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59-42-7

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59-42-7 Usage

Description

This synthetic drug has both chemical and pharmacological similarities to norepinephrine. A characteristic quality of phenylephrine is the distinctly expressed selectivity to α- adrenoreceptors, especially α1-adrenoreceptors. Although phenylephrine increases the contractibility of blood vessels, in practical terms it is not considered a cardiostimulant.

Chemical Properties

White or almost white, crystalline powder.

Uses

Different sources of media describe the Uses of 59-42-7 differently. You can refer to the following data:
1. L-Phenylephrine is an adrenergic α1A receptor agonist (Ki = 1.4 μM) that demonstrates selectivity against the α1B and α1C receptor subtypes (Kis = 23.9 and 47.8 μM, respectively). By stimulating adrenergic α1 receptors, L-phenylephrine can induce aortic smooth muscle contractions, although reported relative affinity and potency values in rabbit are 5-fold weaker compared to that of L-norepinephrine. This compound is frequently used to precontract smooth muscle in preparations designed to study the properties of various vasodilator agents. Because L-phenylephrine acts on adrenergic α1 receptors in the arterioles of the nasal mucosa to produce constriction, it has been examined clinically as an oral decongestant.
2. Phenylephrine is used in hypotension, paroxysmal supraventricular tachycardia, and shock. It is also used locally, particularly in the form of nasal spray, for relieving edema.

Definition

ChEBI: A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.

Brand name

Afrin 4 Hour Nasal Spray (Schering-Plough Health Care); Biomydrin (Parke-Davis); Mydfrin (Alcon); Neo-Synephrine (Sterling Health U.S.A.); Nostril (Boehringer Ingelheim);Fenox;Forte;Isopto;Minims;Visadron.

General Description

(Neo-Synephrine, a prototypical selectivedirect-acting 1-agonist) differs from E only inlacking a p-OH group. It is orally active, and its DOA isabout twice that of E because it lacks the catechol moietyand thus is not metabolized by COMT. However, its oralbioavailability is less than 10% because of its hydrophilicproperties (log P=0.3), intestinal 3 -O-glucuronidation/sulfation and metabolism by MAO. Lacking the p-OHgroup, it is less potent than E and NE but it is a selectiveα1-agonist and thus a potent vasoconstrictor. It is usedsimilarly to metaraminol and methoxamine for hypotension.Another use is in the treatment of severe hypotensionresulting from either shock or drug administration. It alsohas widespread use as a nonprescription nasal decongestantin both oral and topical preparations. When applied tomucous membranes, it reduces congestion and swelling byconstricting the blood vessels of the membranes. In theeye, it is used to dilate the pupil and to treat open-angleglaucoma. In addition, it is used in spinal anesthesia toprolong the anesthesia and to prevent a drop in blood pressureduring the procedure. It is relatively nontoxic and produceslittle CNS stimulation. Metaraminol is just anotherexample.

Clinical Use

Phenylephrine is a potent direct-acting α1-agonist with clinical effects similar to those of noradrenaline. It causes widespread vasoconstriction with an increase in arterial pressure, reflex bradycardia and decrease in cardiac output. It may be administered by i.v. bolus (50–100μg boluses) and i.v. infusion (50–150μgmin –1) to maintain arterial pressure during general anaesthesia or other causes of low SVR. It may also be used topically as a nasal decongestant or mydriatic. There is some evidence suggesting a paradoxical reduction in cerebral oxygen delivery.

Safety Profile

Poison by ingestion, subcutaneous, intravenous, intraperitoneal, and intraduodenal routes. Human systemic effects by ocular route: blood pressure increase. An experimental teratogen. Other experimental reproductive effects. A nasal decongestant. When heated to decomposition it emits toxic fumes of NOx.

Synthesis

Phenylephrine, 1-(3-hydroxyphenyl)-2-methylaminoethanol (11.1.16), which differs from epinephrine, in that it does not have a hydroxyl group at C4 of the aromatic ring, is synthesized by an analogous scheme of making epinephrine; however, instead of using ω-chloro-3,4-dihydroxyacetophenone, ω-chloro-3-dihydroxyacetophenone is used [11,22,23].

Veterinary Drugs and Treatments

Phenylephrine has been used to treat hypotension and shock (after adequate volume replacement), but many clinicians prefer to use an agent that also has cardiostimulatory properties. Phenylephrine is recommended for use to treat hypotension secondary to drug overdoses or idiosyncratic hypotensive reactions to drugs such as phenothiazines, adrenergic blocking agents, and ganglionic blockers. Its use to treat hypotension resulting from barbiturate or other CNS depressant agents is controversial. Phenylephrine has been used to increase blood pressure to terminate attacks of paroxysmal supraventricular tachycardia, particularly when the patient is also hypotensive. Phenylephrine has been used to both treat hypotension and prolong the effects of spinal anesthesia. Ophthalmic uses of phenylephrine include use for some diagnostic eye examinations, reducing posterior synechiae formation, and relieving pain associated with complicated uveitis. It has been applied intranasally in an attempt to reduce nasal congestion.

in vitro

in neonatal rat cardiomyocytes, 50 μm l-phenylephrine treatment could protect cells from apoptosis induced by hypoxia (95% n2 and 5% co2) and serum deprivation through α-adrenergic receptor stimulation [2]. besides, in neural progenitor cells (npcs), 10 μm l-phenylephrine could increase npcs proliferation by approximately 160% [3]. furthermore, in cultured rat neonatal cms (ncms), l-phenylephrine could increase cross-sectional area, and significantly increase il-6 mrna levels, while decreasing pgc1α mrna levels [4].

in vivo

studies in sprague-dawley male rats found that, local infiltration of l-phenylephrine could induce cutaneous anesthesia in a dose dependent manner, which could be significantly inhibited by α1-adrenergic receptor antagonists [5].

target

adrenergic α1a receptor

references

[1] lomasney j w, cotecchia s, lorenz w, et al. molecular cloning and expression of the cdna for the alpha 1a-adrenergic receptor. the gene for which is located on human chromosome 5.[j]. journal of biological chemistry, 1991, 266(10): 6365-6369.[2] zhu h, mcelweewitmer s, perrone m, et al. phenylephrine protects neonatal rat cardiomyocytes from hypoxia and serum deprivation-induced apoptosis.[j]. cell death & differentiation, 2000, 7(9): 773-784.[3] hiramoto t, ihara y, watanabe y, et al. α-1 adrenergic receptors stimulation induces the proliferation of neural progenitor cells in vitro[j]. neuroscience letters, 2006, 408(1): 25-28.[4] planavila a, redondo i, hondares e, et al. fibroblast growth factor 21 protects against cardiac hypertrophy in mice[j]. nature communications, 2013.[5] shieh j, chu c, wang j, et al. epinephrine, phenylephrine, and methoxamine induce infiltrative anesthesia via α1-adrenoceptors in rats[j]. acta pharmacologica sinica, 2009, 30(9): 1227-1236.[6] hatton r c, winterstein a g, mckelvey r p, et al. efficacy and safety of oral phenylephrine: systematic review and meta-analysis[j]. annals of pharmacotherapy, 2007, 41(3): 381-390.

Check Digit Verification of cas no

The CAS Registry Mumber 59-42-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 9 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 59-42:
(4*5)+(3*9)+(2*4)+(1*2)=57
57 % 10 = 7
So 59-42-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H13NO2.ClH/c1-10-6-9(12)7-3-2-4-8(11)5-7;/h2-5,9-12H,6H2,1H3;1H/t9-;/m0./s1

59-42-7 Well-known Company Product Price

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  • TCI America

  • (P0395)  L-Phenylephrine  >98.0%(HPLC)(T)

  • 59-42-7

  • 5g

  • 690.00CNY

  • Detail
  • TCI America

  • (P0395)  L-Phenylephrine  >98.0%(HPLC)(T)

  • 59-42-7

  • 25g

  • 1,890.00CNY

  • Detail

59-42-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name phenylephrine

1.2 Other means of identification

Product number -
Other names Mydfrin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:59-42-7 SDS

