ChemicalBook > CAS DataBase List > DL-Mevalonolactone

DL-Mevalonolactone

Product Name: DL-Mevalonolactone
CAS No.: 674-26-0
Chemical Name: DL-Mevalonolactone
Synonyms: NSC 90804;Beta-Hydro;Hyperpure-MVA;MEVALONOLACTONE;DL-MEVALOLACTONE;MEVALONIC LACTONE;DL-MEVALONOLACTONE;(±)-Mevalonolactone;(+/-)-MEVALONOLACTONE;Adeka Mevalonolactone
CBNumber: CB0377087
Molecular Formula: C6H10O3
Formula Weight: 130.14
MOL File: 674-26-0.mol

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DL-Mevalonolactone Property

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)

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Safety

WGK Germany: 3
F: 3-10
HS Code: 29322090

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: M4667
Product name: (±)-Mevalonolactone
Purity: ~97% (titration)
Packaging: 1g
Price: $228
Updated: 2025/07/31

Sigma-Aldrich

Product number: M4667
Product name: (±)-Mevalonolactone
Purity: ~97% (titration)
Packaging: 5g
Price: $730
Updated: 2025/07/31

TCI Chemical

Product number: D0587
Product name: DL-Mevalonolactone
Purity: >98.0%(GC)
Packaging: 100mg
Price: $67
Updated: 2025/07/31

Cayman Chemical

Product number: 20348
Product name: DL-Mevalonolactone
Purity: ≥95%
Packaging: 250mg
Price: $49
Updated: 2024/03/01

Cayman Chemical

Product number: 20348
Product name: DL-Mevalonolactone
Purity: ≥95%
Packaging: 500mg
Price: $92
Updated: 2024/03/01

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DL-Mevalonolactone Chemical Properties,Usage,Production

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.]

References

[1] SéRGIO R DOMINGOS Melanie S Cristóbal Pérez. On the structural intricacies of a metabolic precursor: Direct spectroscopic detection of water-induced conformational reshaping of mevalonolactone.[J]. Journal of Chemical Physics, 2017, 147 12: 124310. DOI: 10.1063/1.4997162
[2] CRISTIANE CECATTO . Mevalonolactone disrupts mitochondrial functions and induces permeability transition pore opening in rat brain mitochondria: Implications for the pathogenesis of mevalonic aciduria[J]. Neurochemistry international, 2017, 108: Pages 133-145. DOI: 10.1016/j.neuint.2017.03.005
[3] NAGENDRA YALURI Tarja K Shalem Modi. Simvastatin induces insulin resistance in L6 skeletal muscle myotubes by suppressing insulin signaling, GLUT4 expression and GSK-3β phosphorylation[J]. Biochemical and biophysical research communications, 2016, 480 2: Pages 194-200. DOI: 10.1016/j.bbrc.2016.10.026

DL-Mevalonolactone Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from DL-Mevalonolactone manufacturers

Hebei Zhuanglai Chemical Trading Co Ltd

Product: DL-Mevalonolactone 674-26-0
Price: US $79.00-38.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20ton
Release date: 2024-11-19

Hebei Chuanghai Biotechnology Co., Ltd

Product: DL-Mevalonolactone 674-26-0
Price: US $30.00-10.00/KG
Min. Order: 50KG
Purity: 99%
Supply Ability: 500000kg
Release date: 2024-10-24

BINBO BIOLOGICAL CO.,LTD

Product: Mevalonolactone 674-26-0
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99.8%
Supply Ability: 1000 kg
Release date: 2024-04-05

674-26-0, DL-MevalonolactoneRelated Search:

Kresoxim-methyl Methyl acrylate Ethyl 2-(Chlorosulfonyl)acetate METSULFURON METHYL D-Glucurone Methyl cellulose Butylated Hydroxytoluene Folic acid DL-Malic acid 1-Hydroxyethylidene-1,1-diphosphonic acid D-(+)-Glucono-1,5-lactone Bensulfuron methyl Methanol CHLOROPHOSPHONAZO III Hyaluronic acid Triclosan Citric acid 3,5-Dihydroxybenzoic acid

DL-MEVALONOLACTONE

β-Hydroxy-β-methyl-δ-valerolactone, (±)-β-Hydroxy-β-methyl-δ-valerolactone, (±)-3-Hydroxy-3-methyl δ-valerolactone, (±)-Mevalolactone, (±)-Mevalonic acid lactone, (±)-Mevalonolactone

(4S)-4-Hydroxy-4-methyltetrahydro-2H-pyran-2-one

(S)-3,5-Dihydroxy-3-methylpentanoic acid δ-lactone

(S)-4β-Hydroxy-4-methyltetrahydro-2H-pyran-2-one

(S)-Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-one

Beta-Hydro

(±)-Mevalonolactone,(±)-β-Hydroxy-β-methyl-δ-valerolactone, (±)-3-Hydroxy-3-methyl δ-valerolactone, DL-Mevalolactone, DL-Mevalonic acid lactone

Tetrahydro-4-hydroxy-4-Methyl-

beta-Hydroxy-beta-methyl-delta-valerolactone DL-Mevalonic Acid Lactone Tetrahydro-4-hydroxy-4-methyl-2-pyrone

tetrahydro-4-hydroxy-4-Methylpyran-2-one

DL-MEVALOLACTONE

DL-MEVALONIC ACID LACTONE

DL-BETA-HYDROXY-BETA-METHYL-DELTA-VALERO-LACTONE

DL-BETA-HYDROXY-BETA-METHYL-GAMMA-VALEROLACTONE

DL-BETA-HYDROXY-BETA-METHYL-G-VALEROLACTONE

DL-3-HYDROXY-3-METHYL DELTA-VALEROLACTONE

BETA-HYDROXY-BETA-METHYL-DELTA-VALEROLACTONE

MEVALONIC ACID LACTONE, DL-

MEVALONIC LACTONE

(+/-)-MEVALONOLACTONE

MEVALONOLACTONE

(+/-)-3-HYDROXY-3-METHYL-5-PENTANOLIDE

(4R)-4-Hydroxy-4-methyl-oxan-2-one

(+/-)-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

D,L-b-Hydroxy-b-methyl-valerolactone

(±)-β-hydroxy-β-methyl-δ-valerolactone

MEVALONIC ACID LACTONE, DL-(RG)

D,L-MEVELONIC ACID LACTONE

DL-B-HYDROXY-B-METHYL-Y-VALEROLACTONE

D,L--Hydroxy--methyl--valerolactone

NSC 90804

(±)-β-Hydroxy-β-methyl-δ-valerolactone, (±)-3-Hydroxy-3-methyl δ-valerolactone, DL-Mevalolactone, DL-Mevalonic acid lactone

dl-mevalonic acid lactone, salt-free

DL-Mevalonolactone &gt

Mevalonolactone, racemic mixture

4-hydroxy-4-methyloxan-2-one

4-Hydroxy-4-methyltetrahydropyran-2-one

Hyperpure-MVA

Adeka Mevalonolactone

DL-Mevalonolactone, 10 mM in DMSO

(±)-Mevalonolactone

674-26-0

Organic Building Blocks

Lactones

Metabolomics

Metabolic Libraries

Lipid Library

Building Blocks

BioChemical

Carbonyl Compounds

Heterocycles, Metabolites & Impurities

Heterocycles

Metabolites & Impurities