156-38-7

Usage

Uses

1. Pharmaceutical Industry:
4-Hydroxyphenylacetic acid is used as a pharmaceutical raw material for the synthesis of cephalosporin antibiotics and antipyretic analgesics. It is also used as a reagent in the acylation of phenols and amines, as well as for the fluorometric determination of oxidative enzymes.
2. Chemical Industry:
In the chemical industry, 4-Hydroxyphenylacetic acid serves as an intermediate for synthesizing atenolol and 3,4-dihydroxyphenylacetic acid.
3. Food Industry:
4-Hydroxyphenylacetic acid is a compound present in olive oil, which is an important fine chemical intermediate with broad prospects for application development.
4. Traditional Medicine:
4-Hydroxyphenylacetic acid is an active component of the Chinese herb Aster tataricus, which has been widely used in China for the treatment of pulmonary diseases, HBV, and carcinoma.
5. Research and Development:
As an active metabolite of amino acid metabolism, 4-Hydroxyphenylacetic acid is utilized in research and development for its potential therapeutic applications in various diseases and conditions.

Referrence

Liu, Zhongyang, et al. "4-Hydroxyphenylacetic Acid Attenuated Inflammation and Edema via Suppressing HIF-1α in Seawater Aspiration-Induced Lung Injury in Rats." International Journal of Molecular Sciences 15.7(2014):12861-84. Ng, T.B.; Liu, F.; Lu, Y.; Cheng, C.H.; Wang, Z. Antioxidant activity of compounds from the medicinal herb Aster tataricus. Comp. Biochem. Physiol. 2003, 136, 109–115.? Du, L.; Mei, H.F.; Yin, X.; Xing, Y.Q. Delayed growth of glioma by a polysaccharide from Aster tataricus involve upregulation of Bax/Bcl-2 ratio, activation of caspase-3/8/9, and downregulation of the Akt. Tumour Biol. 2014, 35, 1819–1825.

Preparation

4-Hydroxyphenylacetic acid is synthesized by diazotization and hydrolysis of 4-aminophenylacetic acid. 4-aminophenylacetic acid and alkali solution are prepared into sodium salt, and then sulfuric acid is added. Cool to 0°C, control the temperature at 0-5°C, and add sodium nitrate solution dropwise, and the reaction is completed for 0.5h. The obtained diazonium was added dropwise to dilute sulfuric acid at 90-95°C for about 1 hour, and the reaction was continued for 1 hour. The reaction solution was decolorized and filtered, cooled and extracted with ethyl acetate, and the extract was recovered with ethyl acetate to obtain 4-Hydroxyphenylacetic acid. The yield is about 85%.

Flammability and Explosibility

Notclassified

Purification Methods

Crystallise the acid from water or Et2O/pet ether. The p-bromophenacyl ester has m 117o (from EtOH). [Beilstein 10 II 112, 10 III 430, 10 IV 543.]

InChI:InChI=1/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)/p-1

Synthetic route

4-Methoxyphenylacetic acid → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With boron tribromide In dichloromethane at -78 - -15℃; for 4h; Inert atmosphere;	99%
With boron tribromide In dichloromethane at -78℃; for 0.5h;	93%
With hydrogen bromide; cetyltributylphosphonium bromide for 7.5h; Heating;	87%

4-(benzyloxy)phenylacetic acid benzyl ester (58609-13-5) → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 3h;	99%

2-(diethylamino)-1-(4-hydroxyphenyl)ethanone hydrochloride → 4-hydroxyphenylacetate (156-38-7) + diethyl amine hydrochloride (660-68-4)

Conditions	Yield
In aq. buffer pH=4 - 7.4; pH-value; Irradiation;	A 99% B 99%

1-(4-hydroxyphenyl)-2-(piperidin-1-yl)ethanone hydrobromide → 4-hydroxyphenylacetate (156-38-7) + piperidine hydrobromide (14066-85-4)

Conditions	Yield
In aq. acetate buffer pH=5.6; pH-value; Irradiation;	A 99% B 99%

