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Malondialdehyde

PubChem CID
10964
Structure
Malondialdehyde_small.png
Malondialdehyde_3D_Structure.png
Molecular Formula
Synonyms
  • Propanedial
  • Malondialdehyde
  • MALONALDEHYDE
  • 542-78-9
  • Malonyldialdehyde
Molecular Weight
72.06 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-18
Description
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].
Malonaldehyde has been reported in Capsicum annuum, Brassica oleracea, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Malondialdehyde.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

propanedial
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

WSMYVTOQOOLQHP-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C(C=O)C=O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

OCHCH2CHO
C3H4O2
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DrugBank ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 ICSC Number

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 NCI Thesaurus Code

2.3.12 Nikkaji Number

2.3.13 RTECS Number

2.3.14 RXCUI

2.3.15 Wikidata

2.3.16 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Malonaldehyde
  • Malondialdehyde
  • Malondialdehyde, Sodium
  • Malonylaldehyde
  • Malonyldialdehyde
  • Propanedial
  • Sodium Malondialdehyde

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
72.06 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
-0.6
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
72.021129366 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
72.021129366 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
34.1 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
5
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
34.2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid (needles); [NIOSH]
Solid
NEEDLES.
Solid (needles).

3.2.2 Color / Form

Solid (needles)
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 190

3.2.3 Melting Point

72 °C
161 °F

3.2.4 LogP

-1.16

3.2.5 Decomposition

When heated to decomposition it emits acrid smoke and irritating fumes.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2789

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Aldehydes

3.4.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 2
Source of Spectrum
RCM-29-1076-MDA
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Va-0-0-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 FDA National Drug Code Directory

7.2 Drug Labels

Active ingredient and drug

7.3 Biomarker Information

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 Absorption, Distribution and Excretion

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.
BIRD RP, DRAPER HH; LIPIDS 17 (8): 519 (1982)
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.
SIU GM, DRAPER HH; LIPIDS 17 (5): 349 (1982)

9.2 Metabolism / Metabolites

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.
NIEHAUS WG JR, SAMUELSSON B; EUR J BIOCHEM 6 (1): 126 (1968)
(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.
SIU GM, DRAPER HH; LIPIDS 17 (5): 349 (1982)
Two aldehyde dehydrogenases in the rat-liver cytosol fraction account for virtually all of the metabolizing activity for malonaldehyde.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V71 1040 (1999)
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.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V71 1040 (1999)
Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

9.3 Biochemical Reactions

10 Use and Manufacturing

10.1 Uses

Sources/Uses
Used in scientific research; [HSDB] Produced during lipid peroxidation and other reactions in mammals; Used as index for rancidity in foods; [Merck Index] Found in many foods (at high levels if rancid); [IARC]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
RESEARCH COMPOUND
IARC MONOGRAPHS 1972-PRESENT V36 p.164
Naturally produced by the body (endogenous).

10.2 Methods of 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
IARC MONOGRAPHS 1972-PRESENT V36 p.164

10.3 U.S. Production

NO COMMERCIAL PRODUCTION
IARC MONOGRAPHS 1972-PRESENT V36 p.164

10.4 U.S. Imports

(1986) No Data

10.5 U.S. Exports

(1986) No Data

11 Identification

11.1 Analytic Laboratory Methods

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.
BIRD RP ET AL; DETERMINATION OF MALONALDEHYDE IN BIOLOGICAL MATERIALS BY HIGH-PRESSURE LIQUID CHROMATOGRAPHY; ANAL BIOCHEM 128(1) 240 (1983)

12 Safety and Hazards

12.1 Hazards Identification

12.1.1 Fire Hazards

Not combustible.

12.1.2 Hazards Summary

Evidence of injury to the liver and pancreas in mice experiments when added to drinking water at 500 mg/kg body weight per day; [HSDB] No listed effects of short-term or long-term exposure; [ICSC] May cause skin, eye, and respiratory tract irritation; Excessive exposure may cause CNS depression; [Merck Index] Causes muscle weakness, dyspnea, and cyanosis in oral lethal-dose study of rats; Causes other gastrointestinal and liver changes and inflammation, necrosis, or scarring of bladder in 90-day oral study of mice; [RTECS] See ALDEHYDES
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.

