Showing Compound Phenoxyacetic acid (FDB008245)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:59 UTC

Update date

2019-11-26 03:02:20 UTC

Primary ID

FDB008245

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Phenoxyacetic acid

Description

Phenoxyacetic acid, also known as phenoxyacetate or POA, belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative. Phenoxyacetic acid is a sweet and sour tasting compound. Phenoxyacetic acid has been detected, but not quantified in, cocoa and cocoa products and cocoa beans (Theobroma cacao). This could make phenoxyacetic acid a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Phenoxyacetic acid.

CAS Number

122-59-8

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Glycol acid phenyl ether	ChEBI
Phenoxacetic acid	ChEBI
Phenoxyacetate	ChEBI
Phenoxyessigsaeure	ChEBI
Phenoxyethanoic acid	ChEBI
POA	ChEBI
Phenoxacetate	Generator
Phenoxyethanoate	Generator
POA CPD	MeSH
2-Phenoxy-acetic acid	HMDB
FEMA 2872	HMDB
Glycolic acid phenyl ether	HMDB
Glycolic acid, phenyl ether	HMDB
Glycollic acid phenyl ether	HMDB
O-Phenylglycolic acid	HMDB
Phenoxy acetic acid	HMDB
Phenoxy-acetic acid	HMDB
Phenxoyacetic acid	HMDB
Phenyl ether glycolic acid	HMDB
Phenoxyacetic acid	KEGG
Phenoxyacetate derivative	Generator
Acetic acid, 2-phenoxy-	biospider
Acetic acid, phenoxy-	biospider
O-phenylglycolic acid	biospider
Phenylglycolic acid, o-	biospider

Predicted Properties

Property	Value	Source
Water Solubility	5.24 g/L	ALOGPS
logP	1.48	ALOGPS
logP	1.29	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.7	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	38.61 m³·mol⁻¹	ChemAxon
Polarizability	14.93 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H8O3

IUPAC name

2-phenoxyacetic acid

InChI Identifier

InChI=1S/C8H8O3/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)

InChI Key

LCPDWSOZIOUXRV-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)COC1=CC=CC=C1

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

Classification

Description

Belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Phenoxyacetic acid derivatives

Alternative Parents

Substituents

Phenoxyacetate
Phenoxy compound
Phenol ether
Alkyl aryl ether
Monocarboxylic acid or derivatives
Ether
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

monocarboxylic acid (CHEBI:8075 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Theobroma cacao

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Molecular messenger:

Neurotransmitter

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 63.15%; H 5.30%; O 31.55%	DFC
Melting Point	Mp 98-99°	DFC
Boiling Point	Bp 285° dec.	DFC
Experimental Water Solubility	12 mg/mL at 10 oC	CHIOU,CT et al. (1977)
Experimental logP	1.34	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 5.12	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Phenoxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-0ufr-9300000000-7ad28b74c9749c6a27fb	Spectrum
GC-MS	Phenoxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-00rl-2920000000-ccf47f028186b228d236	Spectrum
GC-MS	Phenoxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-00ku-3910000000-809db140994c447b1314	Spectrum
GC-MS	Phenoxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-0ufr-9300000000-7ad28b74c9749c6a27fb	Spectrum
GC-MS	Phenoxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-00rl-2920000000-ccf47f028186b228d236	Spectrum
GC-MS	Phenoxyacetic acid, non-derivatized, GC-MS Spectrum	splash10-00ku-3910000000-809db140994c447b1314	Spectrum
Predicted GC-MS	Phenoxyacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0k96-9600000000-0b1c392df3d6c30c93ed	Spectrum
Predicted GC-MS	Phenoxyacetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0609-9210000000-e9bbb8d403c568e9a2f1	Spectrum
Predicted GC-MS	Phenoxyacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-2900000000-8b8c5b741f385415e1bb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9100000000-27d995b989f69c80f2ec	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-6f469cdc95e10cb50c99	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-d3491d871372f4c0b4ad	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-60b44595fb61c23d6b2f	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-10882b67af18ede7a438	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-0900000000-e21c3daae68a323b89c8	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fbi-9400000000-a7b4ff30d1892c67113d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-ee72908afbf7bb97e335	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-179cbb3fbb78fa35dec7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ke9-9700000000-671d63b736938e0ce289	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-0900000000-354976721016ca0ec09d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-9500000000-42bcfb8ed625596a4c60	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-0472014d1afd9430461d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-aa3e4aa5a7bfc3b3c832	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1900000000-45a1aa986c61c7039bc6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-973545fead4d7effef6c	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

8075

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB31609

CRC / DFC (Dictionary of Food Compounds) ID

DDX10-N:DDX10-N

EAFUS ID

2982

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

06Y

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1033781

SuperScent ID

19188

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sour	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Phenoxyacetic acid (FDB008245)

Structure for FDB008245 (Phenoxyacetic acid)