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501-97-3

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501-97-3 Usage

Chemical Properties

Pale-Yellow Crystals

Uses

Different sources of media describe the Uses of 501-97-3 differently. You can refer to the following data:
1. 3-(4-Hydroxyphenyl)propionic acid is uses as pharmaceutical intermediates,it is also used as a sensitive fluorogenic substrate for oxidases such as horseradish peroxidase.
2. Sensitive fluorogenic substrate for oxidases such as horseradish peroxidase
3. Antioxidant

Definition

ChEBI: A hydroxy monocarboxylic acid consisting of propionic acid having a 4-hydroxyphenyl group at the 3-position.

Purification Methods

3-p-Hydroxyphenylpropionic acid (phloretic acid) [501-97-3] M 166.2, m 129-130o, 131 -1 3 3o, pKEst(1)~4.7, pKEst(2)~10.1. Crystallise phloretic acid from ether or H2O. [Beilstein 10 IV 631.]

Check Digit Verification of cas no

The CAS Registry Mumber 501-97-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 1 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 501-97:
(5*5)+(4*0)+(3*1)+(2*9)+(1*7)=53
53 % 10 = 3
So 501-97-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)/p-1

501-97-3 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (A14567)  3-(4-Hydroxyphenyl)propionic acid, 99%   

  • 501-97-3

  • 10g

  • 377.0CNY

  • Detail
  • Alfa Aesar

  • (A14567)  3-(4-Hydroxyphenyl)propionic acid, 99%   

  • 501-97-3

  • 50g

  • 1192.0CNY

  • Detail
  • Alfa Aesar

  • (A14567)  3-(4-Hydroxyphenyl)propionic acid, 99%   

  • 501-97-3

  • 250g

  • 4768.0CNY

  • Detail

501-97-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name phloretic acid

1.2 Other means of identification

Product number -
Other names Benzenepropanoic acid, 4-hydroxy-

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:501-97-3 SDS

501-97-3Synthetic route

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In methanol under 760 Torr; Ambient temperature;100%
With hydrogen; palladium on activated charcoal In methanol100%
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃;99%
para-coumaric acid
7400-08-0

para-coumaric acid

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With 5% Pd(II)/C(eggshell); hydrogen In methanol; water for 3h;99%
Stage #1: para-coumaric acid With palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In ethyl acetate at 25℃; for 12h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride In water
99%
With palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In ethyl acetate at 25℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction;99%
3-[4-(2,4-Dimethyl-benzyloxy)-phenyl]-propionic acid
84253-22-5

3-[4-(2,4-Dimethyl-benzyloxy)-phenyl]-propionic acid

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol under 3040 Torr; for 15h;98%
3-(4-hydroxyphenyl)propionic acid benzyl ester
31770-76-0

3-(4-hydroxyphenyl)propionic acid benzyl ester

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With aluminum oxide for 0.15h; microwave irradiation;92%
4-hydroxy-3,5-di-tert-butylphenylpropionic acid
20170-32-5

4-hydroxy-3,5-di-tert-butylphenylpropionic acid

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With hydrogen bromide for 2h; Heating;92%
3-(4-hydroxyphenyl)propanoic acid amide
23838-70-2

3-(4-hydroxyphenyl)propanoic acid amide

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With water; sodium hydroxide at 80℃; for 4h; Green chemistry;91.5%
methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate
6386-38-5

methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With hydrogen bromide Heating;91%
(E)-4-benzyloxycinnamic acid
6272-45-3

(E)-4-benzyloxycinnamic acid

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With hydrogen; platinum89%
acrylonitrile
107-13-1

acrylonitrile

phenol
108-95-2

phenol

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With hydrogenchloride; aluminum (III) chloride at 180 - 200℃; under 5250.53 - 7500.75 Torr; Temperature;87.5%
3-(4-iodophenyl)propionic acid
1643-29-4

3-(4-iodophenyl)propionic acid

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With copper(I) oxide; 1D-1-O-Methyl-muco-inostol; sodium hydroxide In water at 100℃; for 6h;79%
With copper(I) oxide; 1-D-O-Methyl-chiro-inositol; sodium hydroxide In water at 100℃; for 6h;79%
3-(4-hydroxyphenyl)propionic acid methyl ester
5597-50-2

3-(4-hydroxyphenyl)propionic acid methyl ester

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
In water Alkaline conditions;70.2%
jones reagent

jones reagent

dihydro-p-coumaryl aldehyde
20238-83-9

dihydro-p-coumaryl aldehyde

dichromic acid
13530-68-2

dichromic acid

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
In sulfuric acid; ethyl acetate; acetone63.1%
3-(4-methoxyphenyl)propanoic acid
1929-29-9

