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M4667

Sigma-Aldrich

(±)-Mevalonolactone

~97% (titration)

Synonym(s):

(±)-β-Hydroxy-β-methyl-δ-valerolactone, (±)-3-Hydroxy-3-methyl δ-valerolactone, DL-Mevalolactone, DL-Mevalonic acid lactone

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About This Item

Empirical Formula (Hill Notation):
C6H10O3
CAS Number:
674-26-0
Molecular Weight:
130.14
Beilstein/REAXYS Number:
80960
EC Number:
211-615-0
MDL number:
MFCD00006648
UNSPSC Code:
12352108
PubChem Substance ID:
24896934
NACRES:
NA.25

assay

~97% (titration)

storage temp.

−20°C

SMILES string

CC1(O)CCOC(=O)C1

InChI

1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3

InChI key

JYVXNLLUYHCIIH-UHFFFAOYSA-N

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General description

Alkaline hydrolysis of mevalonolactone gives mevalonate. Mevalonate is a precursor of farnesyl and geranylgeranyl pyrophosphates. These pyrophosphates are required for protein prenylation.

Application

(±)-Mevalonolactone is used to:
  • study the effect of statin on the prenylation of Ras and Rho GTPases
  • analyse the isoprenoid biosynthesis pathways in Listeria monocytogenes
  • study the the effects of statins on proliferation and migration of HUVECs (HGF-induced human umbilical vein endothelial cells)

Other Notes

May also be liquid!

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The effects of different types of statins on proliferation and migration of HGF-induced Human Umbilical Vein Endothelial Cells (HUVECs).
Burgazli KM
European Review for Medical and Pharmacological Sciences, 17, 2874-2883 (2013)
Coenzyme Q 10 production in recombinant Escherichia coli strains engineered with a heterologous decaprenyl diphosphate synthase gene and foreign mevalonate pathway.
Zahiri HS
Metabolic engineering, 8, 406-416 (2006)
Analysis of the isoprenoid biosynthesis pathways in Listeria monocytogenes reveals a role for the alternative 2-C-methyl-D-erythritol 4-phosphate pathway in murine infection.
Begley M
Infection and Immunity, 76, 5392-5401 (2008)
Akira Honda et al.
Journal of lipid research, 48(5), 1212-1220 (2007-02-03)
We have developed a new sensitive and specific nonradioisotope assay method to measure the activity of HMG-CoA reductase, the rate-controlling enzyme in the cholesterol biosynthetic pathway. This method was based upon a stable isotope dilution technique by liquid chromatography-tandem mass
Jenna Waldron et al.
Annals of clinical biochemistry, 48(Pt 3), 223-232 (2011-03-01)
Mevalonic acid (MVA) is synthesized at an early and rate-limiting step in the biosynthesis of cholesterol by the enzyme hydroxymethylglutaryl coenzyme A (HMG-CoA) reductase, and is a useful measure of statin efficacy or treatment. A liquid chromatography-tandem mass spectrometry (LC-MS/MS)
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Articles

Cholesterol Biosynthesis

Biosynthesis of cholesterol generally takes place in the endoplasmic reticulum of hepatic cells and begins with acetyl- CoA, which is mainly derived from an oxidation reaction in the mitochondria. Acetyl-CoA and acetoacetyl-CoA are converted to 3-hydroxy- 3-methylglutaryl-CoA (HMG-CoA) by HMG-CoA synthase.

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