42558-50-9

Basic information

• Product Name: (+)-METHYL (S)-3-HYDROXYPENTANOATE
• Synonyms: METHYL L-(S)-3-HYDROXYPENTANOATE;(+)-METHYL (S)-3-HYDROXYPENTANOATE;METHYL (S)-3-HYDROXYPENTANOATE;(+)-METHYL (S)-3-HYDROXYVALERATE;(S)-(+)-METHYL 3-HYDROXYPENTANOATE;Methyl (S)-3-hydroxy-pentanoateMethyl (S)-3-Hydroxyvalerate;(S)-3-hydroxypentanoate
• CAS NO: 42558-50-9
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.16
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds
• Mol File: 42558-50-9.mol
• Article Data: 91

Chemical Properties

• Boiling Point: 203.949 °C at 760 mmHg
• Flash Point: 76 °C
• Appearance: /
• Density: 1.029 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.065mmHg at 25°C
• Refractive Index: n20/D 1.427
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 13.95±0.20(Predicted)
• BRN: 4655381
• CAS DataBase Reference: (+)-METHYL (S)-3-HYDROXYPENTANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-METHYL (S)-3-HYDROXYPENTANOATE(42558-50-9)
• EPA Substance Registry System: (+)-METHYL (S)-3-HYDROXYPENTANOATE(42558-50-9)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 3
• Hazardous Substances Data: 42558-50-9(Hazardous Substances Data)

Usage

Description

(+)-METHYL (S)-3-HYDROXYPENTANOATE, also known as Methyl (S)-lactate or L-Hydroxypentanoic acid methyl ester, is a chiral chemical compound with the molecular formula C6H12O3. It is a clear, colorless liquid characterized by a fruity odor. This enantiomer of (–)-methyl (R)-3-hydroxypentanoate exhibits optical activity due to its chiral nature. Primarily, it serves as a synthetic intermediate in the production of various organic compounds, and is commonly used in the manufacturing of pharmaceuticals, flavors, and fragrances.

Uses

Used in Pharmaceutical Industry:
(+)-METHYL (S)-3-HYDROXYPENTANOATE is used as a synthetic intermediate for the production of various pharmaceuticals. Its chiral nature allows for the creation of specific drug molecules that can interact differently with biological targets, leading to more effective treatments.
Used in Flavor and Fragrance Industry:
(+)-METHYL (S)-3-HYDROXYPENTANOATE is used as a key component in the development of flavors and fragrances due to its fruity odor. It contributes to the creation of unique scents and tastes in various consumer products, such as food, beverages, and cosmetics.
Used in Chemical Synthesis:
(+)-METHYL (S)-3-HYDROXYPENTANOATE is used as a versatile building block in the synthesis of a wide range of organic compounds. Its reactivity and chirality make it a valuable asset in the development of new chemical entities for various applications.
Safety Precautions:
It is important to handle and store (+)-METHYL (S)-3-HYDROXYPENTANOATE with caution, as it may pose safety hazards if not managed properly. Proper safety measures should be taken to minimize risks associated with its use.

InChI:InChI=1/C6H12O3/c1-3-5(7)4-6(8)9-2/h5,7H,3-4H2,1-2H3/t5-/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 53538-53-7 (3R)-3-hydroxypentanoic acid 
• 2689-69-2 methyl tetrahydrothiophen-3-one-2-carboxylate 
• 92445-22-2 octyl (-)-3-hydroxypentanoate 
• 96120-11-5 methyl (R)-3-tetrahydropyranyloxypentanoate 
• 67-56-1 methanol 
• 92445-22-2 octyl (3S)-(+)-3-hydroxypentanoate 
• 84231-00-5 (2R,3S)-Tetrahydro-3-hydroxy-2-thiophencarbonsaeure-methylester 
• 109462-42-2 methyl (R)-3,4-epoxybutyrate 
• 1576-86-9 2-pentenal 
• 1373154-28-9 (S)-methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate 
• 3724-55-8 methyl but-3-enoate 
• 97234-06-5 methyl (S)-5-phenylthio-3-hydroxypentanoate 
• 97189-78-1 methyl (S)-5-phenylthio-3-tetrahydropyranyloxypentanoate 

Downstream Products

• 95338-08-2 methyl (3R)-3-(3',5'-dinitrobenzoyloxy)-pentanoate 
• 100235-80-1 methyl (2R,3R)-3-(3',5'-dinitrobenzoyloxy)-2-methylpentanoate 
• 849482-37-7 (R)-3-Benzyloxymethoxy-pentanoic acid methyl ester 
• 256486-03-0 (R)-3-Benzyloxy-pentanoic acid methyl ester 
• 774216-22-7 methyl (S)-3-(phenylamino)valerate 

Relevant articles and documents

General chemoenzymatic route to two-stereocenter triketides employing assembly line ketoreductases

Modular polyketide synthases (PKSs) are enzymatic assembly lines that fuse carbon fragments into complex chiral products. Here, their synthetic logic is employed to chemoenzymatically generate two-stereocenter triketides. Each of the four stereoisomers was constructed in a stereocontrolled manner using C-acylation and two PKS ketoreductases possessing opposite stereoselectivities.

Copper-Catalyzed Asymmetric Conjugate Additions of Bis(pinacolato)diboron and Dimethylzinc to Acyl- N-methylimidazole Michael Acceptors: A Highly Stereoselective Unified Strategy for 1,3,5,... n (OH, Me) Motif Synthesis

A unified strategy for the construction of prevalent 1,3,5,...n (OH, Me) motifs based on consecutive copper-catalyzed asymmetric conjugate borylation (ACB) and methylation (ACA) reactions involving α,β-unsaturated 2-acyl-N-methylimidazoles is described. Good yields and high diastereoselectivities have been obtained in ACA and ACB reactions for both matched and mismatched pairs as illustrated in the synthesis of syn/anti and anti/anti (Me, OTBS, Me) and (OH, OTBS, Me) motifs.

Chiral BINAP-based hierarchical porous polymers as platforms for efficient heterogeneous asymmetric catalysis

Two vinyl-functionalized chiral 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) ligands, (S)-4,4′-divinyl-BINAP and (S)-5,5′-divinyl-BINAP, were successfully synthesized. Chiral BINAP-based porous organic polymers (POPs), denoted as 4-BINAP@POPs and 5-BINAP@POPs, were efficiently prepared via the copolymerization of vinyl-functionalized BINAP with divinyl benzene under solvothermal conditions. Thorough characterization using nuclear magnetic resonance spectroscopy, thermogravimetric analysis, extended X-ray absorption fine structure analysis, and high-angle annular dark-field scanning transmission electron microscopy, we confirmed that chiral BINAP groups were successfully incorporated into the structure of the materials considered to contain hierarchical pores. Ru was introduced as a catalytic species into the POPs using different synthetic routes. Systematic investigation of the resultant chiral Ru/POP catalysts for heterogeneous asymmetric hydrogenation of β-keto esters revealed their excellent chiral inducibility as well as high activity and stability. Our work thereby paves a path towards the use of advanced hierarchical porous polymers as solid chiral platforms for heterogeneous asymmetric catalysis.