MESACONIC ACID supplier | CasNO.498-24-8

Name
Mesaconic acid
EINECS 207-859-2
CAS No. 498-24-8
Article Data77
CAS DataBase
Density 1.387 g/cm³
Solubility 26.3g/L(18 oC)
Melting Point 200-202 ºC
Formula C5H6 O4
Boiling Point 336.6 °C at 760 mmHg
Molecular Weight 130.1
Flash Point 171.5 °C
Transport Information
Appearance
Safety Moderately toxic by intraperitoneal route. When heated to decomposition it emits acrid smoke and fumes.
Risk Codes R36/37/38
Molecular Structure
Hazard Symbols
Synonyms 2-Butenedioicacid, 2-methyl-, (E)-; Mesaconic acid (6CI,8CI); (2E)-2-Methyl-2-butenedioicacid; (E)-Citraconic acid; 2-Methylfumaric acid; Citronic acid; Methylfumaricacid; NSC 65438; trans-1-Propene-1,2-dicarboxylic acid;trans-2-Methyl-2-butenedioic acid
PSA 74.60000
LogP 0.10190

Synthetic route

: 2409-52-1
diethylitaconate

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
Stage #1: diethylitaconate With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating; Stage #2: With hydrogenchloride for 3h; Heating;	80%

: 97-65-4
2-methylenesuccinic acid

A: 79-41-4
poly(methacrylic acid)

B: 498-23-7
citraconic acid

C: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
With 5% Pt/Al2O3; sodium hydroxide In water at 250℃; for 1h; Reagent/catalyst; Temperature; Inert atmosphere;	A 68% B n/a C n/a
With sodium hydroxide In water at 180℃; under 112511 Torr; for 0.241667h;	A 27.26 %Spectr. B 36.48 %Spectr. C 16.23 %Spectr.
With sodium hydroxide at 280℃; for 0.0583333h;	A 57.08 %Chromat. B 5.91 %Chromat. C 5.72 %Chromat.
With sodium hydroxide at 250℃; for 0.25h; Reagent/catalyst;

...Expand

: 77-92-9
citric acid

A: 79-41-4
poly(methacrylic acid)

B: 498-23-7
citraconic acid

C: 498-24-8
Mesaconic acid

D: 97-65-4
2-methylenesuccinic acid

Conditions

Conditions	Yield
With 4-methoxy-phenol; triphenylphosphine In water at 225℃; under 20686.5 Torr; for 1.5h; Temperature; Glovebox; Inert atmosphere;	A 24.1% B n/a C n/a D n/a
With sodium hydroxide at 250℃; for 0.25h; Reagent/catalyst;

...Expand

: 59107-74-3
3-bromo-4-methyl-2,5-furandione

A: 498-24-8
Mesaconic acid

B: 498-21-5, 636-60-2
2-methylbutanedioic acid

Conditions

Conditions	Yield
With water; zinc

: 64-17-5
ethanol

: 498-23-7
citraconic acid

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
Rate constant;

: 41138-18-5
2-methyl-fumaramide

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
With hydrogenchloride

: 498-23-7
citraconic acid

: furan-2,3,5(4H)-trione pyridine (1:1)

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
beim Kochem die entstehende Itaconsaeure;

: 498-23-7
citraconic acid

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
at 180 - 200℃;
Quantum yield; Irradiation;
With diethyl ether; chloroform; bromine an der Sonne;

: 498-23-7
citraconic acid

A: 498-24-8
Mesaconic acid

B: 97-65-4
2-methylenesuccinic acid

Conditions

Conditions	Yield
With sodium hydroxide

: 498-23-7
citraconic acid

A: 498-24-8
Mesaconic acid

B: 79-10-7
acrylic acid

C: 74-99-7
prop-1-yne

Conditions

Conditions	Yield
bei der Elektrolyse von citraconsaeurem Kalium.Electrolysis;

...Expand

: 498-21-5, 636-60-2
2-methylbutanedioic acid

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
nach Verfuetterung im Hundeorganismus;

: 691-83-8
diethyl citraconate

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
With potassium hydroxide

: 5469-23-8, 19371-95-0, 20515-34-8, 20515-35-9, 37951-41-0
(RS,SR)-2,3-dibromo-2-methyl-succinic acid

