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Chemical Structure| 530-57-4 Chemical Structure| 530-57-4
Chemical Structure| 530-57-4

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Syringic acid, a natural product isolated and purified from the herbs of Michelia spaerantha C.Y.Wu, is an antimitogenic and chemo-sensitizing agent for human colorectal cancer, reduces oxidative stress and neuronal degeneration in treatment of cerebral ischemia and pretreatment of spinal cord ischemia/reperfusion, and exerts its chemotherapeutic and chemo-sensitizing effects through an array of mechanisms including cell-cycle arrest, apoptosis induction, inhibition of cell proliferation, cell migration, angiogenesis, NFκB DNA-binding and proteasome activities.

Synonyms: 3,5-dimethyl ether Gallic Acid; NSC 2129; 3,5-dimethoxy-4-hydroxy Benzoic Acid

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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 Syringic acid

CAS No. :530-57-4
Formula : C9H10O5
M.W : 198.17
SMILES Code : O=C(O)C1=CC(OC)=C(O)C(OC)=C1
Synonyms :
3,5-dimethyl ether Gallic Acid; NSC 2129; 3,5-dimethoxy-4-hydroxy Benzoic Acid
MDL No. :MFCD00002552
InChI Key :JMSVCTWVEWCHDZ-UHFFFAOYSA-N
Pubchem ID :10742

Safety of Syringic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Syringic 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 [ 530-57-4 ]

[ 530-57-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 530-57-4 ]
  • [ 2478-38-8 ]
  • 2
  • [ 3337-62-0 ]
  • [ 530-57-4 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; sodium; copper(I) iodide; In N-methyl-acetamide; methanol; EXAMPLE 29 3,5-Dimethoxy-4-hydroxybenzoic acid (syringic acid) <strong>[3337-62-0]3,5-Dibromo-4-hydroxybenzoic acid</strong> (60 g) was treated with sodium methoxide in methanol (prepared by dissolving 32 g sodium in 300 ml methanol), cuprous iodide (7.5 g) and dimethylformamide (300 ml) under the same conditions as described for 2,6-dibromo-4-t-butylphenol in Example 9. 34.5 g (theory 39.5 g) of a solid m.p. 210°-6° C. (literature: 204°-5° C. for the dimethoxy compound) was isolated and this was proved by NMR to be 80percent 3-bromo-4-hydroxy-5-methoxybenzoic acid, 10percent title product and 10percent starting material (50percent total replacement of Br).
  • 3
  • [ 530-57-4 ]
  • [ 6638-05-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogen; sodium sulfate;Co(II, III) tetrachlorocatechol catalyst; at 320 - 345℃; under 2311.54 Torr; for 2.25h;Sealed reactor; Example DDimethoxy Cresol Formation; The reaction equipment consisted of a 6 long.x.2 diameter steel reactor fit with a thermocouple, a one eighth inch diameter stainless steel line for hydrogen gas introduction, a one eighth inch line for product vapor removal in series with a gas vent line. The reactor was wrapped with a thick layer of fiber mat insulation to maintain a uniform temperature throughout the reaction chamber. One piece of carbon steel, each 2.x.3/4.x.0.032 plus the ground reactants, 3.013 g of syringic acid plus 0.0120 g Co(II, III) tetrachlorocatechol catalyst plus 0.356 g Na2SO4, were placed in a 30 mL glass vial that was set into the vertical reactor and the reactor top was sealed closed. Hydrogen gas was introduced into the reactor at a flow rate of 10 mL/minute to flush air from the reactor. After flushing the reactor was pressurized to 30 psig with hydrogen gas heated to 320° C. to 345° C. for a period of two hours and fifteen minutes. The reactor was flushed with a short burst of hydrogen, by sharp pressure drops followed by re-pressurization, every 5 to 10 minutes to sweep out water vapor. Once the reactor was cool it was opened and 1.334 g (53percent) crude liquid dimethoxy cresol was recovered.
With hydrogen; sodium sulfate; at 320 - 345℃; under 2311.54 Torr; for 2.25h; Example D Dimethoxy Cresol Formation [0023] The reaction equipment consisted of a 6? long×2? diameter steel reactor fit with a thermocouple, a one eighth inch diameter stainless steel line for hydrogen gas introduction, a one eighth inch line for product vapor removal in series with a gas vent line. The reactor was wrapped with a thick layer of fiber mat insulation to maintain a uniform temperature throughout the reaction chamber. One piece of carbon steel, each 2?×?×0.032? plus the ground reactants, 3.013 g of syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) plus 0.0120 g Co(II)-Co(III)-Co(II) tetrachlorocatechol activator plus 0.356 g Na2SO4 promoter, were placed in a 30 mL glass vial that was set into the vertical reactor and the reactor top was sealed closed. Hydrogen gas was introduced into the reactor at a flow rate of 10 mL/minute to flush air from the reactor. After flushing the reactor was pressurized to 30 psig with hydrogen gas heated to 320° C. to 345° C. for a period of two hours and fifteen minutes. The reactor was flushed with a short burst of hydrogen, by sharp pressure drops followed by re-pressurization, every 5 to 10 minutes to sweep out water vapor. Once the reactor was cool it was opened and 1.334 g (53percent) crude liquid dimethoxy cresol was recovered.
 

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