3-Phenylpropionic acid

Base Information

• Chemical Name: 3-Phenylpropionic acid
• CAS No.: 501-52-0
• Molecular Formula: C9H10O2
• Molecular Weight: 150.177
• Hs Code.: 29163900
• European Community (EC) Number: 207-924-5
• NSC Number: 9272
• UNII: 5Q445IN5CU
• DSSTox Substance ID: DTXSID2047064
• Nikkaji Number: J2.601H
• Wikipedia: Phenylpropanoic_acid
• Wikidata: Q4358522
• Metabolomics Workbench ID: 37413
• ChEMBL ID: CHEMBL851
• Mol file: 501-52-0.mol

Synonyms:3-phenyl propionic acid;3-phenylpropanoic acid;3-phenylpropionate;3-phenylpropionic acid;3-phenylpropionic acid, sodium salt;beta-phenylpropionate;dihydrocinnamic acid;hydrocinnamic acid

Chemical Property of 3-Phenylpropionic acid

Chemical Property:

• Appearance/Colour: white to off-white crystalline mass, powder or crystals and/or chunk
• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 45-48 °C(lit.)
• Refractive Index: 1.542
• Boiling Point: 279.999 °C at 760 mmHg
• PKA: 4.66(at 25℃)
• Flash Point: 170.045 °C
• PSA: 37.30000
• Density: 1.126 g/cm³
• LogP: 1.70380
• Storage Temp.: 2-8°C
• Solubility.: ethanol: soluble50mg/mL, clear, colorless to faintly yellow
• Water Solubility.: Soluble in water
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 150.068079557
• Heavy Atom Count: 11
• Complexity: 126

Purity/Quality:

99% ^*data from raw suppliers

Hydrocinnamic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC=C(C=C1)CCC(=O)O
• Description: 3-Phenylpropionic acid is a carboxylic acid that belongs to the class of phenylpropanoids. Also referred as hydrocinnamic acid, the chemical is a white crystalline solid with a sweet fatty smell of rose musk cinnamon at room temperature. 3-Phenylpropionic acid is soluble in both water and alcohol. It is widely used in food additives, cosmetics, and pharmaceuticals.
• Uses: Food Industry 3-Phenylpropionic acid is utilized in the food industry as a preservative as well as to maintain the original quality of aroma of frozen foods. It is also used for flavoring and restoring original color to food. 3-Phenylpropionic acid is added to shelved foods to prevent microorganisms from deteriorating the food. It also acts as an antioxidant to prolong the life of foodstuff in shelves. 3-Phenylpropionic acid is also used as a food sweetener. 3-Phenylpropionic acid acts as an emulsifier as it can keep water and oil mixtures separated. 3-Phenylpropionic acid can be added in food for technological reasons in wide range such as processing, manufacturing, packaging, treatment, transportation, and storage. Cosmetics 3-Phenylpropionic acid is used in beautifying products such as bath gels, detergent powders, and fabric softeners as it gives a floral scent. It is also used as a flavour for mouthwashes and toothpastes. Used in the compositions for the treatment of blood disorders using α-methylhydrocinnamic acid. Hydrocinnamic acid was used in the synthesis of three medium-chain acyl-Coenzyme A′s i.e. 3-phenylpropionyl-CoA from mixed anhydrides of fatty acids. Hydrocinnamic acid is inhibitor of carboxypeptidase. Hydrocinnamic acid was used in the synthesis of three medium-chain acyl-Coenzyme A?s i.e. 3-phenylpropionyl-CoA from mixed anhydrides of fatty acids.