ω-amino-4-hydroxyacetophenone hydrochloride (19745-72-3) → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
In aq. acetate buffer pH=5.6; pH-value; Irradiation;	99%

p-Coumaric Acid (7400-08-0) → 4-hydroxyphenylacetate (156-38-7) + p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With β-D-glucose; oxygen for 18h; Reagent/catalyst; Enzymatic reaction;	A n/a B 97.3%

aqueous sulphuric acid + 4-hydroxymandelic acid sodium salt monohydrate + aqueous chromic chloride → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With zinc In water; paraffin oil	97%

(4-chloro-phenyl)-acetic acid methyl ester (52449-43-1) → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With sodium hydroxide	96%

BrH*C9H11NO2 → 4-hydroxyphenylacetate (156-38-7) + methylammonium bromide (6876-37-5)

Conditions	Yield
In water pH=5.6; pH-value; Irradiation;	A 95% B 95%

2-fluoro-1-(4-hydroxyphenyl)ethanone → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
In acetonitrile Quantum yield; Solvent; UV-irradiation;	95%

4-cyanomethylphenol (14191-95-8) → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With benzene-1,2-dicarboxylic acid at 250℃; under 7600 Torr; for 0.5h; microwave irradiation;	92%
With hydrogenchloride
With potassium hydroxide
With sodium hydroxide In water; toluene

2-bromomethyl-2-(4'-hydroxyphenyl)-1,3-dioxolane (182296-61-3) → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With sodium hydroxide In water at 95℃; for 0.666667h;	90%

2-chloromethyl-5,5-dimethyl-2-(4-hydroxyphenyl)-1,3-dioxane → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With sodium hydroxide In water at 95℃; for 1h;	88%

2-bromomethyl-5,5-dimethyl-2-(4-hydroxyphenyl)-1,3-dioxane → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With sodium hydroxide In water at 90 - 95℃; for 0.666667h;	88%

2-(4-hydroxyphenyl)acetamide (17194-82-0) → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With phthalic anhydride at 240 - 250℃; under 3040 Torr; for 1h; Hydrolysis;	86%

C15H15NO5S → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With sodium tetrahydroborate; trifluoroacetic acid In dichloromethane at 15 - 25℃;	85.5%

4-hydroxymandelic acid sodium salt monohydrate → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With concentrated aqueous hydrochloric acid; palladium In water	85%

(4-iodophenyl)acetic acid (1798-06-7) → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With copper(I) oxide; 1D-1-O-Methyl-muco-inostol; sodium hydroxide In water at 100℃; for 6h;	84%
With copper(I) oxide; 1-D-O-Methyl-chiro-inositol; sodium hydroxide In water at 100℃; for 6h;	84%

p-hydroxyphenethyl alcohol (501-94-0) → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With sodium hydroxide; oxygen; lead acetate; palladium on activated charcoal In water at 90℃; under 3800 Torr; for 3h;	80.5%
With lithium aluminium tetrahydride

4-Hydroxyphenylpyruvic acid (156-39-8) → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With sodium perborate In water for 48h; Ambient temperature;	80%
Multi-step reaction with 2 steps 1: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction 2: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction View Scheme
With oxygen; ascorbic acid

p-hydroxyphenacyl chloride (6305-04-0) → 4-hydroxyphenylacetate (156-38-7) + 1,4-bis(4-hydroxyphenyl)butan-1,4-dione (108791-64-6) + 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With methyloxirane In water; acetonitrile for 4h; Irradiation;	A 75% B 10% C 5%

Sodium; (S)-hydroxy-(4-hydroxy-phenyl)-acetate → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With formic acid; phosphoric acid; sodium hydrogensulfite In water at 100℃; under 3750.3 Torr; for 9h; 1.1 mol HCOOH;	73%

2-bromomethyl-5,5-dimethyl-2-(4-hydroxyphenyl)-1,3-dioxane → 4-hydroxyphenylacetate (156-38-7) + 2,2-dimethyl-3-hydroxypropyl (4-hydroxyphenyl acetate)

Conditions	Yield
With potassium acetate In water at 95 - 100℃; for 1h;	A 11.7% B 69.3%

