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Merck

M4667

(±)-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
UNSPSC Code:
12352108
NACRES:
NA.25
PubChem Substance ID:
24896934
EC Number:
211-615-0
Beilstein/REAXYS Number:
80960
MDL number:
MFCD00006648
Assay:
~97% (titration)

Key Documents

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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

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

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCH6322
BCCH8327
BCBX5655
BCBX4250
BCBT8228

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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)
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)
Mareike Bongers et al.
eLife, 9 (2020-03-13)
Volatile isoprenoids produced by plants are emitted in vast quantities into the atmosphere, with substantial effects on global carbon cycling. Yet, the molecular mechanisms regulating the balance between volatile and non-volatile isoprenoid production remain unknown. Isoprenoids are synthesised via sequential
Tomoyuki Nishimoto et al.
Toxicology and applied pharmacology, 223(1), 39-45 (2007-06-30)
High-dose statin treatment has been recommended as a primary strategy for aggressive reduction of LDL cholesterol levels and protection against coronary artery disease. The effectiveness of high-dose statins may be limited by their potential for myotoxic side effects. There is
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