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CAS No. :1135-24-6 MDL No. :MFCD00004400
Formula : C10H10O4 Boiling Point : -
Linear Structure Formula :- InChI Key :KSEBMYQBYZTDHS-HWKANZROSA-N
M.W : 194.18 Pubchem ID :445858
Synonyms :
Coniferic acid;4-hydroxy-3-Methoxycinnamic Acid;Ferulic Acid, Methyl ferulate, trans-Ferulic acid, Coniferic acid, NSC 2821, NSC2821, NSC-2821;NSC 674320;NSC 51986;NSC 2821;Fumalic Acid
Chemical Name :3-(4-Hydroxy-3-methoxyphenyl)acrylic acid

Safety of [ 1135-24-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1135-24-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 1135-24-6 ]
  • Downstream synthetic route of [ 1135-24-6 ]

[ 1135-24-6 ] Synthesis Path-Upstream   1~8

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Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 1977
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Reference: [1] Chemical and Pharmaceutical Bulletin, 2011, vol. 59, # 11, p. 1425 - 1429
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  • [ 1080-12-2 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 12, p. 2594 - 2611
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YieldReaction ConditionsOperation in experiment
99% With palladium on activated charcoal; hydrogen In methanol at 50℃; for 4 h; To a stirred suspension of ferulic acid (25g, 128.74mmol) in methnol (200ml), Pd/C (3.75g) was added and the mixture was hydrogenated in 1.2 Mpa of hydrogen pressure for 4h at 50oC. After cooled to room temperature, the mixture was filtered and vacuumed to get white solid (25g, 99percent). 1H NMR (400 MHz, CDCl3) δ 6.76 (d, J = 7.8 Hz, 1H), 6.62 (m, 2H), 3.79 (s, 3H), 2.81 (t, J = 7.7 Hz, 2H), 2.58 (t, J = 7.7 Hz, 2H). ESI-MS m/z: 195.1 [M - H].
99% With palladium on activated charcoal; hydrogen In methanol at 50℃; for 4 h; Pd/C (3.75 g) was added to a stirred suspension of ferulic acid(25 g, 128.74 mmol) in methanol (200 ml), and the mixture was hydrogenated at a hydrogen pressure of 1.2 MPa for 4 h at 50 C. After cooling to room temperature, the mixture was filtered and vacuumed to obtain a white solid (25 g, 99percent). 1H NMR (400 MHz,CDCl3) d 6.76 (d, J 7.8 Hz, 1H), 6.62 (m, 2H), 3.79 (s, 3H), 2.81 (t,J 7.7 Hz, 2H), 2.58 (t, J 7.7 Hz, 2H). ESI-MS m/z: 195.1 [MH].
3.12 mmol at 37℃; for 16 h; Microbiological reaction Strains were reactivated in two subsequent growths (o/n, anaerobiosis, 37 °C) in 10 ml MRS freshly supplemented with 0.05percent cystein (MRS-Cys). MRS-Cys medium (10 ml) was supplemented with sterile filtered FA at a concentration of 3 mM and then inoculated at 2percent from the re-activated culture and grown at 37 °C under anaerobic conditions. After 16 h, the cultures were centrifuged and the supernatants filtered through a 0.22 μηη syringe filter and analyzed by Ultra-Performance Liquid Chromatography (UPLC). FA and DHFA were separated using a C18-column Acquity UPLC BEH C18 1.8 μιτι, 2.1 mm x 150 mm (Waters AG, Baden-Dattwil, Switzerland). The system consisted of an UPLC-PDA system, equipped with binary gradient pump and a Photodiode Array detector (PDA) (Waters AG, Baden-Dattwil, Switzerland). Samples were kept at 10 °C during the analysis and the chromatography was done at 40 °C. Elution was performed with a flow rate set at 0.5 ml/min and a gradient of solvent A (water) and B (acetonitrile), both acidified with 1percent acetic acid. UPLC analysis was started with 3percent of solvent B. This condition was maintained for 1.8 min and then the percentage of solvent B was linearly increased to 15percent within 5.4 min, to 21 percent within 2.7 min and finally to 90percent within 0.1 min; 90percent solvent B was maintained for 2 min, then initial conditions were reached within 0.1 min and the column equilibrated in 3percent solvent B for 3.9 min. The detection was monitored with the PDA set at 280 nm. (0037) As shown in table 1 below, other bacteria were able to completely metabolize FA, however, the maximum yield (100 percent) of DHFA production was reached only with Lactobacillus johnsonii CNCM 1-1225. Some strains were able to transform FA, but not exclusively to DHFA. It is expected (but not measured) that these strains converted at least some of the FA into other metabolites. Table 1 (0038) (0039) Lactobacillus johnsonii CNCM 1-1225 is more effective than other strains at converting ferulic acid to dihydroferulic acid, including the type strain of Lactobacillus plantarum which has previously been shown to nnetabolise ferulic acid into DHFA [Knockaert (2012)]
Reference: [1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 1, p. 81 - 86
[2] Tetrahedron Letters, 2010, vol. 51, # 44, p. 5753 - 5756
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 13, p. 4462 - 4466
[4] European Journal of Medicinal Chemistry, 2014, vol. 87, p. 429 - 439
[5] Journal of the American Chemical Society, 2017, vol. 139, # 10, p. 3767 - 3773
