Propanedial, ion(1-), sodium
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Propanedial, ion(1-), sodium
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CAS No:
24382-04-5
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Formula:
C3H3O2.Na
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Chemical Name:
Propanedial, ion(1-), sodium
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Synonyms:
Propanedial,ion(1-),sodium;Malonaldehyde,ion(1-),sodium;Malonaldehyde,sodium deriv.;Sodium malondialdehyde;Malonaldehyde sodium salt;Propanedial sodium;Sodium β-oxyacrolein;(E)-3-Hydroxyacrolein sodium salt;2-Propenal,3-hydroxy-,sodium salt,(E)-;2-Propenal,3-hydroxy-,sodium salt,(2E)-;1977-31-7;5388-46-5;76888-01-2;82995-28-6;122129-91-3;128766-18-7;133767-33-6;143413-46-1;170453-21-1;219517-51-8;442687-07-2
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CAS No:
Description
Malonaldehyde, sodium salt is a light yellow powder. (NTP, 1992)|Solid|NEEDLES.|Solid (needles).
Malonaldehyde, sodium salt is a light yellow powder. (NTP, 1992)|Malonaldehyde is a dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form. It has a role as a biomarker.|Malonaldehyde is the dialdehyde of [malonic acid].|Malondialdehyde is an organic compound with the formula CH2(CHO)2, and a byproduct of lipid metabolism in the body. Malondialdehyde, a highly reactive compound, is one of the many reactive electrophile species that cause toxic stress in cells and form covalent protein adducts, called advanced lipoxidation end products (ALE). This compound also forms mutagenic DNA adducts when it reacts with deoxyadenosine and deoxyguanosine in DNA. Malondialdehyde is also found in many foods and is present in high levels in rancid foods.|The dialdehyde of malonic acid.
Propanedial, ion(1-), sodium Basic Attributes
72.06 g/mol
72.021129366 g/mol
4Y8F71G49Q
1632
DTXSID90202556
C94711
Solid (needles)
Characteristics
34.1 Ų
-1.16
232 °F (decomposes) (NTP, 1992)|72.0 °C|72°C|72 °C|161°F
greater than or equal to 100 mg/mL at 68.9° F (NTP, 1992)
Water soluble.
Aldehydes
MALONALDEHYDE, SODIUM SALT is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation. This chemical is sensitive to light and heat. Dilute aqueous solutions (1%) are stable when stored at -4° F in the dark for 7 days.
Safety Information
TX6475000
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Proteins [Note: Pure compound is stable under neutral conditions, but not under acidic conditions].
DHHS/NTP; Toxicology & Carcinogenesis Studies of Malonaldehyde, Sodium Salt (3-Hydroxy-2-propenal, sodium salt) in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 331 (1988) NIH Publication No. 88-1792 /Malonaldehyde, sodium salt/
Flash point data for this compound are not available; however, it is probably combustible. (NTP, 1992)|Not combustible.
Fires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)|In case of fire in the surroundings, use appropriate extinguishing media.
SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light, and store it in a freezer. (NTP, 1992)
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. The worker should wash daily at the end of each work shift. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.|Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]|For more Personal Protective Equipment (PPE) (Complete) data for MALONALDEHYDE (6 total), please visit the HSDB record page.|(See protection codes)
The worker should immediately wash the skin when it becomes contaminated.|The worker should wash daily at the end of each work shift.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.|Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.|For more Preventive Measures (Complete) data for MALONALDEHYDE (6 total), please visit the HSDB record page.
NIOSH considers maloaldehyde to be a potential occupational carcinogen.|NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concn.
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
A harmful concentration of airborne particles can be reached quickly.
Use ventilation, local exhaust or breathing protection.
Protective gloves.
Wear safety goggles.
