17407-55-5

Basic information

• Product Name: (S)-(+)-2-HYDROXY-3-METHYLBUTYRIC ACID
• Synonyms: (S)-(+)-2-HYDROXY-3-METHYLBUTANOIC ACID;(S)-(+)-2-HYDROXY-3-METHYLBUTYRIC ACID;(S)-2-HYDROXY-3-METHYLBUTYRIC ACID;L-ALPHA-HYDROXYISOVALERIC ACID;2S-HYDROXY-3-METHYL-BUTANOIC ACID;2-HYDROXY-3-METHYLBUTYRIC ACID;3-METHYL-2-HYDROXY-BUTANOIC ACID;(S)-(+)-2-HYDROXY-3-METHYLBUTYRIC ACID, 99% (99% EE/GLC)
• CAS NO: 17407-55-5
• Molecular Formula: C₅H₁₀O₃
• Molecular Weight: 118.13
• EINECS: 223-697-5
• Product Categories: pharmacetical;Aliphatics;Carboxylic Acids;chiral;Carboxylic Acids
• Mol File: 17407-55-5.mol
• Article Data: 40

Chemical Properties

• Melting Point: 68-70 °C(lit.)
• Boiling Point: 124-125 °C13 mm Hg(lit.)
• Flash Point: 112℃
• Appearance: White/Powder
• Density: 1.136
• Vapor Pressure: 0.00793mmHg at 25°C
• Refractive Index: 1.4641 (estimate)
• Storage Temp.: 2-8°C
• PKA: 3.87±0.16(Predicted)
• BRN: 1721140
• CAS DataBase Reference: (S)-(+)-2-HYDROXY-3-METHYLBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2-HYDROXY-3-METHYLBUTYRIC ACID(17407-55-5)
• EPA Substance Registry System: (S)-(+)-2-HYDROXY-3-METHYLBUTYRIC ACID(17407-55-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 17407-55-5(Hazardous Substances Data)

Usage

Chemical Properties

white fine crystalline powder

Uses

A useful chiral building block for peptide synthesis. Used in the preparation of the cytotoxic didemnin cyclopeptides and of the antineoplastic agent dolastatin 15.

InChI:InChI=1/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/p-1/t4-/m0/s1

Upstream product

• 56-23-5 tetrachloromethane 
• 18556-89-3 3-methyl-2-oxobutanal 
• 88246-66-6 1,1-bis(trimethylsilyloxy)-3-methyl-1-butene 
• 10323-40-7 2-bromoisovaleric acid 
• 10303-64-7 2-hydroxy-4-methylpentanoic acid 
• 75-30-9 2-iodo-propane 
• 95-92-1 oxalic acid diethyl ester 
• 7664-93-9 sulfuric acid 
• 112757-19-4 (+)-N-(α-hydroxy-isovaleryl)-glycine 
• 123-91-1 1,4-dioxane 
• 72-18-4 L-valine 
• 41029-44-1 isopropyl triflate 
• 134001-65-3 (S)-2-Hydroxy-3,N-dimethyl-butyramide 
• 1187551-28-5 grassystatin A 

Downstream Products

• 759-05-7 3-methyl-2-ketobutanoic acid 
• 78-84-2 isobutyraldehyde 
• 17407-56-6 (R)-2-Hydroxy-3-methylbutyric acid 
• 54639-27-9 N-phenyl-2-hydroxy-3-methyl-butanamide 
• 24347-63-5 methyl (S)-2-hydroxy-3-methylbutanoate 
• 2528-17-8 α-hydroxy-isovaleric acid t-butyl ester 
• 83490-55-5 N-Benzyl-2-hydroxy-3-methylbutyrohydroxamsaeure 
• 83490-54-4 N-Ethyl-2-hydroxy-3-methylbutyrohydroxamsaeure 
• 78-83-1 2-methyl-propan-1-ol 
• 124-38-9 carbon dioxide 
• 134816-19-6 (S)-Hiva-(S)-Phe-OMe 
• 142350-55-8 benzyl N-<(2S)-2-hydroxy-isovaleryl>-L-phenylalaninate 
• 73604-33-8 L-α-hydroxyisovaleryl-Leu-Val-Phe-OCH3 
• 87063-73-8 5-Isopropyl-2,2-dimethyl-[1,3]dioxolan-4-one 

