(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid
- CAS No.
- 94050-90-5
- Chemical Name:
- (R)-(+)-2-(4-Hydroxyphenoxy)propionic acid
- Synonyms
- D-HPPA;(R)-2-(4-HYDROXYPHENOXY)PROPIONIC ACID;(R)-(+)-2-(4-Hydroxy;Hydroxy phenyl propionate;Phenyl Acetate Impurity 24;HYDROXYPHENOXYPROPIONIC ACID;(R)-(+)-2-(4-Hydroxyphenoxy);(-)-p-Hydroxyhydratropic acid;(R)-(+)-2-(4-Hydroxyphenoxy)Pr;R-(+)-2-(HYDROXYPHENOXY)PROPIONIC
- CBNumber:
- CB6711601
- Molecular Formula:
- C9H10O4
- Molecular Weight:
- 182.17
- MOL File:
- 94050-90-5.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/10/25 16:21:11
| 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) |
(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid Chemical Properties,Uses,Production
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 Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Aether Industries Limited | +91-261-6603130 +91-2616603130 | Gujarat, India | 145 | 58 | Inquiry |
| ARRKEM LIFE SCIENCES PRIVATE LIMITED | +91-8148739767 +91-8148739767 | Telangana, India | 347 | 58 | Inquiry |
| Bhagiradha Chemicals & Industries Limited | -23619165.88 | Andhra Pradesh, India | 2 | 58 | Inquiry |
| S. Amit Speciality Chemicals Pvt. Ltd. | 91-22-40013003 | Maharashtra, India | 177 | 58 | Inquiry |
| Bhagiradha Chemicals & Industries Limited (BCIL) | 91-40-42221212 | Hyderabad, India | 4 | 58 | Inquiry |
| Aether Industries Limited | 91-261-3303000 | Gujarat, India | 27 | 58 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6257 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6100 | 58 | Inquiry |
| Rensun Pharmaceuticals Pvt Ltd. | 91-22-28223755 | Maharashtra, India | 152 | 58 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6768 | 58 | Inquiry |
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