Meglutol | CAS#503-49-1 | antilipemic agent

MedKoo Cat#: 598962 | Name: Meglutol

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Description:

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

Meglutol is an antilipemic agent which lowers cholesterol, triglycerides, serum beta-lipoproteins and phospholipids. It acts by interfering with the enzymatic steps involved in the conversion of acetate to hydroxymethylglutaryl coenzyme A as well as inhibiting the activity of HYDROXYMETHYLGLUTARYL COA REDUCTASES which is the rate limiting enzyme in the biosynthesis of cholesterol.

Chemical Structure

Meglutol

CAS#503-49-1

Theoretical Analysis

MedKoo Cat#: 598962

Name: Meglutol

CAS#: 503-49-1

Chemical Formula: C6H10O5

Exact Mass: 162.0528

Molecular Weight: 162.14

Elemental Analysis: C, 44.45; H, 6.22; O, 49.34

Price and Availability

Size	Price	Availability
100mg	USD 295.00	2 Weeks
250mg	USD 550.00	2 Weeks
500mg	USD 950.00	2 Weeks

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Synonym

Meglutol; HMGA; NSC 361411; NSC-361411; NSC361411; CB-337; CB 337; CB337;

IUPAC/Chemical Name

3-hydroxy-3-methylpentanedioic acid

InChi Key

NPOAOTPXWNWTSH-UHFFFAOYSA-N

InChi Code

InChI=1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10)

SMILES Code

O=C(O)CC(C)(O)CC(O)=O

Appearance

Solid powder

Purity

>98% (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

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Meglutol is an antilipemic agent which lowers cholesterol, triglycerides, serum beta-lipoproteins and phospholipids, and inhibits the activity of hydroxymethylglutarryl CoA reductases, which is the rate limiting enzyme in the biosynthesis of cholesterol.

In vitro activity:

In vivo rat experiments showed that intraperitoneal administration of HMG (meglutol) and MGA decreased the activities of the respiratory chain complex II and creatine kinase (CK), whereas HMG also decreased the activity of complex II-III. Furthermore, HMG and MGA injection increased reactive species production and carbonyl formation, and decreased glutathione concentrations. Reference: Free Radic Res. 2016 Sep;50(9):997-1010. https://pubmed.ncbi.nlm.nih.gov/27430492/

In vivo activity:

The present work investigated the in vitro effect of 3-hydroxy-3-methylglutarate (HMG) that accumulates in 3-hydroxy-3-methylglutaryl-CoA lyase deficiency (HMGLD) on important parameters of oxidative stress in rat cerebral cortex. It was observed that HMG induced lipid peroxidation by significantly increasing chemiluminescence and levels of thiobarbituric acid-reactive substances (TBA-RS). HMG also induced protein oxidative damage in cortical supernatants, which was reflected by increased carbonyl content and sulfhydryl oxidation. Reference: J Neurosci Res. 2008 Feb 15;86(3):683-93. https://pubmed.ncbi.nlm.nih.gov/17941049/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	185.02
	DMSO	140.0	863.45
	Ethanol	5.0	30.84
	PBS (pH 7.2)	10.0	61.68

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 162.14 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.

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. da Rosa MS, Seminotti B, Ribeiro CA, Parmeggiani B, Grings M, Wajner M, Leipnitz G. 3-Hydroxy-3-methylglutaric and 3-methylglutaric acids impair redox status and energy production and transfer in rat heart: relevance for the pathophysiology of cardiac dysfunction in 3-hydroxy-3-methylglutaryl-coenzyme A lyase deficiency. Free Radic Res. 2016 Sep;50(9):997-1010. doi: 10.1080/10715762.2016.1214952. Epub 2016 Aug 23. PMID: 27430492. 2. da Rosa MS, da Rosa-Junior NT, Parmeggiani B, Glänzel NM, de Moura Alvorcem L, Ribeiro RT, Grings M, Wajner M, Leipnitz G. 3-Hydroxy-3-Methylglutaric Acid Impairs Redox and Energy Homeostasis, Mitochondrial Dynamics, and Endoplasmic Reticulum-Mitochondria Crosstalk in Rat Brain. Neurotox Res. 2020 Feb;37(2):314-325. doi: 10.1007/s12640-019-00122-x. Epub 2019 Nov 13. PMID: 31721046. 3. Leipnitz G, Seminotti B, Haubrich J, Dalcin MB, Dalcin KB, Solano A, de Bortoli G, Rosa RB, Amaral AU, Dutra-Filho CS, Latini A, Wajner M. Evidence that 3-hydroxy-3-methylglutaric acid promotes lipid and protein oxidative damage and reduces the nonenzymatic antioxidant defenses in rat cerebral cortex. J Neurosci Res. 2008 Feb 15;86(3):683-93. doi: 10.1002/jnr.21527. PMID: 17941049.

In vitro protocol:

In vivo protocol:

1. da Rosa MS, da Rosa-Junior NT, Parmeggiani B, Glänzel NM, de Moura Alvorcem L, Ribeiro RT, Grings M, Wajner M, Leipnitz G. 3-Hydroxy-3-Methylglutaric Acid Impairs Redox and Energy Homeostasis, Mitochondrial Dynamics, and Endoplasmic Reticulum-Mitochondria Crosstalk in Rat Brain. Neurotox Res. 2020 Feb;37(2):314-325. doi: 10.1007/s12640-019-00122-x. Epub 2019 Nov 13. PMID: 31721046. 2. Leipnitz G, Seminotti B, Haubrich J, Dalcin MB, Dalcin KB, Solano A, de Bortoli G, Rosa RB, Amaral AU, Dutra-Filho CS, Latini A, Wajner M. Evidence that 3-hydroxy-3-methylglutaric acid promotes lipid and protein oxidative damage and reduces the nonenzymatic antioxidant defenses in rat cerebral cortex. J Neurosci Res. 2008 Feb 15;86(3):683-93. doi: 10.1002/jnr.21527. PMID: 17941049.

