27372-03-8

Basic information

• Product Name: 3-Hydroxy-2-methylbutanoic Acid
• Synonyms: 3-Hydroxy-2-Methylbutanoic Acid Ethyl Ester;3-Hydroxy-2-methylbutanoic Acid (Mixture of Diastereomers);(+/-)-ETHYL 3-HYDROXY-2-METHYLBUTYRATE
• CAS NO: 27372-03-8
• Molecular Formula: C₇H₁₄O₃
• Molecular Weight: 118.1311
• Product Categories: Aliphatics
• Mol File: 27372-03-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 215.7°C at 760 mmHg
• Flash Point: 83.8°C
• Appearance: /
• Density: 1.002g/cm³
• Vapor Pressure: 0.0316mmHg at 25°C
• Refractive Index: 1.43
• Storage Temp.: Refrigerator
• Solubility: Dichloromethane, Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 14.51±0.20(Predicted)
• CAS DataBase Reference: 3-Hydroxy-2-methylbutanoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-2-methylbutanoic Acid(27372-03-8)
• EPA Substance Registry System: 3-Hydroxy-2-methylbutanoic Acid(27372-03-8)

Safety Data

• Hazardous Substances Data: 27372-03-8(Hazardous Substances Data)

Usage

Description

3-Hydroxy-2-methylbutanoic Acid is an organic compound with the molecular formula C5H10O3. It is a derivative of hydroxybutanoic acid, featuring a methyl group at the second carbon and a hydroxyl group at the third carbon. 3-Hydroxy-2-methylbutanoic Acid is known for its versatile chemical properties, making it a valuable component in various applications across different industries.

Uses

Used in Organic Synthesis:
3-Hydroxy-2-methylbutanoic Acid is used as a key intermediate in the synthesis of various organic compounds. Its unique structural features allow for a wide range of chemical reactions, making it a valuable building block for the development of new molecules with potential applications in pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
3-Hydroxy-2-methylbutanoic Acid is used as a starting material for the synthesis of pharmaceutical compounds. Its ability to undergo various chemical transformations enables the creation of novel drug candidates with potential therapeutic applications.
Used in Flavor and Fragrance Industry:
3-Hydroxy-2-methylbutanoic Acid is used as a component in the development of new flavors and fragrances. Its unique chemical properties allow for the creation of distinct scents and tastes, contributing to the diversity of products in this industry.
Used in Chemical Research:
3-Hydroxy-2-methylbutanoic Acid is used as a research tool in the study of various chemical reactions and processes. Its unique structural features make it an interesting subject for investigation, potentially leading to new discoveries and advancements in the field of chemistry.

InChI:InChI=1/C7H14O3/c1-4-10-7(9)5(2)6(3)8/h5-6,8H,4H2,1-3H3

Upstream product

• 82731-69-9 2,3-epoxy-2-methyl-butyric acid ethyl ester 
• 117268-79-8 sodium phenylseleno(triethyl)borate 
• 50313-58-1 2-ethoxycarbonylmethyl-oxiranecarboxylic acid ethyl ester 
• 64-17-5 ethanol 
• 108-05-4 vinyl acetate 

