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Chemical Structure| 621-82-9 Chemical Structure| 621-82-9
Chemical Structure| 621-82-9

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Cinnamic acid can stimulate insulin secretion and improve glucose tolerance.

Synonyms: 3-Phenylacrylic acid; β-Phenylacrylic acid

4.5 *For Research Use Only !

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Product Citations

Product Citations

Scott, Jared Lee ;

Abstract: Breast cancer (BC) is the second greatest contributor to the death of women, second only to heart disease, and is the most common type of cancer. BC treatments involve the administration of adjuvant chemotherapies which often have side effects that prevent patients from completing the full course of drugs or the refusal to take these potentially lifesaving treatments. Many chemotherapy drugs are developed from plants, and some plant extracts can exhibit significant anticancer activities while also having less toxic side effects. However, these potential "plant therapeutics" suffer from poor oral bioavailability. The Apiaceae plant family consists of several species that are used as culinarily spices including anise, celery, cumin, and coriander, all of which have demonstrated antioxidant, chemopreventive, and anticancer activities. One method to improve the systemic distribution of anticancer phytochemicals is their encapsulation in naturally produced membrane bound nanoparticles known as exosomes. Exosomes are produced by most eukaryotic organisms, as well as some prokaryotes, and are involved in cell-to-cell communication through the delivery of proteins, nucleic acids, and small molecules from one cell to another. Exosomes are found in many extracellular fluids including blood, urine, and milk. Bovine milk exosomes represent a scalable source of exosomes that are already present in the human diet and have been explored as a drug delivery system that can increase effectiveness and improve bioavailability. To enhance the loading potential and anticancer bioactivity of Apiaceae phytochemicals, an acid hydrolysis (AH) of the glycoside compounds present in ethanolic spice extracts was performed on eight ethanolic spice extracts. The antiproliferative effects of AH extracts and exosomal formulations were assayed with three model types of BC cells. Cumin was characterized in greater detail as these extracts had the highest concentration of terpenoids and alkaloids while also having significant concentrations of phenolics and responded well to AH with increased antiproliferative activity and exosomal loading. Extracts and exosomal formulations exhibited broad antiproliferative effects with lower IC50s in the extracts delivered with exosomes. The phytochemical contents of AH-cumin extracts and exosomal formulations were assayed with HPLC-DAD, LC-MS/MS, and GC-MS, while the potential anticancer mechanisms of these treatments were investigated in triple negative BC (TNBC). AHcumin extracts were determined to have numerous phenolic compounds, many of which have known anticancer mechanisms, in addition to several alkaloids and lipid compounds, some of which have activities that could contribute to the anticancer effects observed. Mechanistically, AH-cumin extracts and exosomal formulations were shown to interact with multidrug resistance proteins and inhibit lipid metabolism in TNBC cells. These results indicate that acid hydrolyzed cumin extracts delivered through exosome nanoparticles represent a possible avenue towards the development of novel treatments for TNBC, the hardest type of BC to treat.

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Product Details of Cinnamic acid

CAS No. :621-82-9
Formula : C9H8O2
M.W : 148.16
SMILES Code : O=C(O)/C=C/C1=CC=CC=C1
Synonyms :
3-Phenylacrylic acid; β-Phenylacrylic acid
MDL No. :MFCD00004369

Safety of Cinnamic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Cinnamic 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 [ 621-82-9 ]

[ 621-82-9 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 2298-36-4 ]
  • [ 621-82-9 ]
  • {4-[(E)-(3-Phenyl-acryloyl)amino]-phenoxy}-acetic acid [ No CAS ]
  • 3
  • [ 621-82-9 ]
  • [ 54925-64-3 ]
  • [ 345647-22-5 ]
  • 4
  • [ 621-82-9 ]
  • [ 480-39-7 ]
  • 5
  • [ 14019-62-6 ]
  • [ 621-82-9 ]
  • [ 294177-65-4 ]
  • 6
  • [ 2026-70-2 ]
  • [ 621-82-9 ]
  • N-methyl-N-(3-(trifluoromethyl)phenyl)cinnamamide [ No CAS ]
  • 8
  • [ 3321-92-4 ]
  • [ 621-82-9 ]
  • C17H12Cl2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; trichlorophosphate; at 20℃;Cooling with ice; General procedure: Phosphoryl chloride (POCl3; 20 mmol) was added slowly to a 100 mL SNRB flask containing a mixture of I (5.5 mmol) and the appropriate 2'-hydroxyacetophenone (5 mmol) in pyridine (30 mL). The flask was placed in an ice bath and the reaction mixture was left overnight, with constant stirring at room temperature. The reaction mixture was then poured into 100 mL cold, dilute HCl in a 250 mL EF, followed by extraction with ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product obtained was further purified by open column chromatography.
  • 9
  • [ 2026-70-2 ]
  • [ 621-82-9 ]
  • [ 1439401-79-2 ]
  • [ 1439401-80-5 ]
  • 10
  • [ 14752-66-0 ]
  • [ 621-82-9 ]
  • [ 36603-45-9 ]
YieldReaction ConditionsOperation in experiment
79% With dipotassium peroxodisulfate; oxygen; In N,N-dimethyl-formamide; at 100℃; for 12h; General procedure: A mixture of cinnamic acid 1 (1.0 mmol), K2S2O8 (1.5 mmol) and sodium sulfinate 2 (1.5 mmol) in DMF (5 mL) was stirred at 100 oC under ambient air for 12 h. Upon completion of the reaction (monitored by TLC), the mixture was extracted with EtOAc (3 x 15 mL). The combined organic phase was dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (EtOAc/n-hexane, 1:4) to afford an analytically pure sample of β-keto sulfones 3.
 

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