1730-92-3

Basic information

• Product Name: (S)-(+)-3-Methylpentanoic acid
• Synonyms: (S)-(+)-3-METHYLPENTANOIC ACID;(S)-3-METHYL-PENTANOIC ACID;(S)-Methylvaleric acid;(S)-3-Methyl-pentanoic;(S)-3-Methylvaleric Acid;(3S)-3-methylpentanoic acid
• CAS NO: 1730-92-3
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.16
• Product Categories: pharmacetical
• Mol File: 1730-92-3.mol

Chemical Properties

• Boiling Point: 198.999 °C at 760 mmHg
• Flash Point: 88.369 °C
• Appearance: /
• Density: 0.948 g/cm³
• Storage Temp.: 2-8°C
• PKA: 4.80±0.10(Predicted)
• CAS DataBase Reference: (S)-(+)-3-Methylpentanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-3-Methylpentanoic acid(1730-92-3)
• EPA Substance Registry System: (S)-(+)-3-Methylpentanoic acid(1730-92-3)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 1730-92-3(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
(S)-(+)-3-Methylpentanoic acid is used as a precursor for the production of esters, which are essential ingredients in creating artificial flavors and perfumes. Its ability to contribute unique scents and tastes makes it a valuable component in this industry.
Used in Pharmaceutical Industry:
(S)-(+)-3-Methylpentanoic acid is utilized in the development and production of pharmaceuticals, serving as a key building block for various medicinal compounds. Its versatility in chemical synthesis allows for the creation of a wide range of pharmaceutical products.
Used in Food Preservation:
(S)-(+)-3-Methylpentanoic acid is used as a preservative in the food industry to maintain the freshness and quality of various products. Its antimicrobial properties help control microbial growth, ensuring the safety and longevity of food items.
Used in Industrial Microbial Control:
(S)-(+)-3-Methylpentanoic acid is employed in various industrial applications to control microbial growth. Its antimicrobial properties make it an effective solution for preserving products and preventing contamination, particularly in industries such as cosmetics, personal care, and household products.

Upstream product

• 5773-63-7 (+)-(S)-3-methylpentanenitrile 
• 73-32-5 L-isoleucine 
• 53254-65-2 (-)-2-(10-Pinen-2-yl)-butan-1,4-diol 
• 53254-68-5 C₂₈H₃₆O₆S₂ 
• 1122577-96-1 (S)-3-methylpentanoic acid ((1'S,2'S)-2'-hydroxy-1'-methyl-2'-phenylethyl)(methyl)amide 
• 137-32-6 (+/-)-2-methyl-1-butanol 
• 137-32-6 (-)-2-Methylbutan-1-ol 
• 124-38-9 carbon dioxide 
• 534-00-9 (+)-1-bromo-2-methylbutane 
• 534-00-9 (S)-2-methylbutyl bromide 
• 2313-61-3 (2R+2S,4S)-4-methyl-2-hexanol 
• 53254-54-9 (R)-((1R)-pin-2-en-10-yl)-succinic acid-anhydride 
• 104282-47-5 (E)-Pent-2-enoic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104651-08-3 N-<(E)-3-methyl-2-pentenoyl>bornane-10,2-sultam 

Downstream Products

• 178685-26-2 (S)-3-Methyl-pentanoic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-hydroxy-3-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-4-yl ester 
• 178685-29-5 (S)-3-Methyl-pentanoic acid (2R,3R,4S,5S,6R)-6-acetoxymethyl-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-4-hydroxy-5-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester 
• 178685-30-8 (S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-4-((S)-2-methyl-butyryloxy)-5-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester 
• 134628-47-0 (S)-3-Methyl-pentanoic acid (S)-3-methyl-2-(toluene-4-sulfonyloxymethyl)-pentyl ester 
• 134628-51-6 benzyl (5S,1'S)-4-benzyloxycarbonyl-5-methyl-2-(1'-methylpropyl)heptanoate 
• 134679-82-6 (2R,4S)-2,4-Bis-((S)-sec-butyl)-pentanedioic acid dibenzyl ester 
• 13777-67-8 (S)-4-methyl-hexan-2-one semicarbazone 
• 106793-38-8 (s)-4'-(2-methylbutylcarbonyloxy)phenol 
• 1122577-96-1 (S)-3-methylpentanoic acid ((1'S,2'S)-2'-hydroxy-1'-methyl-2'-phenylethyl)(methyl)amide 
• 1449396-57-9 C₁₉H₃₁NO₂ 
• 5870-68-8 (S)-3-methyl-pentanoic acid ethyl ester 
• 178685-23-9 (S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-2-methyl-butyryloxy)-4-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester 
• 178685-28-4 (S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-4-allyloxy-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester 
• 178685-25-1 (S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-2-acetoxymethyl-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-(4-methoxy-benzyloxy)-3-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-4-yl ester 

