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PHENOXYACETIC ACID

CAS: 122-59-8
European Community (EC) Number: 204-556-7
IUPAC Name: 2-phenoxyacetic acid
Molecular Weight: 152.15
Molecular Formula: C6H5OCH2COOH or C8H8O3

Phenoxyacetic acid is a monocarboxylic acid that is the O-phenyl derivative of glycolic acid.
A metabolite of 2-phenoxyethanol, Phenoxyacetic acid is used in the manufacture of pharmaceuticals, pesticides, fungicides and dyes.
Phenoxyacetic acid has a role as a human xenobiotic metabolite, an Aspergillus metabolite, a plant growth retardant and an allergen.
Phenoxyacetic acid is a monocarboxylic acid and an aromatic ether.
Phenoxyacetic acid derives from a glycolic acid.
Phenoxyacetic acid is a conjugate acid of a phenoxyacetate.

Phenoxyacetic acid appears as light tan powder or white solid.

Phenoxyacetic acid, POA, is a white solid with the formula of C8H8O3.
Although not itself usefully active as an herbicide, Phenoxyacetic acid forms the part-structure of many phenoxy herbicide derivatives including MCPA and 2,4-D.

Phenoxyacetic acid is an O-phenyl derivative of glycolic acid.
Phenoxyacetic acid is both a monocarboxylic acid and an aryl ether.
Phenoxyacetic acids preparation from sodium phenolate and sodium chloroacetate in hot water was first reported in 1880.

The phenolate anion reacts via nucleophilic attack on the methylene carbon of the chloroacetic acid, forming an ether bond.

Phenoxyacetic acid is a white or clear crystalline compound at room temperature.
When impure, Phenoxyacetic acid can appear to be a light tan to brown.
Phenoxyacetic acid has a solubility in water of 12 g/L and is highly soluble in organic solvents including ethanol, diethyl ether and benzene.
Phenoxyacetic acid is a weak acid and weak base with a pKa of 3.7.

Phenoxyacetic acid has found minor uses as a food additive and perfume component and is categorised as "generally recognised as safe" in these applications.

Phenoxyacetic acids are very important chemicals because of their wide distribution and extensive use as plant growth regulators.
2,4-diphenoxyacetic acid (2,4-D) is used as agricultural herbicides against broad leaf weeds in cereal crop farm as well as on pastures and lawns, in parks, and on golf courses. Chlorophenoxyacetic acid (CPA) is used worldwide as a plant growth regulator for agricultural and non-agrieultural purposes.
Typically, Phenoxyacetic acid is employed on a large scale for weed control on cereal crops and lawns.
Adsorption of phenoxyacetic acids onto solid adsorbents is very important, since it can effectively remove pollutants from aqueous stream.

The first phenoxyacetic acid was 2,4-D, developed in the early 1940s.
Phenoxyacetic acid was followed by several other derivatives, the common structural element being a chloro-substituted phenoxy group usually attached to the β-carbon of an aliphatic carboxylic acid (acetic acid, propionic acid, butyric acid).

The main molecular structure of phenoxy acid herbicides contains phenoxyacetic acid, phenoxy propionic acid, and aryloxy-phenoxy propionic acid.
Most effective on caulines and leaves, the common characteristics of these herbicides include high selectivity, broad spectrum, low dosage, low cost, and safety.
Phenoxy acid herbicide is safe for humans, livestock, and the environment when normal dosages are used.
However, the synthesis of 2,4,5-trichlorophenoxyacetic acid (2,4,5-T) generates dioxin, which is a strong teratogen.
2,4,5-T is, therefore, restricted or banned in many countries.
Phenoxy acid herbicides mainly include 2,4-D, MCPA, diclofop-methyl, and fluazifop-butyl.

Phenoxyacetic acid is a herbicide and its photodegradation using TiO2 as photocatalyst has been studied.
Selective separation of penicillin V from phenoxyacetic acid using liquid membranes consisting of 1,2-dichloroethane and Amberlite LA-2 as carrier has been studied.

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.
In humans, phenoxyacetic acid is involved in the rosiglitazone metabolism pathway.
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.
Phenoxyacetic acid is a primary metabolite.
Primary metabolites are metabolically or physiologically essential metabolites.
They are directly involved in an organism’s growth, development or reproduction.
Based on a literature review a small amount of articles have been published on Phenoxyacetic acid.

A monocarboxylic acid that is the O-phenyl derivative of glycolic acid.
A metabolite of 2-phenoxyethanol, it is used in the manufacture of pharmaceuticals, pesticides, fungicides and dyes.

Phenoxyacetic acid is found in cocoa and cocoa products.
Phenoxyacetic acid is a flavouring ingredient. Phenoxyacetic acid is on the FDA list of approved food additives.

SYNONYMS:

PHENOXYACETIC ACID

2-phenoxyacetic acid

122-59-8

Phenoxyethanoic acid

Acetic acid, phenoxy-

Phenoxy acetic acid

Glycolic acid phenyl ether

Glycol acid phenyl ether

o-Phenylglycolic acid

Phenoxyacetate

Glycollic acid phenyl ether

Acetic acid, 2-phenoxy-

Acide phenoxyacetique

Glycolic acid, phenyl ether

Phenoxyessigsaeure

Phenylglycolic acid, O-

Phenyl ether glycolic acid

Phenoxy-Acetic Acid

2-phenoxy-acetic acid

Acide phenoxyacetique [French]

POA

phenoxacetic acid

NSC 9810

MFCD00004296

UNII-YRC253429Q

CHEBI:8075

2-phenoxyethanoic acid

YRC253429Q

NCGC00091151-01

DSSTox_CID_5873

Phenoxyacetic acid, 98+%

DSSTox_RID_77956

DSSTox_GSID_25873

CAS-122-59-8

FEMA No. 2872

CCRIS 7275

EINECS 204-556-7

BRN 0907949

AI3-06295

Phenoxyacetc acd

Phenxoyacetic acid

2-(phenoxy)acetic acid

Phenoxyacetic acid, 98%

ACMC-1BC4K

bmse000742

Epitope ID:122699

SCHEMBL8127

4-06-00-00634 (Beilstein Handbook Reference)

MLS002454438

CHEMBL173521

DTXSID9025873

FEMA 2872

LCPDWSOZIOUXRV-UHFFFAOYSA-

NSC9810

HMS1783L04

HMS3039A16

ZINC331715

HY-Y0267

NSC-9810

Tox21_111092

Tox21_201854

Tox21_303164

ANW-17998

BBL015276

Phenoxymethylpenicillin EP Impurity B

SBB040522

STK300005

AKOS000103786

Tox21_111092_1

BS-3837

MCULE-5625991303

NCGC00091151-02

NCGC00091151-04

NCGC00257086-01

NCGC00259403-01

SMR001372021

CS-0013736

FT-0658304

FT-0673712

P0107

ST45061459

C02181

D70383

AC-907/25014208

Q904253

SR-01000854537

J-004833

J-523928

SR-01000854537-2

Phenoxyacetic acid, PESTANAL(R), analytical standard

Z57182011

F0777-0784

06Y