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
With potassium iodide und (Kupfer);

: 97-65-4
2-methylenesuccinic acid

: furan-2,3,5(4H)-trione pyridine (1:1)

: 498-24-8
Mesaconic acid

: 97-65-4
2-methylenesuccinic acid

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
With water at 180 - 200℃;
With sodium hydroxide
Multi-step reaction with 2 steps 1: sodium hydroxide / 0.06 h / 280 °C 2: sodium hydroxide / 0.02 h / 270 °C View Scheme

: 20469-57-2
bromomethyl-succinic acid

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
With potassium hydroxide

: 616-02-4
citraconic acid anhydride

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
With water; nitric acid beim Eindampfen bis zum Beginn der Entwicklung roter Daempfe;
With nitric acid durch Eindampfen bis zum Beginn der Entwicklung roter Daempfe;
Multi-step reaction with 2 steps 1: H2SO4 2: alcoholic KOH-solution View Scheme
Multi-step reaction with 2 steps 1: bromine / 150 °C / beim Erhitzen im geschlossenen Rohr 2: zinc; water View Scheme

: 88-20-0
o-toluenesulfonic acid

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
With water; platinum Electrolysis.bei der Elektrolytischen Oxydation an Platin-Anoden;
With water; lead dioxide Electrolysis.bei der Elektrolytischen Oxydation an Blei(IV)-oxyd-Anoden;

: 553-97-9
2-Methyl-1,4-benzoquinone

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
With sulfuric acid at 10 - 12℃; bei der elektrolytischen Oxydation an einer PbO2-Anode;

: 104-15-4
toluene-4-sulfonic acid

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
at 70 - 75℃;

: 2792-66-7
α-methyl-DL-aspartic acid

: 623-11-0
1-methyl-4-nitrosobenzene

: 77-78-1
dimethyl sulfate

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
(+-)-2-amino-2-methyl-succinic acid;

...Expand

: 642-92-2, 1114-07-4, 2955-50-2, 4846-45-1, 5941-19-5, 6061-13-8, 6667-60-3, 7298-96-6, 31571-69-4, 86562-29-0, 121570-10-3, 127001-58-5
D,L-threo-β-methylaspartic acid

: 623-11-0
1-methyl-4-nitrosobenzene

: 77-78-1
dimethyl sulfate

: 498-24-8
Mesaconic acid

...Expand

: 77-92-9
citric acid

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
Kochen des Destillationsprodukts (welches Citraconsaeure und Itaconsaeure bezw. deren Anhydride enthaelt) mit 10prozentiger Natronlauge;

: 3120-04-5
3-methyl-1-phenylpyrrole-2,5-dione

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
With hydrogenchloride

: 6061-13-8
(2S,3S)-3-methylaspartic acid

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
With L-threo-3-methylaspartate ammonia-lyase In various solvent(s) Mechanism; enzymic ammonia elimination, different pH, labeled comp.;
In water at 20℃; Michaelis and catalytic center activity constants for deamination reaction by 3-methylaspartase from Morganella morganii strain YG-0601; pH 9.7; effect of various organic or inorganic compounds;
In water at 20℃; Michaelis and catalytic center activity constants for deamination reaction by 3-methylaspartase from Citrobacter sp. strain YG-0504; pH 9.7; effects of various organic or inorganic compounds;
With 3-methylaspartase; magnesium chloride In water Mechanism; Kinetics; various pL; also in D2O; primary deuterium and solvent isotope effects;
With 3-methylaspartase; potassium chloride; 2-amino-2-hydroxymethyl-1,3-propanediol; magnesium chloride In water at 30℃; Mechanism; Kinetics; various pL; also in D2O; isotope effects;

: 7298-96-6
erythro-β-methyl-L-aspartate

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
With L-threo-3-methylapartase; magnesium(II); potassium ion In water at 30℃; for 24h; Rate constant; Product distribution; Mechanism; pH 9.0; Km, deuterium isotope effects;
With 3-methylaspartase deamination reaction, different enzyme concentrations, kinetic parameters: KM, Vmax;

: 2880-58-2
2-methoxy-1,4-benzoquinone

A: 498-24-8
Mesaconic acid

B: 141-82-2
malonic acid

C: 110-15-6
succinic acid

D: 144-62-7
oxalic acid

Conditions

Conditions	Yield
With sodium hydroxide; oxygen at 90℃; under 7500.6 Torr; for 3h; Product distribution;

