19367-38-5

Basic information

• Product Name: Methyl 4-hydroxycinnamate
• Synonyms: TIMTEC-BB SBB002393;METHYL 4-HYDROXYCINNAMATE;METHYL 4-COUMARATE;METHYL COUMARATE;METHYL P-HYDROXYCINNAMATE;METHYL 3-(4-HYDROXYPHENYL)ACRYLATE;METHYL 3-HYDROXYCINNAMATE;Methyl 4-hydroxyphenylacrylate
• CAS NO: 19367-38-5
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.18
• Product Categories: Aromatic Esters;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 19367-38-5.mol
• Article Data: 56

Chemical Properties

• Melting Point: 138-140°C
• Boiling Point: 306.6 °C at 760 mmHg
• Flash Point: 132.8 °C
• Appearance: Off-white to pale orange solid
• Density: 1.197 g/cm³
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.82±0.13(Predicted)
• CAS DataBase Reference: Methyl 4-hydroxycinnamate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-hydroxycinnamate(19367-38-5)
• EPA Substance Registry System: Methyl 4-hydroxycinnamate(19367-38-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 19367-38-5(Hazardous Substances Data)

Usage

Description

Methyl 4-hydroxycinnamate is a derivative of cinnamic acid, characterized by its off-white to pale orange solid appearance. It is known for its antifungal properties and is utilized in various applications due to its ability to inhibit the growth of certain fungi.

Uses

Used in Pharmaceutical Industry:
Methyl 4-hydroxycinnamate is used as an antifungal agent for its effectiveness against various strains of Aspergillus, including Aspergillus flavus, Aspergillus terreus, and Aspergillus niger. It plays a crucial role in the structure-antifungal activity relationship study, aiding in the development of new antifungal drugs and treatments.
Used in Agricultural Industry:
In the agricultural sector, Methyl 4-hydroxycinnamate is employed as a protective agent against fungal infections that can damage crops and reduce their yield. Its antifungal properties help in controlling the growth of harmful fungi, ensuring better crop health and increased productivity.
Used in Cosmetics Industry:
Methyl 4-hydroxycinnamate is also utilized in the cosmetics industry as a preservative due to its antifungal and antimicrobial properties. It helps in extending the shelf life of cosmetic products by preventing the growth of fungi and bacteria that can cause spoilage and degradation of the product.
Used in Food Industry:
In the food industry, Methyl 4-hydroxycinnamate serves as an additive to enhance the shelf life and quality of perishable items. Its antifungal properties help in preventing the growth of mold and other fungi that can spoil food products, ensuring their freshness and safety for consumption.
Overall, Methyl 4-hydroxycinnamate is a versatile compound with a wide range of applications across different industries, primarily due to its antifungal properties and ability to enhance the quality, safety, and shelf life of various products.

Upstream product

• 110-16-7 maleic acid 
• 77-78-1 dimethyl sulfate 
• 108-95-2 phenol 
• 67-56-1 methanol 
• 35047-20-2 2-diazo-3-(4-hydroxyphenyl)propanoic acid methyl ester 
• 71-23-8 propan-1-ol 
• 75-89-8 2,2,2-trifluoroethanol 
• 55226-78-3 methyl 4-acetoxycinnamate 
• 67-63-0 isopropyl alcohol 
• 540-38-5 p-Iodophenol 
• 292638-85-8 acrylic acid methyl ester 
• 123-08-0 4-hydroxy-benzaldehyde 
• 106-41-2 4-bromo-phenol 
• 7400-08-0 para-coumaric acid 

Downstream Products

• 6049-54-3 3-amino-3-(4-hydroxyphenyl)propionic acid 
• 59576-98-6 (E)-p-coumaric amide 
• 70193-44-1 (E)-3-{4-[3-(4-Chloro-phenoxy)-2-oxo-propoxy]-phenyl}-acrylic acid methyl ester 
• 60377-05-1 3-<4'-(2-Methoxycarbonylvinyl)-phenoxy>-1-(4'-chlorphenoxy)-propanol-(2) 
• 60377-35-7 3-<4'-(2-Methoxycarbonylvinyl)-phenoxy>-1-(4'-chlorphenylmercapto)-propanol-(2) 
• 60377-23-3 (E) Methyl-4-(3-(4-Chloroanilino)-2-Hydroxypropoxy)-Benzoate 
• 60377-25-5 (Z)-3-{4-[3-(4-Chloro-phenylamino)-2-hydroxy-propoxy]-phenyl}-acrylic acid methyl ester 
• 66498-17-7 (E)-3-(4-{2-[4-(2,4-Dichloro-phenoxy)-phenoxy]-propionyloxy}-phenyl)-acrylic acid methyl ester 
• 3843-74-1 methyl 3,4-dihydroxycinnamate 
• 866417-47-2 methyl {4'-[3''-(methyl prop-2''(E)-enoate)]phenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate 
• 7400-08-0 para-coumaric acid 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 81609-53-2 methyl 4-octyloxy-cinnamate 
• 126148-70-7 methyl 4-decyloxy-cinnamate 

Relevant articles and documents

Nitrification inhibitors from the root tissues of Brachiaria humidicola, a tropical grass

Nitrification inhibitory activity was found in root tissue extracts of Brachiaria humidicola, a tropical pasture grass. Two active inhibitory compounds were isolated by activity-guided fractionation, using recombinant Nitrosomonas europaea containing luxAB genes derived from the bioluminescent marine gram-negative bacterium Vibrio harveyi. The compounds were identified as methyl-p-coumarate and methyl ferulate, respectively. Their nitrification inhibitory properties were confirmed in chemically synthesized preparations of each. The IC50 values of chemically synthesized preparations were 19.5 and 4.4 μM, respectively. The ethyl, propyl, and butyl esters of p-coumaric and ferulic acids inhibited nitrification, whereas the free acid forms did not show inhibitory activity.

