23508-35-2

Basic information

• Product Name: (S)-3-(4-HYDROXYPHENYL)-2-HYDROXYPROPIONIC ACID
• Synonyms: (S)-2-HYDROXY-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID;(S)-3-(4'-HYDROXYPHENYL)-2-HYDROXY-PROPANOIC ACID;(S)-3-(4-HYDROXYPHENYL)-2-HYDROXYPROPIONIC ACID;(S)-3-(4-HYDROXYPHENYL)LACTIC ACID;(2S)-2-HYDROXY-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID;(2S)-3-(4-HYDROXYPHENYL)-2-HYDROXYPROPIONIC ACID;(S)-3-(4-Hydroxyphenyl)Lactic;(S)-3-(4-Hysroxyphenyl)-2-hydroxypropionoicacid
• CAS NO: 23508-35-2
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.17
• Mol File: 23508-35-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 165-168 °C
• Boiling Point: 414.439 °C at 760 mmHg
• Flash Point: 218.597 °C
• Appearance: /
• Density: 1.405 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.617
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.80±0.10(Predicted)
• CAS DataBase Reference: (S)-3-(4-HYDROXYPHENYL)-2-HYDROXYPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(4-HYDROXYPHENYL)-2-HYDROXYPROPIONIC ACID(23508-35-2)
• EPA Substance Registry System: (S)-3-(4-HYDROXYPHENYL)-2-HYDROXYPROPIONIC ACID(23508-35-2)

Safety Data

• Hazardous Substances Data: 23508-35-2(Hazardous Substances Data)

Usage

General Description

(S)-3-(4-HYDROXYPHENYL)-2-HYDROXYPROPIONIC ACID, also known as caffeic acid, is a natural organic compound found in various plants. It is a hydroxycinnamic acid that belongs to the phenolic group of compounds and is a potent antioxidant. Caffeic acid has been shown to have anti-inflammatory and neuroprotective effects, and may also have potential anti-cancer properties. It is commonly found in foods such as coffee, fruits, vegetables, and wine, and is considered to be a beneficial dietary component due to its antioxidant and potential health-promoting properties.

InChI:InChI=1/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)/t8-/m0/s1

Synthetic route

4-Hydroxyphenylpyruvic acid (156-39-8) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

Conditions	Yield
With triethylamine; B-chlorodiisopinocampheylborane In tetrahydrofuran	92%
With triethylamine; B-chlorodiisopinocampheylborane In tetrahydrofuran at -30℃; optical yield given as %ee;	78%
Stage #1: 4-hydroxyphenylpiruvic acid With triethylamine In N,N-dimethyl-formamide at -40℃; for 0.166667h; Stage #2: With B-chlorodiisopinocampheylborane In tetrahydrofuran; N,N-dimethyl-formamide at -20 - 20℃; for 12.5h; enantioselective reaction;	71%

(S)-3-(4-hydroxy-phenyl)-2-methoxy-propionic acid sodium salt → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

Conditions	Yield
With hydrogenchloride; sodium iodide at 110℃; for 24h;	91%

(S)-2-ethoxy-3-(4-methoxyphenyl)propanoic acid (343880-41-1) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + (S)-2-hydroxy-3-(4-methoxyphenyl)propanoic acid (33173-34-1)

Conditions	Yield
With boron tribromide In dichloromethane at -10℃;	A 7% B 90%

(S)-2-ethoxy-3-(4-methoxyphenyl)propanoic acid (343880-41-1) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid (325793-65-5)

Conditions	Yield
With hydrogen iodide In water	A 10% B 80%

L-tyrosine (60-18-4) → 4-Hydroxyphenylpyruvic acid (156-39-8) + (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

Conditions	Yield
With formate dehydrogenase; oxygen; ammonium formate; NADH In aq. phosphate buffer at 21℃; under 750.075 Torr; for 7h; pH=7; Concentration; Enzymatic reaction; stereoselective reaction;	A 2 %Chromat. B 80%

(S)-3-(4-(benzyloxy)phenyl)-2-hydroxypropanoic acid (162919-37-1) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