...Expand

: 112365-92-1
(2S,3S)-<3-2H>-3-methylaspartic acid

: 498-24-8
Mesaconic acid

Conditions

Conditions	Yield
With 3-methylaspartase deamination reaction, different enzyme concentrations, kinetic parameters: KM, Vmax;
With 3-methylaspartase; magnesium chloride In water Mechanism; Kinetics; various pL; also in D2O; primary deuterium and solvent isotope effects;
With 3-methylaspartase; potassium chloride; 2-amino-2-hydroxymethyl-1,3-propanediol; magnesium chloride In water at 30℃; Mechanism; Kinetics; various pL; also in D2O; isotope effects;

: 77-92-9
citric acid

A: 638-18-6
diethyl 3-hydroxypentanedioate

B: 498-24-8
Mesaconic acid

C: 499-12-7
1 propene 1,2,3 tricarboxylic acid

D: 97-65-4
2-methylenesuccinic acid

E: 616-02-4
citraconic acid anhydride

F: 2170-03-8
itaconic acid anhydride

Conditions

Conditions	Yield
With Sn/Pb solder at 150 - 210℃;

...Expand

: 59107-74-3
3-bromo-4-methyl-2,5-furandione

: 7732-18-5
water

zinc turnings: zinc turnings

A: 498-24-8
Mesaconic acid

B: 498-21-5, 636-60-2
2-methylbutanedioic acid

...Expand

: 498-24-8
Mesaconic acid

: 498-21-5, 636-60-2
2-methylbutanedioic acid

Conditions

Conditions	Yield
With formic acid; (bppm)Rh(1,1,1,5,5,5,-hexafluoroacetylacetonate); triethylamine In dimethylsulfoxide-d6 at 30℃; for 8h;	100%
With samarium diiodide In tetrahydrofuran for 0.0833333h; Ambient temperature;	88%
With phenylsilane; C12H23N2O2P In tetrahydrofuran at 23℃; for 2h;	86%

: 498-24-8
Mesaconic acid

: 2174-58-5
L-malic acid

Conditions

Conditions	Yield
With formic acid; TETRACYCLINE; paraquat dichloride In water at 45℃; for 30h; Clostridium formicoaceticum;	99%

: 64-17-5
ethanol

: 498-24-8
Mesaconic acid

: 2418-31-7
(E)-2-methyl-but-2-enedioic acid diethyl ester

Conditions

Conditions	Yield
With sulfuric acid for 3h; Reflux;	90%
With sulfuric acid for 16h; Heating;	81%
With sulfuric acid at 20℃; Reflux;	68%
With hydrogenchloride
With sulfuric acid; benzene

: 498-24-8
Mesaconic acid

: 6061-13-8
(2S,3S)-3-methylaspartic acid

Conditions

Conditions	Yield
With β-methyl aspartase; potassium chloride; ammonium chloride; magnesium chloride In water at 32℃; pH=9;	90%
With ammonium hydroxide; 3-methylaspartate ammonia-lyase; sodium chloride; magnesium chloride at 30℃; for 50h;	69%
With β-methylaspartase; ammonium chloride; ammonia; sodium chloride; magnesium chloride In water at 30℃; for 18h;	66%

: 67-56-1
methanol

: 498-24-8
Mesaconic acid

: 617-53-8
mesaconic acid dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid for 5h; Reflux; Inert atmosphere;	87%
With thionyl chloride at 0℃; for 2h; Reflux;	76%
With sulfuric acid for 12h; Heating;	75%

: 498-24-8
Mesaconic acid

: 31571-69-4
(2S,3RS)-3-methylaspartic acid

Conditions

Conditions	Yield
In water at 30℃; 0.2 M NH4Cl, 0.02 M MgCl2, 0.01 M KCl, methylaspartase, pH 9.0, several days;	86%

: 498-24-8
Mesaconic acid

: C5H8(2)HNO4

Conditions

Conditions	Yield
at 30℃; D2O, 0.2 M NH4Cl, 0.02 M MgCl2, 0.01 M KCl, methylaspartase, pD 8.6, several days;	86%

