Basic information
- Standard SMILES
O=C(O)CCc1ccccc1- InChIKey
XMIIGOLPHOKFCH-UHFFFAOYSA-N- Molecular formula
- C9H10O2
- Average molar mass
- 150.17 g/mol
- Monoisotopic mass
- 150.06807956
Overview
3-phenylpropionic acid is a monocarboxylic acid that is propionic acid substituted at position 3 by a phenyl group. It has a role as an antifungal agent, a plant metabolite and a human metabolite. It is a member of benzenes and a monocarboxylic acid. It is functionally related to a propionic acid. It is a conjugate acid of a 3-phenylpropionate.
Names & identifiers
- Preferred name
- Benzenepropanoic acid
- IUPAC
- 3-phenylpropanoic acid
- English name
- 3-Phenylpropionic acid
- Molecular formula
- C9H10O2
- Molecular weight
- 150.17
Names & synonyms
Show more names
Database identifiers
- CAS
501-52-0- PubChem CID
- 107
- DTXSID
DTXSID2047064- ChEMBL
CHEMBL851- ChEBI
CHEBI:28631- UNII
- 5Q445IN5CU
- EC Number
- 207-924-5
- Nikkaji
- J2.601H
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 126
Experimental & physicochemical properties
LogP
1.84
1.91
Food Additives
FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Food
Solubility
5.9 mg/mL
slightly soluble in water; soluble in oils
moderately soluble (in ethanol)
Boiling Point
280.00 °C. @ 760.00 mm Hg
280 °C
Physical Description
White solid; [Merck Index] Off-white or white crystalline powder; [Alfa Aesar MSDS]
Solid
White crystalline solid, faint, sweet, somewhat balsamic and coumarin-like odour
Physicochemical properties
- Melting point
- 45 · 45-48 °C (lit.)
- Boiling point
- 280 °C · 280 °C (lit.)
- Density
- 1.071 g/mL · 1.071 g/mL at 25 °C (lit.)
- vapor pressure
- 0.356 Pa · 0.356Pa at 25℃
- FEMA
- 2889 · 2889 | 3-PHENYLPROPIONIC ACID
- refractive index
- 1.5408 · 1.5408 (estimate)
- FLAVIS Number
- 8.032 · 08.032 | 3-Phenylpropionic acid
- Flash point
- 230 °F · >230 °F
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 0.6 % · 0.6% soluble in water, soluble in alcohol, Propylene glycol, Glycerin and oils
- form
- Liquid
- pka
- 4.66 · 4.66(at 25℃)
- Specific Gravity
- 1.071 · 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
- Water Solubility
- Soluble in water
- Merck
- 14 · 14,4784
- JECFA Number
- 646 · 646
- BRN
- 907515 · 907515
- Major Application
- 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
- 1.153 at · 1.153 at 25℃
- CAS DataBase Reference
- 501 · 501-52-0(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 3 · 3-PHENYLPROPIONIC ACID
- EWG's Food Scores
- 2 · 2
- FDA UNII
- 5 Q445IN5CU · 5Q445IN5CU
- NIST Chemistry Reference
- 3 · 3-Phenylpropanoic acid(501-52-0)
- EPA Substance Registry System
- Hydrocinnamic acid (501-52-0)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 22 · 22-24/25-37/39-26
- WGK Germany
- 3 · 3
- RTECS
- 8600000 · DA8600000
- TSCA
- TSCA listed
- HS Code
- 29163900 · 29163900
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 95.6% (238 of 249) of all reports.
Not Classified
Aggregated GHS information provided per 249 reports by companies from 8 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Benzenepropanoic acid
Commission 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/33212
3-Phenylpropionic acid: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- DA8600000
- hs_code
- 29163900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 22-24/25-37/39-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Pharmacology
Uses & manufacturing
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Applications
Description3-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.
UsesFood 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.
OccurrenceReported 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.
UsesUsed 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 DescriptionHydrocinnamic 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 methods
PreparationHydrogenation 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.
PreparationBy reduction of cinnamic acid using sodium amalgam.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A monocarboxylic acid that is propionic acid substituted at position 3 by a phenyl group.
Related reactions
Linked notes
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