1730-91-2

Usage

Uses

Used in Chemical Synthesis:
(S)-(+)-2-Methylbutyric acid is used as a chiral starting reagent for various synthetic preparations. Its unique chiral properties make it a valuable component in the creation of different compounds, particularly in the pharmaceutical and chemical industries.
Used in Pheromone Production:
In the field of chemical ecology, (S)-(+)-2-Methylbutyric acid is used in the preparation of stereoisomers of (R)-lavandulyl (S)-2-methylbutanoate and (R)-maconelliyl (S)-2-methylbutanoate. These compounds are female sex pheromones found in the pink hibiscus mealybug, an invasive insect species. The production and use of these pheromones can aid in the management and control of this pest by disrupting their mating behavior.
Used in Pharmaceutical Industry:
(S)-(+)-2-Methylbutyric acid, due to its chiral nature, can be utilized in the development of enantiomer-specific drugs. Enantiomer-specific drugs are designed to interact with biological targets in a way that only one enantiomer is effective, leading to more targeted and potentially safer medications.
Used in Flavor and Fragrance Industry:
The chiral properties of (S)-(+)-2-Methylbutyric acid can also be exploited in the creation of specific flavors and fragrances. Chiral compounds often have distinct smells or tastes, and the (S)-enantiomer may provide unique sensory characteristics that can be valuable in the development of new products in this industry.

Purification Methods

Purify the acid by distilling it in vacuo [Sax & Bergmann J Am Chem Soc 77 1910 1955, Doering & Aschner J Am Chem Soc 75 393 1953 ]. The methyl ester is formed by addition of diazomethane and has b 112-115o/760mm, [] D +21.1o (c 1.7, MeOH). [Beilstein 2 IV 888.]

InChI:InChI=1/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)/t4-/m1/s1

Upstream product

• 595-84-6 2-ethyl-2-methylmalonic acid 
• 147-71-7 D-tartaric acid 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 319-78-8 D-Isoleucine 
• 73-32-5 L-isoleucine 
• 56-40-6 glycine 
• 147-85-3 L-proline 
• 109-52-4 valeric acid 
• 116-53-0 2-Methylbutanoic acid 
• 80-59-1 Tiglic acid 
• 6565-55-5 (S,S,S)-1,3,5-Tris(1-methylpropyl)benzol 
• 134773-09-4 (R)-2-tert-Butyl-3-((S)-2-methyl-butyryl)-2,3-dihydro-1H-pyrimidin-4-one 
• 77397-07-0 (S)-1-((S)-2-Hydroxymethyl-pyrrolidin-1-yl)-2-methyl-butan-1-one 
• 63157-98-2 (S)-(-)-N-1-phenylethyl-(S)-(+)-2-methylbutyramide 

Downstream Products

• 10307-60-5 (S)-2-methylbutyric acid methyl ester 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 27763-54-8 (S)-2-methylbutanoyl chloride 
• 16725-76-1 (S)-2-methyl-1-phenylbutan-1-one 
• 99296-46-5 (S)-2-methyl-butyric acid-(4-nitro-phenyl ester) 
• 37878-21-0 (S)-N-<(S)-2-Methyl-1-oxobutyl>phenylalanin 
• 131267-65-7 2,1',3',4',6'-Penta-O-benzyl-6-O-(4-methoxybenzyl)-3,4-di-O-<(S)-2-methylbutyryl>sucrose 
• 131267-59-9 3-O-Allyl-2,1',3',4',6'-penta-O-benzyl-6-O-(4-methoxybenzyl)-4-O-<(S)-2-methylbutyryl>sucrose 
• 131284-46-3 2,1',3',4',6'-Penta-O-benzyl-6-O-decanoyl-4-O-isobutyryl-3-O-<(S)-2-methylbutyryl>sucrose 
• 108712-66-9 (S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester 
• 90344-20-0 (S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-{2-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester 
• 84131-91-9 (S)-(+)-2-methylbutyric anhydride 
• 78018-27-6 (S)-(+) 14-(2-Methylbutyryl)dictyocarpine 
• 78039-66-4 S-(+)-14-(2-Methylbutyryl)browniine, Glaucedine 

Relevant academic research and scientific papers

Asymmetric hydrogenation of an α-unsaturated carboxylic acid catalyzed by intact chiral transition metal carbonyl clusters-diastereomeric control of enantioselectivity

Twenty clusters of the general formula [(μ-H)2Ru3(μ3-S)(CO)7(μ-P-P?)] (P-P? = chiral diphosphine of the ferrocene-based Walphos or Josiphos families) have been synthesised and characterised. The clusters have be

Asymmetric [2,3]-Wittig rearrangements with chiral, phosphorus anion-stabilizing groups

The [2,3]-Wittig rearrangement of a chirally-modified phosphorus stabilized anion proceeds readily and with excellent diastereo- and enantioselectivity for alkyloxymethyl and (Z)-2-butenyloxymethyl derivatives.

