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Glyceraldehyde
Glyceraldehyde SR Clough, Haley & Aldrich, Inc., Bedford, NH, USA Ó 2014 Elsevier Inc. All rights reserved. l
Chemical Abstracts Service Registry Number: 367-47-5 Synonyms: DL-Glyceraldehyde; 2,3-Dihydroxypropanal; a,bDihydroxypropionaldehyde; Glyceric aldehyde; Glycerose; 2,3-Dihydroxypropionaldehyde l Chemical Formula: C3H6O3 l Chemical Structure: l
significant concentrations of this compound. Because it is a solid at room temperature, exposure would be anticipated to occur only through contact with the skin or by inhalation of airborne dust. Skin exposure may also occur from contact with aqueous solutions (40%) of glyceraldehyde.
Toxicokinetics
Glyceraldehyde can exist as two different isomers (enantiomers), D-glyceraldehyde and L-glyceraldehyde, which are ‘mirror images’ of each other.
Background Glyceraldehyde is a simple sugar (monosaccharide) compound with chemical formula C3H6O3. It is an intermediate compound in the metabolism of carbohydrates, principally when a molecule of fructose (a common sugar in fruits) is hydrolyzed by enzymes to form one molecule of dihydroxyacetone phosphate and one molecule of glyceraldehyde. The word glyceraldehyde is derived from glycerine and aldehyde, as glyceraldehyde is merely glycerine with one hydroxymethylene group.
Uses Glyceraldehyde is a sweet colorless crystalline solid with a molecular weight of 90.08 g mol 1. The solubility in water is 29 200 mg l 1. It is used in nutrition; in the preparation of polyesters and adhesives; as a cellulose modifier; and in the tanning of leather. It is also used in biochemical research as the ‘D’ stereoisomer is used as ‘reference’ chemical because it is one of the simplest molecules to compare against other molecules, such as sugars and amino acids. The conformation of the alcohol and aldehyde groups around the central carbon of Dglyceraldehyde helps scientists evaluate the structure and nomenclature (identity) of other simple sugars, such as glucose. This makes glyceraldehyde an important tool and reference standard for the biochemist.
As glyceraldehyde is a normal metabolic intermediate in humans, it cannot be readily categorized as a ‘toxic’ chemical. Given a large enough exposure or dose, any chemical can result in toxic injury. As with any aldehyde/alcohol, very high air concentrations or accidental ingestion of large amounts would be expected to overwhelm the body’s natural defenses and produce an adverse effect (e.g., eye, nose, and lung irritation from airborne dust). Glyceraldehyde is a chemical that occurs naturally in living organisms, including humans. It is an intermediate in the metabolism of fructose. In the liver, fructose is converted to fructose-1-phosphate by the enzyme fructokinase. Fructose-1-phosphate is then converted to two three-carbon molecules, glyceraldehyde and dihydroxyacetone phosphate, by the enzyme fructose-1-phosphate aldolase. Glyceraldehyde is then converted into glyceraldehyde-3-phosphate by the enzyme glyceraldehyde kinase. Glyceraldehyde-3-phosphate is a high-energy intermediate that provides the body with a way of extracting energy to make ATP, which can then be used to power other metabolic functions, such as muscle contraction. Following exposure and absorption of small to moderate doses, glyceraldehyde would be easily assimilated via this normal carbohydrate metabolic capacity.
Mechanism of Toxicity Glyceraldehyde has only been shown to be toxic in cell cultures where excess concentrations apparently interfere with normal mechanisms of carbohydrate metabolism, possibly by forming by-products induced by reactive oxygen species.
Acute and Short-Term Toxicity (Animal/Human)
Environmental Fate and Behavior Because this chemical is a metabolic intermediate and could easily be utilized by microorganisms, a release or spill of this compound into the general environment would not be expected to have any long-term adverse effects as the half-life in soil or water would be expected to be very brief.
The median lethal dose (LD50) for glyceraldehyde in rats is 2 g kg 1, which places it in the category of slightly to moderately toxic. The chemical is also slightly toxic by the intraperitoneal route. No other data are available on animal toxicity.