Relevant articles and documents

Naphthyl 3,4,6-tri-O-methyl-β-D-glucopyranoside as a chiral auxiliary in an asymmetric 1,4-addition reaction

Naphthyl 3,4,6-tri-O-methyl-β-D-glucopyranoside, easily synthesized from tri-O-acetyl-D-glucal, has been applied as a chiral auxiliary in an asymmetric Michael addition to the 2-O-crotonate. A very high facial diastereoselection (>95%) was obtained. No diastereoselection was observed when 1,3,4,6-tetra-O-methyl-β-D-glucopyranoside was used as the chiral auxiliary. A stereochemical model, taking into account steric shielding and π-stacking effects, is proposed on the basis of the observed results.

Stereoselective synthesis of belactosin C and its derivatives using a catalytic proline catalyzed crossed-aldol reaction

A highly practical and concise stereoselective total synthesis of belactosin C and synthetic variants was achieved using an S-proline catalyzed crossed-aldol reaction as the key step.

Effect of chiral substituents on the secondary structure of poly(N-alkynylamides)

Optically active N-alkynylamides (S)-HC≡C(CH2) aNHCO(CH2)bCH(CH3)CH 2CH3 (1: a = 1, b = 0; 2: a = 1, b = 1; 3: a = 1, b = 2; 4: a = 1, b = 3; 5: a = 2, b = 0; 6: a = 2, b = 1; 7: a = 3, b = 0), having several numbers of methylene spacers between the ethynyl group and chiral carbon or amide group, and (S)-HC≡C(CH2)2OCOCH 2CH(CH3)CH2CH3 (8) were polymerized with (nbd)Rh+[η6-C6H5B --(C6H5)3] to afford the corresponding polymers with moderate molecular weights (Mn = 11 000-21 000) in 67-99% yields. The 1H NMR spectra demonstrated that the resulting polymers had stereoregular structures (cis content = 79-100%). CD, UV-vis, and IR spectroscopic studies revealed that the position of the amide group and chiral center strongly affects the pitch and stability of helical structure of the polymers, and intramolecular hydrogen bonding is formed between the amide groups in CHCl3. By comparison with the results of CD measurements and molecular orbital calculation, the sign of Cotton effect and the relationship between the screw sense of poly(N-propargylamides) was elucidated.

Differential Effects of β3- versus β2-Amino Acid Residues on the Helicity and Recognition Properties of Bim BH3-Derived α/β-Peptides

Oligomers containing α- and β-amino acid residues (α/β-peptides) have been shown to mimic the α-helical conformation of conventional peptides when the unnatural residues are derived from β3-amino acids or cyclic β-amino acids, but the impact of incorporating β2 residues has received little attention. The effects of β2 residues on the conformation and recognition behavior of α/β-peptides that mimic an isolated α-helix were investigated. This effort has focused on 26-mers based on the Bim BH3 domain; a set of isomers with identical α/β backbones that differ only in the placement of certain side chains along the backbone (β3 vs. β2 substitution) was compared. Circular dichroism data suggest that β2 residues can be helix-destabilizing relative to β3 residues, although the size of this effect seems to depend on side chain identity. Binding data show that β3→β2 substitution at sites that contact a partner protein, Bcl-xL, can influence affinity in a way that transcends effects on helicity.

Novel iridium complex of spirophosphine-carboxylic acid, preparation method and application thereof

The invention relates to an iridium complex of spirophosphine-carboxylic acid, a preparation method and application thereof. The iridium complex of spirophosphine-carboxylic acid is a compound with a structure shown as formula (I), wherein n=0-3; and the values of R1, R2, R3, R4, R5, R6 and R7 are defined as claim 1. Substituted 7-carboxyl-7'-diarylphosphino-1, 1'-spirobiindane is taken as the ligand to from carboxylic acid anion under the action of alkali, and then complexation with an iridium precursor is carried out to obtain different iridium/spirophosphine-carboxylic acid complexes. The iridium complex of spirophosphine-carboxylic acid provided by the invention can catalyze the asymmetric hydrogenation reaction of a variety of unsaturated carboxylic acids, and show high activity and enantioselectivity, thus having good industrialization prospects. (formula (I)).