: 498-24-8
Mesaconic acid

: 127-65-1
chloroamine-T

: C12H15NO7S

Conditions

Conditions	Yield
	81%

: 67-56-1
methanol

: 498-24-8
Mesaconic acid

: 84569-14-2
citraconic acid dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid Heating;	80%

: 498-24-8
Mesaconic acid

: 71-36-3
butan-1-ol

: 22644-91-3
(E)-2-methylbut-2-enedicarboxylic acid dibutyl ester

Conditions

Conditions	Yield
With sulfuric acid for 3h; Reflux;	75%

: 498-24-8
Mesaconic acid

: C72H122N16O22

: C149H246N32O46

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 2.5h;	70%

: zinc(II) nitrate hexahydrate

: 498-24-8
Mesaconic acid

: 7732-18-5
water

: 16375-56-7
4-[2-(1-naphtalenyl)ethenyl]-pyridine

: 2C17H13N*H2O*Zn(2+)*C5H4O4(2-)

Conditions

Conditions	Yield
With triethylamine In methanol; ethanol	70%

...Expand

: 498-24-8
Mesaconic acid

: 6236-09-5
(S)-citramalic acid

Conditions

Conditions	Yield
With formaldehyd; TETRACYCLINE; paraquat dichloride In water at 37℃; for 24h; Clostridium formicoaceticum, phosphate buffer;	69.8%
mit Hilfe eines Mesaconase-Praeparats;

: 939-23-1
p-phenylpyridine

: cadmium(II) nitrate tetrhydrate

: 498-24-8
Mesaconic acid

: bis{(mesaconato)bis(4-phenylpyridyl)cadmium(II)}

Conditions

Conditions	Yield
With triethylamine In methanol; ethanol; water for 168h;	65%

...Expand

: 498-24-8
Mesaconic acid

: 7298-96-6
erythro-β-methyl-L-aspartate

Conditions

Conditions	Yield
With 3-methylaspartase enzymic amination in protium oxide;	61%
Multi-step reaction with 4 steps 1: 86 percent / H2O / 30 °C / 0.2 M NH4Cl, 0.02 M MgCl2, 0.01 M KCl, methylaspartase, pH 9.0, several days 2: 99 percent / aq. K2CO3 3: diethyl ether 4: 55 percent / HCl, AcOH / Heating View Scheme

: 498-24-8
Mesaconic acid

: (2S,3S)-2-Hydrazino-3-methylsuccinic acid

Conditions

Conditions	Yield
With potassium chloride; hydrazine hydrate; magnesium chloride at 30℃; for 72h; 3-methylaspartase (EC 4.3.1.2);	61%
With potassium and magnesium ions; hydrazine In water for 72h; 3-methylaspartase;	41%

: 498-24-8
Mesaconic acid

: 112365-92-1
(2S,3S)-<3-2H>-3-methylaspartic acid

Conditions

Conditions	Yield
With ammonium hydroxide; potassium chloride; water-d2; magnesium chloride In water at 30℃; for 48h; with 3-methylaspartase;	60%
With 3-methylaspartase; water-d2 enzymic amination;	60%

: aluminum(III) nitrate nonahydrate

: 498-24-8
Mesaconic acid

: C5H4O4(2-)*Al(3+)*HO(1-)*3H2O

Conditions

Conditions	Yield
With urea In water at 150℃; for 3h; Autoclave;	60%

: 498-24-8
Mesaconic acid

: 94594-90-8
(2R)-bornane-10,2-sultam

: 827628-67-1
(E)-1,4-Bis-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-methyl-but-2-ene-1,4-dione

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	50%

: 498-24-8
Mesaconic acid

: 74-89-5
methylamine

: (2S,3S)-N,3-Dimethylaspartic acid

Conditions

Conditions	Yield
With potassium chloride; magnesium chloride at 30℃; for 168h; 3-methylaspartase (EC 4.3.1.2);	40%
With potassium and magnesium ions In water for 72h; 3-methylaspartase;	35%

: 498-24-8
Mesaconic acid

: 74-89-5
methylamine

: (2S,3S)-N,3-Dimethyl(3-(2)H)aspartic acid

Conditions

Conditions	Yield
With potassium chloride; water-d2; magnesium chloride at 30℃; for 168h; 3-methylaspartase (EC 4.3.1.2);	40%

