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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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1 G
$228.00
5 G
$600.95
10 G
$829.60

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1 G
$228.00
5 G
$600.95
10 G
$829.60

About This Item

Empirical Formula (Hill Notation):
C6H10O3
CAS Number:
Molecular Weight:
130.14
Beilstein/REAXYS Number:
80960
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.25

$228.00


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assay

~97% (titration)

Quality Level

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.[1] Mevalonate is a precursor of farnesyl and geranylgeranyl pyrophosphates. These pyrophosphates are required for protein prenylation.[2]

Application

(±)-Mevalonolactone is used to:
  • study the effect of statin on the prenylation of Ras and Rho GTPases[2]
  • analyse the isoprenoid biosynthesis pathways in Listeria monocytogenes[3]
  • study the the effects of statins on proliferation and migration of HUVECs (HGF-induced human umbilical vein endothelial cells)[4]

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)


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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)
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)
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)
Russell P Swift et al.
PLoS pathogens, 16(2), e1008316-e1008316 (2020-02-15)
Malaria parasites rely on a plastid organelle for survival during the blood stages of infection. However, the entire organelle is dispensable as long as the isoprenoid precursor, isopentenyl pyrophosphate (IPP), is supplemented in the culture medium. We engineered parasites to
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)

Articles

Cholesterol biosynthesis starts in the hepatic endoplasmic reticulum with acetyl-CoA, yielding 3-hydroxy-3-methylglutaryl-CoA via HMG-CoA synthase.

Questions

1–3 of 3 Questions  
  1. What chemical/s is this product soluble in for resuspension into a liquid form and at what concentration? I am wanting to add this to cell culture media.

    1 answer
    1. This product is soluble at a concentration of 0.5 g in 5 mL of 95% ethanol, equivalent to 100 mg/mL.

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  2. Why did M4667, (±)-Mevalonolactone, arrive as a liquid?

    1 answer
    1. As noted on the Sigma Aldrich web page for product M4667, (±)-Mevalonolactone, this product "may also be a liquid".  The melting point for this chemical is 26-28°C, which is approximately room temperature.  Because of this, the product may arrive as a liquid, but if stored at -20°C it should return to a solid/semi-solid state.  This product does not arrive in solution and will not have a concentration value.

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  3. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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