Meglutol

Base Information

• Chemical Name: Meglutol
• CAS No.: 503-49-1
• Molecular Formula: C6H10 O5
• Molecular Weight: 162.142
• Hs Code.: 2918199090
• European Community (EC) Number: 207-971-1
• NSC Number: 760412,361411
• UNII: CLA99KCD53
• DSSTox Substance ID: DTXSID90198304
• Nikkaji Number: J6.212J
• Wikipedia: Meglutol
• Wikidata: Q524670
• NCI Thesaurus Code: C174659
• Pharos Ligand ID: DAUTQGXC7X8C
• Metabolomics Workbench ID: 37215
• ChEMBL ID: CHEMBL50444
• Mol file: 503-49-1.mol

Synonyms:3 Hydroxy 3 methylglutaric Acid;3 Hydroxy 3 methylpentanedioic Acid;3-Hydroxy-3-methylglutaric Acid;3-Hydroxy-3-methylpentanedioic Acid;Acid, 3-Hydroxy-3-methylglutaric;Acid, 3-Hydroxy-3-methylpentanedioic;beta Hydroxy beta Methylglutarate;beta-Hydroxy-beta-Methylglutarate;Meglutol

Chemical Property of Meglutol

Chemical Property:

• Appearance/Colour: Off-white powder with chunks
• Vapor Pressure: 1.35E-08mmHg at 25°C
• Melting Point: 105-108 °C(lit.)
• Refractive Index: 1.4230 (estimate)
• Boiling Point: 354.3 °C at 760 mmHg
• PKA: 3.95±0.10(Predicted)
• Flash Point: 182.2 °C
• PSA: 94.83000
• Density: 1.417 g/cm³
• LogP: -0.31320
• Storage Temp.: −20°C
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 162.05282342
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Hydroxy-3-methylpentane-1,5-dioicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(=O)O)(CC(=O)O)O
• Recent ClinicalTrials: Role of Aromatase Inhibitor to Enhance Ovulation in Poor Responder During Induction With Short Antagonist Protocol in Cases of ICSI
• Description: Meglutol (β-hydroxy-β-methylglutaric acid; HMG) is a hypolipidemic agent that acts via the inhibition of cholesterol synthesis a t the stage of HMG-CoAreductase, blocking the conversion of HMG-CoA to mevalonate. This conversion is the rate-limiting step in cholesterol biosynthesis and is the point of physiological feedback control; as such, it appears to be the ideal locus of action for a hypolipidemic agent. Investigational compounds that act by this mechanism include the natural products compactin and mevinolin.
• Uses: antihyperlipoproteinemia 3-Hydroxy-3-methylpentane-1,5-dioic Acid (cas# 503-49-1) is a compound useful in organic synthesis.

Technology Process of Meglutol

There total 41 articles about Meglutol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

3-methyl-1,3,5-pentanetriol (7564-64-9) → meglutol (503-49-1)

Guidance literature:

In acetic acid butyl ester; nitric acid;

Reference yield: 76.0%

mevalonolactone (674-26-0,503-48-0) → meglutol (503-49-1)

Guidance literature:

With nitric acid; sodium nitrite; at 35 - 40 ℃; for 5h;

DOI:10.1007/BF00605192

Reference yield: 70.0%

7-O-retronecanol (88205-12-3) → meglutol (503-49-1) + retronecanol (567-39-5)

Guidance literature:

With barium dihydroxide; In water; for 1h; Heating;

upstream raw materials:

1,1-diallylethanol

Ethyl 3-hydroxy-5,5-dimethoxy-3-methylpentanoate

3-hydroxy-3-methyl-glutaric acid diethyl ester

4-methyl-3,6-dihydro-2H-pyran

Downstream raw materials:

3-hydroxy-3-methylglutaric anhydride

D,L-mevalonic acid

dimethyl 3-hydroxy-3-methylglutarate

3-methyl-1,3,5-pentanetriol

Refernces

• 1、 Tolkacheva,Shashkov,Chirva. "Steroidal glycosides from Allium cyrillii Bulbs". . p. 272 - 275. Retrieved 2012.
• 2、 Yavrouian, Andre H.,Sanchez, Robert A.,Pollard, John K.,Metzner, E. Kurt. "Hydrolysis of 3-Hydroxy-3-methylglutaronitrile; A Convenient Synthesis of 3-Hydroxy-3-methylglutaric Acid". . p. 791 - 793. Retrieved 1981.
• 3、 Mattocks, Robin A.,Nwude, Nwankwo. "PYRROLIZIDINE ALKALOIDS FROM CROTALARIA LACHNOSEMA AND C. NARAGUTENSIS". . p. 3289 - 3292. Retrieved 1988.
• 4、 Walker, Paul D.,Williams, Christopher,Weir, Angus N. M.,Wang, Luoyi,Crosby, John,Race, Paul R.,Simpson, Thomas J.,Willis, Christine L.,Crump, Matthew P.. "Control of β-Branching in Kalimantacin Biosynthesis: Application of 13C NMR to Polyketide Programming". supporting information. p. 12446 - 12450. Retrieved 2019/08/16.
• 5、 -. "POLYMERS PREPARED FROM MEVALONOLACTONE AND DERIVATIVES". . . Retrieved 2016/06/06.