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94050-90-5

94050-90-5 Structure

94050-90-5 Structure
IdentificationMore
[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 PropertiesBack 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 Rotation]

[α]20/D +58°, c = 1 in methanol
[Cosmetics Ingredients Functions]

SKIN CONDITIONING
[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 DataBack Directory
[Symbol(GHS) ]

Corrosion (GHS05)
GHS05
[Signal word ]

Danger
[Hazard statements ]

H318
[Precautionary statements ]

P280-P305+P351+P338
[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
[REACH Registrations]

Inactive
[HS Code ]

29189900
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Eye Dam. 1
Hazard InformationBack 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.
Spectrum DetailBack Directory
[Spectrum Detail]

(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid(94050-90-5)MS
(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid(94050-90-5)1HNMR
(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid(94050-90-5)13CNMR
(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid(94050-90-5)IR1
(R)-(+)-2-(4-Hydroxyphenoxy)propionic acid(94050-90-5)IR2
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

94050-90-5(sigmaaldrich)
[TCI AMERICA]

(R)-(+)-2-(4-Hydroxyphenoxy)propionic Acid,>98.0%(GC)(T)(94050-90-5)
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