maleic acid
cis-1,2-ethylenedicarboxylic acid
 
Notes:
Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). The molecule consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 degree centigrade) is also much lower than that of fumaric acid (287 degree centigrade). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place at the expense of intermolecular interactions. Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid is a reactant in many Diels-Alder reactions. [HMDB]
  • Charkit Chemical
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    • Penta International Corporation
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      13-02000 MALEIC ACID
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    • TCI AMERICA
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      M0006 Maleic Acid >99.0%(T)
       
Synonyms   Articles   Notes   Search
(Z)-but-2-enedioic acid (Click)
CAS Number: 110-16-7Picture of molecule
ECHA EINECS - REACH Pre-Reg: 203-742-5
FDA UNII: 91XW058U2C
Nikkaji Web: J2.446E
Beilstein Number: 0605762
MDL: MFCD00063177
XlogP3: -0.30 (est)
Molecular Weight: 116.07268000
Formula: C4 H4 O4
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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DG SANTE Food Contact Materials: maleic acid
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Physical Properties:
Appearance: white crystalline solid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 1.59000 @  25.00 °C.
Melting Point: 130.00 to  131.00 °C. @ 760.00 mm Hg
Boiling Point: 355.00 to  356.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.000005 mm/Hg @ 25.00 °C. (est)
Flash Point: 361.00 °F. TCC ( 183.00 °C. ) (est)
logP (o/w): -0.480
Soluble in:
 water, 4.41E+05 mg/L @ 25 °C (exp)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: buffering agents
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Suppliers:
Aceto
MALEIC ACID (DSM)
BOC Sciences
For experimental / research use only.
but-2-enedioic acid >98%
Charkit Chemical
MALEIC ACID
Covalent Chemical
Maleic Acid
ExtraSynthese
For experimental / research use only.
Maleic Acid
Penta International
MALEIC ACID NF& EP GRADE
Penta International
MALEIC ACID
Prinova
Maleic Acid
Santa Cruz Biotechnology
For experimental / research use only.
Maleic Acid ≥99%
Sigma-Aldrich
For experimental / research use only.
Maleic acid ReagentPlus®, ≥99.0% (HPLC)
TCI AMERICA
For experimental / research use only.
Maleic Acid >99.0%(T)
Viachem
Maleic Acid
Odor: bland
Use: It is employed in the manufacture of phthalic-type alkyd and polyester resins, surface coatings, copolymers, plasticizers, lubricant additives and agricultural chemicals; in adhesives and sealants; as a preservative for oils and fats; organic synthesis; dyeing and finishing wool, cotton and silk; and preparing the maleate salts of antihistamines and similar drugs.
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50  708 mg/kg
BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 7-4/1970

oral-mouse LD50  2400 mg/kg
Biochemical Journal. Vol. 34, Pg. 1196, 1940.

Dermal Toxicity:
skin-rabbit LD50 1560 mg/kg
BEHAVIORAL: TREMOR
BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 7-4/1970

Inhalation Toxicity:
inhalation-rat LC50 > 720 mg/m3/1H
BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 7-4/1970

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Safety in Use Information:
Category: cosmetic agents
Recommendation for maleic acid usage levels up to:
 not for fragrance use.
 
