3609-48-1

Basic information

• Product Name: 3-Hydroxy-3,3-diphenylpropionic acid
• Synonyms: 3-Hydroxy-3,3-diphenylpropionic acid
• CAS NO: 3609-48-1
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.2699
• Mol File: 3609-48-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 209-211℃
• Boiling Point: 418.3°Cat760mmHg
• Flash Point: 220.9°C
• Appearance: /
• Density: 1.243g/cm³
• Vapor Pressure: 9.58E-08mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: 3-Hydroxy-3,3-diphenylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-3,3-diphenylpropionic acid(3609-48-1)
• EPA Substance Registry System: 3-Hydroxy-3,3-diphenylpropionic acid(3609-48-1)

Safety Data

• Hazardous Substances Data: 3609-48-1(Hazardous Substances Data)

Usage

Description

3-Hydroxy-3,3-diphenylpropionic acid, also known as (R)-(-)-3-Hydroxy-3,3-diphenylpropionic acid, is a chiral aromatic compound with a molecular formula C15H14O3. It is a white crystalline powder that is insoluble in water but soluble in organic solvents. 3-Hydroxy-3,3-diphenylpropionic acid is known for its unique properties and reactivity, making it a versatile molecule in various scientific and industrial applications.

Uses

Used in Asymmetric Synthesis:
3-Hydroxy-3,3-diphenylpropionic acid is used as a chiral auxiliary in asymmetric synthesis for its ability to induce enantioselectivity in chemical reactions. This property is crucial for the production of enantiomerically pure compounds, which are essential in pharmaceuticals and agrochemicals where the biological activity of a compound can be highly dependent on its stereochemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Hydroxy-3,3-diphenylpropionic acid is used for the preparation of certain drugs. Its chiral center and aromatic nature make it a valuable building block in the synthesis of biologically active molecules, contributing to the development of new medications with improved efficacy and selectivity.
Used in Material Science:
3-Hydroxy-3,3-diphenylpropionic acid has potential applications in the field of material science. Its unique structural features and reactivity are being explored for the development of new materials with specific properties, such as chiral polymers or materials with tailored optical, electronic, or mechanical characteristics.
Used in Resolving Enantiomeric Mixtures:
3-Hydroxy-3,3-diphenylpropionic acid is used as a resolving agent for enantiomeric mixtures. It can help in the separation of enantiomers, which is important in various chemical and pharmaceutical processes where the desired biological activity or chemical property is associated with a specific enantiomer.
Overall, 3-Hydroxy-3,3-diphenylpropionic acid is a multifaceted compound with applications spanning across asymmetric synthesis, pharmaceuticals, material science, and enantiomeric resolution, making it a valuable asset in the fields of chemistry and biotechnology.

InChI:InChI=1/C15H14O3/c16-14(17)11-15(18,12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,18H,11H2,(H,16,17)

Upstream product

• 119-61-9 benzophenone 
• 105-39-5 chloroacetic acid ethyl ester 
• 64-19-7 acetic acid 
• 121669-92-9 C₆H₁₁BrO₃ 
• 32858-84-7 β-hydroxy-β,β-diphenyl-methyl propionate 
• 530-48-3 1,1-Diphenylethylene 
• 124-38-9 carbon dioxide 
• 4165-79-1 1,1-diphenyl-3-buten-1-ol 
• 7664-93-9 sulfuric acid 
• 58518-25-5 4,4-diphenyl-oxetane-2,2-dicarbonitrile 
• 67-64-1 acetone 
• 105-36-2 ethyl bromoacetate 
• 88681-52-1 3,3-diphenyl-β-peroxypropiolactone 
• 950-17-4 1,1-diphenyl-2-chloroethan-1-ol 

