3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid

Base Information

• Chemical Name: 3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid
• CAS No.: 1135-24-6
• Molecular Formula: C10H10O4
• Molecular Weight: 194.187
• Hs Code.: DERIVATION
• DSSTox Substance ID: DTXSID5040673
• Wikidata: Q51617501
• Metabolomics Workbench ID: 130644
• ChEMBL ID: CHEMBL3185646
• Mol file: 1135-24-6.mol

Synonyms:(E/Z)-ferulic acid;3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid;C10H10O4;DTXSID5040673;4-Hydroxy-3-methoxy cinnammic acid;Spectrum_001256;SpecPlus_000547;Spectrum2_001394;Spectrum3_001434;Spectrum4_001897;KBioGR_002459;KBioSS_001736;DivK1c_006643;SPBio_001408;CHEMBL3185646;KBio1_001587;KBio2_001736;KBio2_004304;KBio2_006872;KBio3_002388;3-methoxy4-hydroxy cinnamic acid;4-hydroxyl-3-methoxycinnamic acid;CHEBI:193350;2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, (2Z)-;3-methoxy-4-hydroxy cinnamic acid;3-methoxy-4-hydroxy-cinnamic acid;4-hydroxy-3-methoxy-cinnamic acid;HMS3655P22;AKOS028109905;NCGC00094889-05;NCI60_002312;SY013625;LS-123655;3-(4-hydroxy-3-methoxyphenyl)-acrylic acid;FT-0601239;FT-0646300;3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid;(E/Z)-Ferulic acid 1000 microg/mL in Acetone;3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoic acid;3- (4-hydroxy-3-methoxyphenyl) -2-propenoic acid;Q51617501;1-Acetate 3,5-Bis(4-chlorobenzoate)-2-deoxy-D-erythro-pentofuranose

Chemical Property of 3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid

Chemical Property:

• Appearance/Colour: Pale Yellow Solid
• Vapor Pressure: 3.34E-06mmHg at 25°C
• Melting Point: 168-172 °C(lit.)
• Refractive Index: 1.5168 (estimate)
• Boiling Point: 372.3 °C at 760 mmHg
• PKA: 4.58±0.10(Predicted)
• Flash Point: 150.5 °C
• PSA: 66.76000
• Density: 1.316 g/cm³
• LogP: 1.49860
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: soluble
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 224

Purity/Quality:

98%, ^*data from raw suppliers

Ferulic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)O)O
• Chemical Structure and Natural Sources: Ferulic acid (4-hydroxy-3-methoxycinnamic acid) is a phenolic acid found in various plants, including Angelica sinensis, Cimicifuga heracleifolia, and Lignsticum chuangxiong. It is conjugated with mono- and oligosaccharides, polyamines, lipids, and polysaccharides in plants and is rarely found in a free state.; Common sources of ferulic acid include commelinid plants (rice, wheat, oats, and pineapple), grasses, grains, vegetables, fruits, beans, seeds of coffee, artichoke, peanut, and nuts.
• Physiological Functions and Benefits: Ferulic acid possesses various physiological functions, including antioxidant, antimicrobial, anti-inflammatory, anti-thrombosis, and anticancer activities. It protects against coronary disease, lowers cholesterol levels, and increases sperm viability.; Due to its low toxicity and numerous health benefits, ferulic acid is widely used in the pharmaceutical, food, and cosmetics industries.
• Biological Synthesis and Metabolic Pathways: Ferulic acid is formed in plants through the shikimate pathway, starting from aromatic amino acids such as l-phenylalanine and l-tyrosine. Phenylalanine and tyrosine are converted into cinnamic and p-coumaric acid, respectively, before being further hydroxylated and methylated to form ferulic acid. Ferulic acid and other aromatic compounds participate in lignin formation in plants, contributing to cell wall rigidity.
• Chemical Synthesis and Structure: Ferulic acid was first chemically synthesized and structurally confirmed in 1925. It contains an unsaturated side chain with both cis and trans isomeric forms.; The resonance-stabilized phenoxy radical in ferulic acid accounts for its effective antioxidant activity, making it capable of terminating free radical chain reactions.
• Industrial and Commercial Applications: Extraction of ferulic acid offers business opportunities for industries involved in drugs, functional foods, and nutraceuticals. Ferulic acid is used in the production of vanillin, preservatives, food gels, edible films, sports foods, and skin protection agents. Its incorporation in skin care formulations provides photoprotective effects, delays skin photoaging processes, and brightens the skin.
• General Description: Ferulic acid is a phenolic compound with a propenylbenzene structure, known for its antioxidant properties and industrial significance. It can undergo dimerization under acidic conditions to form phenylindane derivatives, where the methoxy group's position influences diastereoselectivity. Additionally, ferulic acid has been utilized in the synthesis of multifunctional anti-Alzheimer hybrids due to its ability to contribute antioxidant and anti-amyloid effects, demonstrating its potential in therapeutic applications.