12.2 Safety and Hazard Properties

12.2.1 NIOSH Recommendations

NIOSH considers maloaldehyde to be a potential occupational carcinogen.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 190
NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concn.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 190

12.3 First Aid Measures

Inhalation First Aid
Fresh air, rest. Refer for medical attention.
Skin First Aid
Rinse and then wash skin with water and soap.
Eye First Aid
Rinse with plenty of water for several minutes (remove contact lenses if easily possible).
Ingestion First Aid
Rinse mouth. Give one or two glasses of water to drink.

12.3.1 First Aid

(See general first aid procedures)

Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.

Skin: Water flush immediately - If this chemical contacts the skin, immediately flush the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and flush the skin with water. Get medical attention promptly.

Breathing: Respiratory support

Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

12.4 Fire Fighting

In case of fire in the surroundings, use appropriate extinguishing media.

12.5 Accidental Release Measures

12.5.1 Spillage Disposal

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.

12.5.2 Disposal Methods

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.

12.5.3 Preventive Measures

The worker should immediately wash the skin when it becomes contaminated.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 190
The worker should wash daily at the end of each work shift.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 190
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 190
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 190
For more Preventive Measures (Complete) data for MALONALDEHYDE (6 total), please visit the HSDB record page.

12.6 Exposure Control and Personal Protection

12.6.2 Permissible Exposure Limit (PEL)

none

12.6.3 Immediately Dangerous to Life or Health (IDLH)

NIOSH considers malonaldehyde to be a potential occupational carcinogen.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 190

Ca [N.D.]

See: IDLH INDEX

12.6.4 Inhalation Risk

A harmful concentration of airborne particles can be reached quickly.

12.6.5 Personal Protective Equipment (PPE)

Wear appropriate personal protective clothing to prevent skin contact.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 190
Wear appropriate eye protection to prevent eye contact.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 190
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.
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 190
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. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 190
For more Personal Protective Equipment (PPE) (Complete) data for MALONALDEHYDE (6 total), please visit the HSDB record page.

(See personal protection and sanitation codes)

Skin: Prevent skin contact - Wear appropriate personal protective clothing to prevent skin contact.

Eyes: Prevent eye contact - Wear appropriate eye protection to prevent eye contact.

Wash skin: When contaminated/Daily

Remove: When wet or contaminated

Change: Daily - Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

Provide: Eyewash, Quick drench

12.6.6 Respirator Recommendations

NIOSH

At concentrations above the NIOSH REL, or where there is no REL, at any detectable concentration:

(APF = 10,000) Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode

(APF = 10,000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus

Escape:

(APF = 50) Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister

Any appropriate escape-type, self-contained breathing apparatus

Important additional information about respirator selection

12.6.7 Preventions

Inhalation Prevention
Use ventilation, local exhaust or breathing protection.
Skin Prevention
Protective gloves.
Eye Prevention
Wear safety goggles.
Ingestion Prevention
Do not eat, drink, or smoke during work.

12.7 Stability and Reactivity

12.7.1 Hazardous Reactivities and Incompatibilities

Proteins [Note: Pure compound is stable under neutral conditions, but not under acidic conditions].
NIOSH. NIOSH Pocket Guide to Chemical Hazards. DHHS (NIOSH) Publication No. 97-140. Washington, D.C. U.S. Government Printing Office, 1997., p. 190

12.8 Other Safety Information

12.8.1 Special Reports

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/

13 Toxicity

13.1 Toxicological Information

13.1.1 Toxicity Summary

Uremic toxins such as malondialdehyde are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).
A7868: Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. PMID:25041433
A7869: Young GH, Wu VC: KLOTHO methylation is linked to uremic toxins and chronic kidney disease. Kidney Int. 2012 Apr;81(7):611-2. doi: 10.1038/ki.2011.461. PMID:22419041

13.1.2 NIOSH Toxicity Data

13.1.3 Evidence for Carcinogenicity

Evaluation: No epidemiological data relevant to the carcinogenicity of malonaldehyde were available. There is limited evidence in experimental animals for the carcinogenicity of malonaldehyde. Overall evaluation: Malonaldehyde is not classifiable as to its carcinogenicity to humans (Group 3)
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V71 1045 (1999)

13.1.4 Carcinogen Classification

1 of 2
IARC Carcinogenic Agent
Malonaldehyde
IARC Carcinogenic Classes
Group 3: Not classifiable as to its carcinogenicity to humans
IARC Monographs

