7400-08-0

Basic information

• Product Name: p-Hydroxy-cinnamic acid
• Synonyms: 4-hydroxylcinnamic acid;Alkaline ceramidase;Anti-PHCA antibody produced in rabbit;ACER3;Alkaline CDase 3;Alkaline ceramidase 3;Alkaline dihydroceramidase SB89;Alkaline phytoceramidase
• CAS NO: 7400-08-0
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.16
• EINECS: 231-000-0
• Product Categories: Cinnamic acid
• Mol File: 7400-08-0.mol
• Article Data: 241

Chemical Properties

• Melting Point: 214 °C (dec.)(lit.)
• Boiling Point: 251.61°C (rough estimate)
• Flash Point: 177.284 °C
• Appearance: Light yellow to beige crystalline powder
• Density: 1.2132 (rough estimate)
• Vapor Pressure: 7.19E-05mmHg at 25°C
• Refractive Index: 1.5380 (estimate)
• Storage Temp.: -20°C
• Solubility: Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.65±0.10(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: p-Hydroxy-cinnamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: p-Hydroxy-cinnamic acid(7400-08-0)
• EPA Substance Registry System: p-Hydroxy-cinnamic acid(7400-08-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37/39-22
• WGK Germany: 2
• RTECS: GD9095000
• Hazardous Substances Data: 7400-08-0(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow to beige crystalline powder with aroma, soluble in methanol, ethanol, DMSO and other organic solvents, derived from synthesis.

Uses

4-Hydroxycinnamic acid is the hydroxy derivative of Cinnamic Acid with antioxidant properties. It is a is a major component of lignocellulose. Studies suggest that 4-Hydroxycinnamic acid may reduce the risk of cancer by reducing the formation of carcinogenic nitrosamines. A recent study reports that 4-Hydroxycinnamic acid may act as a chemical castrator in bees by altering the epression of genes required for ovary development. This compound is common in pollen a major constituent of the worker bee diet, but it is not found in queen bees'royal jelly.

Application

p-Hydroxycinnamic acid is mainly used as an intermediate in the pharmaceutical and perfume industries. It can react with dimethyl sulfate to produce p-anisaldehyde, react with acetaldehyde to produce p-hydroxycinnamaldehyde, and further oxidize it to produce cinnamic acid. This product can be directly oxidized to produce 4-Hydroxybenzoic acid and reduction to produce 4-Hydroxybenzyl alcohol.

Definition

ChEBI: 4-coumaric acid is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate.

Hazard

Moderately toxic.

Safety Profile

Moderarely toxic by intraperitoneal route. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and fumes. See also COUMARIN

InChI:InChI=1/C9H8O3/c1-6(9(11)12)7-2-4-8(10)5-3-7/h2-5,10H,1H2,(H,11,12)

Synthetic route

malonic acid (141-82-2) + 4-hydroxy-benzaldehyde (123-08-0) → p-Coumaric Acid (7400-08-0)

Conditions	Yield
With piperidine; pyridine for 1h; Knoevenagel-Doebner-Stobbe Reaction; Reflux;	98%
With ammonium acetate for 0.05h; Irradiation;	97%
With aluminum oxide; lithium chloride for 0.0833333h; Doebner condensation; microwave irradiation;	97%

(E)-4-iodocinnamic acid (113641-76-2) → p-Coumaric Acid (7400-08-0)

Conditions	Yield
With copper(I) oxide; 1-D-O-Methyl-chiro-inositol; sodium hydroxide In water at 100℃; for 6h;	88%

5-O-(E)-p-coumaroylquinic acid ethyl ester (1443678-33-8) → p-Coumaric Acid (7400-08-0) + D-(-)-quinic acid (77-95-2)

Conditions	Yield
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h;	A n/a B 2.5 mg

2'-O-acetyl-3-O-(E)-p-coumaroylsucrose → D-Fructose (57-48-7) + D-glucose (50-99-7) + p-Coumaric Acid (7400-08-0)

Conditions	Yield
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h;

3',6'-di-O-acetyl-3-O-(E)-p-coumaroylsucrose → D-Fructose (57-48-7) + D-glucose (50-99-7) + p-Coumaric Acid (7400-08-0)

Conditions	Yield
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h;