59-42-7Synthetic route

(S)-phenylephrine
614-03-9

(S)-phenylephrine

Phenylephrin
59-42-7

Phenylephrin

Conditions
ConditionsYield
Stage #1: (S)-phenylephrine With sulfuric acid; acetic anhydride at 105℃; for 12h; Walden inversion;
Stage #2: With water at 95℃; for 3h; Walden inversion; optical yield given as %ee; enantioselective reaction;
99%
With sulfuric acid; acetic anhydride und Erhitzen des Reaktionsprodukts mit wss.Salzsaeure und anschliessend mit wss.Ammoniak;
(R)-phenylephrine-(R)-naproxen
1280541-42-5

(R)-phenylephrine-(R)-naproxen

Phenylephrin
59-42-7

Phenylephrin

Conditions
ConditionsYield
Stage #1: (R)-phenylephrine-(R)-naproxen With hydrogenchloride In water; toluene at 75 - 80℃; for 0.5h; pH=< 2;
Stage #2: With ammonium hydroxide In water at 1 - 15℃; pH=~ 9; Product distribution / selectivity;
90%
α-methylamino-m-hydroxy-acetophenone sulfate

α-methylamino-m-hydroxy-acetophenone sulfate

Phenylephrin
59-42-7

Phenylephrin

Conditions
ConditionsYield
Stage #1: α-methylamino-m-hydroxy-acetophenone sulfate With hydrogen; (((R)-1-diphenylphosphino-2-[((S)-α-(N,N-dimethylamino)-o-diphenylphosphino-phenyl)methyl]ferrocene)-η5-2,4-dimethyl-pentadienyl)-ruthenium(II) iodide In methanol at 70℃; under 23272.3 Torr; for 48h;
Stage #2: With ammonium hydroxide In water at 65℃; for 0.0833333h; pH=~ 4.8 - 9;
88.7%
Phenylephrine
1477-63-0

Phenylephrine

Phenylephrin
59-42-7

Phenylephrin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Lg-tartaric acid
2: acetic acid anhydride; sulfuric acid / und Erhitzen des Reaktionsprodukts mit wss.Salzsaeure und anschliessend mit wss.Ammoniak
View Scheme
Multi-step reaction with 2 steps
1.1: methanol / 2 h / 20 - 65 °C / Resolution of racemate
2.1: hydrogenchloride / toluene; water / 0.5 h / 75 - 80 °C / pH < 2
2.2: 1 - 15 °C / pH ~ 9
View Scheme
3-Hydroxyphenyl-ω-methylaminoacetophenone hydrochloride
94240-17-2

3-Hydroxyphenyl-ω-methylaminoacetophenone hydrochloride

A

(S)-phenylephrine
614-03-9

(S)-phenylephrine

B

Phenylephrin
59-42-7

Phenylephrin

Conditions
ConditionsYield
With potassium hydroxide; hydrogen; [(R)-P-Phos RuCl2 (R)-DAIPEN] In water; isopropyl alcohol at 65℃; under 21002.1 Torr; for 1h; Product distribution / selectivity;A n/a
B n/a
With hydrogen; [(S)-Cl-MeO-Biphep RuCl2](dmf)n In methanol at 75℃; under 22502.3 Torr; for 18h; Product distribution / selectivity;A n/a
B n/a
With hydrogen; [RuCl-(S)-P-Phos(p-cymene)]Cl In methanol at 75℃; under 22502.3 Torr; for 18h; Product distribution / selectivity;A n/a
B n/a
3-Hydroxyphenyl-ω-methylaminoacetophenone hydrochloride
94240-17-2

3-Hydroxyphenyl-ω-methylaminoacetophenone hydrochloride

Phenylephrin
59-42-7

Phenylephrin

Conditions
ConditionsYield
With RuCl2[(S)-xylyl-2,2,6,6’-tetramethoxy-4,4’-bis(diphenylphosphino)-3,3-bipyridine][(R)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine]; hydrogen; potassium hydroxide In water; isopropyl alcohol at 65℃; under 21752.2 - 24752.5 Torr; for 2.25h; Autoclave; optical yield given as %ee; enantioselective reaction;
(R)-1-(3-methoxyphenyl)-2-nitroethanol

(R)-1-(3-methoxyphenyl)-2-nitroethanol

Phenylephrin
59-42-7

Phenylephrin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 5%-palladium/activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr
2: dichloromethane / 0 °C
3: boron tribromide / dichloromethane / 24 h / 0 °C
View Scheme
C10H15NO2
747358-03-8

