed by distillation. The principal disadvantage of the method is the need for relatively large volumes of water.
U.S. Production

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >10 million - 50 million 1990 >10 million - 50 million 1994 >10 million - 50 million 1998 >10 million - 50 million 2002 >10 million - 50 million
Acetic acid, hydroxy- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Consumption Patterns

Total annual consumption worldwide is ca. 2000-3000 t of solution

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents that soften, separate, and cause desquamation of the cornified epithelium or horny layer of skin. They are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases.
【Therapeutic Uses】
Keratolytic Agents
Glycolic acid is a member of the alpha-hydroxy acid (AHA) family, which ... has been used for centuries as a cutaneous rejuvenation treatment. Recently it has proved to be a versatile peeling agent and it is now widely used to treat many defects of the epidermis and papillary dermis in a variety of strengths, ranging from 20% to 70%, depending on the condition being treated. People of almost any skin type and color are candidates, and almost any area of the body can be peeled... [Murad H et al; Dermatol Clin 13 (2): 285-307 (1995)]
【Biomedical Effects and Toxicity】
The penetration of 10% aq. glycolic acid, adjusted to pH 3.8 using either ammonium or sodium hydroxide, was examined using separated Yucatan minipig epidermis and full thickness hairless mouse skin. A 200 uL-aliquot of each formulation was applied to an area of a Franz diffusion cell, and glycolic acid was analyzed using liquid scintillation counting. Using an occlusive patch, penetration was linear with a lag time of less than 15 mm. After 8 hr, 0.8 and 1.6% of the ammonium and sodium salts penetrated, respectively, using the pig skin model and 1.8 and 2.3% of the ammonium and sodium salts penetrated, respectively, using the mouse skin model. Under open patch conditions, penetration was not linear and lag time was greater than 15 mm. Using the pig skin model, 1.1 and 0.7% of the ammonium and sodium salts penetrated, respectively, and using the mouse skin model, 0.6 and 0.9% of the ammonium and sodium salts penetrated, respectively.
The skin penetration of (14)C-glycolic acid was studied using an in vitro system in which a cream formulation was applied to pig skin at a dose of 5 mg/0.79 sq cm skin without an occlusive patch. It was determined that 3.1% of the applied glycolic acid penetrated the skin.
Two female rhesus monkeys were dosed orally with 4 mL/kg of 500 mg/kg homogenous 1-(14)C-glycolic acid, 0.73 uC/mmol, in aq. solution via stomach tube. Urine was collected at intervals of 0-8, 8-24, 24-48, 48-72, and, for one monkey, 72-96 hr. Over a 72 hr period one animal excreted, as a percentage of the dose, 53.2% (14)C, 51.4% of which was excreted in the urine; 51.4% of the dose was excreted in the first 24 hr. The second animal excreted a total of 42.2% (14)C over 96 hr, 36.6% of which was excreted in the urine; 34.1% of the dose was excreted in the first 24 hr. (The greater amount of fecal radioactivity observed for this monkey could have been due to urinary radioactivity contamination.) Very little of the dose was converted to radioactive glyoxylic, hippuric, or oxalic acid.
Skin penetration of 10% aq. Glycolic acid was determined in vitro using human female (age 87 years) abdominal skin. The aq. solution was prepared by adding 0.8 mL 12.473% glycolic acid solution to 0.2 mL of (2-(14)C) glycolic acid solution, 44 mCi/mmol or 250 iCi/mL that contained 0.216 mg glycolic acid. The pH of a mixture containing 0.8 mL of the 12.473% glycolic acid solution and 0.2 mL of water was 3.72. Skin integrity was assessed by determining the permeability coefficient of tritiated water. Twenty uL of 10% aq. glycolic acid solution, 2 mg active, was placed on the stratum corneum surface; 13 replicates were used. Samples of 200 uL, which were taken 1, 2, 4, 6, 8, and 24 hr after application, were counted using a liquid scintillation counter. The skin surface was rinsed 3 times after the 24 hr sample was taken. The average total absorption over 24 hr 2.6 +/= 0.37 ug/sq cm representing 0.15 +/= 0.02% of the applied dose. A lag time of approximately 3.8 hr was followed by a period of steady-state diffusion at a rate of 0.13 ug/sq cm/hr. After 24 hr, 48 +/= 0.05% of the dose was recovered in the skin and 0.15 +/= 0.02% was found in the receptor phase. Total recovery was 102.9% +/= 2.9%.