Conditions	Yield
With hydrogen; 10 percent Pd/C In methanol; ethyl acetate for 20h; atmospheric pressure;	70%

tyrosine (556-02-5) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

›Tyr (556-02-5, 556-03-6, 34537-57-0, 55520-40-6, 96946-98-4, 60-18-4) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

L-tyrosine (60-18-4) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

Conditions	Yield
With nitric acid
durch Einwirkung von Bacillus subtilis in Gegenwart von Phosphaten;
With bacterium subtilis
With barium nitrite; sulfuric acid

4-amino-L-phenylalanine (943-80-6) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

Conditions	Yield
With hydrogenchloride; sodium nitrite 1.) 0 deg C, overnight, 2.) reflux, 15 min; Yield given. Multistep reaction;

4-Hydroxyphenylpyruvic acid (156-39-8) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + (R)-3-(4-hydroxyphenyl)lactic acid (89919-57-3)

Conditions	Yield
With triethylamine; B-chlorodiisopinocampheylborane In tetrahydrofuran 1.) -20 deg C, 5 min; 2.) 20 deg C, then 0 deg C, 3 h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
With triethylamine; B-chlorodiisopinocampheylborane In tetrahydrofuran Title compound not separated from byproducts;
With C20H34BCl; triethylamine In tetrahydrofuran at 20℃; for 12h; Overall yield = 70 percent; Overall yield = 299 mg;	A n/a B n/a

inactive form → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

Conditions	Yield
With water; MORPHIN

methyl 2-dihydroxy-3-(4-methoxyphenyl)propanoate (856899-98-4) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

Conditions	Yield
With sodium hydroxide In ethanol for 3h;

4-methoxy-benzaldehyde (123-11-5) + indenyl magnesium bromide → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.2: Microbiological reaction 2.1: 100 percent / H2 / Pd/C / ethyl acetate / 16 h / 20 °C / 2327.17 Torr 3.1: aq. NaOH / ethanol / 3 h View Scheme

(2S,3R)-methyl p-methoxycinnamate epoxide (137173-40-1) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / H2 / Pd/C / ethyl acetate / 16 h / 20 °C / 2327.17 Torr 2: aq. NaOH / ethanol / 3 h View Scheme

(S)-2-acetoxy-3-(4-(benzyloxy)phenyl)propanoic acid (267228-34-2) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / 0.1 mol/l LiOH / tetrahydrofuran / 20 h / 20 °C 2: 70 percent / H2 / 10 percent Pd/C / ethyl acetate; methanol / 20 h / atmospheric pressure View Scheme

ethyl 2-ethoxy-3-(4-methoxyphenyl)-2-propenoate → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid (325793-65-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; ethanol / toluene 2: hydrogen; 5%-palladium/activated carbon / Isopropyl acetate / 3 h / 22 - 25 °C / 3000.3 Torr / Autoclave; Inert atmosphere 3: Isopropyl acetate / 0.17 h / 45 - 47 °C 4: hydrogen iodide / water View Scheme

ethyl 2-ethoxy-3-(4-methoxyphenyl)-2-propenoate → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + (S)-2-hydroxy-3-(4-methoxyphenyl)propanoic acid (33173-34-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; ethanol / toluene 2: hydrogen; 5%-palladium/activated carbon / Isopropyl acetate / 3 h / 22 - 25 °C / 3000.3 Torr / Autoclave; Inert atmosphere 3: Isopropyl acetate / 0.17 h / 45 - 47 °C 4: boron tribromide / dichloromethane / -10 °C View Scheme

(Z)-2-ethoxy-3-(4-methoxyphenyl)propenoic acid (1214260-73-7) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid (325793-65-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen; 5%-palladium/activated carbon / Isopropyl acetate / 3 h / 22 - 25 °C / 3000.3 Torr / Autoclave; Inert atmosphere 2: Isopropyl acetate / 0.17 h / 45 - 47 °C 3: hydrogen iodide / water View Scheme

