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MedKoo Cat#: 573945 | Name: Mevalonolactone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mevalonolactone is a chemical that can be used in the preparation of a vitamin E.

Chemical Structure

Mevalonolactone
Mevalonolactone
CAS#19115-49-2

Theoretical Analysis

MedKoo Cat#: 573945

Name: Mevalonolactone

CAS#: 19115-49-2

Chemical Formula: C6H10O3

Exact Mass: 130.0630

Molecular Weight: 130.14

Elemental Analysis: C, 55.37; H, 7.75; O, 36.88

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Synonym
(-)-(R)-Mevalonic acid lactone, (-)-(R)-Mevalonolactone, (-)-Mevalonolactone, (3R)-Mevalonolactone, Mevalonolactone
IUPAC/Chemical Name
2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-
InChi Key
JYVXNLLUYHCIIH-ZCFIWIBFSA-N
InChi Code
1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3/t6-/m1/s1
SMILES Code
C[C@]1(CCOC(=O)C1)O
Appearance
Solid powder
Purity
>90% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Mevalonolactone is a chemical that can be used in the preparation of a vitamin E.
In vitro activity:
This work aims at describing the effects of accumulating mevalonolactone, mostly produced by a dehydration reaction due to mevalonic acid accumulation, using an in vitro cellular model mimicking the glial component of the central nervous system (human glioblastoma U-87 MG cells). In order to mimic its progressive increase, occurring during the disease, U-87 MG cells have been treated repeatedly with growing doses of mevalonolactone, followed by the assessment of oxidative stress response (evaluated by measuring SOD2 and HemeOX expression levels), ROS production, mitochondrial damage and inflammatory response (evaluated by measuring IL1B expression levels). These results suggest that protracted treatments with mevalonolactone induce oxidative stress with augmented ROS production and mitochondrial damage accompanied by membrane depolarization. Reference: Neurochem Int. 2018 Nov;120:233-237. https://pubmed.ncbi.nlm.nih.gov/29753116/
In vivo activity:
In the present study, administration of mevalonolactone to rats caused a rapid inhibition of HMG-CoA reductase activity. The increased phosphorylation of reductase kinase was catalyzed by reductase kinase kinase, which was significantly elevated (3- to 4-fold) after the administration of mevalonolactone to rats. Mevalonolactone administration was also associated with a significant inhibition of phosphoprotein phosphatase activity, which dephosphorylates both HMG-CoA reductase (activation) and reductase kinase (inactivation). These results indicate that mevalonolactone administration to rats in vivo was associated with an inhibition of HMG-CoA reductase activity by two mechanisms: (i) an increase in the degree of phosphorylation of both HMG-CoA reductase and reductase kinase due to increased activity of reductase kinase kinase; (ii) a decrease in the dephosphorylation of both HMG-CoA reductase and reductase kinase secondary to inhibition of phosphoprotein phosphatase activity. Reference: Proc Natl Acad Sci U S A. 1984 Dec;81(23):7293-7. https://pubmed.ncbi.nlm.nih.gov/6594693/

Preparing Stock Solutions

The following data is based on the product molecular weight 130.14 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Gratton R, Tricarico PM, Celsi F, Crovella S. Prolonged treatment with mevalonolactone induces oxidative stress response with reactive oxygen species production, mitochondrial depolarization and inflammation in human glioblastoma U-87 MG cells. Neurochem Int. 2018 Nov;120:233-237. doi: 10.1016/j.neuint.2018.05.003. Epub 2018 May 9. PMID: 29753116. 2. Cecatto C, Amaral AU, da Silva JC, Wajner A, Godoy KDS, Ribeiro RT, Gonçalves AM, Vargas CR, Wajner M. Mevalonolactone disrupts mitochondrial functions and induces permeability transition pore opening in rat brain mitochondria: Implications for the pathogenesis of mevalonic aciduria. Neurochem Int. 2017 Sep;108:133-145. doi: 10.1016/j.neuint.2017.03.005. Epub 2017 Mar 9. PMID: 28284974. 3. Beg ZH, Stonik JA, Brewer HB Jr. In vivo modulation of rat liver 3-hydroxy-3-methylglutaryl-coenzyme A reductase, reductase kinase, and reductase kinase kinase by mevalonolactone. Proc Natl Acad Sci U S A. 1984 Dec;81(23):7293-7. doi: 10.1073/pnas.81.23.7293. PMID: 6594693; PMCID: PMC392132. 4. Edwards PA, Lan SF, Tanaka RD, Fogelman AM. Mevalonolactone inhibits the rate of synthesis and enhances the rate of degradation of 3-hydroxy-3-methylglutaryl coenzyme A reductase in rat hepatocytes. J Biol Chem. 1983 Jun 25;258(12):7272-5. PMID: 6863245.
In vitro protocol:
1. Gratton R, Tricarico PM, Celsi F, Crovella S. Prolonged treatment with mevalonolactone induces oxidative stress response with reactive oxygen species production, mitochondrial depolarization and inflammation in human glioblastoma U-87 MG cells. Neurochem Int. 2018 Nov;120:233-237. doi: 10.1016/j.neuint.2018.05.003. Epub 2018 May 9. PMID: 29753116. 2. Cecatto C, Amaral AU, da Silva JC, Wajner A, Godoy KDS, Ribeiro RT, Gonçalves AM, Vargas CR, Wajner M. Mevalonolactone disrupts mitochondrial functions and induces permeability transition pore opening in rat brain mitochondria: Implications for the pathogenesis of mevalonic aciduria. Neurochem Int. 2017 Sep;108:133-145. doi: 10.1016/j.neuint.2017.03.005. Epub 2017 Mar 9. PMID: 28284974.
In vivo protocol:
1. Beg ZH, Stonik JA, Brewer HB Jr. In vivo modulation of rat liver 3-hydroxy-3-methylglutaryl-coenzyme A reductase, reductase kinase, and reductase kinase kinase by mevalonolactone. Proc Natl Acad Sci U S A. 1984 Dec;81(23):7293-7. doi: 10.1073/pnas.81.23.7293. PMID: 6594693; PMCID: PMC392132. 2. Edwards PA, Lan SF, Tanaka RD, Fogelman AM. Mevalonolactone inhibits the rate of synthesis and enhances the rate of degradation of 3-hydroxy-3-methylglutaryl coenzyme A reductase in rat hepatocytes. J Biol Chem. 1983 Jun 25;258(12):7272-5. PMID: 6863245.
1: Gratton R, Tricarico PM, Celsi F, Crovella S. Prolonged treatment with mevalonolactone induces oxidative stress response with reactive oxygen species production, mitochondrial depolarization and inflammation in human glioblastoma U-87 MG cells. Neurochem Int. 2018 Nov;120:233-237. doi: 10.1016/j.neuint.2018.05.003. Epub 2018 May 9. PubMed PMID: 29753116. 2: Cecatto C, Amaral AU, da Silva JC, Wajner A, Godoy KDS, Ribeiro RT, Gonçalves AM, Vargas CR, Wajner M. Mevalonolactone disrupts mitochondrial functions and induces permeability transition pore opening in rat brain mitochondria: Implications for the pathogenesis of mevalonic aciduria. Neurochem Int. 2017 Sep;108:133-145. doi: 10.1016/j.neuint.2017.03.005. Epub 2017 Mar 9. PubMed PMID: 28284974. 3: Scopel M, Abraham WR, Antunes AL, Henriques AT, Macedo AJ. Mevalonolactone: an inhibitor of Staphylococcus epidermidis adherence and biofilm formation. Med Chem. 2014 May;10(3):246-51. PubMed PMID: 24111986.