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Maleic acid

Names

[ CAS No. ]:
110-16-7

[ Name ]:
Maleic acid

[Synonym ]:
(2Z)-2-Butenedioic acid
2-Butenedioic acid, (2Z)-
cis-2-Butenedioic Acid
2-Butenedioicacid (2Z)-
MFCD00063177
EINECS 203-742-5
Maleic acid
cis-Butenedioic acid,Toxilic acid
Maleic acid [NA2215]
(2Z)-But-2-enedioic acid

Biological Activity

[Description]:

Maleic Acid is a Glutamate Decarboxylase (GAD) inhibitor of E. coli and L. monocytogenes.

[Related Catalog]:

Natural Products >> Acids and Aldehydes
Research Areas >> Infection

[Target]

Human Endogenous Metabolite

GAD


[In Vitro]

The MICs of WT 10403S for the acids (e.g., Maleic Acid) are 34 mM, 25 mM, 31 mM and 30 mM which correspond to pH values prior to growth of 4.84, 5.14, 5.32 and 5.02 respectively. Of all compounds tested, Maleic Acid is the least inhibitory despite acting at a lower pH (4.84). The most acid resistant (10403S) and the weakest (EGD-e) strain are challenged with 8.6 mM and 4.3 mM of each organic acid at pH 3 and 3.3 respectively. On both strains, Maleic Acid is the most bactericidal[2].

[References]

[1]. Fonda ML, et al. Glutamate decarboxylase. Substrate specificity and inhibition by carboxylic acids. Biochemistry. 1972 Mar 28;11(7):1304-9.

[2]. Paudyal R, et al. A novel approach in acidic disinfection through inhibition of acid resistance mechanisms; Maleic acid-mediated inhibition of glutamate decarboxylase activity enhances acid sensitivity of Listeria monocytogenes. Food Microbiol. 2018 Feb;69:96-104.


[Related Small Molecules]

3-Methyladenine | Hydrocortisone | Acetylcysteine(N-acetylcysteine) | Retinoic acid | Melatonine | Dinoprostone | Nicotinamide | Adenosine triphosphate | 4-Acetamidophenol | Prostaglandin E1 | Dehydroepiandrosterone | Corticosterone | Progesterone | Docosahexaenoic Acid | NAD+

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
355.5±25.0 °C at 760 mmHg

[ Melting Point ]:
134-138ºC

[ Molecular Formula ]:
C4H4O4

[ Molecular Weight ]:
116.072

[ Flash Point ]:
183.0±19.7 °C

[ Exact Mass ]:
116.010956

[ PSA ]:
74.60000

[ LogP ]:
-0.01

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.526

[ Storage condition ]:
Store at RT.

[ Stability ]:
Stable. Combustible. Incompatible with strong oxidizing agents, bases.

[ Water Solubility ]:
790 g/L (25 ºC)

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
OM9625000
CHEMICAL NAME :
Maleic acid
CAS REGISTRY NUMBER :
110-16-7
BEILSTEIN REFERENCE NO. :
0605762
LAST UPDATED :
199710
DATA ITEMS CITED :
13
MOLECULAR FORMULA :
C4-H4-O4
MOLECULAR WEIGHT :
116.08
WISWESSER LINE NOTATION :
QV1U1VQ -C

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
708 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - muscle weakness Gastrointestinal - ulceration or bleeding from stomach
TYPE OF TEST :
LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>720 mg/m3/1H
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2400 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
1560 mg/kg
TOXIC EFFECTS :
Behavioral - tremor

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Human Fibroblast
DOSE/DURATION :
20 mmol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 183,89,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84505 No. of Facilities: 1840 (estimated) No. of Industries: 22 No. of Occupations: 27 No. of Employees: 17036 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84505 No. of Facilities: 2076 (estimated) No. of Industries: 36 No. of Occupations: 45 No. of Employees: 30064 (estimated) No. of Female Employees: 11590 (estimated)

Safety Information

[ Symbol ]:

GHS05, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302 + H312-H315-H317-H318-H335

[ Precautionary Statements ]:
P280-P301 + P312 + P330-P305 + P351 + P338 + P310

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R22;R36/37/38

[ Safety Phrases ]:
S26-S28-S37

[ RIDADR ]:
UN 2215

[ WGK Germany ]:
1

[ RTECS ]:
OM9625000

[ Packaging Group ]:
III

[ HS Code ]:
2917190090

Precursor & DownStream

Customs

[ HS Code ]: 2917190090

[ Summary ]:
2917190090 acyclic polycarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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