(±)-Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-on

Bezeichnung:(±)-Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-on

CAS-Nr674-26-0

Englisch Name:DL-Mevalonolactone

CBNumberCB0377087

SummenformelC6H10O3

Molgewicht130.14

MOL-Datei674-26-0.mol

Synonyma

(±)-Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-on

(±)-Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-on physikalisch-chemischer Eigenschaften

Schmelzpunkt	28 °C(lit.)
Siedepunkt	145-150 °C5 mm Hg(lit.)
alpha	-1.0～+1.0°(20℃/D)(c=5, C2H5OH)
Dichte	1.1066 (rough estimate)
Brechungsindex	n20/D 1.473(lit.)
Flammpunkt	>230 °F
storage temp.	-20°C
Löslichkeit	Chloroform (Sparingly), DMSO (Slightly), Ethyl Acetate, Methanol (Slightly)
Aggregatzustand	Oil
pka	13.57±0.20(Predicted)
Farbe	Pale Yellow to Dark Brown
Merck	14,6163
BRN	80960
Stabilität	Hygroscopic
InChIKey	JYVXNLLUYHCIIH-UHFFFAOYSA-N
CAS Datenbank	674-26-0(CAS DataBase Reference)
NIST chemische Informationen	Dl-mevalonic acid lactone(674-26-0)

Sicherheit

WGK Germany	3
F	3-10
HS Code	29322090

DL-Mevalonolactone Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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.
Chemische Eigenschaften
Pale Yellow Oil
Verwenden
(±)-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)
Verwenden
HMG CoA substrate
Verwenden
A metabolite from endophytes of the medicinal plant Erythrina crista-galli.
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
Allgemeine Beschreibung
Alkaline hydrolysis of mevalonolactone gives mevalonate. Mevalonate is a precursor of farnesyl and geranylgeranyl pyrophosphates. These pyrophosphates are required for protein prenylation.
läuterung methode
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 Upstream-Materialien And Downstream Produkte

(±)-Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-on Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

674-26-0, DL-Mevalonolactone Verwandte Suche:

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