ChemFOnt: Showing chemical card for Phenylpropiolic acid (CFc000001589)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:15 UTC

Chemfont ID

CFc000001589

Molecule Identification

Common Name

Phenylpropiolic acid

Definition

Phenylpropiolic acid is an acetylenic compound that is propynoic acid in which the acetylenic hydrogen is replaced by a phenyl group. It is an alpha,beta-unsaturated monocarboxylic acid, an acetylenic compound and a member of benzenes. It derives from a propynoic acid. Phenylpropiolic acid is one of a number of phenylpropanoid, natural products occurring in plants pathways involved in plant resistance providing building units of physical barriers against pathogen invasion, synthesizing an array of antibiotic compounds, and producing signals implicated in the mounting of plant resistance. (PMID 15199968 ). Phenylpropiolic acid is a cis-pyrrolidinone that has been tested as an inhibitors of type II 17beta-hydroxysteroid dehydrogenase for the treatment of osteoporosis. (PMID 16806919 ). Phenylpropiolic acid (C6H5CCCO2H) is formed by the action of alcoholic potash on cinnamic acid dibromide (C6H5CHBrCHBrCO2H), crystallizes in long needles or prisms which melt at 136–137 °C. When heated with water to 120 °C, it yields phenylacetylene (C6H5CCH). Chromic acid oxidizes it to benzoic acid; zinc and acetic acid reduce it to cinnamic acid, C6H5CH=CHCO2H, whilst sodium amalgam reduces it to hydrocinnamic acid, C6H5CH2CH2CO2H. Ortho-nitrophenylpropiolic acid, NO2C6H4CCCO2H, prepared by the action of alcoholic potash on ortho-nitrocinnamic acid dibromide, crystallizes in needles which decompose when heated to 155–156 °C. It is readily converted into indigo.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Phenylpropiolic acid	ChEBI
3-Phenylpropynoic acid	ChEBI
beta-Phenylpropargylic acid	ChEBI
Phenylacetylene monocarboxylic acid	ChEBI
Phenylacetylenecarboxylic acid	ChEBI
Phenylpropynoic acid	ChEBI
3-Phenylpropiolate	Generator
3-Phenylpropynoate	Generator
b-Phenylpropargylate	Generator
b-Phenylpropargylic acid	Generator
beta-Phenylpropargylate	Generator
Β-phenylpropargylate	Generator
Β-phenylpropargylic acid	Generator
Phenylacetylene monocarboxylate	Generator
Phenylacetylenecarboxylate	Generator
Phenylpropynoate	Generator
Phenylpropiolate	Generator
3-Phenyl-2-propynoate	HMDB
3-Phenyl-2-propynoic acid	HMDB
3-Phenyl-propiolate	HMDB
3-Phenyl-propiolic acid	HMDB
Phenyl-(8ci)propiolate	HMDB
Phenyl-(8ci)propiolic acid	HMDB
Phenyl-propiolate	HMDB
Phenyl-propiolic acid	HMDB
Phenylpropioplate	HMDB
Phenylpropioplic acid	HMDB

Chemical Formula

C₉H₆O₂

Average Molecular Weight

146.1427

Monoisotopic Molecular Weight

146.036779436

IUPAC Name

3-phenylprop-2-ynoic acid

Traditional Name

phenylpropiolic acid

CAS Registry Number

637-44-5

SMILES

OC(=O)C#CC1=CC=CC=C1

InChI Identifier

InChI=1S/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11)

InChI Key

XNERWVPQCYSMLC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0002359)
Cell membrane (HMDB: HMDB0002359)

Source

Exogenous

Exogenous (HMDB: HMDB0002359)

Endogenous

Plant

Plant (HMDB: HMDB0002359)

Process

Not Available

Role

Industrial application

Drug (HMDB: HMDB0002359)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	1.7	ALOGPS
logP	2.15	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	2.77	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	38.45 m³·mol⁻¹	ChemAxon
Polarizability	14.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon