3069-52-1

Basic information

• Product Name: tert-Butyl L-2-hydroxy-4-methylpentanoate
• Synonyms: tert-Butyl L-2-hydroxy-4-methylpentanoate;(S)-tert-butyl 2-hydroxy-4-methylpentanoate
• CAS NO: 3069-52-1
• Molecular Formula: C₁₀H₂₀O₃
• Molecular Weight: 188.26
• Mol File: 3069-52-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 206°C at 760 mmHg
• Flash Point: 72.5°C
• Appearance: /
• Density: 0.963g/cm³
• Vapor Pressure: 0.0574mmHg at 25°C
• Refractive Index: 1.44
• PKA: 13.07±0.20(Predicted)
• CAS DataBase Reference: tert-Butyl L-2-hydroxy-4-methylpentanoate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl L-2-hydroxy-4-methylpentanoate(3069-52-1)
• EPA Substance Registry System: tert-Butyl L-2-hydroxy-4-methylpentanoate(3069-52-1)

Safety Data

• Hazardous Substances Data: 3069-52-1(Hazardous Substances Data)

Usage

General Description

Tert-Butyl L-2-hydroxy-4-methylpentanoate is an organic compound with the molecular formula C12H24O3. It is a clear, colorless liquid with a fruity odor, commonly used as a flavoring and fragrance ingredient in various consumer products, including perfumes, lotions, and food items. This chemical is derived from the esterification of tert-butyl alcohol and L-2-hydroxy-4-methylpentanoic acid, resulting in a compound with a wide range of applications in the cosmetics and food industry. Tert-Butyl L-2-hydroxy-4-methylpentanoate is known for its pleasant aroma and is considered safe for use at low concentrations in consumer products.

InChI:InChI=1/C10H20O3/c1-7(2)6-8(11)9(12)13-10(3,4)5/h7-8,11H,6H2,1-5H3

Upstream product

• 3069-51-0 L-α-Acetoxyisocapronsaeure-tert-butylester 
• 13748-90-8 (S)-2-hydroxyl-3,3-dimethylbutyric acid 
• 75-65-0 tert-butyl alcohol 
• 61-90-5 L-leucine 
• 3069-50-9 O-acetyl-L-α-hydroxyisocapric acid 
• 75716-87-9 tert-butyl 4-methyl-2-oxopentanoate 

Downstream Products

• 733769-90-9 (S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid tert-butyl ester 
• 38184-57-5 Z-Leu-OLeu-OH 
• 1309439-90-4 C₂₃H₃₅NO₆S 
• 1201096-13-0 C₂₃H₃₅NO₆ 
• 3069-55-4 Benzyloxycarbonyl-D-valyl-D-leucyl-L-α-hydroxyisocapronsaeure-tert.-butylester 
• 380886-45-3 D-p-chlorophenyl 2-phthalimidoxy-4-methylpentanoamide 
• 380886-40-8 D-tert-butyl 2-p-chlorophenylcarbonyl-aminoxy-4-methylpentanoate 

Relevant articles and documents

α-Aminoxy Oligopeptides: Synthesis, Secondary Structure, and Cytotoxicity of a New Class of Anticancer Foldamers

α-Aminoxy peptides are peptidomimetic foldamers with high proteolytic and conformational stability. To gain an improved synthetic access to α-aminoxy oligopeptides we used a straightforward combination of solution- and solid-phase-supported methods and obtained oligomers that showed a remarkable anticancer activity against a panel of cancer cell lines. We solved the first X-ray crystal structure of an α-aminoxy peptide with multiple turns around the helical axis. The crystal structure revealed a right-handed 28-helical conformation with precisely two residues per turn and a helical pitch of 5.8 ?. By 2D ROESY experiments, molecular dynamics simulations, and CD spectroscopy we were able to identify the 28-helix as the predominant conformation in organic solvents. In aqueous solution, the α-aminoxy peptides exist in the 28-helical conformation at acidic pH, but exhibit remarkable changes in the secondary structure with increasing pH. The most cytotoxic α-aminoxy peptides have an increased propensity to take up a 28-helical conformation in the presence of a model membrane. This indicates a correlation between the 28-helical conformation and the membranolytic activity observed in mode of action studies, thereby providing novel insights in the folding properties and the biological activity of α-aminoxy peptides.

Benzotriazole-mediated syntheses of depsipeptides and oligoesters

Reactions of O-Pg(α-hydroxyacyl)benzotriazoles with (a) unprotected α-hydroxycarboxylic acids, (b) amino acids, and (c) amines afforded, respectively, chirally pure (a) oligoesters, (b) depsidipeptides, and (c) amide conjugates (yields 52-94%). N-Pg(α-Ami

Zinc-catalyzed enantiospecific sp3-sp3 cross-coupling of α-hydroxy ester triflates with grignard reagents

(Chemical Equation Presented) Zinc chloride does the trick and efficiently catalyzes the enantiospecific cross-coupling of α-hydroxy ester triflates with Grignard reagents under mild conditions. Enantiopure α-hydroxy esters are directly available from the chiral pool or by diazotization of α-amino acids. Substantial variations in both reacting partners are tolerated making this methodology an attractive alternative to enolate alkylation featuring a reversal of polarity.