(Z)-2-ethoxy-3-(4-methoxyphenyl)propenoic acid (1214260-73-7) → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + (S)-2-hydroxy-3-(4-methoxyphenyl)propanoic acid (33173-34-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen; 5%-palladium/activated carbon / Isopropyl acetate / 3 h / 22 - 25 °C / 3000.3 Torr / Autoclave; Inert atmosphere 2: Isopropyl acetate / 0.17 h / 45 - 47 °C 3: boron tribromide / dichloromethane / -10 °C View Scheme

2-ethoxy-3-(4-methoxyphenyl)propanoic acid → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid (325793-65-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Isopropyl acetate / 0.17 h / 45 - 47 °C 2: hydrogen iodide / water View Scheme

2-ethoxy-3-(4-methoxyphenyl)propanoic acid → (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + (S)-2-hydroxy-3-(4-methoxyphenyl)propanoic acid (33173-34-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: Isopropyl acetate / 0.17 h / 45 - 47 °C 2: boron tribromide / dichloromethane / -10 °C View Scheme

methanol (67-56-1) + (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) → (S)-3-(4-hydroxyphenyl)-2-hydroxypropionyl methyl ester (123359-33-1)

Conditions	Yield
With hydrogenchloride at 20℃; for 2h;	100%

1-Decanol (112-30-1) + (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) → C19H30O4

Conditions	Yield
With sulfuric acid at 80℃; for 2h;	95%

1-dodecyl alcohol (112-53-8) + (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) → C21H34O4

Conditions	Yield
With sulfuric acid at 80℃; for 2h;	91%

(S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + acetic anhydride (108-24-7) → C13H14O6

Conditions	Yield
With pyridine at 20℃; for 3h;	90%
With pyridine
With dmap; triethylamine In dichloromethane at 21℃; for 3h;
With dmap In ethyl acetate at 30℃; for 1h;

3-(5-bromopentoxy)-estra-1,3,5(10)-triene-17β-ol (22034-75-9) + (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) → C32H42O6

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h;	84%

(S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + butan-1-ol (71-36-3) → (S)-latifolicinin A

Conditions	Yield
With sulfuric acid at 80℃; for 2h;	82%

(S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + N,0-dimethylhydroxylamine (1117-97-1) → (S)-2-hydroxy-3-(4-hydroxyphenyl)-N-methoxy-N-methylpropanamide (915396-55-3)

Conditions	Yield
Stage #1: N,0-dimethylhydroxylamine With 4-methyl-morpholine In dichloromethane at 0℃; for 0.0833333h; Stage #2: (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 14.0833h; chemoselective reaction;	79%

(S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + hexan-1-ol (111-27-3) → C15H22O4

Conditions	Yield
With sulfuric acid at 80℃; for 2h;	69%

ethanol (64-17-5) + (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) → latifolicinin B (267228-41-1)

Conditions	Yield
With sulfuric acid at 80℃; for 2h;	66%

(S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + 1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) → C19H26O4

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h;	64%

octanol (111-87-5) + (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) → C17H26O4

Conditions	Yield
With sulfuric acid at 80℃; for 2h;	64%

farnesyl bromide (24163-93-7, 24163-94-8, 28290-41-7, 56881-57-3, 6874-67-5) + (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) → C24H34O4

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h;	42%

(S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + methyl N2-(((R)-2-amino-4-phenylbutanoyl)-D-prolyl)-Nω-nitro-D-argininate → methyl N2-(((2R)-2-((S)-2-hydroxy-3-(4-hydroxyphenyl)propanamido)-4-phenylbutanoyl)-L-prolyl)-Nω-nitro-D-argininate

Conditions	Yield
With 4-methyl-morpholine; O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	31%

(S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + urea (57-13-6) + oidium lactis → 4-Hydroxyphenylpyruvic acid (156-39-8)

(S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) → (R)-3-(4-hydroxyphenyl)lactic acid (89919-57-3)

Conditions	Yield
With BIS-TRIS buffer; Lactobacillus halotolerans DSM 20190 In water at 42℃; for 24h; pH=6;

(S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + benzyl chloride (100-44-7) → (S)-3-(4-Benzyloxy-phenyl)-2-hydroxy-propionic acid benzyl ester

Conditions	Yield
With potassium carbonate In ethanol for 24h; Heating;
With potassium carbonate In ethanol for 18h;

