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

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

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

• 73489-84-6 3-hydroxy-3-methyl-glutaric acid diethyl ester 
• 36838-71-8 4-methylene-tetrahydro-pyran 
• 72060-94-7 1,3-dicyano-2-methyl-2-hydroxypropane 
• 123688-62-0 lobatoside D 
• 25201-40-5 1,1-diallylethanol 
• 2018-45-3 4-(β-hydroxyethyl)-4-methyl-1,3-dioxane 
• 16302-35-5 4-methyl-3,6-dihydro-2H-pyran 
• 19115-49-2 (R)-mevalonolactone 
• 1158964-28-3 malvidin 3-O-[6-O-(3-hydroxy-3-methylglutaroyl)-β-D-glucopyranoside] 
• 89622-82-2 ditert.-butyl 3-methyl-3-hydroxy-glutarate 
• 7440-44-0 pyrographite 
• 7564-64-9 3-methyl-1,3,5-pentanetriol 
• 128811-87-0 5-chloro-3-hydroxy-3-methylvaleric acid 
• 128811-86-9 4-(β-chloroethyl)-4-methyl-1,3-dioxane 

Downstream Products

• 56652-39-2 dimethyl 3-hydroxy-3-methylglutarate 
• 34695-32-4 3-hydroxy-3-methylglutaric anhydride 
• 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

Steroidal glycosides from Allium cyrillii Bulbs

Two spirostanol saponins, one of which was a new compound, were isolated among the steroidal glycosides of Allium cyrillii Ten. Bulbs. The structures of these glycosides were established using chemical and spectral analytical methods as β-D-glycopyranosyl-(1 →2)-[β-D-xylopyranosyl-(1 →3)]-β-D-glucopyranosyl-(1 →4)-β-D-galactopyranosyl- (1→3)-(25R)-5α-spirostan-2α,3β-diol and β-D-glucopyranosyl-(1→2)-[4-O-(3-hydroxy-3-methylglutaryl) -β-D-xylopyranosyl-(1 →3)]-β-D-glucopyranosyl-(1 →4)-β-D-galactopyranosyl-(1→3)-(25R)-5α-spirostan-2α, 3β-diol.

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.

PYRROLIZIDINE ALKALOIDS FROM CROTALARIA LACHNOSEMA AND C. NARAGUTENSIS

Crotalaria lachnosema, from Nigeria, was found to contain two pyrrolizidine alkaloids, dicrotaline and its acetyl derivative, the natural occurrence of which is reported for the first time.The major alkaloid in C. naragutensis was nilgirine, together with integerrimine, usaramine and a new alkaloid, acetyl integerrimine.Key Word Index - Crotalaria lachnosema; C. naragutensis; pyrrolizidine alkaloid; dicrotaline; acetyl dicrotaline; integerrimine; acetyl integerrimine; nilgirine; usaramine.

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.

Control of β-Branching in Kalimantacin Biosynthesis: Application of 13C NMR to Polyketide Programming

The presence of β-branches in the structure of polyketides that possess potent biological activity underpins the widespread importance of this structural feature. Kalimantacin is a polyketide antibiotic with selective activity against staphylococci, and its biosynthesis involves the unprecedented incorporation of three different and sequential β-branching modifications. We use purified single and multi-domain enzyme components of the kalimantacin biosynthetic machinery to address in vitro how the pattern of β-branching in kalimantacin is controlled. Robust discrimination of enzyme products required the development of a generalisable assay that takes advantage of 13C NMR of a single 13C label incorporated into key biosynthetic mimics combined with favourable dynamic properties of an acyl carrier protein. We report a previously unassigned modular enoyl-CoA hydratase (mECH) domain and the assembly of enzyme constructs and cascades that are able to generate each specific β-branch.

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.

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.

Statin-like principles of bergamot fruit (Citrus bergamia): Isolation of 3-hydroxymethylglutaryl flavonoid glycosides

The 3-hydroxy-3-methylglutaryl neohesperidosides of hesperetin (brutieridin, 1) and naringenin (melitidin, 2) were isolated and detected from the fruits of bergamot (Citrus bergamia). The structures of these compounds were determined by spectroscopic and

An unusual acylated malvidin 3-glucoside from flowers of Impatiens textori Miq. (Balsaminaceae)

Acylated malvidin 3-glucoside was isolated from the purple flowers of Impatiens textori Miq. as a major anthocyanin component along with malvidin 3-(6″-malonyl-glucoside). Its structure was elucidated to be malvidin 3-O-[6-O-(3-hydroxy-3-methylglutaryl)-β