Downstream Products

• 80-59-1 Tiglic acid 
• 565-63-9 Angelic acid 
• 139564-43-5 Aethyl-3-acetoxy-2-methylbutyrat 
• 121404-73-7 (2R,3S)-(+)-ethyl-2-methyl-3-hydroxybutanoate benzylether 
• 7505-94-4 ethyl 3-hydroxy-2,2-dimethylbutanoate 
• 5837-78-5 Ethyl tiglate 
• 697751-89-6 (2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-butyric acid ethyl ester 
• 871028-89-6 4-nitrobenzoic acid (1S,2R)-2-ethoxycarbonyl-1-methylpropyl ester 
• 780772-18-1 (2R,3S)-2-Methyl-3-[4-(4,4,5,5,6,6,7,7,7-nonafluoro-heptyloxy)-benzyloxy]-butyraldehyde 
• 780772-27-2 (2R,4S,5S)-4,5-Dimethyl-2-[4-(4,4,5,5,6,6,7,7,7-nonafluoro-heptyloxy)-phenyl]-[1,3]dioxane 
• 780773-47-9 (2S,3S)-2-Methyl-3-[4-(4,4,5,5,6,6,7,7,7-nonafluoro-heptyloxy)-benzyloxy]-butan-1-ol 
• 780772-41-0 (E)-(2S,6S,7S)-2,6-Dimethyl-7-[4-(4,4,5,5,6,6,7,7,7-nonafluoro-heptyloxy)-benzyloxy]-oct-4-enal 
• 780772-49-8 (E)-(2R,6S,7S)-2,6-Dimethyl-7-[4-(4,4,5,5,6,6,7,7,7-nonafluoro-heptyloxy)-benzyloxy]-oct-4-enal 
• 780772-37-4 (E)-(2S,6S,7S)-2,6-Dimethyl-7-[4-(4,4,5,5,6,6,7,7,7-nonafluoro-heptyloxy)-benzyloxy]-oct-4-en-1-ol 

Relevant articles and documents

Hepta-, hexa-, penta-, tetra-, and trisaccharide resin glycosides from three species of Ipomoea and their antiproliferative activity on two glioma cell lines

Six new partially acylated resin glycosides were isolated from convolvulin of Ipomoea purga, Ipomoea stans, and Ipomoea murucoides (Convolvulaceae). The structures of compounds 1–6 were elucidated by a combination of NMR spectroscopy and mass spectrometry. The structure of jalapinoside B (1) consists of a hexasaccharide core bonded to an 11-hydroxytetradecanoic (convolvulinic) acid forming a macrolactone acylated by a 2-methylbutanoyl, a 3-hydroxy-2-methylbutanoyl, and a quamoclinic acid B units. Purginoic acid A (2) contains a hexasaccharide core bonded to a convolvulinic acid acylated by a 3-hydroxy-2-methylbutanoyl unit. Stansin A (4) is an ester-type heterodimer, and consists of two stansoic acid A (3) units, acylated by 2-methylbutanoic and 3-hydroxy-2-methylbutanoic acids. The site of lactonization was located at C-3 of Rhamnose, and the position for the ester linkage of the monomeric unit B on the macrolactone unit A was established as C-4 of the terminal rhamnose. Compounds 5 and 6 are glycosidic acids. Murucinic acid II (5) is composed of a pentasaccharide core bonded to an 11-hydroxyhexadecanoic (jalapinolic) acid, acylated by an acetyl unit. Stansinic acid I (6) is a tetrasaccharide core bonded to a jalapinolic acid, acylated by 2-methylbutanoyl and 3-hydroxy-2-methylbutanoyl units. Preliminary testing showed the cytotoxicity of compounds 1–6 toward OVCAR and UISO-SQC-1 cancer cell lines. In addition, compound 1 showed an antiproliferative activity on glioma C6 and RG2 tumor cell lines. Copyright

The organoselenium-mediated reduction of α,β-epoxy ketones, α,β-epoxy esters, and their congeners to β-hydroxy carbonyl compounds: Novel methodologies for the synthesis of aldols and their analogues

Novel methods for the reduction of α,β-epoxy ketones, α,β-epoxy esters (glycidic esters), and their congeners to β-hydroxy carbonyl compounds (aldols) by the use of organoselenium reagents are described. The reagents, a sodium phenylseleno(triethyl)borate complex Na[PhSeB(OEt)3] easily prepared by reduction of (PhSe)2 with NaBH4 in EtOH and benzeneselenol (PhSeH) generated in situ from the borate complex by addition of acetic acid, have been demonstrated to serve as excellent reducing agents for these transformations. The organoselenium-mediated reduction of α,β-epoxy carbonyl compounds regiospecifically occurs at the α-carbon to produce a wide variety of cyclic (intramolecular) aldols as well as acyclic (intermolecular) ones in excellent yields. Quantitative mechanistic studies have revealed that the organoselenium-mediated reduction proceeds via an α-substitution process in contrast to the common electron transfer reducing agents.