General Description
White crystals or shiny white odorless crystalline powder. pH of 0.1 molar solution: 2.7. Very acid taste.
Reactivity Profile
SUCCINIC ACID(110-15-6) reacts exothermically to neutralize bases, both organic and inorganic. Can react with active metals to form gaseous hydrogen and a metal salt. Such reactions are slow in the dry, but systems may absorb water from the air to allow corrosion of iron, steel, and aluminum parts and containers. Reacts slowly with cyanide salts to generate gaseous hydrogen cyanide. Reacts with solutions of cyanides to cause the release of gaseous hydrogen cyanide. May generate flammable and/or toxic gases and heat with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. May react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Can be oxidized exothermically by strong oxidizing agents and reduced by strong reducing agents. May initiate polymerization reactions.
Air & Water Reactions
Slightly water soluble.
Fire Hazard
Flash point data for this compound are not available. SUCCINIC ACID is probably combustible.
Definition
A crystalline carboxylic
acid, HOOC(CH2)2COOH, that occurs in
amber and certain plants. It forms during
the fermentation of sugar (sucrose).
Definition
ChEBI: An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.
Production Methods
Succinic acid can be produced 1) by oxidation of Butanediol-1,4 with
Nitric acid.
2) by oxidation of Tetrahydrofuran with
Nitric acid.
3) by hydrogenation of Fumaric acid or
Maleic acid.
Biotechnological Production
Traditionally, succinic acid is produced by petrochemical synthesis using the
precursor maleic acid. However, there are some microorganisms that are
able to produce succinic acid (e.g. Actinobacillus succinogenes, Anaerobiospirillum
succiniciproducens and Mannheimia succiniciproducens). Maximum product
concentrations of 106 g.L-1 with a yield of 1.25 mol of succinic acid per mole of
glucose and a productivity of 1.36 g.L-1.h-1 have been achieved by growing A.
succinogenes on glucose . A high productivity of 10.40 g.L-1.h-1 has been
reached with A. succinogenes growing on a complex medium with glucose in a
continuous process with an integrated membrane bioreactor-electrodialysis process.
In this process, the product concentration has been 83 g.L-1 . Moreover,
metabolic engineering methods were used to develop strains (e.g. C.
glutamicum, E. coli, S. cervisiae and Y. lipolytica) with high productivity and titer
as well as low byproduct formation. For example, growing C.
glutamicum strain DldhA-pCRA717 on a defined medium with glucose, a high
productivity of 11.80 g.L-1.h-1 with a yield of 1.37 mol of succinic acid per mole
of glucose and a titer of 83 g.L-1 has been reported after 7 h. An extended
cultivation resulted in a product concentration of 146 g.L-1 after 46 h.
Flammability and Explosibility
Nonflammable
Biochem/physiol Actions
Succinic acid is a byproduct of anaerobic fermentation in microbes. It is a dicarboxylic acid and an intermediate in Kreb′s cycle. Polymorphism in succinate dehydrogenase leads to succinate accumulation. High levels of succinate impairs 2-oxoglutarate epigenetic signalling. Succinate levels may modulate tumor progression. Succinate inhibits histone demethylation and may contribute to epigenetic changes. Succinate is crucial for interleukin-1 β (IL-1β) synthesis during inflammation and immune signalling.
Biotechnological Applications
Succinic acid and its derivatives are used as flavoring agents for food and beverages. This acid could be used as feedstock for dyes, insecticides, perfumes, lacquers, as well as in the manufacture of clothing, paint, links, and fibers (McKinlay et al. 2007). Succinic acid is widely used in medicine as an antistress, antihypoxic, and immunity-improving agent, in animal diets, and as a stimulator of plant growth. It is also a component of bio-based polymers such as nylons or polyesters (Kamzolova et al. 2012b). Succinate esters are precursors for the known petrochemical products such as 1,4-butanediol, tetrahydrofuran, c-butyrolactone, and various pyrrolidinone derivatives (Bechthold et al. 2008).
Succinic acid production by Y. lipolytica was reported for the first time when it was grown on ethanol under aerobic conditions and nitrogen limitation. Succinic acid amount was 63.4 g/L as the major product of batch fermentation in this process. However, the disadvantage was low yield of succinic acid on ethanol (58 %), and a high cost of production (Kamzolova et al. 2009).
Kamzolova et al. developed a novel process for the production of succinic acid. It includes the synthesis of a-ketoglutaric acid by a thiamine-auxotrophic strain Y. lipolytica VKMY-2412 from n-alkanes, and subsequent oxidation of the acid by hydrogen peroxide to succinic acid. The concentration of succinic acid and its yield were found to be 38.8 g/L and 82.45 % of n-alkane consumed, respectively (Kamzolova et al. 2012b).
Succinic acid production was also studied by genetically modified strains using glucose and glycerol as substrates. Yuzbashev et al. constructed temperaturesensitive mutant strains with mutations in the succinate dehydrogenase encoding gene SDH1 by in vitro mutagenesis-based approach. Then, the mutants were used to optimize the composition of the media for selection of transformants with the deletion in the SDH2 gene. The defects of each succinate dehydrogenase subunit prevented the growth on glucose, but the mutant strains grew on glycerol and produced succinate in the presence of the buffering agent CaCO3. Subsequent selection of the strain with deleted SDH2 gene for increased viability was allowed to obtain a strain that is capable to accumulate succinate at the level of more than 450 g/L with buffering and more than 17 g/L without buffering. Therefore, a reduced succinate dehydrogenase activity can lead to an increased succinate production (Yuzbashev et al. 2010). Y. lipolytica is able to produce succinic acid at low pH values. High amounts of succinate can be achieved by genetic engineering (Otto et al. 2013).
Carcinogenicity
Monosodium succinate was
given to groups of 50 male and 50 female Fischer 344 rats
in drinking water at levels of 0%, 1%, or 2% for 2 years. No
toxic lesion specifically caused by long-term administration
of monosodium succinate was detected, and no dose-related
increase was found in the incidence of tumors in any organ or
tissue. The incidence of C-cell tumors of the thyroid gland of
females that received 2% solution was apparently, but not
significantly, higher than that in controls. Because C-cell
tumors are commonly occurring spontaneous tumors in aging
female rats of this strain and the incidence of C-cell tumors in
the female control group was lower than that of historical
controls for the testing laboratory, the authors concluded that
this lesion was not treatment related.
Purification Methods
Wash it with diethyl ether. Crystallise it from acetone, distilled water, or tert-butanol. Dry it under vacuum over P2O5 or conc H2SO4. Also purify it by conversion to the disodium salt which, after crystallisation from boiling water (charcoal), is treated with mineral acid to regenerate the succinic acid. The acid is then recrystallised and dried in a vacuum. [Beilstein 2 H 606, 2 IV 1908.]
