Mevalonic acid

Mevalonic acid
IUPAC name (3R)-3,5-Dihydroxy-3-methylpentanoic acid
Identifiers
CAS number	150-97-0
Jmol-3D images	Image 1
SMILES C[C@@](O)(CCO)CC(=O)O
Properties
Molecular formula	C6H12O4
Molar mass	148.16 g mol−1
Y acid (verify) (what is: Y/N?) 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. This compound is of major pharmaceutical importance. Drugs, such as the statins, stop the production of mevalonate by inhibiting HMG-CoA reductase.^[1]

Chemistry

Mevalonic acid is very soluble in water and in polar organic solvents. It exists in equilibrium with the lactone, called mevalonolactone, 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. Mevalonic acid is the primary precursor of isopentenyl pyrophosphate (IPP), that is in turn the basis for all terpenoids. Mevalonic acid is chiral and the (3R)-enantiomer is the only one that is biologically active.

Mevalonate pathway

References

1. ^ Endo, A. (1992). "The discovery and development of HMG-CoA reductase inhibitors". Journal of Lipid Research 33 (11): 1569–1582. PMID 1464741.