Volume 36: (1985) Allyl Compounds, Aldehydes, Epoxides and Peroxides

Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

Volume 71: (1999) Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide (Part 1, Part 2, Part 3)

2 of 2
Carcinogen Classification
3, not classifiable as to its carcinogenicity to humans. (L135)

13.1.5 Health Effects

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

13.1.6 Exposure Routes

The substance can be absorbed into the body by ingestion.
inhalation, skin absorption, ingestion, skin and/or eye contact
Endogenous, Ingestion, Dermal (contact)

13.1.7 Symptoms

Inhalation Exposure
Cough.
Eye Exposure
Redness.
irritation eyes, skin, respiratory system; central nervous system depression; [potential occupational carcinogen]
As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

13.1.8 Target Organs

Eyes, skin, respiratory system, central nervous system

13.1.9 Cancer Sites

[in animals: thyroid gland tumors]

13.1.10 Adverse Effects

Neurotoxin - Other CNS neurotoxin

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

13.1.11 Acute Effects

13.1.12 Treatment

Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

13.1.13 Human Toxicity Excerpts

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.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V71 1040 (1999)

13.1.14 Non-Human Toxicity Excerpts

DESPITE ITS LOW UPTAKE AND RAPID OXIDATION TO CARBON DIOXIDE, TREATMENT OF PRIMARY RAT SKIN FIBROBLAST CULTURES WITH 1X10-3 MOLAR (14)C-MALONALDEHYDE FOR 24 HR PRODUCED A LATENT INHIBITION OF (14)C-LABELED GLUCOSE OXIDATION.
BIRD RP, DRAPER HH; LIPIDS 17 (8): 519 (1982)
EXPOSURE OF PRIMARY RAT SKIN FIBROBLAST CULTURES TO 1X10(-3) AND 1X10(-4) MOLAR MALONALDEHYDE GAVE DOSE-DEPENDENT PRODUCTION OF MICRONUCLEI. CHROMOSOMAL ABERRATIONS WERE PRODUCED IN 14 AND 34% OF METAPHASES, RESPECTIVELY. AT 24 HR, THE CORRESPONDING FREQUENCIES WERE 46 AND 52%. DOSE-DEPENDENT INCREASES IN ANEUPLOIDY WERE SEEN AT GREATER THAN OR EQUAL TO 1X10(-4) MOLAR MALONALDEHYDE.
BIRD RP, DRAPER HH; MUTAT RES 101 (3): 237 (1982)
MALONDIALDEHYDE, THE MOST STUDIED PRODUCT OF LIPID PEROXIDATION, WAS INVESTIGATED FOR POSSIBLE INHIBITORY EFFECTS ON ALDH FOR RAT LIVER MITOCHONDRIA. MALONDIALDEHYDE WAS A POTENT INHIBITOR OF THE ENZYME. THE ENZYME WAS EQUALLY SENSITIVE TO INHIBITION WHEN INTACT MITOCHONDRIAL PREPARATIONS WERE COMPARED WITH DISRUPTED MITOCHONDRIA. EXTENT OF INHIBITION DEPENDED ON MALONDIALDEHYDE CONCN AND TIME OF INCUBATION; HIGH CONCN COMPLETELY AND IRREVERSIBLY INHIBITED LOW KM MITOCHONDRIAL ALDH. THE RATE OF ALDH INACTIVATION WAS BIPHASIC, WITH RAPID AND SLOWER RATES BOTH DEPENDENT ON MALONDIALDEHYDE CONCN.
HJELLE JJ ET AL; TOXICOL LETT 14 (1-2): 35 (1982)
RAW AND COOKED MEAT WITH 30% FAT HAD HIGHER MALONALDEHYDE LEVELS THAN THE MEAT WITH 10% FAT. MALONALDEHYDE VALUES WERE HIGHER IN THE COOKED PATTIES THAN IN THE RAW. AMES TEST REVERTANT NUMBERS WERE HIGHER FOR THE EXTRACT FROM PATTIES COOKED TO 95 °C AT 218 °C THAN THOSE COOKED TO 83 °C AT 175 °C. REVERTANT NUMBERS WERE NOT DIFFERENT FOR PATTIES AT THE TWO DIFFERENT FAT LEVELS. GENERALLY THE LOWER COOKING TEMPERATURE RESULTED IN LOWER COOKING LOSSES, LOWER MALONALDEHYDE LEVELS, AND REVERTANT NUMBERS THAN DID THE HIGHER TEMPERATURES.
GODWIN SL MC; DISS ABSTR INT B 1982 42 (11): 4347 (1981)
For more Non-Human Toxicity Excerpts (Complete) data for MALONALDEHYDE (15 total), please visit the HSDB record page.