Chronic Toxicity (Animal/Human) Exposure and Exposure Monitoring Only persons involved in the manufacture and production of glyceraldehyde would be expected to be exposed to
752
No studies were found that documented chronic toxicity following prolonged exposure to elevated levels of glyceraldehyde.
Encyclopedia of Toxicology, Volume 2
http://dx.doi.org/10.1016/B978-0-12-386454-3.00393-6
Glyceraldehyde
753
Immunotoxicity
Ecotoxicology
A comprehensive search on the adverse immunotoxic effects of glyceraldehyde on the immune system could not find any studies in the public domain.
No records are available in the US Environmental Protection Agency ECOTOX database for glyceraldehyde. An environmental spill of glyceraldehyde would not be anticipated to adversely affect soils, vegetation, water bodies, or wetlands as the compound would be quickly assimilated by native organisms (principally bacteria and algae).
Reproductive Toxicity A comprehensive search on the adverse reproductive effects of glyceraldehyde could not find any studies in the public domain.
Genotoxicity A comprehensive search on the adverse genotoxic effects of glyceraldehyde could not find any studies in the public domain.
Other Hazards As pure glyceraldehyde is a powder and a carbohydrate, in areas where glyceraldehyde dusts might be expected, care should be taken to keep these areas free from ignition sources, such as sparks from static electricity.
Exposure Standards and Guidelines Carcinogenicity Glyceraldehyde is not listed as a carcinogen by the National Toxicology Program, the Occupational Safety and Health Administration, or the International Agency for Research on Cancer.
There are no regulatory exposure standards or guidelines published for glyceraldehyde.
See also: Butyraldehyde; Formaldehyde; Food Additives; Food Safety and Toxicology; Glycerol.
Clinical Management Persons who are exposed to high concentrations of glyceraldehyde dusts/powder in air should vacate or be removed from the source and seek fresh air. Medical attention should be sought. Treatment should be similar to first aid following any high-level chemical exposure; irrigation of the eyes with copious amounts of water, washing of exposed skin with soap and water, and supportive therapy following ingestion.
Further Reading British Industrial Biological Research Association, 1990. Toxicity Profile of Glyceraldehyde. British Industrial Biological Research Association, Carshalton, UK.
Chemical Abstracts Service Registry Number: 367-47-5 Synonyms: DL-Glyceraldehyde; 2,3-Dihydroxypropanal; a,bDihydroxypropionaldehyde; Glyceric aldehyde; Glycerose; 2,3-Dihydroxypropionaldehyde l Chemical Formula: C3H6O3 l Chemical Structure: l
significant concentrations of this compound. Because it is a solid at room temperature, exposure would be anticipated to occur only through contact with the skin or by inhalation of airborne dust. Skin exposure may also occur from contact with aqueous solutions (40%) of glyceraldehyde.
Toxicokinetics
Glyceraldehyde can exist as two different isomers (enantiomers), D-glyceraldehyde and L-glyceraldehyde, which are ‘mirror images’ of each other.
Background Glyceraldehyde is a simple sugar (monosaccharide) compound with chemical formula C3H6O3. It is an intermediate compound in the metabolism of carbohydrates, principally when a molecule of fructose (a common sugar in fruits) is hydrolyzed by enzymes to form one molecule of dihydroxyacetone phosphate and one molecule of glyceraldehyde. The word glyceraldehyde is derived from glycerine and aldehyde, as glyceraldehyde is merely glycerine with one hydroxymethylene group.
Uses Glyceraldehyde is a sweet colorless crystalline solid with a molecular weight of 90.08 g mol 1. The solubility in water is 29 200 mg l 1. It is used in nutrition; in the preparation of polyesters and adhesives; as a cellulose modifier; and in the tanning of leather. It is also used in biochemical research as the ‘D’ stereoisomer is used as ‘reference’ chemical because it is one of the simplest molecules to compare against other molecules, such as sugars and amino acids. The conformation of the alcohol and aldehyde groups around the central carbon of Dglyceraldehyde helps scientists evaluate the structure and nomenclature (identity) of other simple sugars, such as glucose. This makes glyceraldehyde an important tool and reference standard for the biochemist.
