3843-74-1

Basic information

• Product Name: METHYL CAFFEATE
• Synonyms: METHYL CAFFEATE;METHYL 3,4-DIHYDROXYCINNAMATE;CAFFEIC ACID METHYL ESTER;3,4-DIHYDROXYCINNAMIC ACID METHYL ESTER;TIMTEC-BB SBB000325;3-(3,4-Dihydroxyphenyl)acrylic acid methyl ester;3-(3,4-Dihydroxyphenyl)propenoic acid methyl ester;Caffeic acid methyl
• CAS NO: 3843-74-1
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• Product Categories: Aromatic Esters
• Mol File: 3843-74-1.mol
• Article Data: 124

Chemical Properties

• Melting Point: 158-161°C
• Boiling Point: 368℃
• Flash Point: 80 °C
• Appearance: Slightly yellowish solid
• Density: 1.318
• Vapor Pressure: 6.38E-06mmHg at 25°C
• Refractive Index: 1.5168 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Acetonitrile (Slightly), Dimethylformamide, DMSO, Ethyl Acetate, Methanol (Sligh
• PKA: 8.71±0.18(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: METHYL CAFFEATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL CAFFEATE(3843-74-1)
• EPA Substance Registry System: METHYL CAFFEATE(3843-74-1)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 3843-74-1(Hazardous Substances Data)

Usage

Description

Caffeic acid methyl ester is an ester of a naturally occurring phenolic compound found in P. amplexicaule var. sinense and S. torvum fruits. At 40 mg/kg, it demonstrates antihyperglycemic and antidiabetic activity in diabetic rats, upregulating GLUT4 and regenerating pancreatic β-cells. At 10 mg/kg, it can induce anti-inflammatory and antinociceptive effects in rat models of edema and pain, inhibiting nitric oxide and prostaglandin E2 production, as well as tumor necrosis factor-α release.

Chemical Properties

slightly yellowish solid

Uses

Inhibitor of protein tyrosine kinase

Definition

ChEBI: An alkyl caffeate ester formed by the formal condensation of caffeic acid with methyl alcohol.

InChI:InChI=1/C10H10O4/c1-14-10(13)5-3-7-2-4-8(11)9(12)6-7/h2-6,11-12H,1H3

Upstream product

• 67-56-1 methanol 
• 7664-93-9 sulfuric acid 
• 331-39-5 caffeic acid 
• 16695-14-0 Malonic acid monomethyl ester 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 61276-17-3 Acteoside 
• 75-36-5 acetyl chloride 
• 71038-25-0 methyl (E)-3-(3,4-bis(benzyloxy)phenyl)acrylate 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 331-39-5 caffeic acid 
• 124-41-4 sodium methylate 
• 100976-84-9 ethyl 3,4-diacetoxycinnamate 
• 14534-61-3 4,5-di-O-caffeoylquinic acid 
• 2450-53-5 3,5-di-O-caffeoylquinic acid 

Downstream Products

• 3598-22-9 methyl 3-(3,4-dihydroxyphenyl)propionate 
• 1202-41-1 (E)-3-(3,4-dihydroxyphenyl)acrylamide 
• 22139-58-8 3-(3,4-dihydroxy-phenyl)-acrylic acid N'-(2-morpholin-4-yl-ethyl)-hydrazide 
• 4657-38-9 methyl 3-ethoxy-4-hydroxycinnamate 
• 40918-96-5 methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate 
• 92279-07-7 4-(2-Methoxycarbonyl-vinyl)-benzochinon-(1,2) 
• 889471-78-7 (E)-2-(benzyloxy)-4-(3-hydroxyprop-1-en-1-yl)phenol 
• 1093679-73-2 Caffeic acid-3-O-glucuronide 
• 1093679-71-0 Caffeic acid 4-O-glucuronide 
• 1206897-88-2 dimethyl 6,9,10-trihydroxybenzo[k,l]xanthene-1,2-dicarboxylate 
• 1378941-49-1 C₂₁H₂₁NO₇S 
• 3843-74-1 Methyl caffeate 
• 3843-74-1 methyl 3,4-dihydroxycinnamate 

Relevant articles and documents

CESTRIC ACID, A CAFFEIC ACID ESTER FROM CESTRUM EUANTHES

Cestric acid, a new phenolic ester was isolated from leaves of Cestrum euanthes.By means of GC, HPLC, mass spectroscopy, GC/MS, and 13C NMR, it was shown to be an ester of caffeic acid with glucaric acid.The ester occurs as an equilibrium mixture of four isomers.Key Word Index - Cestrum euanthes; Solanaceae; caffeic acid; glucaric acid; phenolic esters; isomers.

