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Mevalonic acid

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Mevalonic acid
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IUPAC name
(3R)-3,5-Dihydroxy-3-methylpentanoic acid
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150-97-0 7pxY ChEBI CHEBI:17710 7pxN ChemSpider 388367 7pxN Jmol-3D images Image KEGG C00418 7pxN PubChem Template:Chembox PubChem/format colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Mevalonic acid (MVA) is a key organic compound in biochemistry. The name is derived from a contraction of dihydroxymethylvalerolactone. The anion of mevalonic acid, which is the predominant form in biological environments is known as mevalonate, and is of major pharmaceutical importance. Drugs such as the statins (which lower levels of cholesterol) stop the production of mevalonate by inhibiting HMG-CoA reductase.[1]

Chemistry

Mevalonic acid is very soluble in water and polar organic solvents. It exists in equilibrium with its lactone form, called mevalonolactone, that is 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.

References

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

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