3-(4-methoxyphenyl)propanoic acid

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 20℃; for 2.5h;59%
With aluminum tri-bromide; toluene
With hydrogen bromide
L-tyrosine
60-18-4

L-tyrosine

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With sodium hydroxide; baker's yeast for 48h;45%
With tyrosine transaminase
3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on
60-82-2

3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on

A

3-(4-hydroxyphenyl)propan-1-ol
10210-17-0

3-(4-hydroxyphenyl)propan-1-ol

B

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

C

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborate In water at 100℃; Product distribution;A 22%
B 8%
C 38%
morpholine
110-91-8

morpholine

4-hydroxypropiophenone
70-70-2

4-hydroxypropiophenone

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With sulfur Erwaermen des Reaktionsprodukts mit aethanol. Natronlauge;
3-(p-hydroxyphenyl)propiononitrile
17362-17-3

3-(p-hydroxyphenyl)propiononitrile

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With potassium hydroxide
3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on
60-82-2

3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on

A

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

B

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With potassium hydroxide
3-(4-aminophenyl)propionic acid
2393-17-1

3-(4-aminophenyl)propionic acid

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
Diazotization;
ethyl 3-(4-methoxyphenyl)propanoate
22767-72-2

ethyl 3-(4-methoxyphenyl)propanoate

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With hydrogen iodide
Conditions
ConditionsYield
With bacterium proteus vulgaris at 37℃;
bei der Einw. eines Bacteriums aus der Gruppe der Pyocyaneen;
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With sodium acetate; acetic anhydride anschliessendes Hydrieren an Raney-Nickel in wss. NaOH;
Multi-step reaction with 3 steps
1: 90 percent / KI, Na2CO3 / acetone / 14 h / Heating
2: 75 percent / pyridine, piperidine / 1 h
3: 89 percent / H2 / Pt
View Scheme
Multi-step reaction with 2 steps
1: 3-amino propanoic acid / pyridine / 0.17 h / 70 °C / Microwave irradiation
2: palladium 10% on activated carbon; hydrogen / ethanol / 0.5 h
View Scheme
4-hydroxypropiophenone
70-70-2

4-hydroxypropiophenone

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With 1,4-dioxane; ammonium polysulfide at 160℃; Behandeln des Reaktionsprodukts mit wss. Salzsaeure;
3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With sulfuric acid bei der elektrolytischen Oxydation;
punarnavoside
106009-02-3

punarnavoside

A

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

B

1-glucopyrano-2-benzyl-4,5-dihydroxybenzene
122738-91-4

1-glucopyrano-2-benzyl-4,5-dihydroxybenzene

Conditions
ConditionsYield
With potassium hydroxide for 4h; Heating;
3-(4-Hydroxy-phenyl)-propionic acid (2aS,4aS,5S,7bS)-1-oxo-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2a,4a,5,7b-tetrahydro-1H-2,6-dioxa-cyclopenta[cd]inden-4-ylmethyl ester

3-(4-Hydroxy-phenyl)-propionic acid (2aS,4aS,5S,7bS)-1-oxo-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2a,4a,5,7b-tetrahydro-1H-2,6-dioxa-cyclopenta[cd]inden-4-ylmethyl ester

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol for 1.33333h;40 mg
4-Iodophenol
540-38-5

4-Iodophenol

3-(trichlorostannyl)propanoic acid
59586-11-7

3-(trichlorostannyl)propanoic acid

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With potassium hydroxide; Pd(dpm)4Cl2 1.) H2O, 2.) H2O, 100 deg C, 3 h; Yield given. Multistep reaction;
3-(4-Hydroxy-phenyl)-propionic acid pentachlorophenyl ester
199444-18-3

3-(4-Hydroxy-phenyl)-propionic acid pentachlorophenyl ester

A

Pentachlorophenol
87-86-5

Pentachlorophenol

B

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

Conditions
ConditionsYield
With potassium hydroxide In 1,4-dioxane at 25℃; Rate constant; 0.1 M ionic strength;
sulfuric acid
7664-93-9

sulfuric acid

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

lead dioxide anode

lead dioxide anode

A

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

B

quinhydrone
106-34-3

quinhydrone

C

p-benzoquinone
106-51-4

p-benzoquinone

D

6-oxy-hydrocoumarin

6-oxy-hydrocoumarin

Conditions
ConditionsYield
bei der elektrolytischen Oxydation;
methanol
67-56-1

methanol

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

3-(4-hydroxyphenyl)propionic acid methyl ester
5597-50-2

3-(4-hydroxyphenyl)propionic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 20℃; for 2h;100%
With sulfuric acid for 2h; Inert atmosphere; Reflux;100%
With thionyl chloride at 0 - 20℃;100%
ethanol
64-17-5