The in vitro percutaneous absorption glycolic acid was determined using human abdominal skin. The skin was mounted in flow-through diffusion cells. Skin viability was maintained and barrier integrity was confirmed prior to application of the test materials. The test formulations were prepared to give an average dose of 0.55 uCi of (14)-C radioactivity per cell. The emulsions were applied to the skin at 3 mg/sq cm of exposed skin in the diffusion cells (exposed skin = 0.64 sq cm). At the end of each experiment, the skin was washed and rinsed three times, and it was tape stripped 10 times to remove the stratum corneum. The remaining epidermis was separated from the dermis using heat. The absorbed radioactivity in the 6 hr receptor fluid fractions and the skin layers was measured by liquid scintillation counting. Glycolic acid was studied using two o/w emulsions, one containing 2% PEG-100 stearate and 1% laureth-4 (Formulation A) and the other containing 2% PEG-100 stearate and 1% ammonium laureth sulfate (Formulation B). The emulsions, containing 5% glycolic acid, were prepared in buffers at pH 3 and 7 and evaluated using skin samples from three subjects for each emulsion. With Formulation A, a much greater amount of glycolic acid was absorbed at a pH of 3 versus 7. Total glycolic acid absorption after 24 hr was 27.2% at pH 3 and 3.47% at pH 7. With the pH 3 formulation, the amount of radioactivity found in the receptor fluid, stratum corneum, viable epidermis, and dermis was 2.6, 5.8, 6.6, and 12.2%, respectively. With Formulation B, the amount of glycolic acid absorbed at pH 3 and 7 was 34.8 and 2.3%, respectively. With the pH 3 formulation, the amount of radioactivity found in the receptor fluid, stratum corneum, viable epidermis, and dermis was 12.2, 2.4, 11.6, and 8.6%, respectively.
The deposition of glycolic acid in a number of vehicles was investigated using male SKH-hr-1 hairless mice. Glycolic acid solutions (40 mg/mL) with trace amounts of (14)C glycolic acid prepared in an aqueous solution, two non-ionic formulations, Non-1 containing glyceyl dilaurate/cholesterol/polyoxyethylene-1 0-stearyl ether and Non-2 containing glyceryl distearate/cholesterol/polyoxyethylene-10-stearyl ether, 30% (w/w) propylene glycol in water (PG/water), an o/w emulsion (80:20 (w/w) aqueous phase to oil phase), and a water-in-oil (w/o) emulsion (45:55 (w/w) water-to-oil). Using at least three animals per formulation per time point, 25 uL the test formulation were applied without an occlusive patch to a 4 sq cm area of the dorsal surface. One hr after application, the site was wiped three times to remove test material. Animals were killed at the time of wiping and 2, 4, and 8 hr later. Full-thickness dorsal skin was excised and the liver and the urinary bladder were removed. The excised skin was repeatedly tape-stripped until it appeared "shiny and glossy", approximately 15 times. The remaining skin, the urinary bladder, and the surface swabs and strips were assayed for glycolic acid content using a scintillation counter. The amount of glycolic acid adhering to the stratum corneum surface was defined as the first two strippings and the amount found in the stratum corneum was defined as strippings 3-15. The accumulation of glycolic acid in the stratum corneum using the different vehicles at 1 and 8 hr was in the following order: aqueous solution = Non-1 = Non-2 >w/o emulsion = o/w emulsion = 30% PG/water solution. The amounts of glycolic acid in the "living skin strata" was significantly greater with Non-1 formulations as compared to all other formulations at all time periods except after 8 hr when Non-1 was similar to Non-2 and the w/o emulsion. The remaining formulations were similar to each other at all time points, with the exception of the 30% PG/water solution which had the poorest deposition at all times. The amount of glycolic acid in the urinary bladder at 8 hr was significantly greater with Non-1 as compared to others. Approximately, 1-2% of the glycolic acid in Non-1 was found in the liver at 8 hr. The combined amounts of glycolic acid found in the living skin strata and urinary bladder were significantly lower at 4 and 8 hr if glycerol was added to the Non-1 formulation.
