3,5-dihydroxy-3-methyl-Pentanoic acid

3,5-dihydroxy-3-methyl-Pentanoic acid Basic information
Product Name:3,5-dihydroxy-3-methyl-Pentanoic acid
Synonyms:3,4-Dihydroxy-3-methylpentanoic acid;3,5-dihydroxy-3-methyl-Pentanoic acid;Mevalonic acid;2,4-Dideoxy-3-C-methylpentonic Acid;3,5-Dihydroxy-3-methylvaleric Acid;D,L-Mevalonic Acid;Hiochic Acid;MK 91
CAS:150-97-0
MF:C6H12O4
MW:148.16
EINECS:
Product Categories:All Aliphatics;Aliphatics;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:150-97-0.mol
3,5-dihydroxy-3-methyl-Pentanoic acid Structure
3,5-dihydroxy-3-methyl-Pentanoic acid Chemical Properties
storage temp. 2-8°C
solubility Soluble in DMSO
form neat
Melting point 151-152 °C(Solv: benzene (71-43-2))
pKa4.33±0.10(Predicted)
Boiling point 364.1±32.0 °C(Predicted)
density 1.263±0.06 g/cm3(Predicted)
Concentration0.1 mCi/ml
SolventEthanol:0.15N NH4OH (1:1)
Specific Activity10-20 Ci/mmol
EPA Substance Registry SystemPentanoic acid, 3,5-dihydroxy-3-methyl- (150-97-0)
Safety Information
WGK Germany 3
Hazardous Substances Data150-97-0(Hazardous Substances Data)
MSDS Information
3,5-dihydroxy-3-methyl-Pentanoic acid Usage And Synthesis
UsesPrecursor in the biosynthesis of cholesterol. Occurs in equilibrium with the d-lactone
DefinitionAnorganic acid, it is an intermediate in the biosyn-thesis of squalene, cholesterol, and coenzyme q inplants and animals.
BiosynthesisMevalonic acid is the primary precursor of an the terpenoids and steroids biosynthesised by plants. It is derived from acetyl CoA through the intermediate formation of acetoacetyl CoA and 3-hydroxy-3-methylglutaryl CoA (HMG CoA), these reactions being catalysed by acetyl CoA acetyltransferase and HMG CoA synthase, respectively. Reduction of HMG CoA, catalysed by HMG CoA reductase, gives mevalonic acid.
The biosynthesis of mevalonic acid
Before the pathway can continue, mevalonic acid must be catalytically phosphorylated by ATP and mevalonic acid kinase. Mevalonic acid kinase activity has been detected in many plants and has been found to be inhibited by such products of the acetate-mevalonate pathway as geranyl, farnesyl, geranylgeranyl and phytyl pyrophosphates. Thus, phosphorylation of mevalonic acid is a primary point at which control of terpenoid and steroid biosynthesis operates. Phosphorylation leads first to the mono- and then to the pyrophosphate. The second phosphorylation is catalysed by phosphomevalonate kinase.

Biochem/physiol ActionsMetabolite of the mevalonate pathway, which plays a key role in the biosynthesis of sterols, dolichol, heme and ubiquinone. Of interest for research in the disease areas oncology, autoimmune diseases, artherosclerosis and Alzheimer disease, as well as for inherited deficiencies of mevalonate kinase.
3,5-dihydroxy-3-methyl-Pentanoic acid Preparation Products And Raw materials

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