C10H15NO2

Phenylephrin
59-42-7

Phenylephrin

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 0℃; for 24h;
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Phenylephrin
59-42-7

Phenylephrin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2,6-dimethylpyridine; copper(II) choride dihydrate; C50H54N2O6 / ethanol; dichloromethane / 30 h / 20 °C
2: 5%-palladium/activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr
3: dichloromethane / 0 °C
4: boron tribromide / dichloromethane / 24 h / 0 °C
View Scheme
(R)-2-N-tert-butoxycarbonyl-N-methylamino-1-(3-nitrophenyl)ethanol

(R)-2-N-tert-butoxycarbonyl-N-methylamino-1-(3-nitrophenyl)ethanol

Phenylephrin
59-42-7

Phenylephrin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper acetylacetonate; sodium tetrahydroborate / isopropyl alcohol; ethanol / 17 h / 30 °C / Inert atmosphere
2: hydrogenchloride; sodium nitrite / water / 0 - 120 °C
View Scheme
(R)-2-N-tert-butoxycarbonyl-N-methylamino-1-(3-aminophenyl)ethanol

(R)-2-N-tert-butoxycarbonyl-N-methylamino-1-(3-aminophenyl)ethanol

Phenylephrin
59-42-7

Phenylephrin

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 0 - 120℃;51.7 mg
Phenylephrin
59-42-7

Phenylephrin

phenylephrine hydrochloride
61-76-7

phenylephrine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol at 55 - 65℃; for 0.5h; Product distribution / selectivity;84.5%
With hydrogenchloride In water; isopropyl alcohol pH=7 - 8; enantioselective reaction;3.35 g
Phenylephrin
59-42-7

Phenylephrin

calcium carbide
75-20-7

calcium carbide

A

3-(2,2,3-trimethyl-oxazolidin-5-yl)-phenol
60052-56-4

3-(2,2,3-trimethyl-oxazolidin-5-yl)-phenol

B

m-(TRIMETHYLACETOXY)-α-[(METHYLAMINO)METHYL]BENZYL ALCOHOL HYDROCHLORIDE

m-(TRIMETHYLACETOXY)-α-[(METHYLAMINO)METHYL]BENZYL ALCOHOL HYDROCHLORIDE

Conditions
ConditionsYield
In acetoneA 70%
B n/a
3-naphthyl-1-phenyl-5-(5-fluoro-2-nitrophenyl)-2-pyrazoline

3-naphthyl-1-phenyl-5-(5-fluoro-2-nitrophenyl)-2-pyrazoline

Phenylephrin
59-42-7

Phenylephrin

C34H30N4O4

C34H30N4O4

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 4h; Reflux;63.2%
Phenylephrin
59-42-7

Phenylephrin

ethyl isocyanate
109-90-0

ethyl isocyanate

(1R)-1-(3-hydroxyphenyl)-2-<(ethylcarbamoyl)amino>ethanol
110193-48-1

(1R)-1-(3-hydroxyphenyl)-2-<(ethylcarbamoyl)amino>ethanol

Conditions
ConditionsYield
With triethylamine In diethyl ether Ambient temperature;21%
Phenylephrin
59-42-7

Phenylephrin

ethyl isocyanate
109-90-0

ethyl isocyanate

(1R)-1-(3-Hydroxyphenyl)-2-(N-ethylcarbamoyl)amino ethanol
126349-88-0

(1R)-1-(3-Hydroxyphenyl)-2-(N-ethylcarbamoyl)amino ethanol

Conditions
ConditionsYield
With triethylamine In diethyl ether21%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

Phenylephrin
59-42-7

Phenylephrin

(R)-5-(3-hydroxyphenyl)-3-methyl-2-oxazolidone
110193-49-2

(R)-5-(3-hydroxyphenyl)-3-methyl-2-oxazolidone

Conditions
ConditionsYield
With pyridine In dichloromethane at -78℃; for 0.5h;6%
Phenylephrin
59-42-7