4,2',3',6'-tetra-O-acetyl-3-O-(E)-p-coumaroylsucrose (1446205-86-2) → D-Fructose (57-48-7) + D-glucose (50-99-7) + p-Coumaric Acid (7400-08-0)

Conditions	Yield
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h;

1,2',3',4',6'-penta-O-acetyl-3-O-(E)-p-coumaroylsucrose (1392307-46-8) → D-Fructose (57-48-7) + D-glucose (50-99-7) + p-Coumaric Acid (7400-08-0)

Conditions	Yield
With sulfuric acid; water In 1,4-dioxane at 90℃; for 3h;

para-coumaric acid (7400-08-0) → p-Coumaric Acid (7400-08-0)

Conditions	Yield
With iodine In d(4)-methanol at 50℃; for 0.166667h; Time; Green chemistry;

4-Iodophenol (540-38-5) + acrylic acid (79-10-7) → p-Coumaric Acid (7400-08-0)

Conditions	Yield
With palladium diacetate; potassium carbonate In water at 80℃; for 2h;	94%
With potassium carbonate In 1,4-dioxane; water at 80℃; for 12h; Inert atmosphere;	93%
With tetrakis(triphenylphosphine) palladium(0); lithium chloride; potassium hydroxide In water at 85℃; for 3h; Heck Reaction;	95 %Chromat.

L-tyrosine (60-18-4) → p-Coumaric Acid (7400-08-0)

Conditions	Yield
Einw. von Bacillus proteus vulgaris in Ringerscher Loesung;
With 1,3-bis[tris(hydroxymethyl)methylamino]-propane; Arabidopsis thaliana phenylalanine ammonia lyase 1 In water at 37℃; pH=8.4; Enzyme kinetics; Further Variations:; Reagents;
free cell extract of Rhodotorula rubra (ATCC 889) In Tris-HCl buffer pH=8.5; Kinetics; Enzymatic reaction;

kaempferol 3-O-{[(6-O-E-p-coumaroyl)-β-D-glucopyranosyl(1→2)]-α-L-rhamnopyranosyl(1→6)}-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside → p-Coumaric Acid (7400-08-0)

Conditions	Yield
With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness;

quercetin 3-O-[(6-O-E-p-coumaroyl)-β-D-glucopyranosyl(1→2)]-β-D-galactopyranoside-7-O-(2-O-E-caffeoyl)-β-D-glucuropyranoside → p-Coumaric Acid (7400-08-0)

Conditions	Yield
With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness;

quercetin 3-O-[(6-O-E-p-coumaroyl)-β-D-glucopyranosyl-(1→2)]-β-D-galactopyranoside-7-O-β-D-glucuropyranoside → p-Coumaric Acid (7400-08-0)

Conditions	Yield
With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness;

kaempferol 3-O-[(6-O-E-p-coumaroyl)-β-D-glucopyranosyl-(1→2)]-β-D-galactopyranoside-7-O-β-D-glucuropyranoside → p-Coumaric Acid (7400-08-0)

Conditions	Yield
With sodium hydroxide; ascorbic acid at 20℃; for 2h; Darkness;

juglanoside J → p-Coumaric Acid (7400-08-0) + (1S)-1,2,3,4-tetrahydro-8-hydroxy-4-oxonaphthalen-1-yl 6-O-[(3,4,5-trihydroxyphenyl)carbonyl]-β-D-glucopyranoside

Conditions	Yield
With sodium hydroxide at 20℃; for 6h;	A 1.5 mg B 2.8 mg

4-bromo-phenol (106-41-2) + acrylic acid (79-10-7) → p-Coumaric Acid (7400-08-0)

Conditions	Yield
With sodium carbonate; palladium dichloride In water at 100℃; for 2h;	65%
With sodium carbonate; palladium dichloride at 100℃; for 2h;	65%

4-hydroxy-benzaldehyde (123-08-0) → p-Coumaric Acid (7400-08-0)

Conditions	Yield
With hydrogenchloride; malonic acid; aniline In pyridine

1-O-(E)-caffeoyl-2-O-p-(E)-coumaroyl-β-D-glucopyranose → p-Coumaric Acid (7400-08-0)

Conditions	Yield
With hydrogenchloride; water at 90℃; for 3h; Sealed tube;

methyl 4-hydroxycinnamate (3943-97-3) → p-Coumaric Acid (7400-08-0)

