1115-81-7

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-2-METHYLGLUTARIC ACID is used as a key intermediate for the synthesis of various pharmaceuticals, leveraging its chiral properties to create enantiomerically pure compounds that are essential in drug development. (R)-(+)-2-METHYLGLUTARIC ACID's ability to influence the biological activity of medications makes it a crucial component in this industry.
Used in Agrochemical Industry:
In the agrochemical sector, (R)-(+)-2-METHYLGLUTARIC ACID serves as an intermediate in the production of agrochemicals, contributing to the development of effective and targeted pest control solutions.
Used in Flavor and Fragrance Industry:
(R)-(+)-2-METHYLGLUTARIC ACID is utilized as a building block in the creation of flavors and fragrances, where its unique properties can be harnessed to develop novel scents and tastes for various applications.
Used in Research and Development:
(R)-(+)-2-METHYLGLUTARIC ACID is used as a research compound in the fields of medicine and biochemistry, where its chiral nature and reactivity are explored for potential applications in new drug discoveries and biochemical processes.
Used in Chemical Research:
In chemical research, (R)-(+)-2-METHYLGLUTARIC ACID is employed as a chiral building block to investigate the synthesis of complex organic molecules and to understand the role of stereochemistry in chemical reactions.

InChI:InChI=1/C6H10O4/c1-4(6(9)10)2-3-5(7)8/h4H,2-3H2,1H3,(H,7,8)(H,9,10)/t4-/m1/s1

Upstream product

• 18069-17-5 2-methylglutaric acid 
• 57-24-9 strychnidin-10-one 
• 62344-97-2 ethyl 4-cyanopentanoate 
• 92621-62-0 1L-(1,2,4/3)-1-Methyl-2,3,4-cyclohexantriol 
• 75281-35-5 (-)-trans,cis-nepetonic acid 
• 17948-87-7 (R)-2-Carboxymethyl-5-methyl-cyclopent-1-enecarboxylic acid 
• 2857-75-2 (R)-4-methyl-δ-valerolactone 
• 37779-39-8 (-)-(S)-2-methylpentane-1,5-diol 
• 43124-56-7 (+)-isoterpinolene 
• 64-19-7 acetic acid 
• 11005-20-2 Pseudohecogenin 
• 127-09-3 sodium acetate 
• 120057-26-3 gitogenin diacetate 
• 27126-42-7 ethyl 4-bromopentanoate 

Downstream Products

• 33514-22-6 dimethyl (R)-(-)-2-methylglutarate 
• 18545-83-0 (+)-(S)-diethyl 2-methylglutarate 

Relevant academic research and scientific papers

MONOTERPENOIDS-VI. ON THE OPTICAL PURITY OF (+)-CAR-3-ENE FROM PINUS ROXBURGHII, AND THE SOURCE OF RACEMIZATION OF (-)-MENTHOL DERIVED THEREFROM

It is shown that (+)-car-3-ene occurring in the oleoresin from Pinus roxburghii is optically pure.It is also demonstrated that in the production of (-)-menthol from (+)-car-3-ene by the MRC process, partial racemization of (-)-menthol has its origin at the stage of (+)-isoterpinolene.

Palmyrolide A, an unusually stabilized neuroactive macrolide from palmyra atoll cyanobacteria

Palmyrolide A (1) is a new neuroactive macrolide isolated from a marine cyanobacterial assemblage composed of Leptolyngbya cf. and Oscillatoria spp. collected from Palmyra Atoll. It features a rare N-methyl enamide and an intriguing t-butyl branch; the latter renders the adjacent lactone ester bond resistant to hydrolysis. Consistent with its significant suppression of calcium influx in cerebrocortical neurons (IC50 = 3.70 μM), palmyrolide A (1) showed a relatively potent sodium channel blocking activity in neuro-2a cells (IC50 = 5.2 μM), without appreciable cytotoxicity.

Asymmetric hydrodimerization of styrene by a chiral zirconium complex containing a tetradentate [OSSO]-type bis(phenolato) ligand

The chiral non racemic (Λ,R,R)-[OSSO]Zr(CH2Ph) 2 (1a) activated by methylaluminoxane (MAO) and in presence of H 2 produces the chiral hydrodimer (S)-1,3-diphenylbutane with good selectivity respect to the achiral 1,4-diphenylbutane. The absolute configuration of the chiral dimer and the effect of the hydrogen pressure on the ratio between 1,3-diphenylbutane and 1,4-diphenylbutane give useful information about the regiochemistry and stereochemistry of insertion of the styrene into the Zr-H bond.

