19013-37-7

Basic information

• Product Name: DIMETHYL 3-METHYLGLUTARATE
• Synonyms: DIMETHYL 3-METHYLGLUTARATE;3-METHYL-PENTANEDIOIC ACID DIMETHYL ESTER;Dimethyl 3-methylpentanedioate;Glutaric acid, 3-methyl-, dimethyl ester;Methyl 3-methylgutarate;3-Methylglutaric acid dimethyl;3-Methylglutaric acid dimethyl ester;3-Methylpentanedioic acid dimethyl
• CAS NO: 19013-37-7
• Molecular Formula: C₈H₁₄O₄
• Molecular Weight: 174.19
• EINECS: 200-258-5
• Product Categories: C8 to C9;Carbonyl Compounds;Esters
• Mol File: 19013-37-7.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 110 °C19 mm Hg(lit.)
• Flash Point: 207 °F
• Appearance: /
• Density: 1.052 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.11mmHg at 25°C
• Refractive Index: n20/D 1.425(lit.)
• CAS DataBase Reference: DIMETHYL 3-METHYLGLUTARATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL 3-METHYLGLUTARATE(19013-37-7)
• EPA Substance Registry System: DIMETHYL 3-METHYLGLUTARATE(19013-37-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 19013-37-7(Hazardous Substances Data)

Usage

Description

DIMETHYL 3-METHYLGLUTARATE, an ester, is a versatile compound that plays a significant role in the synthesis of various organic compounds and is particularly valuable in the perfume industry due to its contribution to the creation of muscenone, a key ingredient.

Uses

Used in Pharmaceutical Industry:
DIMETHYL 3-METHYLGLUTARATE is used as a synthetic intermediate for the production of (R)and (S)-4-amino-3-methylbutanoic acids. These amino acids are essential in the development of pharmaceuticals, as they are involved in various biological processes and can be used to treat specific medical conditions.
Used in Perfumery:
DIMETHYL 3-METHYLGLUTARATE is used as a building block for the synthesis of (R,Z)-muscenone, an important ingredient in the perfume industry. Its unique scent profile contributes to the creation of various fragrances, making it a valuable component in the formulation of perfumes and colognes.
Used in Enzymatic Synthesis:
DIMETHYL 3-METHYLGLUTARATE is used as a substrate in enantioselective hydrolysis with pig liver esterase, a process that allows for the preparation of optically active compounds, such as verrucarinic acid derivatives. These optically active compounds have potential applications in various fields, including pharmaceuticals and agrochemicals.
Used in Chemoenzymatic Asymmetric Synthesis:
DIMETHYL 3-METHYLGLUTARATE serves as a crucial building block in chemoenzymatic asymmetric synthesis, a technique that combines chemical and enzymatic reactions to produce chiral compounds with high enantioselectivity. This method is widely used in the synthesis of complex molecules, such as pharmaceuticals and natural products, where the stereochemistry of the molecule is crucial for its biological activity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 2132, 1994 DOI: 10.1021/jo00087a033Tetrahedron Letters, 26, p. 5643, 1985 DOI: 10.1016/S0040-4039(01)80908-4

InChI:InChI=1/C8H14O4/c1-6(4-7(9)11-2)5-8(10)12-3/h6H,4-5H2,1-3H3

Upstream product

• 67-56-1 methanol 
• 626-51-7 3-methyl glutaric acid 
• 67030-12-0 3-methylpentanedioyl dichloride 
• 41527-39-3 dimethyl (2E)-pent-2-enedioate 
• 676-58-4 methylmagnesium chloride 
• 52313-87-8 3-methyl-2-pentene-1,5-diacid dimethyl 
• 65844-74-8 2-methylpropan-1,1,3-tricarboxylic acid trimethyl ester 
• 623-43-8 crotonic acid methyl ester 
• 96-32-2 bromoacetic acid methyl ester 
• 88192-98-7 myxopyronin A 
• 1753-40-8 (R)-4-menthen-3-one 
• 5164-76-1 dimethyl glutaconate 
• 82538-51-0 (R)-5,5-dimethoxy-3-methylpentanoic acid methyl ester 
• 1427207-34-8 (4R,6R)-6-(hydroxymethyl)-4-methyltetrahydro-2H-pyran-2-one 

