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:

99% ^*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.

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:

Methyl ferulate

propyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-prop-2-enoate

3,4-Dihydroxybenzoic acid

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

Refernces

• 1、 Li,Zang,Feng,Li,Li. "Synthesis of cinnamic acids catalyzed by expansive graphite under ultrasound". . p. 653 - 656. Retrieved 2001.
• 2、 Chien, Nguyen Quyet,Van Hung, Nguyen,Santarsiero, Bernard D.,Mesecar, Andrew D.,Cuong, Nguyen Manh,Soejarto, D. Doel,Pezzuto, John M.,Fong, Harry H. S.,Tan, Ghee T.. "New 3-O-acyl betulinic acids from Strychnos vanprukii Craib". . p. 994 - 998. Retrieved 2004.
• 3、 Singh, Archana,Mukhopadhyay, Kunal,Ghosh Sachan, Shashwati. "Biotransformation of eugenol to vanillin by a novel strain Bacillus safensis SMS1003". . p. 291 - 303. Retrieved 2019.
• 4、 Zuchowski, Jerzy,Pecio, Lukasz,Stochmal, Anna. "Novel flavonol glycosides from the aerial parts of lentil (Lens culinaris)". . p. 18152 - 18178. Retrieved 2014.
• 5、 Lee, Il Kyun,Jeong, Eun-Kyung,Choi, Sang Un,Hong, Jongki,Lee, Kang Ro. "New flavonol glycosides from Cardamine komarovii". . p. 2615 - 2625. Retrieved 2011.
• 6、 Vance, Carroll P.,Bryan, Jeffrey W.. "PURIFICATION AND PROPERTIES OF CAFFEIC ACID O-METHYLTRANSFERASE FROM ALFALFA ROOT NODULES". . p. 41 - 44. Retrieved 1981.
• 7、 Luo, Qiu-Yan,Li, Wei-Lin,Wu, Li-Qiang. "Acylated flavonol glycosides from Sedum aizoon". . p. 23 - 25. Retrieved 2012.
• 8、 Chung, Mei-Ing,Lai, Mei-Hsun,Yen, Ming-Hong,Wu, Ru-Rong,Lin, Chun-Nan. "Phenolics from Hypericum geminiflorum". . p. 943 - 947. Retrieved 1997.
• 9、 Leont'eva et al.. "". . . Retrieved 1976.
• 10、 Zhang, Lin,Xu, Zhi-Lin,Wu, Chun-Fu,Yang, Jing-Yu,Kano, Yoshihiro,Yuan, Dan. "Two new flavonoid glycosides from Semen Ziziphi Spinosae". . p. 121 - 128. Retrieved 2012.