β-Lactoglobulin Peptide Fragments Conjugated with Caffeic Acid Displaying Dual Activities for Tyrosinase Inhibition and Antioxidant Effect

The regulation of tyrosinase activity and reactive oxygen species is of great importance for the prevention of dermatological disorders in the fields of medicine and cosmetics. Herein, we report a strategy based on solid-phase peptide chemistry for the sy

Mushroom Tyrosinase-Based Enzyme Inhibition Assays Are Not Suitable for Bioactivity-Guided Fractionation of Extracts

Tyrosinase (Tyr) catalyzes the rate-limiting step of melanogenesis in human skin and is thus the main target for treating pigmentation disorders today. This has led to an increased research interest in Tyr inhibitors during the last decades, with a frequent focus on polyphenols. In the early stages of drug discovery, it is typical to avoid the high costs of human Tyr by using the more economic mushroom tyrosinase (mh-Tyr). Since some polyphenols are accepted as substrates by mh-Tyr, the present study aimed to more generally investigate this enzyme's specificity toward polyphenols and to discuss its significance in the context of bioactivity-guided fractionation. Mh-Tyr substrates can change the sample color during an inhibition assay, leading to unreliable inhibition constants or to the discontinuation of a bioactivity-guided fractionation campaign. A data set of 56 natural products was investigated and classified into assay interferers (AIs) and noninterferers, using a spectrophotometric and an LC-ESIHRMS assay. Based on these experimental findings, structure-activity relationships defining AIs were deduced and implemented into an in silico tool that will allow for rapid prescreening in the future. We anticipate that these results will aid in the search for new Tyr inhibitors and contribute to the understanding of this enzyme, as well as its optimal use in pharmacological research.

Development of a clickable designer monolignol for interrogation of lignification in plant cell walls

Lignin is an abundant and essential polymer in land plants. It is a prime factor in the recalcitrance of lignocellulosic biomass to agricultural and industrial end-uses such as forage, pulp and papermaking, and biofuels. To better understand lignifi catio

PHENYLPROPANOID GLYCOSIDES OF PRUNUS SSIORI

Two new bitter phenylpropanoid glucosides, 2-(3,4-methyllenedioxyphenyl)-ethyl-(6-O-caffeoyl)-β-D-glucopyranoside and 3-O-caffeoyl-β-D-fructofuranosyl, 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside, have been isolated together with the know compounds, 6-O-caffeoyl-D-glucopyranoside and 2-(3,4-dihydroxyphenyl)-ethyl-(6-O-caffeoyl)-β-D-glucopyranoside, from the bark of Prunus ssiori.The structures of the isolated compounds have been established by extensive spectroscopic studies. - Key words: Prunus ssiori; Rosaceae; bark; phenylpropanoid glucosides; caffeic acid esters.

Electron-Transfer Reaction of Cinnamic Acids and Their Methyl Esters with the DPPH. Radical in Alcoholic Solutions

The kinetic behavior of cinnamic acids, their methyl esters, and two catechols 1-10 (ArOH) in the reaction with DPPH. in methanol and ethanol is not compatible with a reaction mechanism that involves hydrogen atom abstraction from the hydroxyl

Quinic acid derivatives from Pimpinella brachycarpa exert anti-neuroinflammatory activity in lipopolysaccharide-induced microglia

Five new quinic acid derivatives (1-5), together with 10 known quinic acid derivatives (6-15), were isolated from the MeOH extract of Pimpinella brachycarpa (Umbelliferae). Their structures were established on the basis of spectroscopic analyses including extensive 2D NMR studies (COSY, HMQC and HMBC). Isolated compounds 1-15 were evaluated for their inhibitory activities on nitric oxide (NO) production in an activated murine microglial cell line. Compounds 2, 3, 8 and 11 significantly inhibited NO production without high cell toxicity in lipopolysaccharide (LPS)-activated BV-2 cells, a microglia cell line (IC50 = 4.66, 12.52, 9.04 and 12.11 μM, respectively).

Phenyl glycosides from the leaves of Flacourtia indica (Burm. f.) Merr (Salicaceae)

Thirteen phenolic glycosides, together with fourteen various known compounds, were isolated from the methanolic extract of leaves of Flacourtia indica. Twelve of these were composed of gentisyl or salicyl alcohols, glycosylated on the phenol and acylated on the primary alcohol with various more or less oxidized forms of pyrocatechuic acid. A number of positions on the glucose or on the acid were further acylated by benzoic or cinnamic acid. In addition to these, a glucoside of a phenyl propanoid was also isolated. The gross structures were elucidated by spectroscopic means including 1D and 2D NMR experiments and HR-ESI-MS analyses. Several of these structures, for example, xylosmin, were previously described but it proved extremely difficult to conclude on their exact identity with the absence of clear data on absolute configuration in the literature.

Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents

Protozoal infections are still a global health problem, threatening the lives of millions of people around the world, mainly in impoverished tropical and sub-tropical regions. Thus, in view of the lack of efficient therapies and increasing resistances against existing drugs, this study describes the antiprotozoal potential of synthetic cinnamate ester analogues and their structure-activity relationships. In general, Leishmania donovani and Trypanosoma brucei were quite susceptible to the compounds in a structure-dependent manner. Detailed analysis revealed a key role of the substitution pattern on the aromatic ring and a marked effect of the side chain on the activity against these two parasites. The high antileishmanial potency and remarkable selectivity of the nitro-aromatic derivatives suggested them as promising candidates for further studies. On the other hand, the high in vitro potency of catechol-type compounds against T. brucei could not be extrapolated to an in vivo mouse model.