(S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (23508-35-2) + 4-(3-chloropropoxy)-O-phenylphenol (179020-04-3) → (S)-2-Hydroxy-3-{4-[3-(4-phenoxy-phenoxy)-propoxy]-phenyl}-propionic acid (945292-58-0)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide for 3h; Heating;

Upstream product

• 556-02-5 ?Tyr 
• 60-18-4 L-tyrosine 
• 156-39-8 4-hydroxyphenylpiruvic acid 
• 1214260-73-7 (Z)-2-ethoxy-3-(4-methoxyphenyl)propenoic acid 
• 343880-41-1 (S)-2-ethoxy-3-(4-methoxyphenyl)propanoic acid 
• 267228-34-2 (S)-2-acetyloxy-3-(4-benzyloxyphenyl)propionic acid 
• 137173-40-1 (2S,3R)-methyl p-methoxycinnamate epoxide 
• 123-11-5 4-methoxy-benzaldehyde 
• 856899-98-4 methyl 2-dihydroxy-3-(4-methoxyphenyl)propanoate 
• 162919-37-1 (S)-3-[4-(benzyloxy)phenyl]-2-hydroxypropanoic acid 
• 943-80-6 4-amino-L-phenylalanine 
• 556-02-5 tyrosine 
• 123-08-0 4-hydroxy-benzaldehyde 
• 64896-33-9 (Z)-2-acetamido-3-(p-hydroxyphenyl)-2-propenic acid 

Downstream Products

• 15220-05-0 (+/-)-2-hydroxy-3-(4-hydroxy-3,5-diiodo-phenyl)-propionic acid 
• 35772-94-2 (+/-)-2-hydroxy-3-(4-hydroxy-3,5-dinitro-phenyl)-propionic acid 
• 99358-35-7 2-hydroxy-3-(4-hydroxy-3-nitro-phenyl)-propionic acid 
• 156-39-8 4-hydroxyphenylpiruvic acid 
• 123359-33-1 (S)-3-(4-hydroxyphenyl)-2-hydroxypropionyl methyl ester 

Relevant articles and documents

-

-

Aeruginosins 102-A and B, new thrombin inhibitors from the cyanobacterium Microcystis viridis (NIES-102)

Aeruginosins 102-A and B were isolated from the freshwater cyanobacterium Microcystis aeruginosa (NIES-102). Their structures were elucidated to be 1 and 2 on the basis of 2D NMR data and chemical degradation. These peptides inhibited thrombin potently.

Synthesis of Weinreb amides using diboronic acid anhydride-catalyzed dehydrative amidation of carboxylic acids

The first successful example of the direct synthesis of Weinreb amides using catalytic hydroxy-directed dehydrative amidation of carboxylic acids using the diboronic acid anhydride catalyst is described. The methodology is applicable to the concise syntheses of eight α-hydroxyketone natural products, namely, sattabacin, 4-hydroxy sattabacin, kurasoins A and B, soraphinols A and B, and circumcins B and C.

Latifolicinin A from a Fermented Soymilk Product and the Structure-Activity Relationship of Synthetic Analogues as Inhibitors of Breast Cancer Cell Growth

The functional components in soymilk may vary depending upon the fermentation process. A fermented soymilk product (FSP) obtained by incubation with the microorganisms of intestinal microflora was found to reduce the risk of breast cancer. Guided by the inhibitory activities against breast cancer cells, two cytotoxic compounds, daidzein and (S)-latifolicinin A, were isolated from the FSP by repetitive extraction and chromatography. Latifolicinin A is the n-butyl ester of β-(4-hydroxyphenyl)lactic acid (HPLA). A series of the ester and amide derivatives of (S)-HPLA and l-tyrosine were synthesized for evaluation of their cytotoxic activities. In comparison, (S)-HPLA derivatives exhibited equal or superior inhibitory activities to their l-tyrosine counterparts, and (S)-HPLA amides showed better cytotoxic activities than their corresponding esters. In particular, (S)-HPLA farnesyl amide was active to triple-negative MDA-MB-231 breast cancer cells (IC50 = 27 μM) and 10-fold less toxic to Detroit-551 normal cells.