Downstream Products

• 4457-71-0 3-methylpentane-1,5-diol 
• 63473-60-9 (R)-3-methylpentanedioic acid monomethyl ester 
• 63473-60-9 (S)-5-methoxy-3-methyl-5-oxopentanoic acid 
• 2163-42-0 2-methyl-1.3-propanediol 
• 912293-10-8 C₂₀H₃₆O₄SSi 
• 912293-20-0 C₁₄H₂₂O₄S 
• 912293-11-9 C₁₄H₂₀O₄S 
• 912293-21-1 C₁₅H₂₄O₄S 
• 912293-12-0 C₁₅H₂₂O₄S 
• 853644-39-0 toluene-4-sulfonic acid 5-(4-cyano-phenoxy)-3-methyl-pentyl ester 
• 148054-23-3 3-methylpentane-1,5-diyl bis(4-methylbenzenesulfonate) 
• 708208-66-6 4-[3-methyl-5-(2-oxo-3-pyridin-4-yl-imidazolidin-1-yl)-pentyloxy]-benzonitrile 
• 1027529-98-1 toluene-4-sulfonic acid 3-methyl-5-[4-(2-methyl-2H-tetrazol-5-yl)-phenoxy]-pentyl ester 
• 866750-97-2 toluene-4-sulfonic acid 5-(4'-chloro-biphenyl-4-yloxy)-3-methyl-pentyl ester 

Relevant articles and documents

A Convenient Method for the Preparation of 3-Substituted Glutarate Diesters

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Toward aplyronine payloads for antibody-drug conjugates: Total synthesis of aplyronines A and D

The aplyronines are a family of antimitotic marine macrolides that disrupt cytoskeletal dynamics by dual targeting of both actin and tubulin. Given their picomolar cytotoxicity profile and unprecedented mode of action, the aplyronines represent an excellent candidate as a novel payload for the development of next-generation antibody-drug conjugates (ADCs) for cancer chemotherapy. Enabled by an improved second-generation synthesis of the macrolactone core 5, we have achieved the first total synthesis of the most potent congener aplyronine D together with a highly stereocontrolled synthesis of aplyronine A. To facilitate step economy, an adventurous site-selective esterification of the C7 hydroxyl group was performed to install the N,N,O-trimethylserine pharmacophore to directly afford aplyronines A and D. Toward the assembly of ADCs incorporating an aplyronine warhead, the C29-ester derivative 4 featuring an Fmoc-amino substituted linker attached to the actin-binding tail region was also prepared by adapting this flexible endgame.

Preparation method of high-purity and high-yield monomethyl 3-methylglutarate

The invention relates to a preparation method of high-purity and high-yield monomethyl 3-methylglutarate, and belongs to the field of organic synthesis. The preparation method comprises the followingsteps of (1) esterification reaction: performing esterification reaction on beta-methylglutaric acid and methyl alcohol to obtain beta-dimethyl methylglutarate; (2) alkaline hydrolysis reaction: adding a barium hydroxide methyl alcohol solution into the obtained beta-dimethyl methylglutarate to generate barium salt of the monomethyl 3-methylglutarate; (3) finished product preparation: performing hydrochloric acid acidification, diethyl ether extraction and rectification and purification on the barium salt of the monomethyl 3-methylglutarate to obtain the monomethyl 3-methylglutarate. The prepared monomethyl 3-methylglutarate has the advantages of high yield, high purity and high mono-esterification selectivity. The preparation method is scientific and reasonable; simplicity is realized; the implementation is easy; the method is suitable for industrial mass production.

Two potent OXE-R antagonists: Assignment of stereochemistry

5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is formed by the oxidation of 5-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid (5-HETE), which is a major metabolite of enzymatic oxidation of arachidonic acid (AA). 5-Oxo-ETE is the most potent lipid chemoattractant for human eosinophils. Its actions are mediated by the selective OXE receptor, which is therefore an attractive target in eosinophilic diseases such as allergic rhinitis and asthma. Recently, we have reported two excellent OXE receptor antagonists that have IC50 values at low nanomolar concentrations. Each of these antagonists has a chiral center, and the isolation of the individual enantiomers by chiral high-performance liquid chromatography (HPLC) revealed that in each case one enantiomer is over 300 times more potent than the other. To unambiguously assign the stereochemistry of these enantiomers and to provide access to larger amounts of the active compounds for biological testing, we report here their total synthesis.