Mevalonic acid

Mevalonic acid
IUPAC name	(3R)-3,5-dihydroxy-3-methylpentanoic acid
Identifiers
CAS number	[150-97-0]
SMILES	C[C@@](O)(CCO)CC(=O)O
Properties
Molecular formula	C6H12O4
Molar mass	148.16 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

Mevalonic acid (MVA) is a key organic compound in biochemistry. The anion of mevalonic acid, the predominant form in biological media, is known as mevalonate.

Chemistry

Mevalonic acid is very soluble in water and in polar organic solvents. It exists in equilibrium with the lactone, called mevalolactone, formed by internal condensation of its terminal alcohol and carboxylic acid functional groups.

Biology

Mevalonic acid is a precursor in the biosynthetic pathway, known as the mevalonate pathway, that produces terpenes and steroids. Mevalonate is the primary precursor of isopentenyl pyrophosphate (IPP), that is in turn the basis for all terpenoids. MVA is extensively prochiral and its prochiral character is what makes it an excellent base for a pathway. The 3R enantiomer is the only one that is biologically active.

Mevalonate pathway

References

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