Benzenepropanoic acid
HYDROCINNAMIC ACID · 3-PHENYLPROPANOIC ACID · HYDROXYCINNAMIC ACID · BENZENEPROPANOIC ACID · Phenylpropanoic acid · Benzenepropionic acid · FEMA 2889 · hydrocinnamic
Identifiers & Physical Properties
| CAS No. | 501-52-0 |
|---|---|
| Molecular formula | C9H10O2 |
| Average molar mass | 150.17 g/mol |
| Monoisotopic mass | 150.06807956 g/mol |
| SMILES | O=C(O)CCc1ccccc1 |
| InChIKey | XMIIGOLPHOKFCH-UHFFFAOYSA-N |
| PubChem CID | 107 |
| ChEMBL | CHEMBL851 |
| ChEBI | CHEBI:28631 |
| EC No. | 207-924-5 |
| DTXSID | DTXSID2047064 |
Chemical & Physical Properties
| XLogP | 1.8 |
|---|---|
| Topological polar surface area | 37.3 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 3 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 126 |
| Chemical classes | Other Classes -> Organic Acids |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Angular frequency |
| Fragrances | Fragrance Ingredient (3-Phenylpropionic acid) -> IFRA transparency List |
| LogP (partition coefficient) | 1.841.91 |
| Food additives | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Flavoring agents | EU Flavoring substances |
| Solubility | 5.9 mg/mLslightly soluble in watersoluble in oilsmoderately soluble (in ethanol)0.6% soluble in water, soluble in alcohol, Propylene glycol, Glycerin and oils |
| Boiling point | 280.00 °C. @ 760.00 mm Hg280 °C280 °C (lit.) |
| Melting point | 45 - 48 °C45-48 °C (lit.) |
| Physical Description | White solid[Merck Index] Off-white or white crystalline powder[Alfa Aesar MSDS]White crystalline solid, faint, sweet, somewhat balsamic and coumarin-like odour |
| Dissociation Constants | 4.66 (at 18 °C) |
| Density | 1.071 g/mL at 25 °C (lit.) |
| Vapor pressure | 0.356Pa at 25℃ |
| FEMA | 2889 | 3-PHENYLPROPIONIC ACID |
| Refractive index | 1.5408 (estimate) |
| FLAVIS Number | 08.032 | 3-Phenylpropionic acid |
| Flash point | >230 °F |
| Storage conditions | Sealed in dry,Room Temperature |
| Physical state | Liquid |
| pKa (acidity coefficient) | 4.66(at 25℃) |
| Specific gravity | 1.071 |
| Color | Clear yellow to yellow-green |
| Odor | Very faint, warm-balsamic and sweet odor of Coumarin-Vanillin-type |
| Odor type | floral |
| Biological source | synthetic |
| Merck | 14,4784 |
| JECFA Number | 646 |
| BRN | 907515 |
| Major applications | cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care |
| InChI | 1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11) |
| InChIKey | XMIIGOLPHOKFCH-UHFFFAOYSA-N |
| SMILES | OC(=O)CCc1ccccc1 |
| LogP (partition coefficient) | 1.153 at 25℃ |
| CAS DataBase Reference | 501-52-0(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | 3-PHENYLPROPIONIC ACID |
| EWG's Food Scores | 2 |
| FDA UNII | 5Q445IN5CU |
| NIST Chemistry Reference | 3-Phenylpropanoic acid(501-52-0) |
| EPA Substance Registry System | Hydrocinnamic acid (501-52-0) |
| UNSPSC Code | 85151701 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 22-24/25-37/39-26 |
| Water hazard class (WGK) | 3 |
| RTECS number | DA8600000 |
| TSCA inventory status | TSCA listed |
| Customs code | 29163900 |
| Storage class | 11 - Combustible Solids |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 95.6% (238 of 249) of all reports.Not ClassifiedAggregated GHS information provided per 249 reports by companies from 8 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatory information | Chemical: Benzenepropanoic acidCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 21-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/332123-Phenylpropionic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | Intraperitoneal LD50 (mouse) = 1,202 mg/kg[RTECS] Safe when used as a flavoring agent in food[JECFA] A skin and strong eye irritant[Alfa Aesar MSDS] See Cinnamic aldehyde. |
| Hazard Classes and Categories | Not Classified |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | DA8600000 |
| Customs code | 29163900 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 22-24/25-37/39-26 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H335 |
| REACH registrations | Active |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
Applications & Uses
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.
Occurrence
Reported found in raspberry, guava fruit, Vitis vinifera L., papaya, strawberry fruit, cinnamon, cassia leaf, cheddar cheese, cocoa, beer, cognac, white wine, red wine, special wine, rose apple, mushroom, cloudberry, Boletus edulis, fresh mango, licorice and labdanum.
Uses
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.
General Description
Hydrocinnamic acid forms complexes with uranium(VI) and has been investigated in aqueous solution by attenuated total reflection fourier transform infrared spectroscopy. Hydrocinnamic acids are the major rhizospheric compounds with known growth regulatory activity.
Preparation & Synthesis
Preparation
Hydrogenation of cinnamic acid is used in the preparation of 3-Phenylpropionic acid. Initially, the chemical was prepared by reduction with sodium amalgam in water by electrolysis.
Preparation
By reduction of cinnamic acid using sodium amalgam.