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M4667

Sigma-Aldrich

(±)-Mevalonolactone

~97% (titration)

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Synonym(s):
(±)-β-Hydroxy-β-methyl-δ-valerolactone, (±)-3-Hydroxy-3-methyl δ-valerolactone, DL-Mevalolactone, DL-Mevalonic acid lactone
Empirical Formula (Hill Notation):
C6H10O3
CAS Number:
674-26-0
Molecular Weight:
130.14
Beilstein:
80960
EC Number:
211-615-0
MDL number:
MFCD00006648
PubChem Substance ID:
24896934
NACRES:
NA.25

Assay

~97% (titration)

Quality Level

200

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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This Item
616699605980486604
(±)-Mevalonolactone ~97% (titration)

Sigma-Aldrich

M4667

(±)-Mevalonolactone

Mevalonolactone-(methyl-d3) 99 atom % D, ≥97% (CP)

Sigma-Aldrich

616699

Mevalonolactone-(methyl-d3)

Mevalonolactone-5-13C 99 atom % 13C, 99% (CP)

Sigma-Aldrich

605980

Mevalonolactone-5-13C

Mevalonolactone-2-13C 99 atom % 13C, 98% (CP)

Sigma-Aldrich

486604

Mevalonolactone-2-13C

storage temp.

−20°C

storage temp.

-

storage temp.

-

storage temp.

-

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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(R)-Mevalonic acid 5-phosphate lithium salt 95% (TLC)

Sigma-Aldrich

07841

(R)-Mevalonic acid 5-phosphate lithium salt

(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

Mevinolin from Aspergillus sp. ≥98% (HPLC)

Sigma-Aldrich

M2147

Mevinolin from Aspergillus sp.

Aminohippuric acid United States Pharmacopeia (USP) Reference Standard

USP

1025351

Aminohippuric acid

Mevastatin ≥98% (HPLC), powder or crystals

Sigma-Aldrich

M2537

Mevastatin

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)
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
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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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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