13.1.15 Non-Human Toxicity Values

LD50 Mouse oral 606 mg/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2789
LD50 Rat oral 632 mg/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2789

13.1.16 Ongoing Test Status

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. /Malonaldehyde, sodium salt/ [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=24382-04-5]

13.1.17 National Toxicology Program Studies

... 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/
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 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709

13.2 Ecological Information

13.2.1 Natural Pollution Sources

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.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 164

13.2.2 Artificial Pollution Sources

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)
IARC MONOGRAPHS 1972-PRESENT V36 p.164

13.2.3 Food Survey Values

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.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 164

13.2.4 Plant Concentrations

MALONALDEHYDE HAS BEEN DETECTED IN THE LEAVES OF PEA AND COTTON PLANTS.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V36 164

14 Associated Disorders and Diseases

Disease
Guillain-Barré syndrome
References
PubMed: 20374079
Disease
Smoking
References

PubMed: 6890513, 12194923, 8294547, 15649624, 10636262, 9137998, 19222926, 15878312, 18666198, 18029489, 19036546

Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.

Disease
Uremia
References

PubMed: 2026685, 8087979, 9607216, 17132244, 6520173, 21359215, 15353324, 11865086, 9573551, 10509899, 7482520, 19309105, 24023812, 22626821, 12675874

Merck Manual of Diagnosis and Therapy.

Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.

Geigy Scientific Tables, 8th Rev edition, pp. 80-82. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.

Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.

David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971

National Health and Nutrition Examination Survey (NHANES Survey) 2013

15 Literature

15.1 Consolidated References

15.2 NLM Curated PubMed Citations

15.3 Springer Nature References

15.4 Thieme References

15.5 Wiley References

15.6 Chemical Co-Occurrences in Literature

15.7 Chemical-Gene Co-Occurrences in Literature

15.8 Chemical-Disease Co-Occurrences in Literature

16 Patents

16.1 Depositor-Supplied Patent Identifiers

16.2 WIPO PATENTSCOPE

16.3 Chemical Co-Occurrences in Patents

16.4 Chemical-Disease Co-Occurrences in Patents

16.5 Chemical-Gene Co-Occurrences in Patents

17 Interactions and Pathways

17.1 Protein Bound 3D Structures

17.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

17.2 Chemical-Target Interactions

17.3 Drug-Drug Interactions

17.4 Pathways

18 Biological Test Results

18.1 BioAssay Results

19 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

20 Classification

20.1 MeSH Tree

20.2 NCI Thesaurus Tree

20.3 ChEBI Ontology

20.4 ChemIDplus

20.5 ChEMBL Target Tree

20.6 NORMAN Suspect List Exchange Classification

20.7 EPA DSSTox Classification

20.8 International Agency for Research on Cancer (IARC) Classification

20.9 LOTUS Tree

20.10 EPA Substance Registry Services Tree

20.11 MolGenie Organic Chemistry Ontology

21 Information Sources

  1. CAS Common Chemistry
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  5. FDA Global Substance Registration System (GSRS)
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  11. LOTUS - the natural products occurrence database
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  12. NCI Thesaurus (NCIt)
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    https://publications.iarc.fr/Terms-Of-Use
    IARC Classification
    https://www.iarc.fr/
  20. Japan Chemical Substance Dictionary (Nikkaji)
  21. KEGG
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    https://www.kegg.jp/kegg/legal.html
  22. KNApSAcK Species-Metabolite Database
  23. Natural Product Activity and Species Source (NPASS)
  24. MarkerDB
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    https://markerdb.ca/
  25. Metabolomics Workbench
  26. National Drug Code (NDC) Directory
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    Malonaldehyde
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    https://www.norman-network.com/nds/SLE/
  29. Protein Data Bank in Europe (PDBe)
  30. RCSB Protein Data Bank (RCSB PDB)
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  31. Rhea - Annotated Reactions Database
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  32. SpectraBase
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  43. PATENTSCOPE (WIPO)
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CONTENTS