Conditions	Yield
With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water at 20℃; for 18h; Inert atmosphere; Schlenk technique; Glovebox;	92%

peonidin 3-O-[2-O-(2-O-(trans-sinapoyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] → D-Glucose (2280-44-6) + malonic acid (141-82-2) + p-Coumaric Acid (7400-08-0) + trans-3,5-dimethoxy-4-hydroxycinnamic acid (530-59-6) + peonidin chloride (134-01-0)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 1h;

cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] → D-Glucose (2280-44-6) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + malonic acid (141-82-2) + p-Coumaric Acid (7400-08-0) + cyanidin chloride (528-58-5)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 1h;

peonidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] → D-Glucose (2280-44-6) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + malonic acid (141-82-2) + p-Coumaric Acid (7400-08-0) + peonidin chloride (134-01-0)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 1h;

allivictoside C → p-Coumaric Acid (7400-08-0) + kaempferol 3,7,4'-tri-O-β-D-glucopyranoside

Conditions	Yield
With potassium hydroxide at 20℃; for 12h;

allivictoside E → p-Coumaric Acid (7400-08-0) + kaempferol 3,7,4'-tri-O-β-D-glucopyranoside

Conditions	Yield
With potassium hydroxide at 20℃; for 12h;

p-Coumaric Acid (7400-08-0) → 4-hydroxyphenylpropionic acid (501-97-3)

Conditions	Yield
With hydrogen; platinum(IV) oxide In methanol under 760 Torr; Ambient temperature;	100%
With hydrogen; palladium on activated charcoal In methanol	100%
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃;	99%

methanol (67-56-1) + p-Coumaric Acid (7400-08-0) → methyl 4-hydroxycinnamate (3943-97-3)

Conditions	Yield
With sulfuric acid for 24h; Reflux;	100%
With sulfuric acid for 7h; Heating;	99%
With sulfuric acid for 24h; Reflux;	99%

p-Coumaric Acid (7400-08-0) + acetic anhydride (108-24-7) → 4-acetoxycinnamic acid (27542-85-4)

Conditions	Yield
With pyridine at 20℃;	100%
With pyridine; dmap for 1.5h;	97%
With pyridine at 25℃; for 24h;	95%

p-Coumaric Acid (7400-08-0) + dimethyl sulfate (77-78-1) → 3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3)

Conditions	Yield
Stage #1: p-Coumaric Acid With potassium carbonate In acetone at 20℃; for 0.25h; Stage #2: dimethyl sulfate In acetone at 20℃; for 8h; Heating / reflux;	99%
With potassium carbonate In acetone at 25℃; for 24h;	92%
With potassium carbonate In acetone for 3h; Reflux;	68%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + p-Coumaric Acid (7400-08-0) → 4-hydroxycinnamic acid N-hydroxysuccinimide ester (88492-43-7)

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;	95%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 18h; Ambient temperature;	59%
With diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 2h;	58%

p-Coumaric Acid (7400-08-0) + tert-butyldimethylsilyl chloride (18162-48-6) → (E)-3-(4'-((tert-butyldimethylsilyl)oxy)phenyl)acrylic acid (141222-28-8)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h;	98%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 3h;	98%

p-Coumaric Acid (7400-08-0) → trans-p-coumaric acid-4-O-sulfate

Conditions	Yield
With sulfur trioxide trimethylamine complex; sodium hydrogencarbonate; sodium hydroxide In water at 20℃; for 96h;	99%
With chlorosulfonic acid In pyridine at 20℃;	63%
With D-glucose; aryl sulfotransferase SULT1A1 Rattus norvegicus; isopropyl β-D-thiogalactopyranoside for 96h; Reagent/catalyst; Enzymatic reaction;

p-Coumaric Acid (7400-08-0) → methyl 4-hydroxycinnamate (3943-97-3)

Conditions	Yield
With sulfuric acid In methanol Heating / reflux;	98%
With sulfuric acid In methanol; ethanol; water	61%
With methanol; sulfuric acid

p-Coumaric Acid (7400-08-0) → 4-Vinylphenol (2628-17-3)