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[8] Pharmazie, 2010, vol. 65, # 12, p. 913 - 918
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[10] European Journal of Medicinal Chemistry, 2009, vol. 44, # 1, p. 332 - 344
[11] Chemische Berichte, 1878, vol. 11, p. 656
[12] Journal of the Indian Chemical Society, 1962, vol. 39, # 10, p. 672 - 676
[13] Phytochemistry (Elsevier), 1981, vol. 20, # 6, p. 1543 - 1546
[14] Bulletin de la Societe Chimique de France, 1994, vol. 131, p. 575 - 578
[15] Patent: EP1609360, 2005, A1, . Location in patent: Page/Page column 12
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[17] Patent: EP1640360, 2006, A1, . Location in patent: Page/Page column 58
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[19] Patent: WO2016/162227, 2016, A1, . Location in patent: Page/Page column 12-14
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YieldReaction ConditionsOperation in experiment
100% With hydrogen In tetrahydrofuran a) 3-(4-hydroxy-3-methoxyphenyl)propanoic acid [Show Image] Trans-3-methoxy-4-hydroxycinnamic acid (4 mmol; 784 mg) was dissolved in THF (25 mL) under Argon. Palladium on charcoal (0.4 mmol; 899 mg) was added then the reaction was flushed twice with hydrogen, then left to stir overnight. The reaction mixture was then filtered on celite, then rinsed with ethyl acetate (3*5mL). Concentration yielded the title compound as a light brown solid (785 mg; 4.0 mmol; quantitative yield) used without further purification in the following reactions. MS (ES) m/e 197 (M+H)+ NMR1H (CDCl3) δ (ppm) : 6.84 (d, 1H, J= 7.6 Hz); 6.72 (s, 1H); 6.71 (d, 1H, J = 8.0 Hz); 3.87 (s, 3H); 2.90 (t, 2H, J = 7.6 Hz); 2.66 (t, 2H, J = 7.6 Hz).
100% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 12 h; General procedure:
To a 10mL round-bottom flask containing 5 (2.46g, 15mmol) was added MeOH (45mL), Pd/C (10percent, 750mg).
The mixture was stirred at room temperature for 12h under H2 atmosphere.
Pd/C was filtered and washed with MeOH.
The filtrate was concentrated in vaccum to provide compound 6 as white solid (2.48mg, 99.6percent).
100% With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; A catalytic amount of 10percent Pd/C (0.43 g) was added to a solution of ferulic acid (1, 6.0 g, 30.9 mmol)in degassed EtOAc (100 mL). The reaction flask was then sealed with a rubber septum and freedof air. The reaction mixture was stirred at room temperature (RT) overnight under H2 atmosphere.Upon completion, the reaction mixture was filtered through a bed of celite, and concentrated toafford the known compound 2 [26] (6.1 g, quant.) as an off-white solid: 1H-NMR (400 MHz, CDCl3,which matches the literature [26], Figure S1) 10.50 (very br s, 1H, CO2H), 6.82 (d, J = 7.6 Hz, 1H,aromatic), 6.69 (s, 1H, aromatic), 6.68 (d, J = 7.6 Hz, 1H, aromatic), 5.60 (very br s, 1H, OH), 3.85 (s, 3H,PhOCH3), 2.87 (t, J = 7.2 Hz, 2H, PhCH2CH2CO2H), 2.64 (t, J = 7.2 Hz, 2H, PhCH2CH2CO2H).
98% With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; for 16 h; To a solution of 6(ferulic acid, 1.00 g, 5.155 mmol) in ethyl acetate (20 mL) under H2was added Pd/C (excess). The progress of the reaction was monitored by analyticTLC (10: 1 petroleum ether: Et2O). The solution was stirred for 24hat room temperature. After the completion of reaction, the suspension wasfiltered and filtrate concentrated under reduced pressure to afford pureproduct 7 (0.990 g, 98percent yield) as a colorlesssolid: mp 91-92 oC. 1H NMR (CDCl3) δ 6.86 (d, J= 8.0, 1 H), 6.72 (m, 2 H), 3.89 (s, 3 H), 2.92 (t, J = 7.6, 2 H), 2.67 (t, J =7.6, 2 H); 13 C NMR (CDCl3) 179.3, 146.4, 144.0, 132.0,120.8, 114.4, 111.0, 56.0, 36.0, 32.2; MS:for C10H12O2 calcd 196.07, found 196.0(M+)
89.16% With hydrogen In methanol; ethyl acetate for 5 h; To a solution of 3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid (2Og, 103mmol) in EtOAc (100ml) and MeOH (100ml) was added carefully 10percent Pd/C (2.Og), the reaction mixture was shaken in Parr apparatus for 5hs under 30-40 psi of hydrogen, then the solution was passed through a celite pad and the catalyst was washed with methanol, the filtrate was concentrated and dried at 5O0C under reduced pressure to give product (18g, 89.16percent). LC-MS: m/e 195 (M-I).

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[21] Patent: EP1577290, 2005, A1, . Location in patent: Page/Page column 95
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Reference: [1] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 8, p. 3356 - 3362
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Reference: [1] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 8, p. 3356 - 3362
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Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2181 - 2185
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