alpha-Phenylcinnamic acid

Base Information

• Chemical Name: alpha-Phenylcinnamic acid
• CAS No.: 91-48-5
• Molecular Formula: C15H12O2
• Molecular Weight: 224.259
• Hs Code.: 29163990
• European Community (EC) Number: 202-069-4,840-968-9
• NSC Number: 83528,40614
• UNII: 0PKH62904B
• DSSTox Substance ID: DTXSID00871015
• Nikkaji Number: J414.332I,J3.924A
• Wikipedia: Alpha-Phenylcinnamic_acid
• Wikidata: Q4734916
• ChEMBL ID: CHEMBL1980291
• Mol file: 91-48-5.mol

Synonyms:alpha-phenylcinnamate;alpha-phenylcinnamate, (E)-isomer;alpha-phenylcinnamate, (Z)-isomer

Chemical Property of alpha-Phenylcinnamic acid

Chemical Property:

• Appearance/Colour: light yellow powder
• Vapor Pressure: 4.35E-05mmHg at 25°C
• Melting Point: 172-174 °C(lit.)
• Refractive Index: 1.6530 (estimate)
• Boiling Point: 336.6 °C at 760 mmHg
• PKA: 4.8 in 60% ethanol
• Flash Point: 239.8 °C
• PSA: 37.30000
• Density: 1.198 g/cm³
• LogP: 3.31180
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 224.083729621
• Heavy Atom Count: 17
• Complexity: 281

Purity/Quality:

99% ^*data from raw suppliers

α-Phenylcinnamic Acid ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=C(C2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)/C=C(\C2=CC=CC=C2)/C(=O)O
• Uses: α-Phenylcinnamic Acid, is a 2,3-Diarylpropenoic Acid, which is a selective non-steroidal inhibitors of type-5 17β-hydroxysteroid dehydrogenase (AKR1C3).

Technology Process of alpha-Phenylcinnamic acid

There total 91 articles about alpha-Phenylcinnamic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

formic acid (64-18-6) + diphenyl acetylene (501-65-5) → (E)-2,3-diphenylpropenoic acid (91-48-5)

Guidance literature:

With o-phenylenebis(diphenylphosphine); bis(acetylacetonate)nickel; 2,2-dimethylpropanoic anhydride; In toluene; at 100 ℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere;

Reference yield: 98.0%

methyl (E)-2,3-diphenyl-2-propenoate (36854-27-0) → (E)-2,3-diphenylpropenoic acid (91-48-5)

Guidance literature:

With sodium hydroxide; In N,N-dimethyl-formamide; for 0.75h; Ambient temperature;

Reference yield: 95.0%

carbon dioxide (124-38-9,18923-20-1) + diphenyl acetylene (501-65-5) → (E)-2,3-diphenylpropenoic acid (91-48-5)

Guidance literature:

With manganese; (1,2-dimethoxyethane)dichloronickel(II); Bathocuproine; isopropyl alcohol; In N,N-dimethyl-formamide; at 60 ℃; for 36h; Reagent/catalyst; Temperature; regioselective reaction; Schlenk technique;

DOI:10.1021/jacs.5b05513

upstream raw materials:

pyridine

phenylacetic anhydride

benzaldehyde

(Z)-2,3-diphenylprop-2-enoic acid

Downstream raw materials:

methyl (E)-2,3-diphenyl-2-propenoate

7-hydroxy-2,3-diphenyl-chroman-4-one

(2S)-2,3-diphenylpropanoic acid

(R)-2,3-diphenylpropanoic acid

Refernces

• 1、 Chen, Xiao-Chao,Guo, Lin,Liu, Lei,Liu, Ye,Lu, Yong,Yao, Yin-Qing,Zhao, Xiao-Li. "Hydrocarboxylation of alkynes with formic acid over multifunctional ligand modified Pd-catalyst with co-catalytic effect". . p. 322 - 332. Retrieved 2022/01/06.
• 2、 Peraman, Ramalingam,Meka, Geethavani,Chilamakuru, Naresh Babu,Kutagulla, Vinay Kumar,Malla, Saloni,Ashby, Charles R.,Tiwari, Amit K.,Yiragamreddy, Padmanabha Reddy. "Novel stilbene scaffolds efficiently targetMycobacterium tuberculosisnucleoid-associated protein, HU". . p. 10683 - 10692. Retrieved 2021/06/27.