Mevalonic acid

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Structural formula
Structural formula of R-mevalonic acid
( R ) -evalonic acid
General
Surname Mevalonic acid
other names
  • 3,5-dihydroxy-3-methylpentanoic acid
  • ( R ) -3,5-dihydroxy-3-methylpentanoic acid
  • ( S ) -3,5-dihydroxy-3-methylpentanoic acid
  • ( RS ) -3,5-dihydroxy-3-methylpentanoic acid
  • (+) - 3,5-Dihydroxy-3-methylpentanoic acid
  • (-) - 3,5-Dihydroxy-3-methylpentanoic acid
  • (±) -3,5-dihydroxy-3-methylpentanoic acid
  • D -3,5-dihydroxy-3-methylpentanoic acid
  • L -3,5-dihydroxy-3-methylpentanoic acid
  • DL -3,5-dihydroxy-3-methylpentanoic acid
Molecular formula C 6 H 12 O 4
External identifiers / databases
CAS number 150-97-0
PubChem 439230
ChemSpider 388367
DrugBank DB03518
Wikidata Q241678
properties
Molar mass 148.16 g mol −1
Physical state

firmly

Melting point

28 ° C (lactone form)

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mevalonic acid is a branched chain, saturated hydroxy fatty acid . Their salts are called mevalonates . The compound is chiral and has a stereogenic center . A distinction is therefore made between two optical isomers , the enantiomers ( R ) -evalonic acid and ( S ) -evalonic acid, with ( R ) -evalonic acid occurring naturally. Mevalonic acid is the starting material for isoprenoid biosynthesis.

( S ) -evalonic acid

Whenever "mevalonic acid" is mentioned in this text or in the scientific literature without any additional name ( prefix ), it means ( R ) -evalonic acid.

The corresponding anion is an integral part of the biosynthesis of cholesterol . The formation of mevalonic acid from cytosolic 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) under the catalysis of 3-hydroxy-3-methylglutaryl-coenzyme A reductase ( HMG-CoA reductase ) is a key reaction in the synthesis of Cholesterols (see also figure below).

In plants, mevalonic acid is an important intermediate stage in the synthesis of terpenes (so-called mevalonate pathway ). Around 1955 it was discovered that it can be incorporated very well into cholesterol for the synthesis of markers.

The further conversion takes place by means of the mevalonate kinase to form mevalonic acid phosphate.

The synthesis of mevalonate takes place in the cytosol.

Individual evidence

  1. ^ The Merck Index, 9th Edition, 1976, ISBN 0-911910-26-3 , p. 804.
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ Botany online: Secondary plant substances - isoprenoids / terpenes
  4. ↑ 2.1 Terpene biosynthesis ( Memento from December 27, 2012 in the web archive archive.today )

Web links

Wikibooks: Biochemistry and Pathobiochemistry: Cholesterol Biosynthesis  - Learning and Teaching Materials