The barrier integrity of hairless guinea pig skin after treatment with an alpha hydroxy acid was assessed through in vivo topical application of an oil-in-water emulsion containing 5 or 10% glycolic acid at pH 3.0. The control was a commercial moisturizing lotion, pH 7.8. A dosing regimen for the glycolic acid formulations that was tolerated by the hairless guinea pigs and significantly decreased stratum corneum turnover time was determined using the dansyl chloride staining technique. Once-daily dosing of hairless guinea pig skin for 3 weeks with the glycolic acid formulations resulted in approximately a 36-39% decrease in stratum corneum turnover time compared with the control lotion. After this treatment, hairless guinea pigs were sacrificed for the in vitro measurement of the percutaneous absorption of (14)C hydroquinone and (14)C musk xylol. No significant differences in the 24-hour absorption of either test compound were found for skin treated with the control lotion or the glycolic acid formulations. There were also no significant differences found in the absorption of (3)H water through skin from the different treatment groups. Although no increase in skin penetration occurred after treatment with the glycolic acid formulations, histology revealed approximately a twofold increase in epidermal thickness. Also the number of nucleated cell layers nearly doubled in skin treated with 5% and 10% glycolic acid compared with the control lotion and untreated skin. These studies demonstrate that substantial changes in the structure of hairless guinea pig epidermis can occur without significant effect on skin permeability of two model compounds. [Hood HL et al; Food Chem Toxicol 37 (11): 1105-11 (1999)] PubMed Abstract
Urinary excretion of carbon-14 accounted for 37-52% of (14)C-labelled glycolic acid within 96 hr of oral admin of 500 mg/kg doses to Rhesus monkeys. [MCCHESNEY EW ET AL; FOOD COSMET TOXICOL 10 (5): 655 (1972)] PubMed Abstract
Ethylene glycol toxicity results from its metabolism to glycolic acid and other toxic metabolites. The accumulation of glycolate and the elimination kinetics of ethylene glycol and its metabolites are not well understood, so studies with male Sprague-Dawley rats and mixed breed dogs have been carried out. Ethylene glycol was administered by gavage to rats and dogs which were placed in metabolic cages for urine and blood sample collection at timed intervals. The peak plasma level of ethylene glycol occurred at 2 hr after dosing and that of glycolate between 4-6 hr. The rate of ethylene glycol elimination was somewhat faster in rats with a half-life of 1.7 hr compared to 3.4 hr in dogs. The maximum plasma level of glycolate was greater in rats although the pattern of accumulation was similar to that in dogs. Glycolate disappeared from the plasma at the same time as ethylene glycol, suggesting a slower rate of elimination of the metabolite than that of ethylene glycol. Renal excretion of ethylene glycol was an important route for its elimination accounting for 20-30% of the dose. Renal excretion of glycolate represented about 5% of the dose. Ethylene glycol induced an immediate, but short lived diuresis compared to that in control rats. Minimal clinical effects (mild acidosis with no sedation) were noted at these doses of ethylene glycol (1-2 g/kg) in both rats and dogs. The results indicate that the toxicokinetics of ethylene glycol and glycolate were similar in both species. [Hewlett TP et al; Vet Hum Toxicol 31 (2): 116-20 (1989)] PubMed Abstract
Ethylene glycol (I) and glycolate (glycolic acid) pharmacokinetics were studied in 2 adult patients who had ingested antifreeze; therapy with intravenous ethyl alcohol (II) was also discussed. The patients had maximal ethylene glycol concentrations of 40.9 and 56.9 mmol/L respectively. Both patients survived but with prolonged renal failure. Glycolic acid was the major cause of the metabolic acidosis in both cases; lactate levels were only slightly elevated. Kinetic calculations showed that both ethylene glycol and glycolate were distributed in total body water with plasma half-lives of 8.4 and 7.0 hr respectively. The half-life of ethylene glycol was increased more than 10 fold by ethyl alcohol treatment alone. Calcium oxalate monohydrate crystalluria was dominant in both cases but in one was preceded by a short period with mainly dihydrate excretion; crystalluria was not present upon admission. It was suggested that repetitive urine microscopy in search of needle or envelope shaped crystals should be performed when ethylene glycol intoxication is suspected.