Relevant articles and documents

Pithohirolide, an antimicrobial tetradepsipeptide from a fungus Pithomyces chartarum

Pithohirolide (1), a new depsipeptide, was isolated from an ascomycetous fungus Pithomyces chartarum TAMA 581. The planar structure of 1 was elucidated on the basis of NMR and MS analyses and the absolute configuration was determined by the advanced Marfey’s analysis, chiral-phase HPLC analysis, and synthesis of degradation product. Compound 1 possesses a cyclic structure comprising (S)-2-hydroxy-3-phenylpropanoic acid, (S)-3-hydroxy-3-phenylpropanoic acid, (S)-2-hydroxyisovaleric acid, and N-methyl-l-alanine, connected via three ester and one amide linkages. Compound 1 exhibited antimicrobial activity against Staphylococcus aureus and Saccharomyces cerevisiae at MIC 3.1 μg ml?1.

Rare Streptomyces N-formyl amino-salicylamides inhibit oncogenic K-Ras

During a search for inhibitors of oncogenic K-Ras, we detected two known and two new examples of the rare neoantimycin structure class from a liquid cultivation of Streptomyces orinoci, and reassigned/assigned structures to all based on detailed spectroscopic analysis and microscale C3 Marfey's and C3 Mosher chemical degradation/derivatization/analysis. SAR investigations inclusive of the biosynthetically related antimycins and respirantin, and synthetic benzoxazolone, documented a unique N-formyl amino-salicylamide pharmacophore as a potent inhibitor of oncogenic K-Ras.

Structure revision of isocereulide A, an isoform of the food poisoning emetic Bacillus cereus toxin cereulide

The emetic Bacillus cereus toxin cereulide presents an enormous safety hazard in the food industry, inducing emesis and nausea after the consumption of contaminated foods. Additional to cereulide itself, seven structurally related isoforms, namely the isocereulides A-G, have already been elucidated in their chemical structure and could further be identified in B. cereus contaminated food samples. The newly performed isolation of isocereulide A allowed, for the first time, 1D- and 2D-NMR spectroscopy of a biosynthetically produced isocereulide, revealing results that contradict previous assumptions of an L-O-Leu moiety within its chemical structure. By furthermore applying posthydrolytical dipeptide analysis, amino acid and α-hydroxy acid analysis by means of UPLC-ESITOF- MS, as well as MSn sequencing, the structure of previously reported isocereulide A could be corrected. Instead of the L-O-Leu as assumed to date, one L-O-Ile unit could be verified in the cyclic dodecadepsipeptide, revising the structure of isocereulide A to [(D-O-Leu-D-Ala-L-O-Val-L-Val)2(DO- Leu-D-Ala-L-O-Ile-L-Val)].

Asymmetric Synthesis of Optically Active 3-Cyclohexene-1-carboxylic Acid Utilizing Lactic Ester as a Chiral Auxiliary in the Diastereoselective Diels–Alder Reaction

The optically active 3-cyclohexene-1-carboxylic acid was synthesized through a TiCl4-catalyzed diastereoselective Diels–Alder reaction utilizing lactic acid ester as a chiral auxiliary, which can be removed by washing with H2O. The (S)- and (R)-isomers were both derived from easily available ethyl l-lactate.

Odobromoamide, a terminal alkynyl bromide-containing cyclodepsipeptide from the marine cyanobacterium okeania sp.

The bioassay-guided fractionation of the Okinawan marine cyanobacterium Okeania sp. led to the isolation of the novel cyclodepsipeptide odobromoamide (1). The gross structure of 1 was determined by spectroscopic analyses, and its absolute stereochemistry was determined using a variety of different methods, including chemical derivatization and degradation followed by HPLC analysis. In addition, odobromoamide (1) exhibited broad-spectrum cytotoxicity against a human cancer cell line panel.