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:
Molecular Weight:
130.14
UNSPSC Code:
12352108
NACRES:
NA.25
PubChem Substance ID:
EC Number:
211-615-0
Beilstein/REAXYS Number:
80960
MDL number:
Assay:
~97% (titration)
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
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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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)
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)
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
Svena M Lüdke et al.
Journal of lipid research, 49(12), 2620-2626 (2008-08-02)
The aim of this study was to investigate the possible existence and magnitude of stable carbon isotope discrimination by human 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGR). The catalytic portion of HMGR was expressed and purified. The reaction product mevalonate was lactonized and
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