503-49-1

Basic information

• Product Name: 3-HYDROXY-3-METHYLGLUTARIC ACID
• Synonyms: hmga;lipoglutaren;medroglutaricacid;Meglutol;3-Hydroxymethylglutaric acid;3-HYDROXY-3-METHYLPENTANEDIOIC ACID (HMG);3-Hydroxy-3-methylglutaric acid ,98%;3-Hydroxy-3-Methylglutaric acid >=95%
• CAS NO: 503-49-1
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.14
• EINECS: 207-971-1
• Product Categories: Pharmaceutical Raw Materials;Miscellaneous Reagents;Building Blocks;C6;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 503-49-1.mol
• Article Data: 31

Chemical Properties

• Melting Point: 105-108 °C(lit.)
• Boiling Point: 120 °C / 13mmHg
• Flash Point: 182.2 °C
• Appearance: Off-white powder with chunks
• Density: 1.2132 (rough estimate)
• Vapor Pressure: 1.35E-08mmHg at 25°C
• Refractive Index: 1.4230 (estimate)
• Storage Temp.: −20°C
• PKA: 3.95±0.10(Predicted)
• Merck: 14,5808
• BRN: 1769194
• CAS DataBase Reference: 3-HYDROXY-3-METHYLGLUTARIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-3-METHYLGLUTARIC ACID(503-49-1)
• EPA Substance Registry System: 3-HYDROXY-3-METHYLGLUTARIC ACID(503-49-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 2
• RTECS: MA3753000
• F: 10
• Hazardous Substances Data: 503-49-1(Hazardous Substances Data)

Usage

Description

3-HYDROXY-3-METHYLGLUTARIC ACID, also known as Meglutol or HMG, is a dicarboxylic acid derived from glutaric acid with a hydroxy and a methyl group substitution at the 3rd position. It is a hypolipidemic agent that inhibits cholesterol synthesis at the HMG-CoA reductase stage, making it an ideal target for hypolipidemic agents. It is also found as a plant metabolite in Crotalaria dura and has been identified in the urine of patients with HMG-CoA lyase deficiency. Meglutol is a white solid and is commercially available under the brand name LIPOGLUTAREN.

Uses

Used in Pharmaceutical Industry:
3-HYDROXY-3-METHYLGLUTARIC ACID is used as a hypolipidemic agent for the treatment of hyperlipoproteinemia. It works by inhibiting cholesterol synthesis at the HMG-CoA reductase stage, blocking the conversion of HMG-CoA to mevalonate, which is the rate-limiting step in cholesterol biosynthesis and the point of physiological feedback control.
Used in Organic Synthesis:
3-Hydroxy-3-methylpentane-1,5-dioic Acid (CAS# 503-49-1) is a compound useful in organic synthesis, contributing to the development of various chemical products and applications in different industries.

Originator

Aligarh Muslim Univ. (India)

Synthesis Reference(s)

Synthesis, p. 791, 1981 DOI: 10.1055/s-1981-29596

Purification Methods

Recrystallise the acid from diethyl ether/hexane and dry it under avacuum at 60o for 1hour. [Beilstein 3 IV 1166.]

InChI:InChI=1/C6H10O5/c7-3-4(1-5(8)9)2-6(10)11/h4,7H,1-3H2,(H,8,9)(H,10,11)

Upstream product

• 25201-40-5 1,1-diallylethanol 
• 28891-35-2 Ethyl 3-hydroxy-5,5-dimethoxy-3-methylpentanoate 
• 73489-84-6 3-hydroxy-3-methyl-glutaric acid diethyl ester 
• 16302-35-5 4-methyl-3,6-dihydro-2H-pyran 
• 36838-71-8 4-methylene-tetrahydro-pyran 
• 674-26-0 mevalonolactone 
• 2018-45-3 4-(β-hydroxyethyl)-4-methyl-1,3-dioxane 
• 102040-03-9 tubeimoside I 
• 1158964-28-3 malvidin 3-O-[6-O-(3-hydroxy-3-methylglutaroyl)-β-D-glucopyranoside] 
• 19115-49-2 (R)-mevalonolactone 
• 128811-87-0 5-chloro-3-hydroxy-3-methylvaleric acid 
• 128811-86-9 4-(β-chloroethyl)-4-methyl-1,3-dioxane 
• 81969-90-6 13-epi-dicrotaline 
• 81943-18-2 3-methyl-3-trimethylsilyloxyglutaric anhydride 

Downstream Products

• 150-97-0 D,L-mevalonic acid 
• 56652-39-2 dimethyl 3-hydroxy-3-methylglutarate 
• 73489-84-6 3-hydroxy-3-methyl-glutaric acid diethyl ester 
• 1553-55-5 DL-3-hydroxy-3-methylglutaryl coenzyme A 
• 6247-73-0 S-(4-carboxy-3-methyl-but-2ξ-enoyl)-coenzyme-A 
• 7564-64-9 3-methyl-1,3,5-pentanetriol 
• 480-87-5 (+)-dicrotaline 
• 481-74-3 Chrysophanol 
• 67116-19-2 3-methyl-pentenedioic acid anhydride 
• 674-26-0 mevalonolactone 
• 476-56-2 islandicin 
• 946831-51-2 (3R)-1-[(S)-1-phenylethyl]mevalonamide 
• 176755-40-1 (S)-4-Cyclohexylcarbamoyl-3-hydroxy-3-methyl-butyric acid methyl ester 

Relevant articles and documents

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SYNTHESIS OF MEVALONOLACTONE FROM 4-(β-HYDROXYETHYL)-4-METHYL-1,3-DIOXANE

A method has been developed for obtaining mevalonolactone and 3-hydroxy-3-methylglutaric acid from an industrial waste, 4-(β-hydroxyethyl)-4-methyl-1,3-dioxane.

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FUNGAL METABOLITES XIII : NEW CYTOTOXIC TRITERPENE FROM HEBELOMA SPECIES (BASIDIOMYCETES)

A new cytotoxic lanostane triterpene, named 3-β-acetyl-2-α-(3'-hydroxy-3'-methyl)glutarylcrustulinol, was isolated from Hebeloma crustuliniforme and H. sinapizans.The structure has been elucidated by chemical correlations and spectroscopic evidences.

POLYMERS PREPARED FROM MEVALONOLACTONE AND DERIVATIVES

Described herein polymer precursor compounds (aka polymer building blocks) of derived from biobased compounds, and specifically biobased mevalonolactone and its related derivatives. Through oxidation these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols and polyamides, as well as precursors for glycidyl esters and omega-alkenyl esters. Through reduction, these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols, polycarbonates, as well as precursors for glycidyl ethers and omega-alkenyl ethers. Through nucleophilic ring opening and/or amidation, these biobased precursors can be reacted to yield building blocks for polyester polyols, chain-extender for polyurethanes, or polyester-amides.

NATURAL MOLECULES EXTRACTED FROM BERGAMOT TISSUES, EXTRACTION PROCESS AND PHARMACEUTICAL USE

A natural molecule extracted from a citrus fruit characterized by the fact that its structure is a flavonoid linked to 3-hydroxy-3-methyl glutaric acid and an extraction process in which: the extraction of chopped fruit is conducted in pure or mixed chloroform, ethanol or methanol for a certain time, the filtrate is evaporated to dryness, the residue is submitted to solid phase extraction in order to separate the flavonoidic portion from the other class of compounds, the flavonoid mixture is separated through a preparative HPLC chromatographic system. Pharmaceutical use of the natural molecule extracted from a citrus fruit used as anticholesterol drug.