4-hydroxymandelic acid (1198-84-1) → 4-hydroxyphenylacetate (156-38-7)

Conditions	Yield
With phosphonic Acid; methanesulfonic acid; sodium iodide In water at 40℃; for 48h; Inert atmosphere;	62.2%

2-fluoro-1-(4-hydroxyphenyl)ethanone → 4-hydroxyphenylacetate (156-38-7) + 4-hydroxyphenylacetic acid methyl-d3 ester

Conditions	Yield
In d(4)-methanol; water-d2 Quantum yield; UV-irradiation;	A 39% B 59%

N-[2-(4-hydroxyphenyl)-2-oxoethyl]phenylalanine hydrochloride methyl ester → 4-hydroxyphenylacetate (156-38-7) + 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
In aq. phosphate buffer pH=5.6; pH-value; Irradiation;	A 46% B 55%

triethyl-[2-(4-hydroxyphenyl)-2-oxoethyl]ammonium bromide → 4-hydroxyphenylacetate (156-38-7) + acetaldehyde (75-07-0) + diethylamine (109-89-7) + triethylamine (121-44-8) + 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
In aq. acetate buffer pH=4; pH-value; Irradiation;	A 20% B 24% C 45% D 51% E 18%

ω-amino-4-hydroxyacetophenone hydrochloride (19745-72-3) → 4-hydroxyphenylacetate (156-38-7) + 1,4-bis(4-hydroxyphenyl)butan-1,4-dione (108791-64-6) + 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
In aq. phosphate buffer pH=7.4; pH-value; Irradiation;	A 49% B 8% C 33%

methanol (67-56-1) + 4-hydroxyphenylacetate (156-38-7) → Methyl 4-hydroxyphenylacetate (14199-15-6)

Conditions	Yield
With sulfuric acid Heating;	100%
With sulfuric acid for 8h; Heating;	100%
With sulfuric acid	100%

4-hydroxyphenylacetate (156-38-7) + ethanol (64-17-5) → (4-hydroxy-phenyl)-acetic acid ethyl ester (17138-28-2)

Conditions	Yield
With sulfuric acid for 1h; Heating / reflux;	100%
With sulfuric acid for 2h; Reflux;	98%
With sulfuric acid In water for 8h; Reflux;	98%

4-hydroxyphenylacetate (156-38-7) → 2-(p-hydroxyphenyl)acetyl chloride (37859-23-7)

Conditions	Yield
With thionyl chloride In dichloromethane	100%
With thionyl chloride Heating;
With oxalyl dichloride In chloroform Ambient temperature;

4-hydroxyphenylacetate (156-38-7) + benzyl bromide (100-39-0) → 2-[4-(benzyloxy)benzyl]acetic acid (6547-53-1)

Conditions	Yield
With sodium iodide; potassium hydroxide In ethanol for 20h; Reflux;	100%
With potassium carbonate; tetrabutylammomium bromide In tetrahydrofuran at 30℃; for 0.5h;	93%
With potassium hydroxide In ethanol; water Heating;	67.8%

methanol (67-56-1) + 4-hydroxyphenylacetate (156-38-7) → 3,5-dibromo-4-hydroxyphenylacetic acid methyl ester (212688-02-3)

Conditions	Yield
With bromine	100%

4-hydroxyphenylacetate (156-38-7) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → 2-(4-hydroxyphenyl)-N-methoxy-N-methylacetamide

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; for 1h;	100%
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; for 1h;

4-hydroxyphenylacetate (156-38-7) → 3,4-dihydroxyphenylacetate (102-32-9)

Conditions	Yield
With ascorbic acid In aq. phosphate buffer at 25℃;	99.7%
With Agaricus bisporus; oxygen In aq. phosphate buffer; dichloromethane at 25℃; for 24h; pH=7;	98%
With sodium dihydrogenphosphate at 25℃; for 0.25h; pH=7; Glovebox;	91%

4-hydroxyphenylacetate (156-38-7) + 2-methylbenzene-1,3-diol (608-25-3) → 2,4,4'-trihydroxy-3-methyldeoxybenzoin (139256-03-4)