Conditions	Yield
With 4-methoxy-phenol In water; N,N-dimethyl-formamide at 150℃; for 4h; Solvent;	97%
With 1-methyl-1H-imidazole; sodium hydrogencarbonate for 0.333333h; Heating; microwave irradiation;	94%
With bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate; potassium acetate In DMF (N,N-dimethyl-formamide) at 150℃; for 1.5h; Product distribution / selectivity;	94%

4-benzylpyperidine (31252-42-3) + p-Coumaric Acid (7400-08-0) → (E)-1-(4-benzylpiperidin-1-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	56.5%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	47.7%
Stage #1: p-Coumaric Acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 0.5h; Condensation; Stage #2: 4-benzylpyperidine In tetrahydrofuran at 20℃; Acylation;	19%

p-Coumaric Acid (7400-08-0) + hydroxytyrosol (10597-60-1) → (2E)-3-(4-hydroxyphenyl)-2-propenoic acid 2-(3,4-dihydroxyphenyl)ethyl ester

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 48h;	73%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; Mitsunobu Displacement; chemoselective reaction;	66%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; Schlenk technique; Inert atmosphere;	54%
With Escherichia coli strain B-CP1 at 30℃; for 24h; Microbiological reaction; Enzymatic reaction;

p-Coumaric Acid (7400-08-0) + benzyl bromide (100-39-0) → (E)-4-benzyloxycinnamic acid (6272-45-3)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide	92%
With potassium carbonate In acetone for 12h; Reflux;	92%
With sodium hydroxide In ethanol	82%
With potassium hydroxide In ethanol; water at 20℃; for 72h;	41%
With sodium hydroxide

ethanol (64-17-5) + p-Coumaric Acid (7400-08-0) → ethyl (E)-4-hydroxycinnamate (2979-06-8, 7361-92-4, 7362-39-2)

Conditions	Yield
With sulfuric acid at 60℃;	100%
With sulfuric acid at 65℃; for 18h;	95%
With hydrogenchloride	92%

p-Coumaric Acid (7400-08-0) → (E)-3-(4-hydroxyphenyl)acryloylhydrazide (90557-60-1)

Conditions	Yield
Stage #1: p-Coumaric Acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 25℃; for 2h; Stage #2: With hydrazine hydrate In acetonitrile at 0 - 10℃;	79%
Stage #1: p-Coumaric Acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 2h; Stage #2: With hydrazine hydrate In acetonitrile; cyclohexene at 0 - 10℃;	46%
Stage #1: p-Coumaric Acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 2h; Stage #2: With hydrazine; cyclohexene In acetonitrile at 0 - 20℃; for 1.33333h;	36%
Multi-step reaction with 2 steps 1: 74 percent / Et3N / ethyl acetate / 6 h / Heating 2: 55 percent / N2H4 / CHCl3 / Heating View Scheme

1,2,3,4-tetrahydroisoquinoline (91-21-4) + p-Coumaric Acid (7400-08-0) → (E)-1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	76.7%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	62.7%

2-phenylethanol (60-12-8) + p-Coumaric Acid (7400-08-0) → (2E)-3-(4-hydroxyphenyl)-2-propenoic acid 2-phenylethyl ester

Conditions	Yield
With ytterbium(III) triflate In nitromethane at 120℃; for 1h;	70.6%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 48h;	40%
With Escherichia coli strain B-CP1 at 30℃; for 24h; Microbiological reaction; Enzymatic reaction;

O-2-tetrahydro-2H-pyranhydroxylamine (6723-30-4) + p-Coumaric Acid (7400-08-0) → (E)-3-(4-hydroxyphenyl)-N-((tetrahydro-2H-pyran-2-yl)oxy)acrylamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	84%

propan-1-ol (71-23-8) + p-Coumaric Acid (7400-08-0) → (E)-propyl 3-(4-hydroxyphenyl)acrylate (94530-69-5)

Conditions	Yield
With sulfuric acid for 3h;	72%
With dmap; dicyclohexyl-carbodiimide at 50℃; for 24h;	71%
With sulfuric acid Reflux;	58.43%
	16%
With sulfuric acid

p-Coumaric Acid (7400-08-0) + ethyl chloromethyl ether (3188-13-4) → ethoxymethyl 4-hydroxycinnamate (642471-45-2)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	84%
With triethylamine In dichloromethane at 0℃;	84%

