(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid Struktur

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

Bezeichnung:(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid

CAS-Nr94050-90-5

Englisch Name:(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid

CBNumberCB6711601

SummenformelC9H10O4

Molgewicht182.17

MOL-Datei94050-90-5.mol

(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	145-148 °C (lit.)
alpha	58 º (c=1, MeOH)
Siedepunkt	367.5±17.0 °C(Predicted)
Dichte	1.302±0.06 g/cm3(Predicted)
Brechungsindex	38 ° (C=0.1, MeOH)
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	3.32±0.10(Predicted)
Farbe	Off-White
Optische Aktivität	[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 Datenbank	94050-90-5(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	41
S-Sätze:	26-39
WGK Germany	1
HS Code	29189900

Gefahreninformationscode (GHS)

(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R41:Gefahr ernster Augenschäden.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S39:Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
White to off-white powder or crystal
Verwenden
(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.
Synthese
(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].
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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