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Chemical Structure| 14755-02-3 Chemical Structure| 14755-02-3
Chemical Structure| 14755-02-3

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CAS No.: 14755-02-3

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3-Hydroxycinnamic aci is an aromatic acid that highly abundant in food. And it is a potent antioxidant widely used in food and dietary supplements.

Synonyms: (E)-m-Coumaric acid

4.5 *For Research Use Only !

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Product Details of 3-Hydroxycinnamic acid

CAS No. :14755-02-3
Formula : C9H8O3
M.W : 164.16
SMILES Code : O=C(O)/C=C/C1=CC=CC(O)=C1
Synonyms :
(E)-m-Coumaric acid
MDL No. :MFCD00004390
InChI Key :KKSDGJDHHZEWEP-SNAWJCMRSA-N
Pubchem ID :637541

Safety of 3-Hydroxycinnamic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362

Application In Synthesis of 3-Hydroxycinnamic acid

* 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.

  • Downstream synthetic route of [ 14755-02-3 ]

[ 14755-02-3 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 14755-02-3 ]
  • [ 100-39-0 ]
  • [ 122024-75-3 ]
YieldReaction ConditionsOperation in experiment
92% (￡)-3-(3-(Benzyloxy)phenyl)prop-2-enoic acid (4).3; To a stirred suspension of 3- hydroxycinnamic acid (5.00 g, 30.5 mmol) in EtOH (100 mL) was added 1 M aq. NaOH (65 mL) and the reaction mixture was stirred for 5 min, then treated with benzyl bromide (3.72 mL, 31.1 mmol) and stirred for 14 h at room temperature under N2. The mixture was concentrated under reduced pressure to yield a white solid, which was suspended in water (400 mL) and acidified with cone. aq. HC1. The mixture was filtered and the resulting solid was washed with water and Et20, then dried under high vacuum to give 4 (7.10 g, 92%>) as a white solid: IR (ATR, neat) 3400-2500 (br), 1691, 1629, 1577, 1260 cm"1; 1H NMR (DMSO- d6, 600 MHz) delta 7.49 (d, 1 H, J= 16.0 Hz), 7.46 (app d, 2 H, J= 7.4 Hz), 7.39 (t, 2 H, J= 7.6 Hz), 7.35-7.29 (m, 3 H), 7.22 (d, 1 H, J= 7.6 Hz), 7.03 (dd, 1 H, J= 8.2, 2.3 Hz), 6.56 (d, 1 H, J= 16.0 Hz), 5.14 (s, 2 H); 13C NMR (DMSO-d6, 150 MHz) delta 168.1, 158.7, 142.7, 137.0, 136.1, 130.0, 128.5, 128.0, 127.9, 121.2, 120.9, 116.8, 113.7, 69.3; HRMS (EI) m/z calcd for Ci6Hi403 254.0943, found 254.0950.
  • 2
  • [ 14755-02-3 ]
  • [ 122024-75-3 ]
  • 3
  • [ 14755-02-3 ]
  • [ 155697-42-0 ]
  • 4
  • [ 14755-02-3 ]
  • [ 1421-65-4 ]
  • methyl 3-(3,4-dihydroxyphenyl)-(2S)-2-((2E)-3-(3-hydroxyphenyl)acrylamido)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
41.6% General procedure: To a solution of the corresponding substitutedacid (1 eq, 2.02 mmol) in dichloromethane-N,N-dimethylformamide(DMF) (3 : 1, 20 mL) was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) (1 eq, 2.02 mmol),N,N-diisopropylethylamine (DIEA) (1 eq, 2.02 mmol) andN-hydroxybenzotriazole (HOBt) (1 eq, 2.02 mmol). After themixture was stirred at room temperature for 30 min, correspondingamine (1 eq, 2.02 mmol) and triethylammoniumacetate (TEA) (3 eq, 6.06 mmol) was added. The solution wasstirred at room temperature for 4 h and then extracted withdichloromethane. The organic layer was washed with 1 N HClsolution, saturated NaHCO3 solution, water and brine, driedover Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (ethylacetate-hexane, 1 : 2) to obtain the title compound.
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; General procedure: As shown in Scheme 1, the synthetic route of the analogues (1-7) involved a two-step sequence viamethyl esterification of L-amino acidand amide condensation. 100 muL SOCl2was added in portions to 4 mL methanol at -10 C,then 1 mmol L-amino acid was addedand the mixture was warmed to room temperature and stirred overnight. After thesolvent was removed, 5 mL CH3CN, 500 muL DIPEA (N,N-Diisopropyl ethylamine), 1.1 mmolcorresponding substituted acid and 1.1 mmol HBTU (O-Benzotriazole-N,N,N',N'-tetramethyl-uronium-hexafluorophosphate)was added into the residue. The mixture was stirred for 1 h at room temperatureto finish condensation. The reaction solution was added 20 mL 1 M HCl, andextracted with ethyl acetate (4 × 20 mL). The combined organic phasewas dried over anhydrous Na2SO4 and finally evaporated invacuum. The residue was purified by silica-gel chromatography using mixtures ofPE/EtOAcas eluent to afford compounds 1-7.At this stage, all compounds were fully analyzed and characterized by nuclearmagnetic resonance (NMR), high resolution massspectrum (HRMS).
  • 5
  • [ 14755-02-3 ]
  • [ 7768-28-7 ]
  • C17H16O4 [ No CAS ]
 

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