2538-87-6

Basic information

• Product Name: 3-(4-hydroxyphenyl)acrylaldehyde
• Synonyms: 3-(4-hydroxyphenyl)acrylaldehyde;p-CouMaryl aldehyde;p-Coumaroyl aldehyde
• CAS NO: 2538-87-6
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.15862
• Mol File: 2538-87-6.mol
• Article Data: 25

Chemical Properties

• Melting Point: 140℃
• Boiling Point: 309.4°C at 760 mmHg
• Flash Point: 130.9°C
• Appearance: /
• Density: 1.174g/cm³
• Vapor Pressure: 0.000352mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 9.59±0.26(Predicted)
• CAS DataBase Reference: 3-(4-hydroxyphenyl)acrylaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-hydroxyphenyl)acrylaldehyde(2538-87-6)
• EPA Substance Registry System: 3-(4-hydroxyphenyl)acrylaldehyde(2538-87-6)

Safety Data

• Hazardous Substances Data: 2538-87-6(Hazardous Substances Data)

Usage

Description

3-(4-hydroxyphenyl)acrylaldehyde, also known as p-Coumaraldehyde, is a cinnamaldehyde derivative with a hydroxy group substitution at the 4-position on the phenyl ring. It is a naturally occurring compound found in plants, particularly in cucumbers, and has gained attention for its potential health benefits and applications.

Uses

Used in Pharmaceutical Industry:
3-(4-hydroxyphenyl)acrylaldehyde is used as an antitumor agent for its potential cancer cell growth inhibition properties. It has been shown to significantly inhibit the growth of cancer cells in a dose-dependent manner, making it a promising candidate for further research and development in cancer treatment.
Used in Nutraceutical Industry:
Given its presence in cucumbers and potential health benefits, 3-(4-hydroxyphenyl)acrylaldehyde can be used as a nutraceutical ingredient. It may be incorporated into dietary supplements or functional foods to provide consumers with the health-promoting properties associated with this compound.
Used in Cosmetic Industry:
Due to its antioxidant and anti-inflammatory properties, 3-(4-hydroxyphenyl)acrylaldehyde can be used in cosmetic formulations. It may be employed as an active ingredient in skincare products to help protect the skin from oxidative stress and inflammation, promoting a healthier and more youthful appearance.

InChI:InChI=1/C9H8O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-7,11H/b2-1+

Upstream product

• 58505-83-2 4‐((E)-2-formylvinyl)phenyl acetate 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 540-38-5 p-Iodophenol 
• 59276-27-6 4-(dimethoxymethyl)phenol 
• 501-92-8 4-(prop-2-enyl)phenol 
• 61499-22-7 phenol, 4-(2-propenyl)-, acetate 
• 103909-81-5 (E)-3-(4-(tetrahydro-2H-pyran-2yloxy)phenyl)acryl aldehyde 
• 74189-56-3 4-(tetrahydropyran-2-yloxy)benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 53901-95-4 p-acetoxycinnamoyl chloride 
• 878-00-2 4-formylphenyl acetate 
• 84184-55-4 methyl trans-3-(4-methoxymethoxyphenyl)propenoate 
• 84184-56-5 (E)-3-[4-(methoxymethoxy)phenyl]prop-2-en-1-ol 

Downstream Products

• 847995-35-1 benzoic acid (E)-4-(3-oxoprop-1-enyl)phenyl ester 
• 104286-59-1 4--2-methylbut-2-en-4-olide 
• 73213-61-3 methyl boninenalate 
• 1314759-68-6 C₂₀H₂₂O₂ 
• 1314839-77-4 C₂₂H₂₇NO₃ 
• 1314839-78-5 C₂₃H₂₉NO₃ 
• 1314759-76-6 C₂₂H₂₇NO₃*ClH 
• 1314759-78-8 C₂₃H₂₉NO₃*ClH 
• 1314759-67-5 C₁₉H₂₀O₂ 
• 1612860-92-0 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,4,6-heptatrien-3-one 
• 149365-10-6 4-octyloxycinnamaldehyde 