Renewable benzoxazine monomers from Lignin-like naturally occurring phenolic derivatives

The benzoxazines of three naturally occurring phenylpropanoid phenols: ferulic, coumaric, and phloretic acids, and their esters are described. Benzoxazines with conjugated unsaturated chains exhibit unusual poor thermal stability and degrade partially at the polymerization temperature making necessary the use of a catalyst (BF3.Et2O) to low the polymerization temperature and prevent degradation. Polybenzoxazines are prepared thermally and characterized by DSC and TGA techniques. The resulting materials have superior Tgs when compared with those prepared from an unsubstituted monofuctional benzoxazine due to the additional crosslinking through the ester and carboxylic moieties.

Induction of phenolic compounds in two cultivars of cucumber by treatment of healthy and powdery mildew-infected plants with extracts of Reynoutria sachalinensis

Accumulation of phenolic compounds (p-coumaric, caffeic, and ferulic acids and p-coumaric acid methyl ester) was followed in susceptible (Mustang) and tolerant (Flamingo) cucumber (Cucumis sativus) cultivars. The objective was to determine whether these compounds played a role in resistance against powdery mildew following a prophylactic treatment with Milsana (leaf extracts from the giant knot weed Reynoutria sachalinensis, polygonaceae). This treatment significantly reduced the incidence of powdery mildew in both cultivars. Phenolic compounds were extracted from leaves. In the hydrolyzed fraction containing phenolic aglycones, levels of p-coumaric, caffeic, and ferulic acids and of p-coumaric acid methyl ester increased in all treatments (with leaf extracts of R. Sachalinensis, powdery mildew, or both) except the control, one or two days after treatment. In the fraction containing free phenolics, from the tested compounds, only ferulic acid showed an increase in cv. Flamingo (tolerant), and was particularly evident following treatments. On the other hand, the amounts of hydroxycinnamic acids increased rapidly in the two cultivars following Milsana treatment, suggesting their role in disease reduction. All compounds showed antifungal activity when tested against common pathogens of cucumber (Botrytis cinerea, Pythium ultimum, and P. aphanidermatum), but in general methyl esters were more fungitoxic than their corresponding free acids. This study suggests that cucumber is able to release antifungal compounds that are instrumental in repressing powdery mildew infection. This response is seemingly independent from the level of genetic resistance associated with each cultivar.

Synthesis and Evaluation of PPARδAgonists That Promote Osteogenesis in a Human Mesenchymal Stem Cell Culture and in a Mouse Model of Human Osteoporosis

We synthesized a directed library of compounds to explore the structure-activity relationships of peroxisome proliferator-activated receptor δ(PPARδ) activation relative to mesenchymal stem cell (MSC) osteogenesis. Our scaffold used para-substituted cinnamic acids as a polar headgroup, a heteroatom and heterocycle core connecting units, and substituted phenyl groups for the lipophilic tail. Compounds were screened for their ability to increase osteogenesis in MSCs, and the most promising were examined for subunit specificity using a quantitative PPAR transactivation assay. Six compounds were selected for in vivo studies in an ovariectomized mouse model of human postmenopausal osteoporosis. Four compounds improved bone density in vivo, with two (12d and 31a) having activity comparable to that of GW0742, a well-studied PPARδ-selective agonist. 31a (2-methyl-4-[N-methyl-N-[5-methylene-4-methyl-2-[4-(trifluoromethyl)phenyl]thiazole]]aminocinnamic acid) had the highest selectivity for PPARδcompared to other subtypes, its selectivity far exceeding that of GW0742. Our results confirm that PPARδis a new drug target for possible treatment of osteoporosis via in situ manipulation of MSCs.

BIVALENT LECA INHIBITORS TARGETING BIOFILM FORMATION OF PSEUDOMONAS AERUGINOSA

The present invention relates to divalent compounds binding to LecA. The compounds are useful to block biofilm formation of Pseudomonas aeruginosa. The invention further relates to pharmaceutical compositions comprising these compounds and to therapeutic methods and uses of these compounds, in particular to therapeutic methods and uses for the treatment of Pseudomonas aeruginosa infections in a subject. The invention also relates to imaging of infections, such as biofilms produced by Pseudomonas aeruginosa, by using these divalent compounds.

Preparation method of esmolol hydrochloride intermediate

The invention belongs to the field of organic synthesis of medicines, and particularly relates to a preparation method of a medicine esmolol hydrochloride intermediate for treating hypertension. The synthesis route provided by the invention comprises the following steps: reacting p-bromophenol with methyl acrylate in the presence of a palladium catalyst and a phosphine ligand to generate 3-(4-hydroxyphenyl) methyl acrylate; and hydrogenating the generated 3-(4-hydroxyphenyl) methyl acrylate in the presence of a palladium-carbon catalyst to obtain a target product methyl 4-hydroxyphenylpropionate. The method has the advantages of short reaction steps, cheap and accessible raw materials, simple technique and convenience of operation, and does not need special reaction conditions, thereby being more suitable for industrial production.