Technology Process of 3-Phenylpropionic acid

There total 504 articles about 3-Phenylpropionic 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: 80.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + sodium formate (141-53-7) → ethylbenzene (100-41-4,27536-89-6) + 3-Phenylpropionic acid (501-52-0)

Guidance literature:

With Cyclohexanethiol; 1,3-dicyano-2,4,5,6-tetrakis(N,N-diphenylamino)-benzene; In dimethyl sulfoxide; for 20h; Irradiation; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.1c07562

Reference yield: 73.0%

3-Phenyl-1-propanol (122-97-4) + benzyl alcohol (100-51-6,185532-71-2) → 3-phenyl-propionaldehyde (104-53-0) + benzaldehyde (100-52-7) + benzoic acid (65-85-0,8013-63-6) + 3-Phenylpropionic acid (501-52-0)

Guidance literature:

With sodium tetrahydroborate; 1% Pd/C; water; oxygen; potassium carbonate; In methanol; at 20 ℃; for 12h;

DOI:10.1055/s-0029-1217115

Reference yield: 70.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + carbon dioxide (124-38-9,18923-20-1) → hydratropic acid (492-37-5,2328-24-7) + 3-Phenylpropionic acid (501-52-0)

Guidance literature:

With triethanolamine; tetraethylammonium iodide; In N,N-dimethyl-formamide; at 20 ℃; for 3.5h; under 760.051 Torr; Reagent/catalyst; regioselective reaction; Electrochemical reaction;

DOI:10.1021/jacs.9b13305

upstream raw materials:

pyridine

chloral

2-benzylmalonic acid

3-phenyl-propionaldehyde

Downstream raw materials:

benzaldehyde

4-Phenyl-2-butanone

1,5-diphenyl-3-pentanone

acetone

Refernces

• 1、 Teresa, J. De Pascual,Urones, J. G.,Marcos, I. S.,Nunez, L.,Basabe, P.. "DITERPENOIDS AND FLAVONOIDS FROM CISTUS PALINHAE". . p. 2805 - 2808. Retrieved 1983.
• 2、 Magdalinova,Klyuev. "Hydrogenation of Nitro and Unsaturated Organic Compounds over Catalysts Containing Nanosized Palladium Particles". . p. 1024 - 1030. Retrieved 2017.
• 3、 Bai, Guoyi,Dong, Huixian,Zhao, Zhen,Chu, Hailong,Wen, Xin,Liu, Chen,Li, Fei. "Effect of support and solvent on the activity and stability of NiCoB amorphous alloy in cinnamic acid hydrogenation". . p. 19800 - 19805. Retrieved 2014.
• 4、 lee,Spinks. "". . p. 1005,1006, 1008. Retrieved 1954.
• 5、 Borboa, Lisaedy Garcia,Nunez, Oswaldo. "Amide and lactam hydrolysis of N-(2-hydroxyacetyl)-2-pyrrolidone: Effective catalysis". . p. 737 - 743. Retrieved 2006.
• 6、 Bai, Guoyi,Dong, Huixian,Zhao, Zhen,Wang, Yalong,Chen, Qingzhi,Qiu, Mande. "Preparation of nanoscale Ni-B amorphous alloys and their application in the selective hydrogenation of cinnamic acid". . p. 5012 - 5016. Retrieved 2013.
• 7、 Kanaoka, Shokyoku,Yagi, Naoto,Fukuyama, Yukiko,Aoshima, Sadahito,Tsunoyama, Hironori,Tsukuda, Tatsuya,Sakurai, Hidehiro. "Thermosensitive gold nanoclusters stabilized by well-defined vinyl ether star polymers: Reusable and durable catalysts for aerobic alcohol oxidation". . p. 12060 - 12061. Retrieved 2007.
• 8、 Chen, Cheng,Cheng, Hua,Verpoort, Francis,Wang, Zhi-Qin,Wu, Zhe,Yuan, Ye,Zheng, Zhong-Hui. "Gram-scale synthesis of carboxylic acids via catalytic acceptorless dehydrogenative coupling of alcohols and hydroxides at an ultralow Ru loading". . . Retrieved 2021/12/13.
• 9、 Fu, Qiang,Liang, Fu-Shun,Lou, Da-Wei,Pan, Gao-Feng,Wang, Rui,Wu, Min,Xie, Kai-Jun. "Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process". supporting information. p. 2020 - 2024. Retrieved 2022/03/31.