ethanol

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

3-(4-hydroxy-phenyl)-propionic acid ethyl ester
23795-02-0

3-(4-hydroxy-phenyl)-propionic acid ethyl ester

Conditions
ConditionsYield
With chloro-trimethyl-silane at 25℃; for 24h;100%
With thionyl chloride at 20℃;99%
With sulfuric acid at 20℃; for 4h;99%
propan-1-ol
71-23-8

propan-1-ol

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

3-(4-hydroxyphenyl)propionic acid propyl ester
83281-52-1

3-(4-hydroxyphenyl)propionic acid propyl ester

Conditions
ConditionsYield
With chloro-trimethyl-silane at 25℃; for 24h;100%
With 3 A molecular sieve; sulfuric acid for 72h; Heating;
With hydrogenchloride Heating;
With chloro-trimethyl-silane at 25℃; for 24h;
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

butan-1-ol
71-36-3

butan-1-ol

3-(4-hydroxyphenyl)propionic acid butyl ester

3-(4-hydroxyphenyl)propionic acid butyl ester

Conditions
ConditionsYield
With chloro-trimethyl-silane at 25℃; for 24h;100%
With hydrogenchloride Heating;
With chloro-trimethyl-silane at 25℃; for 24h;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

3-(4-Trimethylsilanyloxy-phenyl)-propionic acid

3-(4-Trimethylsilanyloxy-phenyl)-propionic acid

Conditions
ConditionsYield
With triethylamine hydrochloride; triethylamine In tetrahydrofuran; dichloromethane100%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

sodium 3-(4'-hydroxyphenyl)propionate

sodium 3-(4'-hydroxyphenyl)propionate

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water100%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

benzyl bromide
100-39-0

benzyl bromide

3-(4-benzyloxyphenyl)propanoic acid
50463-48-4

3-(4-benzyloxyphenyl)propanoic acid

Conditions
ConditionsYield
With sodium hydroxide; water; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20 - 80℃;99%
With sodium carbonate; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran; water at 20 - 80℃;99%
Stage #1: 4-hydroxyphenylpropionic acid; benzyl bromide With potassium carbonate In acetone Reflux;
Stage #2: With sodium hydroxide In methanol; water Reflux;
98%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

3-(4-hydroxyphenyl)propan-1-ol
10210-17-0

3-(4-hydroxyphenyl)propan-1-ol

Conditions
ConditionsYield
With borane-THF; Trimethyl borate In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;99%
With sodium tetrahydroborate; Trimethyl borate; dimethyl sulfate In tetrahydrofuran at 20℃; for 1.5h;98%
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃;98%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

benzyl bromide
100-39-0

benzyl bromide

3-(4-hydroxyphenyl)propionic acid benzyl ester
31770-76-0

3-(4-hydroxyphenyl)propionic acid benzyl ester

Conditions
ConditionsYield
With potassium hydrogencarbonate In acetone for 18h; Reflux;99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;94%
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 40℃;91%
With potassium carbonate In N,N-dimethyl-formamide for 15h;88%
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 12h;765 mg
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

3-(4-hydroxyphenyl)propionic acid methyl ester
5597-50-2

3-(4-hydroxyphenyl)propionic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;99%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

methyl 3-(4-methoxyphenyl)propionate
15823-04-8

methyl 3-(4-methoxyphenyl)propionate

Conditions
ConditionsYield
With potassium carbonate In acetone Substitution; Heating;99%
With potassium carbonate In acetone for 48h; Reflux;95%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

2-(3-hydroxypropyl)phenol
1481-92-1

2-(3-hydroxypropyl)phenol

Conditions
ConditionsYield
With borane-THF; Trimethyl borate In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;99%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

benzyl bromide
100-39-0

benzyl bromide

3-(4-benzyloxyphenyl)propionic acid benzyl ester
58608-97-2

3-(4-benzyloxyphenyl)propionic acid benzyl ester

Conditions
ConditionsYield
With sodium hydride; tetra-(n-butyl)ammonium iodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 15h; Heating;98%
Stage #1: 4-hydroxyphenylpropionic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 80℃;
97%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 4h;91%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl 3-(4-hydroxyphenyl)propanoate
116144-68-4

isopropyl 3-(4-hydroxyphenyl)propanoate

Conditions
ConditionsYield
With hydrogenchloride at 22℃; for 12h; Esterification;98%
With hydrogenchloride at 20℃; for 16h;62%
With hydrogenchloride Heating;
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