Downstream Products

• 606-84-8 3,3-diphenylacrylic acid 
• 68434-78-6 3,3-dicyclohexyl-3-hydroxy-propionic acid 
• 71205-89-5 3-hydroxy-3,3-diphenyl-propionic acid-(2-diethylamino-ethyl ester) 
• 32858-84-7 β-hydroxy-β,β-diphenyl-methyl propionate 
• 137074-33-0 1-(3,3-diphenyl-3-hydroxypropanoyl)-4-(pyridin-3-ylcyanomethyl)piperazine 
• 143840-92-0 1-(3,3-diphenyl-3-hydroxypropanoyl)-4-(pyridin-4-ylcyanomethyl)piperazine 
• 530-48-3 1,1-Diphenylethylene 
• 81467-20-1 3,3-diphenyl-3-hydroxypropiohydroxamic acid 
• 13961-05-2 1,1-diphenyl-1,3-propanediol 
• 81467-24-5 3-(2-Hydroxy-2,2-diphenylethyl)-1,4,2-dioxazol-5-on 
• 87058-47-7 3-Benzyloxy-5,6-dihydro-6,6-diphenyl-2H-1,3-oxazin-2,4(3H)-dion 
• 87058-46-6 4-Benzyloxyimino-6,6-diphenyl-1,3-dioxan-2-on 
• 87058-41-1 N-Benzyloxy-3-hydroxy-3,3-diphenylpropanamid 
• 71205-91-9 3-hydroxy-3,3-diphenyl-propionic acid-(2-piperidino-ethyl ester) 

Relevant articles and documents

Docking studies and α-substitution effects on the anti-inflammatory activity of β-hydroxy-β-arylpropanoic acids

Six β -hydroxy-β -aryl propanoic acids were synthesised using a modification of Reformatsky reaction which has already been reported. These acids belong to the aryl propanoic acid class of compounds, structurally similar to the NSAIDs, such as ibuprofen,

Catalytic photocarboxylation of 1,1-diphenylethylene with N,N,N′,N′-tetramethylbenzidine and carbon dioxide

Photocarboxylation of 1,1-diphenylethylene with N,N,N′,N′-tetramethylbenzidine (TMB) in MeCN under bubbling of CO2 proceeded with high catalytic efficiency, giving 3,3-diphenylacrylic acid (DPA) and 3-hydroxy-3,3-diphenylpropionic acid (20). The turnover number (TON=(DPA+20)/TMB) reached 17. Similarly, 1-phenyl-1-cyclohexene yielded cis-2-acetamido-2-phenylcyclohexanecarboxylic acid with TON 5.9. As compared with related N,N-dimethylaniline derivatives, TMB is more resistant to photodecomposition, has the much larger absorbance in the S0→S1 transition, and has the lower quenching efficiency by CO2. Probably these factors are partly responsible for the high TON observed for TMB.

Synthesis and Structure-Activity Relationships of 1-Acyl-4-(2-methyl-3-pyridyl)cyanomethyl)piperazines as PAF Antagonists

A second generation of (cyanomethyl)piperazines, 1-acyl-4-((2-methyl-3-pyridyl)cyanomethyl)piperazines, with increased oral activity was prepared and evaluated in vitro in PAF-induced platelet aggregation assay (PAG) and in vivo in a PAF-induced hypotension test in normotensive rats (HYP).Oral activity was ascertained through a PAF-induced mortality test in mice (MOR).Attachment of a methyl group at position 2 of our earlier pyridine derivatives resulted in an improvement of 1 order of magnitude or greater in the ID50 of the oral test.Three different types of acylsubstituents of similar potency emerge from this work: N-(diphenylmethylamino)acetyl, 3-substituted 3-hydroxy-3-phenylpropionyl, and N-substituted 3-amino-3-phenylpropionyl groups.The most interesting compounds, 26 (UR-12460, PAG IC50 = 0.040 μM, HYP, ID50 = 0.021 mg/kg iv, MOR, ID50 = 0.30 mg/kg po) and 58 (UR-12519, PAG IC50 = 0.041 μM, HYP, ID50 = 0.015 mg/kg iv, MOR, ID50 = 0.044 mg/kg po), compare favorably with WEB-2086.Compounds 26 and 58 were also tested in active anaphylactic shock (AAS) and endotoxin-induced mortality (EIM) tests.On the basis of these data, compounds 26 and 58 have been selected for further pharmacological development.