(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid Chemical Properties

Melting point:

145-148 °C (lit.)

alpha 

58 º (c=1, MeOH)

Boiling point:

367.5±17.0 °C(Predicted)

Density 

1.302±0.06 g/cm3(Predicted)

refractive index 

38 ° (C=0.1, MeOH)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.32±0.10(Predicted)

color 

Off-White

optical activity

[α]20/D +58°, c = 1 in methanol

InChI

InChI=1S/C9H10O4/c1-6(9(11)12)13-8-4-2-7(10)3-5-8/h2-6,10H,1H3,(H,11,12)/t6-/m1/s1

InChIKey

AQIHDXGKQHFBNW-ZCFIWIBFSA-N

SMILES

C(O)(=O)[C@H](OC1=CC=C(O)C=C1)C

CAS DataBase Reference

94050-90-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

26-39

WGK Germany 

1

HS Code 

29189900

MSDS

• Language:English Provider:SigmaAldrich

(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid Usage And Synthesis

Chemical Properties

White to off-white powder or crystal

Uses

(R)-(+)-2-(4-Hydroxyphenoxy)propionic Acid is a degradation product of Cyhalofop-butyl (C989385); an aryloxyphenoxypropionate compound that is used as a herbicide to eliminate grass weeds in rice fields. Cyhalofop-butyl works by selectively inhibiting acetyl CoA carboxylase, an enzyme that is important for the metabolism of fatty acids.

Synthesis

(R)-2-(4-hydroxyphenoxy)propionic acid ((R)-HPOPA) is an essential intermediate for the production of chiral aryloxyphenoxypropionic acid-type herbicides such as clod inafop-propargyl, cyhalofop-butyl, fenoxaprop-p-ethyl, metam ifop, quizalofop-p-ethyl, and quizalofop-p-tefuryl. In general, there are three chemical methods for the preparation of (R)-HPOPA: (1) resolution of racemic HPOPA with alkaloids such as quinine, cinchonine, ephedrine, vauquline or chiral agents such as S-(?)-α-phenylethylamine, L-(+)-chloromethane, R-(+)-α-isopropyl-4-chlorobenzylamine and (2) asymmetric synthesis from L-lactic acids or L-alanine. However, these methods are not always useful for industrial applications because of expensive reagents, problems with enantiopurity of product and low yields. Regioselective hydroxylation of (R)-2-phenoxypropionic acid ((R)-POPA) by microbes is a highly feasible method for the production of (R)-HPOPA, which under mild conditions allows complete transformation of substrate into a single stereoisomeric product with a high yield and without byproduct formation[1-2].

References

[1] Hai-Feng Hu . “A rapid throughput assay for screening (R)-2-(4-hydroxyphenoxy)propionic acid producing microbes.” Journal of microbiological methods 158 (2019): Pages 44-51.
[2] Haiyan Zhou. “An efficient route towards R-2-phenoxypropionic acid synthesis for biotransformative production of R-2-(4-hydroxyphenoxy)propionic acid.” Chinese Journal of Chemical Engineering 32 (2021): Pages 315-323.

(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid(94050-90-5)Related Product Information

• 4-Hydroxybenzoic acid
• 4-Hydroxybenzaldehyde
• Propionic anhydride
• L(+)-Lactic acid
• Propionic acid
• 3-(4-Hydroxyphenyl)propionic acid
• Anisole
• Methylparaben
• 3-(4-Methoxyphenyl)propionic acid
• (Trifluoromethoxy)benzene
• Nandrolone phenylpropionate
• Methyl (R)-(+)-2-(4-hydroxyphenoxy)propanoate
• Butyl (R)-(+)-2-(4-hydroxyphenoxy)propionate
• Ethyl (R)-(+)-2-(4-hydroxyphenoxy)propionate
• Propynyl (R)-(+)-2-(4-hydroxyphenoxy)propionate
• 2-(4-HYDROXYPHENYL)PROPIONIC ACID
• 2-(4-HYDROXYPHENOXY)PROPIONIC ACID HYDRAZIDE
• 2-(p-Hydroxyphenoxy)propionic acid,2-(4-HYDROXYPHENOXY)PROPIONIC ACID