36567-72-3

Basic information

• Product Name: (S)-3-HYDROXY-3-PHENYLPROPANOIC ACID
• Synonyms: (S)-3-HYDROXY-3-PHENYLPROPANOIC ACID;(S)-(-)-3-HYDROXY-3-PHENYLPROPIONIC ACID;(S)-3-HYDROXY-3-PHENYLPROPIONIC ACID;(S)-3-Hydroxybenzenepropanoic acid.;(S)-3-HYDROXY-3-PHENYLPROPANOIC ACID 99%;(S)-(-)-3-Hydroxy-3-phenylpropionic acid, 98+%;(-)-3-Phenylhydracrylic acid;(R)-β-Hydroxybenzenepropanoic acid
• CAS NO: 36567-72-3
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: -0
• Product Categories: Carboxylic Acids;Chiral Building Blocks;Organic Building Blocks
• Mol File: 36567-72-3.mol

Chemical Properties

• Melting Point: 117-120 °C
• Boiling Point: 254.38°C (rough estimate)
• Flash Point: 167.2 °C
• Appearance: White to almost white/Needle-Like Crystals
• Density: 1.1708 (rough estimate)
• Vapor Pressure: 7.14E-05mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 2-8°C
• BRN: 3197773
• CAS DataBase Reference: (S)-3-HYDROXY-3-PHENYLPROPANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-HYDROXY-3-PHENYLPROPANOIC ACID(36567-72-3)
• EPA Substance Registry System: (S)-3-HYDROXY-3-PHENYLPROPANOIC ACID(36567-72-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 36567-72-3(Hazardous Substances Data)

Usage

Chemical Properties

white to almost white needle-like crystals

InChI:InChI=1/C9H10O3/c10-8(6-9(11)12)7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/p-1/t8-/m0/s1

Upstream product

• 357-57-3 brucine 
• 3480-87-3 3-hydroxy-3-phenylpropanoic acid 
• 110-86-1 pyridine 
• 53943-72-9 3-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)-3-oxopropanoic acid 
• 100-52-7 benzaldehyde 
• 5764-85-2 Ethyl 3-hydroxy-3-phenylpropanoate 
• 151963-62-1 (-)-menthyl (S)-3-hydroxy-3-phenylpropanoate 
• 110773-03-0 (R)-2-Phenyl-1,1-di-2-thienyl-1,2-ethandiol-2-acetat 
• 110743-90-3 (R)-1,1-Di-2-naphthyl-2-phenyl-1,2-ethandiol-2-acetat 
• 110743-91-4 (R)-1,1-Bis(2-methoxyphenyl)-2-phenyl-1,2-ethandiol-2-acetat 
• 104720-91-4 (S)-1-((2S,5S)-2,5-Bis-methoxymethoxymethyl-pyrrolidin-1-yl)-3-hydroxy-3-phenyl-propan-1-one 
• 77815-27-1 1-<1-(4-toluensulphonyl)-1-azacyclopentan-2-yl>-3-hydroxy-3-phenyl-1-propanone 
• 95061-48-6 3-Hydroxy-3-phenyl-propionic acid (R)-2-hydroxy-1,2,2-triphenyl-ethyl ester 
• 107289-28-1 (2R,2'S)-2-tert-Butyl-6-(2'-hydroxy-2'-phenylethyl)-4H-1,3-dioxin-4-on 

Downstream Products

• 96854-34-1 (S)-3-phenyl-1,3-propanediol 
• 36615-45-9 methyl (S)-3-hydroxy-3-phenylpropionate 
• 621-82-9 Cinnamic acid 
• 96854-37-4 C₉H₁₁⁽²⁾HO 
• 96895-62-4 (R)-<3-(2)H1>-3-phenylpropionic acid 
• 96854-35-2 2,2-Dimethyl-propionic acid (S)-3-hydroxy-3-phenyl-propyl ester 
• 96854-36-3 2,2-Dimethyl-propionic acid (S)-3-chloro-3-phenyl-propyl ester 
• 96853-97-3 C₁₆H₁₄⁽²⁾HNO₂ 
• 96901-43-8 C₉H₇⁽²⁾HN₂O₆ 
• 96853-98-4 C₂₀H₂₀⁽²⁾HNO₄ 
• 73908-23-3 (R)-2-bromo-1-phenylethanol 
• 33401-74-0 ethyl (3R)-3-hydroxy-3-phenylpropionate 
• 15463-91-9 (-)-3-bromo-3-phenyl-propionic acid 
• 60786-21-2 3-chloro-3-phenylpropanoic acid 

Relevant articles and documents

Sterically congested chiral N-acetyl 2-oxazolidinone as acetyl enolate equivalents in stereoselective aldol reactions

Sterically constrained and highly congested N-acetyl-DMAOx (1a) serves well as a useful chiral acetyl enolate equivalent which permits a diastereoselective and direct approach to 'acetate' aldols (2) including statine derivative.

