Succinic acid

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Succinic acid
Image:Succinic acid.png
Chemical name	butanedioic acid
Other names	succinic acid ethane-1,2-dicarboxylic acid
Chemical formula	C₄H₆O₄
Molecular mass	118.09 g/mol
CAS number	[110-15-6]
Density	1.56 g/cm³
Melting point	185–187 °C
Boiling point	235 °C
SMILES	OC(CCC(O)=O)=O
Disclaimer and references

Succinic acid (IUPAC systematic name: butanedioic acid; historically known as spirit of amber) is a dicarboxylic acid with the formula:

HOOC–CH₂–CH₂–COOH

At room temperature, pure succinic acid is a solid that forms colorless, odorless crystals. It has a melting point of 185 °C and a boiling point of 235 °C. It is a diprotic acid. The anion, succinate, is a component of the citric acid cycle and is capable of donating electrons to the electron transfer chain via the following reaction:

succinate + FAD → fumarate + FADH₂

This is catalysed by the enzyme succinate dehydrogenase (or complex II of the mitochondrial ETC). The complex is a 4 subunit membrane-bound lipoprotein which couples the oxidation of succinate to the reduction of ubiquinone. Intermediate electron carriers are FAD and three Fe₂S_{2_{clusters part of subunit B.}}

Esters of succinic acid are called dialkyl succinates.

1 History
2 Safety
3 References
4 See also
5 External links

[edit] History

Spirit of amber was procured from amber by pulverising and distilling it using a sand bath. It was chiefly used externally for rheumatic aches and pains, and internally in inveterate gleets.

[edit] Safety

The acid is combustible and corrosive, capable of causing burns. "Harmful by inhalation, ingestion and through skin absorption. Wash after handling. Eye contact may cause serious damage."

In nutraceutical form as a food additive and dietary supplement, is safe and approved by the FDA.

[edit] References

This article incorporates content from the 1728 Cyclopaedia, a publication in the public domain.

[edit] See also

Oil of amber, procured by heating succinic acid

v • d • e</span>

Citric Acid Cycle Metabolic Pathway

Malate

Image:Oxaloacetate wpmp.png

Image:S-malate wpmp.png

Image:Fumarate wpmp.png

Image:Succinate wpmp.png

Image:Succinyl-CoA wpmp.png

Image:Biochem reaction arrow reverse NNYY horiz med.png

Image:Biochem reaction arrow reverse NNYN horiz med.png

Image:Biochem reaction arrow reverse NNYY horiz med.png

Acetyl CoA

NADH + H⁺

NAD⁺

H₂O

FADH₂

FAD

CoA + ATP

P_i + ADP

Image:Acetyl co-A wpmp.png

H₂O

Image:Biochem reaction arrow special 1.png

Image:Biochem reaction arrow special 2.png

NADH + H⁺ + CO₂

CoA

NAD⁺

Image:Citrate wpmp.png

H₂O

Image:Cis-Aconitate wpmp.png

H₂O

Image:Threo-Ds-isocitrate wpmp.png

NADP⁺

NADPH + H⁺

Image:Oxalosuccinate wpmp.png

CO₂

Image:2-oxoglutarate wpmp.png

Image:Biochem reaction arrow foward NYNN horiz med.png

Image:Biochem reaction arrow foward YNNN horiz med.png

Image:Biochem reaction arrow foward YYNN horiz med.png

Image:Biochem reaction arrow foward NYNN horiz med.png

Citrate

cis-Aconitate

Isocitrate

Oxalosuccinate

Alpha-ketoglutarate

[edit] External links

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