DL-Mevalonolactone Chemical Properties

Melting point:

28 °C(lit.)

Boiling point:

145-150 °C5 mm Hg(lit.)

alpha 

-1.0～+1.0°(20℃/D)(c=5, C2H5OH)

Density 

1.1066 (rough estimate)

refractive index 

n20/D 1.473(lit.)

Flash point:

>230 °F

storage temp. 

-20°C

solubility 

Chloroform (Sparingly), DMSO (Slightly), Ethyl Acetate, Methanol (Slightly)

form 

Oil

pka

13.57±0.20(Predicted)

color 

Pale Yellow to Dark Brown

Merck 

14,6163

BRN 

80960

Stability:

Hygroscopic

InChIKey

JYVXNLLUYHCIIH-UHFFFAOYSA-N

CAS DataBase Reference

674-26-0(CAS DataBase Reference)

NIST Chemistry Reference

Dl-mevalonic acid lactone(674-26-0)

Safety Information

WGK Germany 

3

F 

3-10

HS Code 

29322090

MSDS

• Language:English Provider:SigmaAldrich

DL-Mevalonolactone Usage And Synthesis

Description

DL-Mevalonolactone is the δ-lactone form of mevalonic acid, a precursor in the mevalonate pathway. It induces depolarization and swelling, decreases NADPH content and aconitase (ACO) activity, and increases malondialdehyde (MDA) production in calcium-loaded rat brain mitochondria. DL-Mevalonolactone reverses decreases in glucose uptake induced by simvastatin (Item Nos. 10010344 | 10010345) in L6 myotubes. Tissue levels and urinary excretion of DL-mevalonolactone are increased in patients with mevalonic aciduria, a disorder characterized by a deficiency in mevalonic kinase activity.

Chemical Properties

Pale Yellow Oil

Uses

A metabolite from endophytes of the medicinal plant Erythrina crista-galli.

Uses

HMG CoA substrate

Uses

(±)-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)

Definition

ChEBI: 4-hydroxy-4-methyl-2-oxanone is a delta-lactone.

Synthesis Reference(s)

Journal of the American Chemical Society, 104, p. 5486, 1982 DOI: 10.1021/ja00384a040
Synthesis, p. 719, 1974 DOI: 10.1055/s-1974-23416

General Description

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

Purification Methods

Purify the lactone via the dibenzyl-ethylenediammonium salt (m 124-125o) [Hofmann et al. J Am Chem Soc 79 2316 1957], or by chromatography on paper or on a Dowex-1 (formate) column. [Bloch et al. J Biol Chem 234 2595 1959.] Store it as the N,N'-dibenzylethylenediamine (DBED) salt, or as the lactone in a sealed container at 0o. [Beilstein 18/1 V 19.]

DL-Mevalonolactone(674-26-0)Related Product Information

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