As glyceraldehyde is a normal metabolic intermediate in humans, it cannot be readily categorized as a ‘toxic’ chemical. Given a large enough exposure or dose, any chemical can result in toxic injury. As with any aldehyde/alcohol, very high air concentrations or accidental ingestion of large amounts would be expected to overwhelm the body’s natural defenses and produce an adverse effect (e.g., eye, nose, and lung irritation from airborne dust). Glyceraldehyde is a chemical that occurs naturally in living organisms, including humans. It is an intermediate in the metabolism of fructose. In the liver, fructose is converted to fructose-1-phosphate by the enzyme fructokinase. Fructose-1-phosphate is then converted to two three-carbon molecules, glyceraldehyde and dihydroxyacetone phosphate, by the enzyme fructose-1-phosphate aldolase. Glyceraldehyde is then converted into glyceraldehyde-3-phosphate by the enzyme glyceraldehyde kinase. Glyceraldehyde-3-phosphate is a high-energy intermediate that provides the body with a way of extracting energy to make ATP, which can then be used to power other metabolic functions, such as muscle contraction. Following exposure and absorption of small to moderate doses, glyceraldehyde would be easily assimilated via this normal carbohydrate metabolic capacity.
Mechanism of Toxicity Glyceraldehyde has only been shown to be toxic in cell cultures where excess concentrations apparently interfere with normal mechanisms of carbohydrate metabolism, possibly by forming by-products induced by reactive oxygen species.
Acute and Short-Term Toxicity (Animal/Human)
Environmental Fate and Behavior Because this chemical is a metabolic intermediate and could easily be utilized by microorganisms, a release or spill of this compound into the general environment would not be expected to have any long-term adverse effects as the half-life in soil or water would be expected to be very brief.
The median lethal dose (LD50) for glyceraldehyde in rats is 2 g kg 1, which places it in the category of slightly to moderately toxic. The chemical is also slightly toxic by the intraperitoneal route. No other data are available on animal toxicity.
Chronic Toxicity (Animal/Human) Exposure and Exposure Monitoring Only persons involved in the manufacture and production of glyceraldehyde would be expected to be exposed to
752
No studies were found that documented chronic toxicity following prolonged exposure to elevated levels of glyceraldehyde.
Encyclopedia of Toxicology, Volume 2
http://dx.doi.org/10.1016/B978-0-12-386454-3.00393-6
Glyceraldehyde
753
Immunotoxicity
Ecotoxicology
A comprehensive search on the adverse immunotoxic effects of glyceraldehyde on the immune system could not find any studies in the public domain.
No records are available in the US Environmental Protection Agency ECOTOX database for glyceraldehyde. An environmental spill of glyceraldehyde would not be anticipated to adversely affect soils, vegetation, water bodies, or wetlands as the compound would be quickly assimilated by native organisms (principally bacteria and algae).
Reproductive Toxicity A comprehensive search on the adverse reproductive effects of glyceraldehyde could not find any studies in the public domain.
Genotoxicity A comprehensive search on the adverse genotoxic effects of glyceraldehyde could not find any studies in the public domain.
Other Hazards As pure glyceraldehyde is a powder and a carbohydrate, in areas where glyceraldehyde dusts might be expected, care should be taken to keep these areas free from ignition sources, such as sparks from static electricity.
Exposure Standards and Guidelines Carcinogenicity Glyceraldehyde is not listed as a carcinogen by the National Toxicology Program, the Occupational Safety and Health Administration, or the International Agency for Research on Cancer.
There are no regulatory exposure standards or guidelines published for glyceraldehyde.
See also: Butyraldehyde; Formaldehyde; Food Additives; Food Safety and Toxicology; Glycerol.
Clinical Management Persons who are exposed to high concentrations of glyceraldehyde dusts/powder in air should vacate or be removed from the source and seek fresh air. Medical attention should be sought. Treatment should be similar to first aid following any high-level chemical exposure; irrigation of the eyes with copious amounts of water, washing of exposed skin with soap and water, and supportive therapy following ingestion.
Further Reading British Industrial Biological Research Association, 1990. Toxicity Profile of Glyceraldehyde. British Industrial Biological Research Association, Carshalton, UK.