57100-28-4

Usage

Uses

Used in Pharmaceutical Industry:
P-Hydroxy-beta-[carboxymethyl]-cinnamic acid is used as a potential pharmaceutical compound for its potential applications in drug development. Its structural features and properties may contribute to the creation of new therapeutic agents.
Used in Biochemical Research:
P-Hydroxy-beta-[carboxymethyl]-cinnamic acid is used as a research compound in biochemistry, where it can be studied for its interactions with other molecules and its potential role in various biological processes.
Used in Lignin Biosynthesis Studies:
P-Hydroxy-beta-[carboxymethyl]-cinnamic acid is used as a model compound in the study of lignin biosynthesis, helping researchers understand the complex organic polymer's formation and its role in plant cell walls.

InChI:InChI=1/C11H10O5/c12-9-3-1-7(2-4-9)8(5-10(13)14)6-11(15)16/h1-5,12H,6H2,(H,13,14)(H,15,16)/b8-5+

Synthetic route

(E)-3-(4-methoxyphenyl)pent-2-enedioic acid (106833-44-7) → trans-sphagnum acid (57100-28-4)

Conditions	Yield
With boron tribromide In dichloromethane 1) -78 deg C to 20 deg C, 2) 20 deg C, 24 h;	84%

3-(4-methoxyphenyl)glutaric acid (33868-91-6) → trans-sphagnum acid (57100-28-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / Br2 / CCl4 / 10 h / Irradiation 2: 84 percent / BBr3 / CH2Cl2 / 1) -78 deg C to 20 deg C, 2) 20 deg C, 24 h View Scheme

ethyl 2,2'-(4-methoxybenzal)bis-acetoacetate (6630-90-6) → trans-sphagnum acid (57100-28-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / 50percent NaOH / ethanol / 3 h / Heating 2: 87 percent / Br2 / CCl4 / 10 h / Irradiation 3: 84 percent / BBr3 / CH2Cl2 / 1) -78 deg C to 20 deg C, 2) 20 deg C, 24 h View Scheme

4-methoxy-benzaldehyde (123-11-5) + (+-)-2-cyano-3-m-tolyl-propionic acid hydrazide → trans-sphagnum acid (57100-28-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / piperidine / ethanol / 20 h / Ambient temperature 2: 93 percent / 50percent NaOH / ethanol / 3 h / Heating 3: 87 percent / Br2 / CCl4 / 10 h / Irradiation 4: 84 percent / BBr3 / CH2Cl2 / 1) -78 deg C to 20 deg C, 2) 20 deg C, 24 h View Scheme

trans-sphagnum acid (57100-28-4) → cis-sphagnum acid (50670-02-5, 57100-28-4)

Conditions	Yield
In methanol Irradiation;

trans-sphagnum acid (57100-28-4) → 4-hydroxy-benzoic acid (99-96-7) + /PBVZE011--290/

Conditions	Yield
With acetate buffer; peroxydase; dihydrogen peroxide for 0.0833333h; in vitro degradation at pH 5; Yield given. Yields of byproduct given;

Upstream product

• 542-05-2 acetonedicarboxylic acid 
• 108-95-2 phenol 
• 33868-91-6 3-(4-methoxyphenyl)glutaric acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 6630-90-6 ethyl 2,2'-(4-methoxybenzal)bis-acetoacetate 
• 106833-44-7 (E)-3-(4-methoxyphenyl)pent-2-enedioic acid 
• 33868-66-5 3-(4-hydroxy-phenyl)-glutaric acid diethyl ester 
• 70410-34-3 3-(4-hydroxyphenyl)pentanedioic acid 
• 857793-72-7 2-bromo-3-(4-hydroxy-phenyl)-glutaric acid diethyl ester 

Downstream Products

• 50670-02-5 cis-sphagnum acid 
• 99-96-7 4-hydroxy-benzoic acid 
• 41251-43-8 diethyl 3-(4-methoxyphenyl)-2-pentenedicarboxylate 
• 33868-91-6 3-(4-methoxyphenyl)glutaric acid 
• 4132-48-3 1-methoxy-4-(1-methylethyl)benzene 
• 4286-23-1 4-isopropenylphenol 
• 149636-52-2 p-hydroxy-3-methyl-trans-cinnamic acid 
• 99-89-8 4-Isopropylphenol 
• 66066-43-1 3-(4-methoxyphenyl)-2-pentenedioic acid 
• 70410-34-3 3-(4-hydroxyphenyl)pentanedioic acid 

Relevant academic research and scientific papers

Syntheses of bryophyte constituents. 8. Sphagnum acid and its degradation products

For Sphagnum acid (1) and its enzymatic degradation product 5-hydroxy-4-(4-hydroxyphenyl)-5H-furan-2-on (2) efficient syntheses on preparative scale were developed. For the (4-hydroxyphenyl)butenolide 2 some characteristic chemical transformations are observed in acidic and basic medium. Johann Ambrosius Barth 1996.