(S)-1-O-tosyl-2,3-O-isopropylideneglycerol
23735-43-5

(S)-1-O-tosyl-2,3-O-isopropylideneglycerol

3-(4-hydroxyphenyl)propionic acid [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester
144256-11-1

3-(4-hydroxyphenyl)propionic acid [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 100℃; for 1h;98%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

dihydrocaffeic acid
1078-61-1

dihydrocaffeic acid

Conditions
ConditionsYield
With Agaricus bisporus; oxygen In aq. phosphate buffer; dichloromethane at 25℃; for 24h; pH=7; Reagent/catalyst;98%
Stage #1: 4-hydroxyphenylpropionic acid With Agaricus bisporus tyrosinase immobilized on polydiallyldimethyl ammonium chloride functionalized oxidized multi-walled carbonanotubes; oxygen In aq. phosphate buffer; dichloromethane at 25℃; for 24h; pH=7.0; Enzymatic reaction;
Stage #2: With sodium dithionite In tetrahydrofuran; water at 25℃; for 0.0833333h; Reagent/catalyst;
98%
With Agaricus bisporus tyrosinase; oxygen; ascorbic acid In water at 20℃; for 24h; pH=7; Na-phosphate buffer; Enzymatic reaction;88%
With sodium dihydrogenphosphate at 25℃; for 0.25h; pH=7; Glovebox;14%
With mushroom tyrosinase In N,N-dimethyl-formamide at 25℃; pH=7; Kinetics; aq. phosphate buffer; Enzymatic reaction;
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

3‐amino‐1‐O‐hexadecyloxy‐2R‐(O–α‐L‐rhamnopyranosyl)‐sn‐glycerol

3‐amino‐1‐O‐hexadecyloxy‐2R‐(O–α‐L‐rhamnopyranosyl)‐sn‐glycerol

3‐(‐3‐(p‐hydroxyphenylpropyl))amido‐1‐O‐hexadecyloxy‐2R‐(O‐α‐L‐rhamnopyranosyl)‐sn‐glycerol

3‐(‐3‐(p‐hydroxyphenylpropyl))amido‐1‐O‐hexadecyloxy‐2R‐(O‐α‐L‐rhamnopyranosyl)‐sn‐glycerol

Conditions
ConditionsYield
With dmap; O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide for 8h;98%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

4-methoxy-aniline
104-94-9

4-methoxy-aniline

3-(4-hydroxyphenyl)-N-(4-methoxyphenyl)propanamide

3-(4-hydroxyphenyl)-N-(4-methoxyphenyl)propanamide

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate In neat (no solvent) at 160 - 165℃; for 2h; Microwave irradiation; Green chemistry;98%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

acetic anhydride
108-24-7

acetic anhydride

3-(4'-acetoxyphenyl)propionic acid
7249-16-3

3-(4'-acetoxyphenyl)propionic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 0 - 20℃;97.1%
Stage #1: 4-hydroxyphenylpropionic acid; acetic anhydride With potassium hydroxide In water for 16h;
Stage #2: With hydrogenchloride In water
96%
With sodium hydroxide In water at 0℃;80%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

1-oxaspiro[4,5]deca-6,9-dien-2,8-dione
4572-26-3

1-oxaspiro[4,5]deca-6,9-dien-2,8-dione

Conditions
ConditionsYield
With phenylbis(2,2,2-trifluoroethoxy)-λ3-iodane; lithium perchlorate In 2,2,2-trifluoroethanol at 20℃; for 0.5h;97%
With phenylbis(2,2,2-trifluoroethoxy)-λ3-iodane In 2,2,2-trifluoroethanol at 20℃; for 0.166667h; Flow reactor;93%
With μ-Oxo-I,I'-bis(trifluoroacetato-O)-I,I'-diphenyldiiodine(III) In acetonitrile at 0℃; for 0.25h;90%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-hydroxyphenyl)-N-methylpropanamide
637358-42-0

N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-hydroxyphenyl)-N-methylpropanamide

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 0 - 20℃;97%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

methyl iodide
74-88-4

methyl iodide

3-(4-hydroxyphenyl)propionic acid methyl ester
5597-50-2

3-(4-hydroxyphenyl)propionic acid methyl ester

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 40℃;96%
Stage #1: 4-hydroxyphenylpropionic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃; for 3h;
95.9%
With potassium hydroxide In dimethyl sulfoxide at 40℃;
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

allyl bromide
106-95-6

allyl bromide

allyl 3-(4-(allyloxy)phenyl)propanoate

allyl 3-(4-(allyloxy)phenyl)propanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;96%
4-chloro-pyridine-2-carbonitrile
19235-89-3