6-chloro-1-hexanol (2009-83-8) + p-Coumaric Acid (7400-08-0) → 4-(6-hydroxyhexyloxy)cinnamic acid (503000-67-7)

Conditions	Yield
Stage #1: p-Coumaric Acid With potassium hydroxide; potassium iodide In ethanol; water for 0.166667h; Stage #2: 6-chloro-1-hexanol In ethanol; water at 30 - 40℃; Heating / reflux;	62%
With 1,3-dimethyl-2-imidazolidinone; potassium carbonate; potassium iodide at 130℃; for 17h;	47%
Stage #1: p-Coumaric Acid With potassium iodide; potassium hydroxide In ethanol; water for 0.166667h; Reflux; Stage #2: 6-chloro-1-hexanol In ethanol; water for 48h; Reflux; Stage #3: With hydrogenchloride In ethanol; water	46.8%

p-Coumaric Acid (7400-08-0) + 4-methoxy-aniline (104-94-9) → C16H15NO3

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide for 6h;	85%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 23℃; for 24h;	78.5%

p-Coumaric Acid (7400-08-0) + Carvacryl chloroacetate → 2-[2-methyl-5-(propan-2-yl)phenoxy]-2-oxoethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Conditions	Yield
With triethylamine; potassium iodide In N,N-dimethyl-formamide at 20℃; for 24h;	80%

1-phenylmethylpiperazine (2759-28-6) + p-Coumaric Acid (7400-08-0) → (E)-1-(4-benzylpiperazin-1-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	63.7%

p-Coumaric Acid (7400-08-0) + hydroxymethylparthenolide (93930-15-5) → ((1aR,7aS,10aS,10bS,E)-1a-methyl-8-methylene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-decahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-5-yl)methyl (E)-3-(4-hydroxyphenyl)acrylate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere;	76%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; Cooling with ice;	69%

p-Coumaric Acid (7400-08-0) + hexan-1-ol (111-27-3) → trans-hexyl 3-(4-hydroxyphenyl)propenoate

Conditions	Yield
Stage #1: p-Coumaric Acid; hexan-1-ol In tetrahydrofuran at 0℃; for 0.5h; Mitsunobu Displacement; Stage #2: With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu Displacement;	36.88%
With di-isopropyl azodicarboxylate; triphenylphosphine In N,N-dimethyl-formamide for 12h; Ambient temperature;	15 mg

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 105-53-3 diethyl malonate 
• 7400-08-0 p-Coumaric Acid 
• 3943-97-3 methyl p-hydroxycinnamate 
• 1225064-68-5 kankanoside H₂ 
• 1899-30-5 trans-3-p-coumaroylquinic acid 
• 117405-49-9 E-4-O-β-D-glucopyranosyl-p-coumaric acid 
• 87099-71-6 3-O-trans-p-coumaroyl-D-quinic acid 
• 1108200-72-1 4-O-(trans-p-coumaroyl)quinic acid 
• 117405-48-8 4-O-β-D-glucopyranosyl-Z-4-hydroxycinnamic acid 
• 1392307-47-9 1,2',3',4',6'-penta-O-acetyl-3-O-(Z)-p-coumaroylsucrose 
• 2538-87-6 trans-p-hydroxycinnamaldehyde 
• 108-24-7 acetic anhydride 
• 140-10-3 (E)-3-phenylacrylic acid 

Downstream Products

• 62718-63-2 4-pentyloxy-trans-cinnamic acid 
• 76457-47-1 4-(3-oxy-[1,2,3]oxadiazol-5-yl)-phenol 
• 29345-55-9 hydroxy-(4-hydroxy-phenyl)-acetaldehyde 
• 6049-54-3 3-amino-3-(4-hydroxyphenyl)propionic acid 
• 501-98-4 (Z)-p-coumaric acid 
• 3943-97-3 methyl 4-hydroxycinnamate 
• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 88-89-1 2,4,6-Trinitrophenol 
• 2628-17-3 4-Vinylphenol 
• 99-96-7 4-hydroxy-benzoic acid 
• 27542-85-4 4-acetoxycinnamic acid 
• 252258-18-7 (E)-3-(4-((methoxycarbonyl)oxy)phenyl)acrylic acid 
• 60345-99-5 (2E)-3-[4-(2-hydroxyethoxy)phenyl]prop-2-enoic acid 

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Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters

Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation

A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.