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M4667

Sigma-Aldrich

(±)-Mevalonolactone

~97% (titration)

Sinónimos:

(±)-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

Fórmula empírica (notación de Hill):
C6H10O3
Número de CAS:
674-26-0
Peso molecular:
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)

Quality Level

200

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)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «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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Artículos

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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