4-chloro-pyridine-2-carbonitrile

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

3-{4-[(2-cyanopyridin-4-yl)oxy]phenyl}propanoic acid
900254-54-8

3-{4-[(2-cyanopyridin-4-yl)oxy]phenyl}propanoic acid

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 72h;95%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

1,3,5-triphenylhexahydro-1,3,5-triazine
91-78-1

1,3,5-triphenylhexahydro-1,3,5-triazine

3-(3-phenyl-3,4-dihydro-2H-1,3-benzoxazin-6-yl)propanoic acid

3-(3-phenyl-3,4-dihydro-2H-1,3-benzoxazin-6-yl)propanoic acid

Conditions
ConditionsYield
With formaldehyd In toluene at 110℃; for 16h;95%
tert-butyl N-(6-aminohexyl)carbamate
51857-17-1

tert-butyl N-(6-aminohexyl)carbamate

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

tert-butyl (6-(3-(4-hydroxyphenyl)propanamido)hexyl)carbamate

tert-butyl (6-(3-(4-hydroxyphenyl)propanamido)hexyl)carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;95%
4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

isopropyl bromide
75-26-3

isopropyl bromide

4-(1-methylethoxy)benzenepropanoic acid (1-methyl)ethyl ester
301224-94-2

4-(1-methylethoxy)benzenepropanoic acid (1-methyl)ethyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 24h;94%
With sodium hydroxide; potassium carbonate In N,N-dimethyl-formamide94%

501-97-3Relevant articles and documents

Chemical constituents from Ginkgo biloba leaves and their cytotoxicity activity

Shu, Penghua,Sun, Mengyuan,Li, Junping,Zhang, Lingxiang,Xu, Haichang,Lou, Yueyue,Ju, Zhiyu,Wei, Xialan,Wu, Wenming,Sun, Na

, p. 269 - 274 (2020)

One novel neoligan glucoside, Ginkgoside B (1), and one new glucose ester, 6-O-(4-hydroxyhydrocinnamoyl)-d-glucopyranose (2), along with nine known compounds (3–11) were isolated from the ethanol extract of Ginkgo biloba leaves. Their structures were elucidated by combination of spectroscopic analyses and alkaline methanolysis. The absolute configuration of compound 1 was determined by single-crystal X-ray diffraction. All the isolated compounds were evaluated for their cytotoxicity activities, and compound 11 exhibited IC50 values of 36.20 and 58.95?μM against 5637 and HeLa cell lines, respectively.

Isolation and characterization of glycosidic tyrosinase inhibitors from typhonium giganteum rhizomes

Shu, Penghua,Zhu, Huiqing,Liu, Wanrong,Zhang, Lingxiang,Li, Junping,Yu, Mengzhu,Fei, Yingying,Cai, Shujing,Li, Ruihua,Wei, Xialan,Yi, Wenhan,Xiao, Fugang

, p. 380 - 387 (2021/06/02)

A new hydrocinnamoyl glucoside, 1-O-(4-hydroxyhydrocinnamoyl)-β-D-glucopyranose (1), together with fifteen known glycosides, including two phenylethanoid glycosides (2–3), two cinnamoyl glycosides (4–5), six phenolic glycosides (6–11), one lignan glycoside (12) and four megastigmane glycosides (13–16) were isolated from a 95% EtOH extract of the Typhonium giganteum rhizomes. The sixteen glycosides were structurally characterized by NMR, HRESIMS, enzymatic hydrolysis and comparison with literature. Upon evaluating inhibitory activities of compounds 1–16 against mushroom tyrosinase at 25 μM, compounds 10 and 11 exhibited obvious inhibitory activities, with %inhibition values of 20.94±0.59%, 23.28±1.09%, respectively, with arbutin used as the positive control (26.21±0.58%).

Copper and L-(?)-quebrachitol catalyzed hydroxylation and amination of aryl halides under air

Bao, Xuefei,Chen, Guoliang,Dong, Jinhua,Du, Fangyu,Li, Hui,Liang, Xinjie,Wu, Ying,Zhang, Yongsheng

supporting information, (2020/08/03)

L-(?)-Quebrachitol, a natural product obtained from waste water of the rubber industry, was utilized as an efficient ligand for the copper-catalyzed hydroxylation and amination of aryl halides to selectively give phenols and aryl amines in water or 95percent ethanol. In addition, the hydroxylation of 2-chloro-4-hydroxybenzoic acid was validated on a 100-g scale under air.

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