537-98-4

Basic information

• Product Name: trans-Ferulic acid
• Synonyms: (E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid;(e)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoicacid;(e)-ferulicacid;3-(4-Hydroxy-3-methoxyphenyl)propenoic acid;Cinnamic acid, 4-hydroxy-3-methoxy-, (E)-;Cinnamic acid, 4-hydroxy-3-methoxy-, trans-;Ferulic acid, trans-;trans-cinnamicaci
• CAS NO: 537-98-4
• Molecular Formula: C10H10O4
• Molecular Weight: 194.18
• EINECS: 208-679-7
• Product Categories: Cinnamic acid;Antioxidant;Biochemistry
• Mol File: 537-98-4.mol
• Article Data: 186

Chemical Properties

• Melting Point: 168-172 °C(lit.)
• Boiling Point: 250.62°C (rough estimate)
• Flash Point: 150℃
• Appearance: slightly yellow/powder
• Density: 1.316(20.0000℃)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.5030 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.58±0.10(Predicted)
• Water Solubility: Soluble in alcohol and hot water.
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,4062
• BRN: 1371483
• CAS DataBase Reference: trans-Ferulic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-Ferulic acid(537-98-4)
• EPA Substance Registry System: trans-Ferulic acid(537-98-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: UD3365500
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 537-98-4(Hazardous Substances Data)

Usage

Description

Trans-Ferulic acid, also known as 4-hydroxy-3-methoxycinnamic acid, is a naturally occurring organic compound found in various plants and is known for its antioxidant and anti-inflammatory properties. It is a solid substance with a molecular formula of C10H10O4 and is characterized by its ability to scavenge free radicals and inhibit the formation of reactive oxygen species.

Uses

Used in Pharmaceutical Applications:
Trans-Ferulic acid is used as an active pharmaceutical ingredient for its antioxidant and anti-inflammatory properties. It is particularly effective in the treatment of various inflammatory conditions and has been shown to have neuroprotective effects.
Used in Food and Beverage Industry:
Trans-Ferulic acid is used as a natural antioxidant in the food and beverage industry to extend the shelf life of products and maintain their quality. It is also used as a flavor enhancer and color stabilizer due to its ability to prevent oxidation and rancidity.
Used in Cosmetics:
Trans-Ferulic acid is used as an ingredient in the cosmetics industry for its antioxidant and anti-aging properties. It is commonly found in skincare products, where it helps to protect the skin from environmental damage and promotes a youthful appearance.
Used in Analytical Applications:
Trans-Ferulic acid is used as a secondary standard in several analytical applications, including pharmaceutical release testing, method development for qualitative and quantitative analyses, and food and beverage quality control testing. It is also used for calibration requirements in various industries.
Used in Synthesis of Biocompatible Antioxidant Polymers:
Trans-Ferulic acid is used in the synthesis of new biocompatible antioxidant polymers, which have potential applications in the medical field. These polymers can be used for drug delivery systems, tissue engineering, and other biomedical applications.
Used in Esterification of Methacrylated Dextran:
Trans-Ferulic acid is used for the esterification of methacrylated dextran, a process that can improve the properties of the resulting polymer and enhance its potential applications in various industries.
Used in Ethanol-Induced Liver Injury Studies:
Trans-Ferulic acid has been used to study the effects of oral administration on ethanol-induced liver injury in C57BL mice. This research can provide valuable insights into the potential therapeutic applications of trans-ferulic acid in the treatment of liver diseases.

Biochem/physiol Actions

Hydroxycinnamic acid found in plant-based foods. Antioxidant.

InChI:InChI=1/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+

Upstream product

• 107668-85-9 helonioside D 
• 34749-55-8 3-(4-acetoxy-3-methoxyphenyl)prop-2-enoic acid 
• 121-33-5 vanillin 
• 97-53-0 4-allylguaiacol 
• 28028-62-8 ethyl ferulate 
• 458-37-7 curcumin 
• 86321-29-1 3-methyl-4-sulfocaffeic acid 
• 2596-47-6 (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid 
• 84976-26-1 O-<5-O-(trans-feruloyl)-α-L-arabinofuranosyl>-(1<*>3)-O-β-D-xylopyranosyl-(1<*>4)-D-xylopyranose 
• 331-39-5 caffeic acid 
• 14031-35-7 S-Adenosyl-L-methionine 
• 117405-51-3 4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside 
• 1014-83-1 cis-ferulic acid 
• 7786-61-0 3-methoxy-4-hydroxystyrene 

Downstream Products

• 1014-83-1 cis-ferulic acid 
• 63358-16-7 3,6-bis-(4-hydroxy-3-methoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1,4-dione 
• 42381-62-4 ethyl (E)-2-(3-(4-hydroxy-3-methoxyphenyl)acrylamido)acetate 
• 77550-11-9 4-cis,8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octane-2,6-dione 
• 72553-14-1 (E)-3-[(1R,2S,7S,8R)-9-((E)-2-Carboxy-vinyl)-6,6,12,12-tetramethoxy-5,11-dioxo-tricyclo[6.2.2.0^2,7]dodeca-3,9-dien-2-yl]-acrylic acid 
• 86341-46-0 acetate of 1-bornyl ferulate 
• 909104-79-6 2-butyl ferulate 
• 109648-34-2 8,8'-diferulic acid 
• 56254-02-5 -3 thiopropene-2 oate de S-phenyle 
• 1318075-54-5 C₃₈H₄₂N₂O₈ 

Relevant articles and documents

Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites

The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had

First total syntheses of four natural bioactive glucosides

The efficient total syntheses of four biologically interesting natural glucosides Ethylconiferin, Butylconiferin, 2’-Butoxyethylconiferin and Balajaponin B, have been achieved for the first time starting from commercially available Vanilline via concise reaction sequence of 8–10 steps with the overall yield of 26–41%. This work definitely laid the foundation for the further pharmacological study of this kind of natural compounds. Meanwhile, currently developed approach could be used as a general synthetic strategy for the syntheses of other monolignol glucosides and their derivatives, and provides an opportunity for further study of the structure-activity relationship of this kind of glucosides.

A Series of Ferulic Acid Amides Reveals Unexpected Peroxiredoxin 1 Inhibitory Activity with in vivo Antidiabetic and Hypolipidemic Effects

Insulin resistance is a major pathophysiological feature in the development of type 2 diabetes (T2DM). Ferulic acid is known for attenuating the insulin resistance and reducing the blood glucose in T2DM rats. In this work, we designed and synthesized a library of new ferulic acid amides (FAA), which could be considered as ring opening derivatives of the antidiabetic PPARγ agonists Thiazolidinediones (TZDs). However, since these compounds displayed weak PPAR transactivation capacity, we employed a proteomics approach to unravel their molecular target(s) and identified the peroxiredoxin 1 (PRDX1) as a direct binding target of FAAs. Interestingly, PRDX1, a protein with antioxidant and chaperone activity, has been implied in the development of T2DM by inducing hepatic insulin resistance. SPR, mass spectrometry-based studies, docking experiments and in vitro inhibition assay confirmed that compounds VIe and VIf bound PRDX1 and induced a dose-dependent inhibition. Furthermore, VIe and VIf significantly improved hyperglycemia and hyperlipidemia in streptozotocin-nicotinamide (STZ-NA)-induced diabetic rats as confirmed by histopathological examinations. These results provide guidance for developing the current FAAs as new potential antidiabetic agents.