| Identification | More | [Name]
(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid | [CAS]
94050-90-5 | [Synonyms]
D-2-(4-HYDROXYPHENOXY)PROPIONIC ACID
D-HPPA
(R)-2-(4-HYDROPHENOXY)PROPIONIC ACID
R-2-(4-HYDROXYPHENOXY)PROPANOIC ACID
(R)-(+)-2-(4-HYDROXYPHENOXY)PROPIONIC ACID
(R)-2-(4-HYDROXYPHENOXY)PROPIONIC ACID
R-(+)-2-(HYDROXYPHENOXY)PROPIONIC
(R)-(+)-2-(HYDROXYPHENOXY)PROPIONIC ACID
（R）-（+）-（4-hydroxyphenoxy)-propionic acid
(2R)-2-(4-hydroxyphenoxy)propanoic acid
(R)-(+)-2-(4-HYDROXYPENOXY)PROPIONIC ACID
HYDROXYPHENOXYPROPIONIC ACID
(R)-(+)-2-(4-Hydroxyphenoxy)Pr
R-(+)-2-(4-HYDROXYPHENYL)PROPIONIC ACID
R-2-(4-Hydroxyphenoxy)propanoic aicd
R-(+)-2-(4-Hydrobenzoxy)propionic acid
(-)-p-Hydroxyhydratropic acid
[R,(-)]-2-(p-Hydroxyphenyl)propionic acid
(R)-2-(p-Hydroxyphenoxy)propionic acid
(S)-2-(4-Hydroxyphenyl)propionic acid | [EINECS(EC#)]
407-960-3 | [Molecular Formula]
C9H10O4 | [MDL Number]
MFCD00274088 | [Molecular Weight]
182.17 | [MOL File]
94050-90-5.mol |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection . | [WGK Germany ]
1
| [HS Code ]
29189900 |
| Hazard Information | Back Directory | [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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