The disposition of dichloroacetic acid (DCA) was investigated in Fischer 344 rats over the 48 hr after oral gavage of 282 mg/kg of 1- or 2-(14C)DCA (1-DCA or 2-DCA) and 28.2 mg/kg of 2-DCA... The major urinary metabolites were glycolic acid, glyoxylic acid, and oxalic acid. DCA and its metabolites accumulated in the tissues and were eliminated slowly.... [Lin EL et al; J Toxicol Environ Health 38 (1): 19-32 (1993)] PubMed Abstract
The accumulation of glycolate and the elimination kinetics of ethylene glycol (EG) /was examined in/ ... male Sprague-Dawley rats and mixed breed dogs... . EG was administered by gavage ... . The peak plasma level of EG occurred at 2 hr after dosing and that of glycolate between 4-6 hr. The rate of EG elimination was somewhat faster in rats with a half-life of 1.7 hr compared to 3.4 hr in dogs. The maximum plasma level of glycolate was greater in rats, although the pattern of accumulation was similar to that in dogs. Glycolate disappeared from the plasma at the same time as EG, suggesting a slower rate of elimination of the metabolite than that of EG. Renal excretion of EG was an important route for its elimination, accounting for 20-30% of the dose. Renal excretion of glycolate represented about 5% of the dose... /Glycolate/ [Hewlett TP et al; Vet Hum Toxicol 31 (2): 116-20 (1989)] PubMed Abstract
1,2-(14)C-Ethylene glycol (EG) was given to female CD (Sprague-Dawley) rats and CD-1 mice in order to determine tissue distribution and metabolic fate after intravenous (iv), peroral (po), and percutaneous (pc) doses. Rats were given doses of 10 or 1000 mg/kg by each route, and additional pc doses of 400, 600 or 800 mg/kg. Mice were also given iv and po doses of 10 or 1000 mg/kg, and intermediate po doses of 100, 200 or 400 mg/kg. Mice were given po doses of 100 or 1000 mg/kg, and both species were given a 50% (w/w) aqueous po dose to simulate antifreeze exposure. For both species, EG is very rapidly and almost completely adsorbed after po doses. ... The tissue distribution of EG following either iv or po routes was essentially the same, with similar percentages recovered for each dose by both routes and for either species. Cutaneously-applied EG was slowly and rather poorly adsorbed in both species, in comparison with po-dose administration, and urinalysis after undiluted po doses indicated that EG probably penetrates rat skin in the parent form. There was an absence in both species of dose-dependent changes in disposition and elimination following the pc application of EG. (14)C-labelled EG, glycolic acid and/or oxalic acid accounted for the majority of the detectable radioactivity in the urine samples from all dose routes in the rat, while glycoaldehyde and glyoxylic acid were not detected in any of the urine fractions evaluated. Similar increases in glycolate production with increasing dose were also observed in mouse urine samples from iv and po dosing. Also, glyoxylate and oxalate were absent from mouse urine... [Frantz SW et al; Xenobiotica 26 (11): 1195-220 (1996)] PubMed Abstract
The kinetics of orally administered ethylene glycol (EG) and its major metabolites, glycolic acid (GA) and oxalic acid (OX), in pregnant (P; gestation day 10 at dosing, GD 10) rats were compared across doses, and between pregnant and nonpregnant (NP) rats. Groups of 4 jugular vein-cannulated female rats were administered 10 (P and NP), 150 (P), 500 (P), 1000 (P), or 2500 (P and NP) mg (13)C-labelled EG/kg body weight. Serial blood samples and urine were collected over 24-hr postdosing, and analyzed for EG, GA, and OX using GC/MS techniques. Pharmacokinetic parameters including Cmax, Tmax, AUC, and beta-t(1/2) were determined for EG and GA. Pregnancy status (GD 10-11) had no impact on the pharmacokinetic parameters investigated. Blood levels of GA were roughly dose-proportional from 10 to 150 mg EG/kg, but increased disproportionately from 500 to 1000 mg EG/kg. EG and GA exhibited dose-dependent urinary elimination at doses > or = 500 mg EG/kg, probably due to saturation of metabolic conversion of EG to GA, and of GA to downstream metabolites. The shift to nonlinear kinetics encompassed the NOEL (500 mg EG/kg) and LOEL (1000 mg EG/kg) for developmental toxicity of EG in rats, providing additional evidence for the role of GA in EG developmental toxicity. The peak maternal blood concentration of GA associated with the LOEL for developmental toxicity in the rat was quite high (363 microg/g or 4.8 mM blood). OX was a very minor metabolite in both blood and urine at all dose levels, suggesting that OX is not important for EG developmental toxicity. [Pottenger LH et al; Toxicol Sci 62 (1): 10-9 (2001)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from a log Kow of -1.11(2) and a regression-derived equation(3), indicates that hydroxyacetic acid is expected to have very high mobility in soil(SRC). The pKa of hydroxyacetic acid is 3.83(4), indicating that this compound will primarily exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of hydroxyacetic acid from moist soil surfaces is not expected to be an important fate process(SRC) given the compound's pKa(4). Hydroxyacetic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 2.0X10-2 mm Hg(6). Hydroxyacetic acid, present at 100 mg/L, reached 86% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(7). Therefore this compound is expected to biodegrade rapidly in soil.
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from a log Kow of -1.11(2) and a regression-derived equation(3), indicates that hydroxyacetic acid is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 3.83(4) indicates hydroxyacetic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydroxyacetic acid, present at 100 mg/L, reached 86% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(8). Therefore this compound is expected to biodegrade rapidly in water.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hydroxyacetic acid, which has an extrapolated vapor pressure of 2.0X10-2 mm Hg at 25 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase hydroxyacetic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5 days(SRC), calculated from its rate constant of 3.1X10-12 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Hydroxyacetic acid does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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