Conformational study of poly(N-propargylamides) having bulky pendant groups

N-Propargylamides having chiral centers at the α-carbon of the amide groups, 1-3, were polymerized with (nbd)Rh+[η6-C6H5B-(C 6H5)3] to afford polymers with moderate molecular weights (Mn = 6000-32 000) in good yield. The 1H NMR spectra demonstrated that the polymers have stereoregular structures (cis = 100%). The polymers were proven to take a helical conformation with an excess of one- handed screw sense in CHCl3, which was supported by their intense CD effects and large optical rotations. It was confirmed that the helical structure was stabilized not only by the steric repulsion but also by the intramolecular hydrogen bonds between the pendant groups. CD spectroscopic study showed that the helical structure is more stable than that of the polymers without a branch at the α-position, which allowed the polymers to exist in the helical state in various solvents. The electronic absorption, CD effects, and optical rotations of the polymers closely correlated to the extent of the hydrogen bonding between the pendant amide groups.

Diastereomeric control of enantioselectivity: Evidence for metal cluster catalysis

Enantioselective hydrogenation of tiglic acid effected by diastereomers of the general formula [(μ-H)2Ru3(μ3-S)(CO) 7(μ-P-P*)] (P-P* = chiral Walphos diphosphine ligand) strongly supports catalysis by intact Ru

Palladium nanoparticle-graphene catalysts for asymmetric hydrogenation

We report for the first time the application of palladium nanoparticle-graphene (Pd/Gn) catalysts in the asymmetric hydrogenation of aliphatic α,β-unsaturated carboxylic acids using cinchonidine as chiral modifier. Pd/Gns were prepared by deposition-preci

Chiral 2-alkylbranched acids, esters and alcohols. Preparation and stereospecific flavour evaluation

Racemic 2-alkylbranched acids are transformed to diastereomeric derivatives with (S)-2-hydroxy-3-phenylpropionic acid-N-methylamide of (S)-(-)-1-phenylethylamine and separated by liquid chromatography to pure diastereoisomers, which are subsequently hydrolyzed to yield optically pure acids. Enantiomeric alcohols are generated by LiAlH4-reduction of the corresponding acids, esters are synthesized by different methods. The odour impression of the enantiomeric compounds is investigated.

Toosendanin relatives, trypanocidal principles from Meliae Cortex

Africa Trypanosomiasis remains a serious health problem, but the approved drugs for this disease are so few that novel trypanocidal compounds are demanded. In search for trypanocidal principles from medicinal plants, we found MeOH extracts of Meliae Cortex with potent activity through the screening from about 300 kinds of methanolic extract. By bioassay-guided fractionation from this extract through the liquid–liquid partition and subsequent chromatographic technique using silica gel and ODS, finally we disclosed toosendanin (1) and its relatives as active principles. These active congeners showed not only potent trypanocidal activity but also little cytotoxicity to display the excellent selective index. Taking the isolated amount as well as trypanocidal activity into consideration, 1 was disclosed to be the responsible active principle in Meliae Cortex. Additionally, the derivatives of 1 were chemically prepared from 1 and bioactivity of them were also evaluated. Through the comparison with their trypanocidal activity among the isolated relatives and the synthesized derivatives of 1, the epoxide moiety was revealed to be essential for their potent trypanocidal activity. Furthermore, 3-O-acetyl group and 7-hydroxyl group were presumed to be important functional groups and introduction of methylpropionyl group into hemiacetal hydroxy moiety was clarified to enhance their typanocidal activity.

Achiral amine additives in the enantioselective hydrogenation of aliphatic α,β-unsaturated acids over cinchonidine-modified Pd/Al 2O3 catalyst

The effect of the achiral amine additive structure was studied on the enantioselective hydrogenation of (E)-2-methyl-2-butenoic acid and (E)-2-methyl-2-hexenoic acid over Pd/Al2O3 catalyst modified by cinchonidine. It was found that

Synthesis and evaluation of a new steroidal BINAP type phosphine

The short and high yielding synthesis of a new cis-configured bissteroidal phosphine 7 is reported. The comparison of these new phosphines as ligands in ruthenium-based hydrogenation catalysts with the previously synthesized diastereomeric trans-configured phosphines 20 shows that the steroid backbone exerts only a minor influence on the enantioselection of the ruthenium catalysts and confirms that the bissteroidal phosphines behave as 'pseudo'-enantiomers in spite of their diastereomeric nature. Evidence is presented that the mode of catalyst preparation, i.e. catalyst structure, is the crucial reaction parameter which mainly determines the enantiomeric excess of the hydrogenation products. (C) 2000 Elsevier Science Ltd.

Eight new diterpenoids and two new nor-diterpenoids from the stems of Croton cascarilloides

From the stems of Croton cascarilloides, eight new diterpenoids, named crotocascarins A-H (1-8), having a crotofolane skeleton were isolated along with two new nor-diterpenoids (9 and 10), named crotocascarins α and β, derived through rearrangement of the crotofolane skeleton. The structures of these compounds were elucidated by means of extensive one- and two-dimensional NMR spectroscopic analyses. The absolute structures of the diterpene moiety were determined by application of the circular dichroism (CD) rule for the γ-lactone ring. The relative structures of the two crotofolanes (1 and 2) and one rearranged compound (9) were confirmed by X-ray crystallographic analyses. Compounds 1, 2 and 9 possessed 2-methylbutyric acid in their molecules, the absolute configuration of which was found to be 2S by comparison of its HPLC behavior with that of an authentic sample. Therefore, the absolute structures of these crotocascarins (1, 2 and 9) were unambiguously determined. The absolute structures of crotofolanes are reported for the first time in this paper.