Solvent-induced chirality switching in the enantioseparation of regioisomeric hydroxyphenylpropionic acids via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol

The enantioseparation of three hydroxyphenylpropionic acid isomers via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol has been demonstrated. The racemates of all three acid isomers were successfully separated with high efficiency (0.56–0.84) after single crystallization. For 2-hydroxy-3-phenylpropionic acid 4, the configuration of the less-soluble salt was controlled by the crystallization solvent: the (R)-4 salt was crystallized from water, while 2-propanol afforded the (S)-4 salt. The chiral recognition mechanism of the three acids was discussed based on the crystal structures of the diastereomeric salts.

Substrate evaluation of rhodococcus erythropolis SET1, a nitrile hydrolysing bacterium, demonstrating dual activity strongly dependent on nitrile sub-structure

Assessment of Rhodococcus erythropolis SET1, a novel nitrile hydrolysing bacterial isolate, has been undertaken with 34 nitriles, 33 chiral and 1 prochiral. These substrates consist primarily of β-hydroxy nitriles with varying alkyl and aryl groups at the β position and containing in several compounds different substituents α to the nitrile. In the case of β-hydroxy nitriles without substitution at the α position, acids were the major products obtained, along with recovered nitrile after biotransformation, as a result of suspected nitrilase activity of the isolate. Unexpectedly, amides were found to be the major hydrolysis product when the β-hydroxy nitriles possessed a vinyl group at this position. To probe this behaviour further, additional related substrates were evaluated containing electron-withdrawing groups at the α position, and amide was also observed upon biotransformation in the presence of SET1. Therefore this novel isolate has also demonstrated NHase activity with nitriles that appears to be substrate-dependent.

Stereoselective acetate aldol reactions of α-silyloxy ketones

TiCl4-mediated aldol reactions of chiral methyl α-silyloxy ketones with a variety of aldehydes provide the corresponding 1,4-syn aldol adducts with moderate to high stereocontrol. This transformation represents a new approach to substrate-controlled acetate aldol reactions and complements the 1,4-anti asymmetric induction produced by the related α-benzyloxy ketones. This new approach could be useful in the design of more efficient syntheses of natural products.

Biotransformation of aromatic ketones and ketoesters with the non-conventional yeast Pichia glucozyma

The non-conventional yeast Pichia glucozyma CBS 5766 has been used for the biotransformation of different aromatic ketones and ketoesters. The growth and biotransformation conditions were optimised for the reduction of acetophenone and under optimised conditions, propiophenone, butyrophenone and valerophenone were reduced to the corresponding (S)-alcohols with high yields and enantioselectivity. Ketoreductase(s) of Pichia glucozyma showed high catalytic activities also towards aromatic β- and γ-ketoesters, being often competitive with esterase(s). These concurrent activities allowed for the preparation of hydroxyesters, hydroxyacids and lactones often in a very selective manner.

Studies toward stereoselective bionanocatalysis on gold nanoparticles

As yet, different enzymes were immobilized on gold nanoparticles both through adsorption and covalent binding. However, there is only one evaluation if such immobilization influenced enzyme enantioselectivity, which is an essential parameter in biocatalys

Asymmetric β-boration of α,β-unsaturated N -acyloxazolidinones by [2.2]paracyclophane-based bifunctional catalyst

An efficient copper-catalyzed asymmetric conjugate boration has been achieved by exploiting a new planar and central chiral bicyclic triazolium ligand. This protocol was highly efficient and gave a variety of chiral secondary alkylboronates in 97-99% ee. A preliminary mechanistic study supports the bifunctional nature of the catalyst.

Reversal of selectivity in acetate aldol reactions of N-acetyl-(S)-4- isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one

Synergistic effects of the exo- and endocyclic chiral centers of an imidazolidinone-based auxiliary were investigated in the perspective of acetate aldol reactions. The reversal in diastereoselectivity was accomplished by lithium and titanium enolate reactions, which proceed through proposed open and closed transitions states, respectively. The aldol adducts were used in the stereoselective synthesis of fluoxetine.

Rhodium-catalyzed asymmetric addition of arylboroxines to β-alkoxyacrylate esters

Asymmetric addition of arylboroxines to β-alkoxyacrylate esters proceeded in the presence of a rhodium complex coordinated with a chiral diene ligand to give high yields of β-alkoxy-β-arylcarboxylic acid esters with very high enantioselectivity.

1,4-syn-Asymmetric induction in the titanium-mediated aldol reactions of chiral methyl α-silyloxy ketones

Good levels of 1,4-syn asymmetric induction are obtained in the TiCl4-mediated aldol reaction of methyl α-silyloxy ketones with achiral aldehydes. Such methodology represents a new approach to the substrate-controlled acetate aldol reaction, which can be useful to design more efficient syntheses of natural products.