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

General Description

(+)-Methyl (S)-3-hydroxypentanoate is a chemical compound with the molecular formula C6H12O3. It is a clear, colorless liquid with a fruity odor, commonly used in the manufacturing of pharmaceuticals, flavors, and fragrances. (+)-METHYL (S)-3-HYDROXYPENTANOATE is an enantiomer of (–)-methyl (R)-3-hydroxypentanoate, and it exhibits optical activity due to its chiral nature. Its primary function is as a synthetic intermediate in the production of various organic compounds. It is also known by the trade names Methyl (S)-lactate and L-Hydroxypentanoic acid methyl ester. Additionally, it is important to handle and store this chemical with caution, as it may pose safety hazards if not managed properly.

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

Upstream product

• 2689-69-2 methyl tetrahydrothiophen-3-one-2-carboxylate 
• 92445-22-2 octyl (-)-3-hydroxypentanoate 
• 95338-08-2 methyl (3R)-3-(3',5'-dinitrobenzoyloxy)-pentanoate 
• 96120-11-5 methyl (R)-3-tetrahydropyranyloxypentanoate 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 56009-31-5 3-hydroxy valeric acid methyl ester 
• 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 
• 1373154-28-9 (S)-methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate 
• 1576-86-9 2-pentenal 
• 3724-55-8 methyl but-3-enoate 
• 97234-06-5 methyl (S)-5-phenylthio-3-hydroxypentanoate 

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 
• 1224722-70-6 (S)-methyl 3-(phenylcarbamoyloxy)pentanoate 
• 849482-28-6 Benzoic acid (R)-1-[(R)-1-((S)-2-{(2R,5S)-5-[(S)-1-((1R,3R)-3-benzyloxymethoxy-1-vinyl-pentyloxycarbonyl)-ethyl]-tetrahydro-furan-2-yl}-1-methyl-ethoxycarbonyl)-ethyl]-allyl ester 
• 849482-31-1 Benzoic acid (S)-1-[(R)-1-((S)-2-{(2R,5S)-5-[(S)-1-((1R,3R)-3-benzyloxymethoxy-1-vinyl-pentyloxycarbonyl)-ethyl]-tetrahydro-furan-2-yl}-1-methyl-ethoxycarbonyl)-ethyl]-allyl ester 
• 849482-29-7 Benzoic acid (E)-(1R,3S,6R,7R,10R,13S,14S)-10-((R)-2-benzyloxymethoxy-butyl)-3,6,13-trimethyl-5,12-dioxo-4,11,17-trioxa-bicyclo[12.2.1]heptadec-8-en-7-yl ester 
• 849482-32-2 Benzoic acid (E)-(1R,3S,6R,7S,10R,13S,14S)-10-((R)-2-benzyloxymethoxy-butyl)-3,6,13-trimethyl-5,12-dioxo-4,11,17-trioxa-bicyclo[12.2.1]heptadec-8-en-7-yl ester 
• 849482-41-3 (E)-(1S,2S,5R,8R,9R,12S,14R)-5-((R)-2-Benzyloxymethoxy-butyl)-8-hydroxy-2,9,12-trimethyl-4,11,17-trioxa-bicyclo[12.2.1]heptadec-6-ene-3,10-dione 
• 849482-43-5 (E)-(1S,2S,5R,8S,9R,12S,14R)-5-((R)-2-Benzyloxymethoxy-butyl)-8-hydroxy-2,9,12-trimethyl-4,11,17-trioxa-bicyclo[12.2.1]heptadec-6-ene-3,10-dione 
• 849482-40-2 (S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (1R,3R)-3-benzyloxymethoxy-1-vinyl-pentyl ester 
• 849482-27-5 (S)-2-[(2S,5R)-5-((S)-2-Hydroxy-propyl)-tetrahydro-furan-2-yl]-propionic acid (1R,3R)-3-benzyloxymethoxy-1-vinyl-pentyl ester 

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.

Stereodiverse Iterative Synthesis of 1,3-Polyol Arrays through Asymmetric Catalytic Hydrogenation. Formal Total Synthesis of (-)-Cyanolide A

An iterative protocol was developed for highly diastereo- and enantioselective construction of high-order 1,3-polyols via iridium-catalyzed asymmetric hydrogenation of β-alkyl-β-keto esters. The protocol involves four operations - asymmetric hydrogenation, hydroxy protection, ester hydrolysis, and C-acylation - and the catalyst loading can be as low as 0.005 mol %. The configurations of all stereogenic centers of 1,3-polyols are controlled by the catalyst. By the use of this protocol, a formal total synthesis of the polyketide cyanolide A was achieved with high diastereoselectivity and enantioselectivity.

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.