Biosynthesis of the myxobacterial antibiotic corallopyronin A

Corallopyronin A is a myxobacterial compound with potent antibacterial activity. Feeding experiments with labelled precursors resulted in the deduction of all biosynthetic building blocks for corallopyronin A and revealed an unusual feature of this metabolite: its biosynthesis from two chains, one solely PKS-derived and the other NRPS/PKS-derived. The starter molecule is believed to be carbonic acid or its monomethyl ester. The putative corallopyronin A biosynthetic gene cluster is a trans-AT-type mixed PKS/NRPS gene cluster, containing a β-branching cassette. Striking features of this gene cluster are a NRPS-like adenylation domain that is part of a PKS-type module and is believed to be responsible for glycine incorporation, as well as split modules with individual domains occurring on different genes. It is suggested that CorB is a transacting ketosynthase and it is proposed that it catalyses the Claisen condensation responsible for the interconnection of the two chains. Additionally, the stereochemistry of corallopyronin A was deduced by a combination of a modified Mosher's method and ozonolysis with subsequent chiral GC analyses.

Sulfated alkenes from the echinus Temnopleurus hardwickii

Three new sulfated alkenes (1-3), trimethylammonium (5R)-5,9-dimethyl-(3E)- 3,8-decadienyl-1-sulfate, dimethylammonium (5R)-5,9-dimethyl-(3E)-3,8- decadienyl-1-sulfate, and 2′-methyl-4′-oxobutan-2-ylammonium (5R)-5,9-dimethyl-(3E)-3,8-decadienyl-1-sulfate

Catalytic asymmetric protonation of chiral calcium enolates via 1,4-addition of malonates

Catalytic asymmetric protonation of chiral calcium enolates was performed. Chiral calcium enolates, prepared in situ from imides and malonates via 1,4-addition in the presence of catalytic amounts of Ca(OEt)2, Ph-PyBox, and achiral phenol, were smoothly protonated to afford adducts bearing tertiary asymmetric carbons in high yields with high enantioselectivities. The adducts were readily converted to optically active 2-substituted 1,5-dicarboxylic acid derivatives.

Sesterterpenoids from the sponge Sarcotragus sp.

Nineteen new sesterterpenoids and eight known compounds were isolated from the sponge Sarcotragus sp. collected from Soheuksan Island, Korea. The structures of these compounds were determined to be linear sesterterpenoids containing furan or related oxygenated functionalities on the basis of combined chemical and spectroscopic analyses. In addition, the configurations of several previously undetermined compounds were assigned. Several compounds exhibited moderate to major antibacterial activity (compounds 1-3, 17, 18) and cytotoxicity (3, 11, 12) against the K562 cell line and inhibitory activity against isocitrate lyase (6, 13).

Terpenoid Chemistry. XXIV (1R)-1-Methoxymyodesert-3-ene, an Iridoid Constituent of Myoporum deserti (Myoporaceae)

A common variety of Myoporum deserti A.Cunn. (Ellangowan Poison Bush) yields an essential oil consisting largely of the iridoid monoterpene, (1R)-1-methoxymyodesert-3-ene, C11H18O2, (1R,4aS,7R,7aR)-1-methoxy-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopentapyran, b.p. 67 deg/2 mm, D - 165 deg.This cyclic acetal is hydrolysed to methanol and a mixture of two epimeric cyclopentanoid dialdehydes which are oxidized to the two epimeric trans, trans-nepetalinic acids and yield (+)-(R)-actinidine with Brady's reagent, (1R)-1-Methoxymyodesert-3-ene is oxidized by ozone/hydrogen peroxide to (1R,2R,5R)-2-acetyl-5-methylcyclopentanecarboxylic acid.Hydrogenation yields mainly (1R)-methoxymyodesertan, hydrolysed by aqueous maleic acid at room temperature to methanol and a cyclic hemiacetal, (1R,4R,4aR,7R,7aR)-4,7-dimethyl-1,3,4,4a,5,6,7,7a-octahydrocyclopentapyran-1-ol.Oxidation of this cis,cis-hemiacetal by bromine in acetate buffer yields a lactone further oxidized by chromic acid to (2R,1',S',2'R,3'R)-2-(2'-carboxy-3'-methylcyclopentyl)-propionic acid. (1R)-1-Methoxymyodesertan, refluxed with aqueous phthalic acid, yields (+)-(4R,4aR,7R)-4,7-dimethyl-3,4,4a,5,6,7-hexahydrocyclopentapyran.Treatment of the hexahydropentapyran, the cis,cis-hemiacetal or (1R)-1-methoxymyodesertan with hydrochloric acid yields a trans,trans-hemiacetal, (1R,4R,4aR,7R,7aS)-4,7-dimethyl-1,3,4,4a,5,6,7,7a-octahydrocyclopentapyran-1-ol,which equilibrates in solution to a mixture of α- and β-anomers.Spectral studies of these and other products establish the configuration of the natural product at C1. (1R)-1-Methoxymyodesert-3-ene is not toxic to sheep as are the β-substituted furans characteristic of most other chemovarieties of M. deserti.