Recommendation for maleic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Scientific Report of EFSA on the risk assessment of salts of authorised acids, phenols or alcohols for use in food contact materials [1]
View page or View pdf
EPI System: View
ClinicalTrials.gov: search
NIOSH International Chemical Safety Cards: search
NLM Hazardous Substances Data Bank: Search
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
NLM Developmental and Reproductive Toxicity: Search
EPA Substance Registry Services (TSCA): 110-16-7
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 444266
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 1
 (Z)-but-2-enedioic acid
Chemidplus: 0000110167
EPA/NOAA CAMEO: hazardous materials
RTECS: 110-16-7
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References:
 (Z)-but-2-enedioic acid
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 110-16-7
Pubchem (cid): 444266
Pubchem (sid): 135018439
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
Golm Metabolome Database: Search
Metabolomics Database: Search
KEGG (GenomeNet): C01384
HMDB (The Human Metabolome Database): HMDB00176
FooDB: FDB008113
Export Tariff Code: 2917.19.2300
Haz-Map: View
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
Formulations/Preparations:
grades of purity: reagent; technical
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
 buffering agents 
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Occurrence (nature, food, other): note
 cacao plant
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 cherry sour cherry fruit
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 lovage root
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 roselle flower
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Synonyms:
(2Z)-but-2-enedioic acid
(Z)-but-2-enedioic acid
cis-but-2-enedioic acid
(2Z)-2-butene dioic acid
(Z)-butene dioic acid
(Z)-2-butene dioic acid
cis-butene dioic acid
(2Z)-2-butenedioic acid
(Z)-butenedioic acid
(Z)-2-butenedioic acid
cis-2-butenedioic acid
2-butenedioic acid (2Z)-
2-butenedioic acid (Z)-
2-butenedioic acid, (2Z)-
2-butenedioic acid, (Z)-
(Z)-1,2-ethylene dicarboxylic acid
cis-1,2-ethylene dicarboxylic acid
cis-1,2-ethylenedicarboxylic acid
1,2-ethylenedicarboxylic acid, (Z)
 maleicacid
 maleinic acid
 malenic acid
 toxilic acid
(Z)-tumaric acid
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Articles:
PubMed: Effects of acid extrusion on the degradability of maize distillers dried grain with solubles in pigs.
PubMed: An in silico toxicogenomics approach for inferring potential diseases associated with maleic acid.
PubMed: Impurity profiling of carbocisteine by HPLC-CAD, qNMR and UV/vis spectroscopy.
PubMed: Quantitative proton nuclear magnetic resonance for the structural and quantitative analysis of atropine sulfate.
PubMed: Ca2+ ion responsive pickering emulsions stabilized by PSSMA nanoaggregates.
PubMed: Metabolic profiling of Chinese tobacco leaf of different geographical origins by GC-MS.
PubMed: CO₂ and O₂ respiration kinetics in hydrocarbon contaminated soils amended with organic carbon sources used to determine catabolic diversity.
PubMed: Self-assembly and emulsification of poly{[styrene-alt-maleic acid]-co-[styrene-alt-(N-3,4-dihydroxyphenylethyl-maleamic acid)]}.
PubMed: Dual-responsive poly(styrene-alt-maleic acid)-graft-poly(N-isopropyl acrylamide) micelles as switchable emulsifiers.
PubMed: Integrated separation process for isolation and purification of biosuccinic acid.
PubMed: Michael acceptor based antiplasmodial and antitrypanosomal cysteine protease inhibitors with unusual amino acids.
PubMed: Comparison of the skin sensitizing potential of unsaturated compounds as assessed by the murine local lymph node assay (LLNA) and the guinea pig maximization test (GPMT).
PubMed: A convenient route to the synthesis of isotopomeric dihydro-2(3H)furanones.
PubMed: Comparative analysis of influence of promoters and inhibitors on in vitro available iron using two methods.
PubMed: Interactions of hydrophobically modified polyelectrolytes with nonionic surfactants.
PubMed: NMR regulatory analysis: determination and characterization of Chinese-herb aristolochic acids.
PubMed: Aqueous photolysis of niclosamide.
PubMed: Development of NMR and raman spectroscopic methods for the determination of the degree of substitution of maleate in modified starches.
PubMed: Modeling solid-to-solid biocatalysis: integration of six consecutive steps.
PubMed: Modulation of allergen-specific immune responses to the major shrimp allergen, tropomyosin, by specific targeting to scavenger receptors on macrophages.
PubMed: Inhibition of renal uptake of indium-111-DTPA-octreotide in vivo.
PubMed: [The kinetics of the excretion of a choline-containing polymer from the body of rats and its effect on the activity of intestinal enzymes].
PubMed: Thermodynamics of the maleate and citraconate hydration reactions catalysed by malease from Pseudomonas pseudoalcaligenes.
PubMed: Analytical method development and preformulation stability studies of L-665,871 (a beta-agonist) in swine feed.
PubMed: Screening for microorganisms producing D-malate from maleate.
PubMed: Maleic acid dimethylester: evaluation of dermal toxicity and genotoxicity.
PubMed: [Analysis of organic residues in the extracts from the food retortable pouch by HPLC].
PubMed: [The effect of maleic acid hydrazide (MH) on the hexose content of potato tubers].
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