Toxicity
LD50 Mouse oral 606 mg/kg|LD50 Rat oral 632 mg/kg
... 2 yr studies of malonaldehyde, sodium salt, were conducted by exposing groups of 50 F344/N rats of each sex at doses of 0, 50, or 100 mg/kg, administered 5 days per week for 103 weeks. Doses of 0, 60, or 120 mg/kg were administered in the same schedule to groups of 50 male and 50 female B6C3F1 mice. Conclusions: Under the conditions of these 2 yr gavage studies, there was clear evidence of carcinogenic activity for male and female F344/N rats administered malonaldehyde, sodium salt, as shown by the increased incidences of follicular cell adenomas or carcinomas (combined) of the thyroid gland. Pancreatic islet cell adenomas were also observed at an increased incidence in low dose male rats. There was no evidence of carcinogenic activity for B6C3F1 mice administered 60 or 120 mg/kg malonaldehyde, sodium salt, in distilled water by gavage 5 days per week for 2 yr. /Malonaldehyde, sodium salt/
MALONALDEHYDE HAS BEEN DETECTED IN LIPID-PEROXIDIZING MICROSOMES AND IS FOUND IN ANIMAL TISSUE AS AN END-PRODUCT OF LIPID PEROXIDATION. IT IS ALSO A SIDE-PRODUCT OF PROSTAGLANDIN AND THROMBOXANE BIOSYNTHESIS. MALONALDEHYDE HAS BEEN DETECTED IN THE LEAVES OF PEA AND COTTON PLANTS.
CONCENTRATIONS OF FREE MALONALDEHYDE IN COMMERCIAL SAMPLES OF REFINED GROUND NUT OILS RANGED FROM 0.04-0.14 mg/kg, AND THE LEVEL IN SUNFLOWER OIL WAS 0.08 mg/kg. THE TOTAL MALONALDEHYDE (FREE AND BOUND) CONCENTRATIONS WERE 0.53-4.36 mg/kg IN GROUND NUT OILS AND 0.98 mg/kg IN SUNFLOWER OIL. INCREASED LEVELS OF MALONALDEHYDE HAVE BEEN FOUND IN HAMBURGER, CHICKEN AND BEEF AS A RESULT OF COOKING UNDER A VARIETY OF CONDITIONS (eg, MICROWAVE, FRYING, BAKING AND BOILING)
MALONALDEHYDE IS FOUND IN MANY FOODSTUFFS AND IS PRESENT AT GENERALLY HIGH LEVELS IN RANCID FOODS. IT HAS BEEN DETECTED IN FISH MEAT, FISH OIL, RANCID SALMON OIL, RANCID NUTS, RANCID FLOUR, ORANGE JUICE ESSENCE, VEGETABLE OIL, FATS, FRESH FROZEN GREEN BEANS, MILK, MILK FAT, RYE BREAD, AND IN RAW, CURED AND COOKED MEATS.
Drug Information
IN PRIMARY RAT SKIN FIBROBLAST CULTURES GROWN IN A MEDIUM CONTAINING 1X10(-5), 1X10(-4), OR 1X10(-3) MOLAR OF 1,3-(14)C MALONALDEHYDE, THERE WAS A LIMITED, CONCENTRATION-DEPENDENT UPTAKE OF MALONALDEHYDE BY 24 HR (APPROXIMATELY 4% AT ALL CONCENTRATIONS). 83-89% OF THE (14)C WAS OXIDIZED TO (14)CO2 BY 24 HR AND APPROXIMATELY 5% WAS RECOVERED IN THE MAJOR LIPIDS. LIMITED CELLULAR UPTAKE OF MALONALDEHYDE MAY EXPLAIN THE TOLERANCE OF CELLS GROWN IN CULTURE TO RELATIVELY HIGH CONCENTRATIONS.|TWELVE HOURS AFTER INTUBATION WITH 1,3-(14)C MALONALDEHYDE, MALE WISTAR RATS SHOWED 60-70%, 5-15% AND 9-17% OF ADMINISTERED RADIOACTIVITY IN EXPIRED CARBON DIOXIDE, FECES AND URINE, RESPECTIVELY. IN VITRO EXPERIMENTS SHOWED METABOLISM TO BE PRIMARILY IN MITOCHONDRIA VIA REACTIONS INVOLVING OXYGEN UTILIZATION AND (14)CO2 PRODUCTION. THE APPARENT KM AND VMAX WERE 0.5 MMOL AND 9.3 NMOL/MIN/MG PROTEIN FOR OXYGEN UPTAKE, RESPECTIVELY, AND 2.0 MMOL AND 2.4 NMOL/MIN/MG PROTEIN FOR (14)CO2 PRODUCTION.
