| Identification | More | [Name]
DL-Mevalonolactone | [CAS]
674-26-0 | [Synonyms]
(+/-)-3-HYDROXY-3-METHYL-5-PENTANOLIDE
(4R)-4-Hydroxy-4-methyl-oxan-2-one
BETA-HYDROXY-BETA-METHYL-DELTA-VALEROLACTONE
DL-3-HYDROXY-3-METHYL DELTA-VALEROLACTONE
DL-BETA-HYDROXY-BETA-METHYL-DELTA-VALERO-LACTONE
DL-BETA-HYDROXY-BETA-METHYL-GAMMA-VALEROLACTONE
DL-BETA-HYDROXY-BETA-METHYL-G-VALEROLACTONE
DL-MEVALOLACTONE
DL-MEVALONIC ACID LACTONE
DL-MEVALONOLACTONE
MEVALONIC ACID LACTONE, DL-
MEVALONIC LACTONE
(+/-)-MEVALONOLACTONE
MEVALONOLACTONE
(+/-)-tetrahydro-4-hydroxy-4-methyl-2h-pyran-2-one
TETRAHYDRO-4-HYDROXY-4-METHYL-2-PYRONE
2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (.+/-.)-
4-Hydroxy-4-methyltetrahydro-2H-pyran-2-one
dl-mevalonic acid lactone, salt-free
D,L-b-Hydroxy-b-methyl-valerolactone | [EINECS(EC#)]
211-615-0 | [Molecular Formula]
C6H10O3 | [MDL Number]
MFCD00006648 | [Molecular Weight]
130.14 | [MOL File]
674-26-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale Yellow Oil | [Melting point ]
28 °C(lit.)
| [alpha ]
-1.0～+1.0°(20℃/D)(c=5, C2H5OH) | [Boiling point ]
145-150 °C5 mm Hg(lit.)
| [density ]
1.1066 (rough estimate) | [refractive index ]
n20/D 1.473(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Sparingly), DMSO (Slightly), Ethyl Acetate, Methanol (Slightly) | [form ]
Oil | [pka]
13.57±0.20(Predicted) | [color ]
Pale Yellow to Dark Brown | [Usage]
A metabolite from endophytes of the medicinal plant Erythrina crista-galli. | [Merck ]
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) |
| Hazard Information | Back Directory | [Description]
DL-Mevalonolactone is the δ-lactone form of mevalonic acid, a precursor in the mevalonate pathway.1 It induces depolarization and swelling, decreases NADPH content and aconitase (ACO) activity, and increases malondialdehyde (MDA) production in calcium-loaded rat brain mitochondria.2 DL-Mevalonolactone reverses decreases in glucose uptake induced by simvastatin (Item Nos. 10010344 | 10010345) in L6 myotubes.3 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.2 | [Chemical Properties]
Pale Yellow Oil | [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)
| [Uses]
A metabolite from endophytes of the medicinal plant Erythrina crista-galli. | [Uses]
HMG CoA substrate | [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. | [storage]
Store at -20°C | [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.] |
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