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Mol Cell Biochem. 2015 Apr;402(1-2):149-55. doi: 10.1007/s11010-014-2322-x. Epub 2015 Jan 4. PubMed PMID: 25557019. 4: Seeka C, Sutthivaiyakit P, Youkwan J, Hertkorn N, Harir M, Schmitt-Kopplin P, Sutthivaiyakit S. Prenylfuranocoumarin-HMGA-flavonol glucoside conjugates and other constituents of the fruit peels of Citrus hystrix and their anticholinesterase activity. Phytochemistry. 2016 Jul;127:38-49. doi: 10.1016/j.phytochem.2016.03.009. Epub 2016 Mar 16. PubMed PMID: 26995149. 5: Fernandes CG, da Rosa MS, Seminotti B, Pierozan P, Martell RW, Lagranha VL, Busanello EN, Leipnitz G, Wajner M. In vivo experimental evidence that the major metabolites accumulating in 3-hydroxy-3-methylglutaryl-CoA lyase deficiency induce oxidative stress in striatum of developing rats: a potential pathophysiological mechanism of striatal damage in this disorder. Mol Genet Metab. 2013 Jun;109(2):144-53. doi: 10.1016/j.ymgme.2013.03.017. Epub 2013 Apr 6. 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PubMed PMID: 6201428. 9: da Rosa MS, Seminotti B, Ribeiro CA, Parmeggiani B, Grings M, Wajner M, Leipnitz G. 3-Hydroxy-3-methylglutaric and 3-methylglutaric acids impair redox status and energy production and transfer in rat heart: relevance for the pathophysiology of cardiac dysfunction in 3-hydroxy-3-methylglutaryl-coenzyme A lyase deficiency. Free Radic Res. 2016 Sep;50(9):997-1010. doi: 10.1080/10715762.2016.1214952. Epub 2016 Aug 23. PubMed PMID: 27430492. 10: Porter EA, van den Bos AA, Kite GC, Veitch NC, Simmonds MS. Flavonol glycosides acylated with 3-hydroxy-3-methylglutaric acid as systematic characters in Rosa. Phytochemistry. 2012 Sep;81:90-6. doi: 10.1016/j.phytochem.2012.05.006. Epub 2012 Jun 20. PubMed PMID: 22721781. 11: Colegate SM, Gardner DR, Davis TZ, Betz JM, Panter KE. Dehydropyrrolizidine alkaloids in two Cryptantha species: including two new open chain diesters one of which is amphoteric. Phytochem Anal. 2013 May-Jun;24(3):201-12. doi: 10.1002/pca.2400. Epub 2012 Oct 15. PubMed PMID: 23070903. 12: Miyazaki S, Kitamura N, Nishio A, Tanaka S, Kayano T, Moriya T, Ichiyanagi T, Shimomura N, Shibuya I, Aimi T. Gymnopilin--a substance produced by the hallucinogenic mushroom, Gymnopilus junonius--mobilizes intracellular Ca(2+) in dorsal root ganglion cells. Biomed Res. 2012 Apr;33(2):111-8. PubMed PMID: 22572385. 13: Fernandes CG, Rodrigues MDN, Seminotti B, Colín-González AL, Santamaria A, Quincozes-Santos A, Wajner M. Induction of a Proinflammatory Response in Cortical Astrocytes by the Major Metabolites Accumulating in HMG-CoA Lyase Deficiency: the Role of ERK Signaling Pathway in Cytokine Release. Mol Neurobiol. 2016 Aug;53(6):3586-3595. doi: 10.1007/s12035-015-9289-9. Epub 2015 Jun 23. PubMed PMID: 26099308. 14: Nishio A, Kitamura N, Tanaka S, Miyazaki S, Ichiyanagi T, Shimomura N, Shibuya I, Aimi T. Multiple effects of gymnopilin on circulatory system of the rat. Biol Pharm Bull. 2012;35(8):1300-5. 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Neurochemical evidence that 3-methylglutaric acid inhibits synaptic Na+,K+-ATPase activity probably through oxidative damage in brain cortex of young rats. Int J Dev Neurosci. 2011 Feb;29(1):1-7. doi: 10.1016/j.ijdevneu.2010.10.007. Epub 2010 Nov 2. PubMed PMID: 21050883. 19: Williamson IP, Rodwell VW. Isolation and purification of 3-hydroxy-3-methylglutaryl-coenzyme A by ion-exchange chromatography. J Lipid Res. 1981 Jan;22(1):184-7. PubMed PMID: 6163836. 20: Yuba E, Harada A, Sakanishi Y, Kono K. Carboxylated hyperbranched poly(glycidol)s for preparation of pH-sensitive liposomes. J Control Release. 2011 Jan 5;149(1):72-80. doi: 10.1016/j.jconrel.2010.03.001. Epub 2010 Mar 4. PubMed PMID: 20206654.