Conditions	Yield
With boron trifluoride diethyl etherate at 110℃; for 0.5h; Heating / reflux;	99%
With boron trifluoride diethyl etherate at 60 - 70℃; for 5h;	97%
With boron trifluoride diethyl etherate at 110℃; for 2h; Inert atmosphere;

4-hydroxyphenylacetate (156-38-7) + 3,5-dimethylaminoaniline (108-69-0) → N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide (131179-77-6)

Conditions	Yield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;	99%
With boric acid In toluene for 18h; Heating;	95%
With pyridine; FI-750-M; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 60℃; for 0.75h; Sealed tube;	86%

(3,4-dichlorophenyl){2-[3-(phenylmethoxy)phenyl]ethyl}amine (295320-01-3) + 4-hydroxyphenylacetate (156-38-7) → N-(3,4-dichlorophenyl)-2-(4-hydroxyphenyl)-N-{2-[3-(phenylmethoxy)phenyl]ethyl}acetamide (295320-03-5)

Conditions	Yield
With anhydrous phosphorus trichloride In chlorobenzene	99%

2-chloro-3-pyridinecarbonitrile (6602-54-6) + 4-hydroxyphenylacetate (156-38-7) → 2-(4-((3-cyanopyridin-2-yl)oxy)phenyl)acetic acid hydrochloride

Conditions	Yield
Stage #1: 2-chloro-3-pyridinecarbonitrile; 4-hydroxyphenylacetate With potassium carbonate In dimethyl sulfoxide at 60℃; for 14h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide	99%

4-hydroxyphenylacetate (156-38-7) + recorcinol (108-46-3) → 2,4,4'-trihydroxy deoxybenzoin (17720-60-4)

Conditions	Yield
With boron trifluoride diethyl etherate at 60 - 70℃; for 1h;	98%
With boron trifluoride diethyl etherate for 0.25h; Acylation; Friedel-Crafts reaction; Heating;	90%
With boron trifluoride diethyl etherate for 0.166667h; Heating;	88%

4-hydroxyphenylacetate (156-38-7) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With sodium tetrahydroborate; Trimethyl borate; dimethyl sulfate In tetrahydrofuran at 20℃; for 1.5h;	98%
With sodium tetrahydroborate; iodine In tetrahydrofuran for 2h; Heating;	88%
With lithium aluminium tetrahydride In tetrahydrofuran at 67℃; for 2.5h;	88%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 4-hydroxyphenylacetate (156-38-7) → 4-hydroxyphenylacetic acid N-hydroxysuccinimide ester (73158-83-5)

Conditions	Yield
With dicyclohexyl-carbodiimide In ethyl acetate	98%
With benzotriazol-1-ol; 1,2-dichloro-ethane In dichloromethane; N,N-dimethyl-formamide	78%
With dicyclohexyl-carbodiimide In 1,4-dioxane	41%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 18h; Ambient temperature;
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 25℃; for 14h; Inert atmosphere;

4-hydroxyphenylacetate (156-38-7) + 4-amino-1-benzylpiperidine (50541-93-0) → N-(1-benzylpiperidin-4-yl)-2-(4-hydroxyphenyl)-acetamide

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In dichloromethane for 2h; Ambient temperature;	98%
Stage #1: 4-hydroxyphenylacetate With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 3h; Stage #2: 4-amino-1-benzylpiperidine In tetrahydrofuran at 20℃; for 24h;	40%

4-hydroxyphenylacetate (156-38-7) + allyl bromide (106-95-6) → allyl (p-allyloxyphenyl)acetate (851318-54-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 48h; Inert atmosphere;	98%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere;	86%
Stage #1: 4-hydroxyphenylacetate With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 2h; Stage #2: allyl bromide In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 4.5h;	65%

5-bromotryptamine (3610-42-2) + 4-hydroxyphenylacetate (156-38-7) → C18H17BrN2O2 (1201916-18-8)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	98%

4-hydroxyphenylacetate (156-38-7) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-(4-((tert-butyldimethylsilyl)oxy)phenyl)acetic acid (114774-40-2)

