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Merck

M4667

(±)-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 CAS:
674-26-0
Peso molecular:
130.14
UNSPSC Code:
12352108
NACRES:
NA.25
PubChem Substance ID:
24896934
EC Number:
211-615-0
Beilstein/REAXYS Number:
80960
MDL number:
MFCD00006648

Nombre del producto

(±)-Mevalonolactone, ~97% (titration)

InChI key

JYVXNLLUYHCIIH-UHFFFAOYSA-N

InChI

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

SMILES string

CC1(O)CCOC(=O)C1

assay

~97% (titration)

storage temp.

−20°C

Quality Level

200

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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)

General description

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

Other Notes

May also be liquid!

Clase de almacenamiento

11 - Combustible Solids

wgk

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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Certificados de análisis (COA)

Lot/Batch Number
BCCH6322
BCCH8327
BCBX5655
BCBX4250
BCBT8228

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

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

    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. 

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

    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.

  6. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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)
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)
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
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