Technology Process of 3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid

There total 188 articles about 3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

p-nitrophenyl ferulate → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4)

Guidance literature:

With ferulic acid esterase from malted Eleusine coracana; In dimethyl sulfoxide; at 37 ℃; for 1h; pH=7.0; Enzyme kinetics;

DOI:10.1021/jf071918d

Reference yield:

cyanidin 3-O-[2-O-(β-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-β-glucopyranosyl)-trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] → 3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + D-xylose (58-86-6) + cyanidin (13306-05-3) + D-glucose (50-99-7) + malonic acid (141-82-2) + para-coumaric acid (7400-08-0,50940-26-6)

Guidance literature:

With hydrogenchloride; water; at 100 ℃; for 2h;

DOI:10.1016/j.phytol.2013.10.004

Reference yield:

cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-β-xylopyranosyl)-6-O-(4-O-(β-glucopyranosyl)-trans-pcoumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] → 3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + D-xylose (58-86-6) + cyanidin (13306-05-3) + D-glucose (50-99-7) + malonic acid (141-82-2) + para-coumaric acid (7400-08-0,50940-26-6)

Guidance literature:

With hydrogenchloride; water; at 100 ℃; for 2h;

DOI:10.1016/j.phytol.2013.10.004

upstream raw materials:

3-(4-acetoxy-3-methoxyphenyl)prop-2-enoic acid

malonic acid

vanillin

(E,E)-3-(4-hydroxy-3-methoxyphenyl)allyl 3-(4-hydroxy-3-methoxyphenyl)acrylate

Downstream raw materials:

3,4-Dihydroxybenzoic acid

3-(4-hydroxy-3-methoxyphenyl)propionic acid

vanillin

3-methoxy-4-hydroxybenzoic acid

Refernces

Novel anti-Alzheimer phenol-lipoyl hybrids: Synthesis, physico-chemical characterization, and biological evaluation

10.1016/j.ejmech.2019.111880

This study investigates the development of 13 new phenol-lipoyl hybrids (SV1-13) as potential anti-Alzheimer agents. The researchers synthesized these hybrids by combining phenolic acids, such as caffeic and ferulic acids, with lipoic acid using various linkers. The phenolic acids and lipoic acid contribute antioxidant and anti-amyloid properties to the hybrids, which are designed to interact with multiple targets involved in Alzheimer's disease progression. The study evaluates the physico-chemical properties, stability in simulated gastrointestinal fluids and human plasma, and biological activities of these hybrids. The results show that SV5, SV9, and SV10 significantly protect SH-SY5Y cells against Aβ1-42-induced neurotoxicity, with SV9 and SV10 demonstrating remarkable antioxidant properties. However, SV5 exhibits the highest stability in human plasma and the best overall pharmacological profile, making it a promising candidate for further development as a multifunctional anti-Alzheimer agent.

Dimerization of ferulic acid and structure determination of phenylindane derivatives

10.1007/s11164-015-2232-x

The research investigates the dimerization of ferulic acid to produce phenylindane derivatives under acidic ethanol conditions. Ferulic acid, a propenylbenzene compound with industrial significance, is the primary starting material. Sulfuric acid serves as the catalyst, and ethanol acts as both a solvent and a reactant in the esterification process. The study aims to explore the reaction conditions that lead to the formation of specific dimerized products, particularly the racemic diastereomers 8a and 8c, and to elucidate their stereochemistry. The researchers found that optimal yields of the major dimer 8a (30–43%) and the minor dimer 8c (approximately 15%) were achieved with 50–60 equivalents of ethanol, 10 equivalents of sulfuric acid, and a reaction time of less than 0.5 hours at reflux temperature. The study concludes that the methoxy group's position on the phenyl ring of ferulic acid plays a crucial role in the diastereoselectivity of the dimerization process. The findings provide valuable insights into the synthesis and structural characteristics of phenylindane derivatives, which have potential applications in pharmaceuticals and other industries.

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