Neutral iridium catalysts with chiral phosphine-carboxy ligands for asymmetric hydrogenation of unsaturated carboxylic acids

We developed neutral iridium catalysts with chiral spiro phosphine-carboxy ligands (SpiroCAP) for asymmetric hydrogenation of unsaturated carboxylic acids. Different from the cationic Crabtree-type catalysts, the iridium catalysts with chiral spiro phosphine-carboxy ligands are neutral and do not require the use of a tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (BArF?) counterion, which is necessary for stabilizing cationic Crabtree-type catalysts. Another advantage of the neutral iridium catalysts is that they have high stability and have a long lifetime in air. The new iridium catalysts with chiral spiro phosphine-carboxy ligands exhibit unprecedented high enantioselectivity (up to 99.4% ee) in the asymmetric hydrogenations of various unsaturated carboxylic acids, particularly for 3-alkyl-3-methylenepropionic acids, which are challenging substrates for other chiral catalysts.

Synthesis of Polysubstituted γ-Butenolides via a Radical Pathway: Cyclization of α-Bromo Aluminium Acetals and Comparison with the Cyclization of α-Bromoesters at High Temperature

Polysubstituted butenolides were obtained in good to high yields from α-bromoesters derived from propargyl alcohols by a one-pot reaction involving the radical cyclization of α-bromo aluminium acetals, followed by the oxidation of the resulting cyclic aluminium acetals in an Oppenauer-type process and migration of the exocyclic C-C bond into the α,β-position. Comparison with the direct cyclization of α-bromoesters at high temperature and under high dilution conditions is described. Deuterium-labelling experiments allowed us to uncover "invisible" 1,5-hydrogen atom transfers (1,5-HATs) that occur during these cyclization processes, together with the consequences of the latter in the epimerization of stereogenic centres. Compared to the classical approach, the cyclization of aluminium acetals proved to be highly chemoselective and its efficiency was illustrated by the short total syntheses of optically enriched γ-butenolides isolated from Plagiomnium undulatum and from Kyrtuhrix maculans.

Design and synthesis of the stabilized analogs of belactosin A with the unnatural cis-cyclopropane structure

The belactosin A analog 2a, having the unnatural cis-cyclopropane structure instead of the trans-cyclopropane structure in belactosin A, is a much more potent proteasome inhibitor than belactosin A. However, its cell growth inhibitory effect is rather lower than that expected from its remarkable proteasome inhibitory effect, probably due to its instability under cellular conditions. We hypothesized that the instability of 2a was due to chemical and enzymatic hydrolysis of the strained β-lactone moiety. Thus, to increase the stability of 2a by chemical modification, its analogs with a sterically more hindered β-lactone moiety and/or cyclopropylic strain-based conformational restriction were designed and synthesized, resulting in the identification of a stabilized analog 6a as a proteasome inhibitor with cell growth inhibitory effects. Our findings suggest that the chemical and biological stability of 2a is significantly affected by the steric hindrance around its β-lactone carbonyl moiety and the conformational flexibility of the molecule.

Efficient synthesis of (2S,3S)-2-ethyl-3-methylvaleramide using (1S,2S)-pseudoephedrine as a chiral auxiliary

An efficient and scaleable synthesis of (2S,3S)-2-ethyl-3-methylvaleramide (1) has been developed starting from inexpensive and readily available L-isoleucine. The key step in this process is an asymmetric alkylation using (1S,2S)-pseudoephedrine as a chiral auxiliary. A practical procedure was developed to remove the sterically hindered pseudoephedrine auxiliary from the amide. The process consists of eight chemical steps and five isolations without any chromatographic purification. It has been successfully implemented to prepare several multikilogram batches of the target compound 1 in 41% overall yield.

Volatile lactones - (5S,S)-5-methyl-3-(methylalkyl)furan-2(5H)-ones - Identified in the submerged cultivation of Streptomyces avermitilis

Six new compounds have been identified in the volatile fractions produced during the submerged cultivation of Streptomyces avermitilis. By recording the GC/MS, GC/FTIR, CD, 1H and 13C NMR data and by performing chemical degradation experiments, these compounds were determined to be (5S,S)-5-methyl-3-(methylalkyl)furan-2(5H)-ones. Herein, the existence of volatile lactones with an anteiso structure of the side-chain is thus documented for the first time. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.