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Itaconic acid

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Identification
Molecular formula
C5H6O4
CAS number
97-65-4
IUPAC name
2-methylenebutanedioic acid
State
State

At room temperature, itaconic acid is in a solid state. It is typically found as crystalline powders or crystals, which are stable under standard conditions.

Melting point (Celsius)
166.00
Melting point (Kelvin)
439.15
Boiling point (Celsius)
268.00
Boiling point (Kelvin)
541.15
General information
Molecular weight
130.10g/mol
Molar mass
130.1020g/mol
Density
1.5730g/cm3
Appearence

Itaconic acid appears as a white crystalline solid at room temperature. The crystals are usually odorless and can exhibit a slightly bitter taste. The solid is typically stable and can absorb moisture when exposed to the atmosphere.

Comment on solubility

Solubility of 2-Methylenebutanedioic Acid (C5H6O4)

2-Methylenebutanedioic acid, also known as maleic acid, exhibits interesting solubility characteristics that are important for its applications in organic synthesis and materials science. Here are some key aspects:

  • Water Solubility: This compound is highly soluble in water, with a solubility exceeding 100 g/L at room temperature. This high solubility is attributed to its ability to form hydrogen bonds with water molecules.
  • Solvent Compatibility: In addition to being soluble in water, 2-methylenebutanedioic acid is also soluble in common organic solvents such as ethanol and acetone, which increases its versatility in various chemical reactions.
  • Effect of pH: The solubility of 2-methylenebutanedioic acid can be influenced by the pH of the solution. In acidic conditions, the compound remains more predominantly in its acidic form, while basic conditions can lead to deprotonation, enhancing solubility further.
  • Temperature Influence: Like many organic acids, the solubility typically increases with temperature, making it easier for the acid to dissolve in warmer solvents.

Moreover, one could note that the solubility properties of 2-methylenebutanedioic acid play a crucial role in various applications, from polymer production to pharmaceuticals, underscoring the importance of understanding solubility in chemistry.

Interesting facts

Interesting Facts about 2-Methylenebutanedioic Acid

2-Methylenebutanedioic acid, commonly known as mesaconic acid, is a fascinating organic compound that belongs to the dicarboxylic acid family. Here are some intriguing aspects of this compound:

  • Biological Relevance: Mesaconic acid is an intermediate in the metabolism of certain microorganisms, showcasing its importance in biochemistry and microbial ecology.
  • Isomeric Forms: This compound has structural isomers, which can lead to diverse properties and reactivities. The ability to exist in different forms underlines the significance of molecular structure in chemical behavior.
  • Applications in Synthesis: Due to its unique structure, 2-methylenebutanedioic acid is utilized in organic synthesis as a building block for various chemical reactions, making it valuable in the development of pharmaceuticals and agrochemicals.
  • Flavor and Fragrance: Compounds similar to mesaconic acid may be found in the flavor and fragrance industry, contributing to specific aromas or taste profiles, demonstrating the link between organic chemistry and sensory experiences.
  • Reactivity: The carboxylic acid functional groups in mesaconic acid make it reactive in several contexts, including esterification and acid-base reactions, which are fundamental in organic synthesis.

In summary, 2-methylenebutanedioic acid not only serves as an important biochemical component but also finds its place in various applications in the world of organic chemistry.

Synonyms
Itaconic acid
97-65-4
2-Methylenesuccinic acid
2-methylidenebutanedioic acid
METHYLENESUCCINIC ACID
Methylenebutanedioic acid
Propylenedicarboxylic acid
Butanedioic acid, methylene-
itaconate
2-Propene-1,2-dicarboxylic acid
Succinic acid, methylene-
2-methylenebutanedioic acid
butanedioic acid, 2-methylene-
MFCD00004260
25119-64-6
HSDB 5308
AI3-16901
NSC 3357
EINECS 202-599-6
DTXSID2026608
CHEBI:30838
NSC-3357
2-Methylene-Succinic Acid
Q4516562YH
ITACONIC ACID [MI]
CHEMBL359159
DTXCID006608
NSC3357
EC 202-599-6
2-METHYLENE,1,4-BUTANEDIOIC ACID (ITACONIC ACID)
CAS-97-65-4
Methylenesuccinate
UNII-Q4516562YH
ITN
Methylenebutanedioate
2-Methylenesuccinate
Propylenedicarboxylate
2-methylenebutanedioate
Succinic acid, methylene
Itaconic acid (Standard)
Itaconic acid, >=99%
bmse000137
Probes1_000076
Probes2_000247
Butanedioic acid, methylene
2-Methylenesuccinic acid #
NCIStruc1_001783
NCIStruc2_000502
2-methylene-butanedioic acid
NCIOpen2_004822
SCHEMBL21523
2Propene1,2dicarboxylic acid
ITACONIC ACID [INCI]
2-Propene-1,2-dicarboxylate
hydron;2-methylidenebutanedioate
HY-Y0520R
Succinic acid, methylene-(8CI)
Itaconic acid, analytical standard
Succinic acid, methylene- (8CI)
HY-Y0520
Tox21_201299
Tox21_303071
BBL011584
BDBM50036216
LMFA01170063
s3095
STL163322
AKOS000118895
2-Hydroxy-3-Naphthoyl-2-Naphthylamine
SB67306
Butanedioic acid,ethylidene-,(E)-(9ci)
NCGC00249019-01
NCGC00257141-01
NCGC00258851-01
AS-11816
CS-0015302
M0223
NS00007642
EN300-18045
C00490
E80791
Q903311
Z57127539
F2191-0234
53EEC7A3-4846-4588-BBC9-CB8846377B96
202-599-6