THIOBARBITURIC ACID-REACTING MATERIAL PRODUCED DURING ENZYMIC MICROSOMAL LIPID PEROXIDATION WAS IDENTIFIED AS MALONALDEHYDE. PHOSPHOLIPID ARACHIDONATE WAS ESTABLISHED AS THE MAJOR SOURCE OF THE MALONALDEHYDE PRODUCED IN THE REACTION.|(14)C-ACETATE APPEARED TO BE THE MAJOR ACCUMULATING METABOLITE IN RAT LIVER MITOCHONDRIAL PREPARATIONS FOLLOWING A 120-MINUTE INCUBATION WITH (14)C-MALONALDEHYDE. A PROBABLE BIOCHEMICAL ROUTE FOR MALONALDEHYDE METABOLISM INVOLVES OXIDATION OF MALONALDEHYDE BY MITOCHONDRIAL ALDEHYDE DEHYDROGENASE FOLLOWED BY DECARBOXYLATION TO PRODUCE CARBON DIOXIDE AND ACETATE.|Two aldehyde dehydrogenases in the rat-liver cytosol fraction account for virtually all of the metabolizing activity for malonaldehyde.|After oral administration of malonaldehyde (158 mg/kg body weight) to rats, increased quantities of formaldehyde, acetaldehyde, acetone and malonaldehyde itself were found in the urine. Additionally, methyl ethyl ketone, not found in control rats, was present in the urine of the animals that had received malonaldehyde.
Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Irritation eyes, skin, respiratory system; central nervous system depression; [potential occupational carcinogen] Target Organs: Eyes, skin, respiratory system, central nervous system (NIOSH, 2016)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)|(See procedures)
Fresh air, rest. Refer for medical attention.
Rinse and then wash skin with water and soap.
Rinse with plenty of water for several minutes (remove contact lenses if easily possible).
Malonaldehyde reacts with DNA to form an adduct with 2'-deoxyguanosine with has been characterized as 3-(2-deoxy-beta-D-erythro-pentofuranosy)pyrimido(1,2-alpha)purin-10(3H)-one (M1G-dR). This adduct is present at quantifiable levels in DNA from many human tissues.
Malonaldehyde
The substance can be absorbed into the body by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact
irritation eyes, skin, respiratory system; central nervous system depression; [potential occupational carcinogen]
Cough.
Redness.
Eyes, skin, respiratory system, central nervous system
Propanedial, ion(1-), sodium Use and Manufacturing
FREE MALONALDEHYDE CAN BE GENERATED FROM/ITS BIS(DIALKYL)ACETALS (eg 1,1,3,3-TETRAETHOXYPROPANE)/BY ACID-CATALYZED HYDROLYSIS WITH DILUTE HYDROCHLORIC ACID OR SHAKING THEM WITH ACID DOWEX 50 ION-EXCHANGE RESIN
RESEARCH COMPOUND
NO COMMERCIAL PRODUCTION
PROCEDURE INVOLVES EXTRACTING THE SAMPLE WITH TRICHLORACETIC ACID, HEATING THE EXTRACT WITH THIOBARBITURIC ACID, SEPARATING THE THIOBARBITURIC ACID-MALONALDEHYDE COMPLEX ON A UBONDPAK(18)C COLUMN, AND MEASURING ABSORBANCE USING A 546-NM INTERFERENCE FILTER. METHOD IS SPECIFIC FOR MALONALDEHYDE IN SEVERAL FOOD AND FEED SAMPLES. A COEFFICIENT OF VARIABILITY OF 7.0% WAS OBTAINED FOR SAMPLES CONTAINING 1-2 UG OF MALONALDEHYDE PER GRAM.
Computed Properties
Molecular Weight:72.06
XLogP3:-0.6
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:72.021129366
Monoisotopic Mass:72.021129366
Topological Polar Surface Area:34.1
Heavy Atom Count:5
Complexity:34.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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