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 16h;	98%
With 1H-imidazole In tetrahydrofuran at 0 - 25℃; for 2h;	82%
With 1H-imidazole In tetrahydrofuran at 0 - 20℃; for 2h;	66%
With 1H-imidazole In tetrahydrofuran at 0 - 20℃; for 1h;	60.7%
Stage #1: 4-hydroxyphenylacetate; tert-butyldimethylsilyl chloride With 1H-imidazole In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: With sodium carbonate In tetrahydrofuran at 20℃; for 1h;	60.7%

4-hydroxyphenylacetate (156-38-7) → (4-hydroxy-3-iodophenyl)acetic acid (19039-15-7)

Conditions	Yield
With Iodine monochloride; acetic acid In dichloromethane at 20℃; for 50h;	98%

4-hydroxyphenylacetate (156-38-7) → (3,5-dibromo-4-hydroxyphenyl)acetic acid (24744-58-9)

Conditions	Yield
With bromine In acetic acid at 15℃; for 96h;	97%
With bromine; acetic acid
With bromine; acetic acid
With bromine In acetic acid

4-hydroxyphenylacetate (156-38-7) + isopropyl alcohol (67-63-0) → iso-propyl 4-hydroxyphenylacetate (41997-33-5)

Conditions	Yield
With sulfuric acid Heating;	97%
With tetrachlorosilane for 7h; Heating;	92%
With Fe(3+)-K-10 montmorillonite clay for 8h; Heating;	90%
With sodium hydrogen sulfate; silica gel at 20℃; for 5.5h; Esterification;	89%
With hydrogenchloride Heating;

4-hydroxyphenylacetate (156-38-7) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → N-(2-(3,4-dimethoxyphenyl)ethyl)-2-(4-hydroxyphenyl)acetamide (10214-84-3)

Conditions	Yield
at 215℃; for 5h;	97%
In neat (no solvent) at 200℃; for 2h; Sealed tube; Inert atmosphere;	91%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;	80.5%

Upstream product

• 104-01-8 4-Methoxyphenylacetic acid 
• 1197-55-3 4-aminophenylacetic acid 
• 60-18-4 L-tyrosine 
• 151562-57-1 1,8-dihydroxy-10-<2-(4-hydroxyphenyl)-1-oxoethyl>-9(10H)-anthracenone 
• 7664-93-9 sulfuric acid 
• 15573-67-8 pisolithin A 
• 10034-85-2 hydrogen iodide 
• 7647-01-0 hydrogenchloride 
• 28116-23-6 N-[(4-hydroxy-phenyl)-acetyl]-glycine 
• 781654-24-8 (4-hydroxyphenyl)thioacetomorpholide 
• 58609-13-5 4-(benzyloxy)phenylacetic acid benzyl ester 
• 104-47-2 p-methoxybenzylnitrile 
• 556-02-5 ?Tyr 
• 103-82-2 phenylacetic acid 

Downstream Products

• 66902-55-4 (4-hydroxy-phenyl)-acetic acid-[3-(2-methyl-piperidino)-propylester]; hydrochloride 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 17138-28-2 (4-hydroxy-phenyl)-acetic acid ethyl ester 
• 110437-21-3 [4-(2-diethylamino-ethoxy)-phenyl]-acetic acid-(2-diethylamino-ethyl ester) 
• 4919-33-9 4-ethoxyphenylacetic acid 
• 106-44-5 p-cresol 
• 51109-27-4 (2,4,5-trihydroxy-phenyl)-acetic acid 
• 1948-39-6 (4-hydroxy-3,5-diiodophenyl)acetic acid 
• 10463-37-3 (4-hydroxy-3,5-dinitro-phenyl)-acetic acid 
• 10463-20-4 4-hydroxy-3-nitrophenylacetic acid 
• 24744-58-9 (3,5-dibromo-4-hydroxyphenyl)acetic acid 
• 38692-80-7 2-(3-bromo-4-hydroxyphenyl)acetic acid 
• 112579-49-4 (4-methoxycarbonyloxy-phenyl)-acetic acid 
• 52426-63-8 (4-ethoxycarbonyloxy-phenyl)-acetic acid 