Phenylephrin

(-)-1-acetoxy-1-(3-acetoxy-phenyl)-2-methylamino-ethane
63991-22-0

(-)-1-acetoxy-1-(3-acetoxy-phenyl)-2-methylamino-ethane

Phenylephrin
59-42-7

Phenylephrin

acetic anhydride
108-24-7

acetic anhydride

(R)-1-acetoxy-1-(3-acetoxy-phenyl)-2-(acetyl-methyl-amino)-ethane
94092-15-6

(R)-1-acetoxy-1-(3-acetoxy-phenyl)-2-(acetyl-methyl-amino)-ethane

bromocyane
506-68-3

bromocyane

Phenylephrin
59-42-7

Phenylephrin

3-(2-imino-3-methyl-oxazolidin-5-yl)-phenol

3-(2-imino-3-methyl-oxazolidin-5-yl)-phenol

Conditions
ConditionsYield
With sodium acetate In methanol
Phenylephrin
59-42-7

Phenylephrin

methyl isocyanate
624-83-9

methyl isocyanate

1-[(R)-2-Hydroxy-2-(3-hydroxy-phenyl)-ethyl]-1,3-dimethyl-urea

1-[(R)-2-Hydroxy-2-(3-hydroxy-phenyl)-ethyl]-1,3-dimethyl-urea

Conditions
ConditionsYield
With triethylamine In diethyl ether Ambient temperature;
Phenylephrin
59-42-7

Phenylephrin

ethyl isocyanate
109-90-0

ethyl isocyanate

ethylcarbamic acid (1R)-2<<(ethylamino)carbonyl>methylamino>ethyl ester
110193-53-8

ethylcarbamic acid (1R)-2<<(ethylamino)carbonyl>methylamino>ethyl ester

Conditions
ConditionsYield
With triethylamine In diethyl ether Ambient temperature;
Phenylephrin
59-42-7

Phenylephrin

1-{(R)-2-Hydroxy-2-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl}-1,3-dimethyl-urea
110193-26-5

1-{(R)-2-Hydroxy-2-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl}-1,3-dimethyl-urea

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / diethyl ether / Ambient temperature
2: 69 percent / cesium carbonate / acetone / 48 h / Heating
View Scheme
Phenylephrin
59-42-7

Phenylephrin

3-Ethyl-1-{(R)-2-hydroxy-2-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl}-1-methyl-urea
110193-25-4

3-Ethyl-1-{(R)-2-hydroxy-2-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl}-1-methyl-urea

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 21 percent / triethylamine / diethyl ether / Ambient temperature
2: 77 percent / cesium carbonate / acetone / 48 h / Heating
View Scheme
Phenylephrin
59-42-7

Phenylephrin

Ethyl-carbamic acid (R)-2-(3,3-diethyl-1-methyl-ureido)-1-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl ester; hydrochloride

Ethyl-carbamic acid (R)-2-(3,3-diethyl-1-methyl-ureido)-1-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl ester; hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / diethyl ether / Ambient temperature
2: 38 percent / cesium carbonate / acetone / 48 h / Heating
View Scheme
Phenylephrin
59-42-7

Phenylephrin

Ethyl-carbamic acid (R)-2-(3,3-diethyl-1-methyl-ureido)-1-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl ester
110193-21-0

Ethyl-carbamic acid (R)-2-(3,3-diethyl-1-methyl-ureido)-1-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / diethyl ether / Ambient temperature
2: 38 percent / cesium carbonate / acetone / 48 h / Heating
View Scheme
Phenylephrin
59-42-7

Phenylephrin

2-dimethylamino-4-phenylpyrimidine-5-carboxylic acid
180283-80-1

2-dimethylamino-4-phenylpyrimidine-5-carboxylic acid

(L)-2-dimethylamino-4-phenylpyrimidine-5-carboxylic acid [2-hydroxy-2-(3-hydroxy-phenyl)ethyl]methyl amide

(L)-2-dimethylamino-4-phenylpyrimidine-5-carboxylic acid [2-hydroxy-2-(3-hydroxy-phenyl)ethyl]methyl amide

Conditions
ConditionsYield
Stage #1: Phenylephrin; 2-dimethylamino-4-phenylpyrimidine-5-carboxylic acid In tetrahydrofuran for 0.166667h;
Stage #2: With 4-methyl-morpholine In tetrahydrofuran for 0.0333333h;
Stage #3: With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In tetrahydrofuran at 20℃; for 4h; Heating / reflux;