: 13520-92-8
ziconium(IV) oxychloride octahydrate

: 498-24-8
Mesaconic acid

: zirconium mesaconate

Conditions

Conditions	Yield
With acetic acid In water at 95℃; for 5h; Microwave irradiation; Green chemistry;	40%

: 67-62-9
O-Methylhydroxylamin

: 498-24-8
Mesaconic acid

: (2S,3S)-N-Methoxy-3-methylaspartic acid

Conditions

Conditions	Yield
With potassium chloride; hydroxylamine; ethylamine; magnesium chloride at 30℃; for 72h; 3-methylaspartase (EC 4.3.1.2);	34%
With potassium and magnesium ions In water for 72h; 3-methylaspartase;

: 498-24-8
Mesaconic acid

: (2S,3S)-N-Hydroxy-3-methylaspartic acid

Conditions

Conditions	Yield
With potassium chloride; hydroxylamine; ethylamine; magnesium chloride at 30℃; for 72h; 3-methylaspartase (EC 4.3.1.2);	19%

: 498-24-8
Mesaconic acid

: 53597-69-6
(1,3,5-triaza-7-phosphaadamantane)

: 3-carboxy-2-methyl-2-(1,3,5-triaza-7-phosphoniatricyclo[3.3.1.13,7]dec-7-yl)propanoate

Conditions

Conditions	Yield
In water at 20℃; for 6574.5h; Solvent; Schlenk technique;	8.5%

: 2811-50-9
7-methoxy-4-vinyl-1,2-dihydronaphthalene

: 498-24-8
Mesaconic acid

: (+/-)-7-methoxy-2-methyl-1,2,3,4,9,10-hexahydro-phenanthrene-1r,2t-dicarboxylic acid

: 109252-62-2
(+/-)-7-methoxy-1-methyl-1,2,3,4,9,10-hexahydro-phenanthrene-1r,2t-dicarboxylic acid

Conditions

Conditions	Yield
With propionic acid

...Expand

: 67-56-1
methanol

: 498-24-8
Mesaconic acid

A: 39529-95-8
(E)-4-methoxy-3-methyl-4-oxobut-2-enoic acid

B: 77044-59-8
(E)-4-methoxy-2-methyl-4-oxobut-2-enoic acid

Conditions

Conditions	Yield
With hydrogenchloride

...Expand

MESACONIC ACID Chemical Properties

Product Name: Mesaconic acid (CAS NO.498-24-8)

Molecular Formula: C₅H₆O₄
Molecular Weight: 130.1g/mol
Mol File: 498-24-8.mol
Einecs: 207-859-2
Melting Point: 200-202 °C(lit.)
Boiling point: 336.6 °C at 760 mmHg
Flash Point: 171.5 °C
Density: 1.387 g/cm³
Surface Tension: 57.4 dyne/cm
Enthalpy of Vaporization: 63.72 kJ/mol
Vapour Pressure: 2.09E-05 mmHg at 25°C
XLogP3-AA: -0.1
H-Bond Donor: 2
H-Bond Acceptor: 4

MESACONIC ACID Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LDLo	intraperitoneal	500mg/kg (500mg/kg)		"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 147, 1954.

MESACONIC ACID Consensus Reports

Reported in EPA TSCA Inventory.

MESACONIC ACID Safety Profile

Moderately toxic by intraperitoneal route. When heated to decomposition it emits acrid smoke and fumes.
Safety Information of Mesaconic acid (CAS NO.498-24-8):
Hazard Codes: Xi
Risk Statements: 36/37/38
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements: 26-36
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing

MESACONIC ACID Specification

Mesaconic acid ,its CAS NO. is 498-24-8,the synonyms is (2E)-2-Methyl-2-butenedioic acid ; 2-Methylfumaric acid ; Butenedioic acid, methyl-, (E)- ; Fumaric acid, methyl- ; Kyselina mesakonova ; kyselinamesakonova ; Mesaconate ; methyl-fumaricaci .

Product Name

Mesaconic acid

Synthetic route

MESACONIC ACID Chemical Properties

MESACONIC ACID Toxicity Data With Reference

MESACONIC ACID Consensus Reports

MESACONIC ACID Safety Profile

MESACONIC ACID Specification

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