Relevant articles and documents

Discovery of novel diphenylbutene derivative ferroptosis inhibitors as neuroprotective agents

Ferroptosis is a regulated and iron-dependent cell death. Ferroptosis inhibitors are promising for treating many neurological diseases. Herein, with phenotypic assays, we discovered a new diphenylbutene derivative ferroptosis inhibitor, DPT. Based on this hit, we synthesized fourteen new diphenylbutene derivatives, evaluated their ferroptosis inhibitory activities in HT22 mouse hippocampal neuronal cells, and found that three compounds exhibited improved inhibitory activities compared with DPT. Among these active compounds, compound 3f displayed the most potent anti-ferroptosis activity (EC50 = 1.7 μM). Further studies demonstrated that 3f is a specific ferroptosis inhibitor. And we revealed that different from the classic ferroptosis inhibitors, 3f blocked ferroptosis by increasing FSP1 protein level. Moreover, 3f can penetrate blood-brain barrier (BBB). In a rat model of ischemic stroke, 3f effectively mitigated cerebral ischemic injury. Therefore, we are confirmed that 3f, as a novel ferroptosis inhibitor with a new scaffold, is promising for further development as an agent against neurological diseases.

The catalytic machinery of the FAD-dependent AtBBE-like protein 15 for alcohol oxidation: Y193 and Y479 form a catalytic base, Q438 and R292 an alkoxide binding site

Monolignol oxidoreductases are members of the berberine bridge enzyme–like (BBE-like) protein family (pfam 08031) that oxidize monolignols to the corresponding aldehydes. They are FAD-dependent enzymes that exhibit the para-cresolmethylhydroxylase-topology, also known as vanillyl oxidase-topology. Recently, we have reported the structural and biochemical characterization of two monolignol oxidoreductases from Arabidopsis thaliana, AtBBE13 and AtBBE15. Now, we have conducted a comprehensive site directed mutagenesis study for AtBBE15, to expand our understanding of the catalytic mechanism of this enzyme class. Based on the kinetic properties of active site variants and molecular dynamics simulations, we propose a refined, structure-guided reaction mechanism for the family of monolignol oxidoreductases. Here, we propose that this reaction is facilitated stepwise by the deprotonation of the allylic alcohol and a subsequent hydride transfer from the Cα-atom of the alkoxide to the flavin. We describe an excessive hydrogen bond network that enables the catalytic mechanism of the enzyme. Within this network Tyr479 and Tyr193 act concertedly as active catalytic bases to facilitate the proton abstraction. Lys436 is indirectly involved in the deprotonation as this residue determines the position of Tyr193 via a cation-π interaction. The enzyme forms a hydrophilic cavity to accommodate the alkoxide intermediate and to stabilize the transition state from the alkoxide to the aldehyde. By means of molecular dynamics simulations, we have identified two different and distinct binding modes for the substrate in the alcohol and alkoxide state. The alcohol interacts with Tyr193 and Tyr479 while Arg292, Gln438 and Tyr193 form an alkoxide binding site to accommodate this intermediate. The pH-dependency of the activity of the active site variants revealed that the integrity of the alkoxide binding site is also crucial for the fine tuning of the pKa of Tyr193 and Tyr479. Sequence alignments showed that key residues for the mechanism are highly conserved, indicating that our proposed mechanism is not only relevant for AtBBE15 but for the majority of BBE-like proteins.

Amino acid derivative, feed composition and application thereof

The invention provides an amino acid derivative, a feed composition and application thereof, and belongs to the technical field of animal feed additives. The amino acid derivative is a compound with astructure shown as a formula (I), and a stereoisomer, a tautomer, a solvate, a metabolite, a feed acceptable salt or a prodrug thereof. In formula (I) shown in the specification, Z is a C1-C3 alkylene group. X is an indole ring group with a structure shown as a formula (II). The formula (II) is shown in the specification, wherein Y is phenyl with the structure shown in the formula (III) shown inthe specification. The amino acid derivative is used as an animal feed additive, and can promote the growth of animals and improve the feed conversion.