59-42-7Relevant articles and documents

Enantioselective synthesis of (S)-phenylephrine by whole cells of recombinant Escherichia coli expressing the amino alcohol dehydrogenase gene from Rhodococcus erythropolis BCRC 10909

Lin, Wei-De,Chen, Chien-Yu,Chen, Huei-Chung,Hsu, Wen-Hwei

, p. 1529 - 1536 (2010)

(R)-phenylephrine [(R)-PE] is an α1-adrenergic receptor agonist that is widely used in over-the-counter drugs to treat the common cold. We found that Rhodococcus erythropolis BCRC 10909 can convert detectable level of 1-(3-hydroxyphenyl)-2-(methylamino) ethanone (HPMAE) to (S)-PE by high performance liquid chromatography tandem mass spectrometry analysis. An amino alcohol dehydrogenase gene (RE_AADH) which possesses the ability to convert HPMAE to (S)-PE was then isolated from R. erythropolis BCRC 10909 and expressed in Escherichia coli NovaBlue. The purified RE_AADH, tagged with 6×His, had a molecular mass of approximately 30kDa and exhibited a specific activity of 0.19μU/mg to HPMAE in the presence of NADPH, indicating this enzyme could be categorized as NADP+-dependent short-chain dehydrogenase reductase. E. coli NovaBlue cell expressing the RE_AADH gene was able to convert HPMAE to (S)-PE with more than 99% enantiomeric excess (ee), 78% yield and a productivity of 3.9mmol(S)-PE/Lh in 12h at 30°C and pH 7. The (S)-PE, recovered from reaction mixture by precipitation at pH 11.3, could be converted to (R)-PE (ee>99%) by Walden inversion reaction. This is the first reported biocatalytic process for the production of (S)-PE from HPMAE.

Recyclable Cu(II)-macrocyclic salen complexes catalyzed nitroaldol reaction of aldehydes: A practical strategy in the preparation of (R)-phenylephrine

Kureshy, Rukhsana I.,Dangi, Balchand,Das, Anjan,Khan, Noor-Ul H.,Abdi, Sayed H.R.,Bajaj, Hari C.

, p. 74 - 79 (2012/10/07)

Chiral macrocyclic salen ligands 1′-3′ derived from 1R,2R-(-)-1,2-diaminocyclohexane, 1R,2R-(+)-1,2-diphenyl-1,2-diaminoethane and (R)-(+)-1,1′-binaphthyl-2,2′-diamine with trigol bis aldehyde were prepared and characterized by microanalysis, 1H NMR, UV/Vis. spectroscopy, optical rotation and mass spectroscopy. Highly enantioselective nitroaldol reaction of various aromatic and aliphatic aldehydes with nitromethane in presence of several bases were carried out in the presence of in situ generated Cu(I)/Cu(II) complexes with chiral macrocyclic salen ligands 1′-3′ at RT. Excellent yields (up to 92% with respect to the aldehyde) of β-nitroalcohols with high enantioselectivity (ee, ~95%) was achieved in case of 3-methoxy- and 4-nitrobenzaldehyde in ca. 30 h with the use of chiral macrocyclic salen ligands 3′ with CuCl2· 2H2O in presence of 2,6-lutidine as a base. Chiral macrocyclic salen catalyst 3 mediated nitroaldol process is recyclable (up to 8 cycles with no significant loss in its performance). This protocol is also used for the synthesis of enantiomerically pure (R)-phenylephrine (α1-adrenergic receptor agonist) via asymmetric nitroaldol reaction of 3-methoxybenzaldehyde in three steps.

METHOD FOR PRODUCING L-PHENYLEPHRINE USING AN ALCOHOL DEHYDROGENASE OF AROMATOLEUM AROMATICUM EBN1 (AZOARCUS SP. EBN1)

-

, (2011/08/02)

The present invention relates to a multi-stage process for producing substituted, optically active alcohols, comprising an enzyme-catalyzed synthesis step, in particular a synthesis step which is catalyzed by an alcohol dehydrogenase. The inventive method is particularly suitable for producing phenylephrine, i.e. 3-[(1R)-1-hydroxy-2-methylamino-ethyl]-phenol.

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