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| | (R)-(+)-2-(4-Hydroxyphenoxy)propionic acid Basic information |
| | (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) |
| Hazard Codes | Xi | | Risk Statements | 41 | | Safety Statements | 26-39 | | WGK Germany | 1 | | HS Code | 29189900 |
| | (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.
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| | (R)-(+)-2-(4-Hydroxyphenoxy)propionic acid Preparation Products And Raw materials |
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