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M4667

Sigma-Aldrich

(±)-Mevalonolactone

~97% (titration)

Sinonimo/i:

(±)-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

Formula empirica (notazione di Hill):
C6H10O3
Numero CAS:
674-26-0
Peso molecolare:
130.14
Beilstein:
80960
Numero CE:
211-615-0
Numero MDL:
MFCD00006648
Codice UNSPSC:
12352108
ID PubChem:
24896934
NACRES:
NA.25

Saggio

~97% (titration)

Temperatura di conservazione

−20°C

Stringa SMILE

CC1(O)CCOC(=O)C1

InChI

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

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Categorie correlate

Descrizione generale

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

Applicazioni

(±)-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)

Altre note

May also be liquid!

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

235.4 °F - closed cup

Punto d’infiammabilità (°C)

113 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
BCBX5655
BCBX4250
BCBT8228
BCBW1902
BCBW0047

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(S)-Mevalonic acid lithium salt analytical standard

Supelco

43987

(S)-Mevalonic acid lithium salt

Mevalonolactone-(methyl-13C) 99 atom % 13C

Sigma-Aldrich

591270

Mevalonolactone-(methyl-13C)

Farnesyl pyrophosphate ammonium salt methanol:ammonia solution, ≥95% (TLC)

Sigma-Aldrich

F6892

Farnesyl pyrophosphate ammonium salt

Mevinolina ≥98% (HPLC)

Sigma-Aldrich

M2147

Mevinolina

Aminohippuric acid United States Pharmacopeia (USP) Reference Standard

USP

1025351

Aminohippuric acid

Mevastatin ≥98% (HPLC), powder or crystals

Sigma-Aldrich

M2537

Mevastatin

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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Articoli

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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