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The oxidizing ability of peroxodisulfate upon complexation inside the Bambusuril macrocycle cavity is inhibited. This dianionic agent can be released on demand from its stable 1:1 complex in water (log Ka=6.9 m?1) by addition of a more strongly bound anion, such as iodide (log Ka=7.1 m?1), which can also be delivered in situ upon irradiation from a 4-hydroxyphenacyl iodide derivative with spatial and temporal precision. The oxidizing properties of peroxodisulfate ions liberated from the complex recover and can take part in subsequent chemical transformations.

A 'photorelease, catch and photorelease' strategy for bioconjugation utilizing a p-hydroxyphenacyl group

A bioorthogonal 'catch and photorelease' strategy, which combines alkyne-azide cycloaddition between p-hydroxyphenacyl azide and alkyne derivatives to form a 1,2,3-triazole adduct and subsequent photochemical release of the triazole moiety via a photo-Favorskii rearrangement, is introduced. The first step can also involve photorelease of a strained alkyne and its Cu-free click reaction with azide.

Facile 1,2-aryl migration of 2-halomethyl-2-(4'-hydroxyphenyl) ketals: A novel single step synthesis of 4-hydroxyphenylacetic acid and its derivatives

1,2-Aryl migration of 1-halomethyl-2-(4-hydroxyphenyl) ketals, obtained from 2-bromomethyl 4-hydroxyacetophenone, under mild basic conditions have been shown to give 4-hydroxyphenylacetic acid or its derivatives which are key intermediates in the preparation of Atenolol, a well known cardiac β-blocker.

SESQUITERTENE LACTONES FROM LACTUCA LACINIATA

From the roots of Lactuca laciniata, six new sesquiterpene lactones, 9α-hydroxyzaluzanin C, 9α-hydroxy-11,13α-dihydrozaluzanin C, lactucopicriside, lactuside A and lactuside B, have been isolated together with known compounds, macrocliniside A, glucozaluzanin C, 11,13-α-dihydroglucozaluzanin C, 11,β,13-dihydrolactucin and dihydrosyntamarin.The structures were establishes by spectral data and X-ray diffraction analysis.Key Word Index - Lactuca laciniata; Compositae; sesquiterpene lactones; 9α-hydroxyzaluzanin C; 9α-hydroxy-11,13α-dihydrozaluzanin C; lactucopicriside; lactulide A; lactuside A; lactuside B.

Sesquiterpene lactones from Ixeris tamagawaensis KITAM. III

Two new germacranolides, ixerins H and I, and three new melampolides, ixerins J, K and L were isolated from the polar and less polar fractions of Ixeris tamagawaensis KITAM., respectively. The structures and stereochemistry were established partly by chemical transformations and mainly by the use of 1H- and 13C-nuclear magnetic resonance spectroscopy.

Formation of Coelenteramine from 2-Peroxycoelenterazine in the Ca2+-Binding Photoprotein Aequorin

Aequorin consists of apoprotein (apoAequorin) and (S)-2-peroxycoelenterazine (CTZ-OOH) and is considered to be a transient-state complex of an enzyme (apoAequorin) and a substrate (coelenterazine and molecular oxygen) in the enzymatic reaction. The degradation process of CTZ-OOH in aequorin was characterized under various conditions of protein denaturation. By acid treatment, the major product from CTZ-OOH was coelenteramine (CTM), but not coelenteramide (CTMD), and no significant luminescence was observed. The counterparts of CTM from CTZ-OOH were identified as 4-hydroxyphenylpyruvic acid (4HPPA) and 4-hydroxyphenylacetic acid (4HPAA) by liquid chromatography/electrospray ionization–time-of-flight mass spectrometry (LC/ESI-TOF-MS). In the luminescence reaction of aequorin with Ca2+, similar amounts of 4HPPA and 4HPAA were detected, indicating that CTM is formed by two pathways from CTZ-OOH through dioxetanone anion and not by hydrolysis from CTMD.