Benzenepropanoic acid

HCID 107CAS 501-52-0

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

hydrocinnamic acid3-phenylpropionic acid501-52-0Benzenepropanoic acidDihydrocinnamic acidBenzenepropionic acid3-Phenyl propionic acid3-Phenyl-propionic acidFEMA No. 2889DTXSID20470645Q445IN5CUNSC-9272
Show more names
HYDROXYCINNAMIC ACIDFEMA 2889hydrocinnamicNSC 9272Hydrocinamic acid
DTXCID0027064CHEBI:28631RefChem:789007207-924-53-Phenylpropanoic acidBenzylacetic acidBETA-PHENYLPROPIONIC ACIDPhenylpropanoic acid

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

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Organic Acids
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesAngular frequency
FragrancesFragrance Ingredient (3-Phenylpropionic acid) -> IFRA transparency List
LogP · 2 items

1.84

1.91

Food Additives · 2 items

FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Food

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)

Safety & regulation

GHS classification

GHS Classification · 3 items

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 · 4 items

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

Hazards SummaryIntraperitoneal 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 CategoriesNot Classified

Safety data

wgk
3
tsca
TSCA listed
rtecs
DA8600000
hs_code
29163900
risk_code
36/37/38
Signal word
Warning

Chemistry & industry

Pharmacology

Tissue LocationsKidney
Cellular LocationsCytoplasm

Uses & manufacturing

UsesUsed as flavoring agent or adjuvant; [FDA]
Use Classification · 6 items

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

General Manufacturing InformationBenzenepropanoic acid: ACTIVE
Applications · 5 items

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Additional notes

DefinitionChEBI: A monocarboxylic acid that is propionic acid substituted at position 3 by a phenyl group.

Related reactions

154 records

Linked notes

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