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[ CAS No. 121-34-6 ] {[proInfo.proName]}

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Chemical Structure| 121-34-6
Chemical Structure| 121-34-6
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Product Citations

Product Citations

Scott, Jared Lee ; DOI:

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 [ 121-34-6 ]

CAS No. :121-34-6 MDL No. :MFCD00002551
Formula : C8H8O4 Boiling Point : -
Linear Structure Formula :C6H3(OH)(COOH)OCH3 InChI Key :WKOLLVMJNQIZCI-UHFFFAOYSA-N
M.W : 168.15 Pubchem ID :8468
Synonyms :
4-hydroxy-3-methoxybenzoic acid
Chemical Name :4-Hydroxy-3-methoxybenzoic acid

Calculated chemistry of [ 121-34-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.92
TPSA : 66.76 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.4
Log Po/w (XLOGP3) : 1.43
Log Po/w (WLOGP) : 1.1
Log Po/w (MLOGP) : 0.74
Log Po/w (SILICOS-IT) : 0.73
Consensus Log Po/w : 1.08

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.02
Solubility : 1.6 mg/ml ; 0.00952 mol/l
Class : Soluble
Log S (Ali) : -2.44
Solubility : 0.615 mg/ml ; 0.00366 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.32
Solubility : 8.1 mg/ml ; 0.0482 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 121-34-6 ]

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 [ 121-34-6 ]

* 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.

  • Downstream synthetic route of [ 121-34-6 ]

[ 121-34-6 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 64-17-5 ]
  • [ 121-34-6 ]
  • [ 617-05-0 ]
YieldReaction ConditionsOperation in experiment
98% With sulfuric acid; for 48h;Inert atmosphere; Reflux; Synthesis of ethyl 4-hydroxy-3-methoxybenzoate: In a round bottomed flask equipped with a nitrogen inlet and a magnetic stir bar, a solution of vanillic acid (10 g, 59.49 mmol) in EtOH (400 mL) was added. To the above solution 600 mg (6.11 mmol) of cone. H2SO4 was added. The mixture was then stirred at reflux temperature for 48 h. The solution was rotary evaporated. Water (100 mL) was then added to the residue and the separated greenish oil was then removed by using separately funnel. Product was then dried in vacuo to obtain 11.45 g (98 %) of ethyl 4-hydroxy-3-methoxybenzoate. 1H NMR (400 MHz, Chloroform-d) delta 7.62 (dd, J= 8.5, 2.1 Hz, 1H), 7.53 (d, J= 1.8 Hz, 1H), 6.91 (d, J= 8.6 Hz, 1H), 4.33 (q, J= 7.1 Hz, 2H), 3.91 (s, 3H), 1.36 (t, J= 7.3 Hz, 3H). HPLC-MS: Expected: 197 (MH+); Found: 197.
98% With sulfuric acid; for 48h;Reflux; Inert atmosphere; In a round bottomed flask equipped with a nitrogen inlet and a magnetic stir bar, a solution of 4-hydroxy-3- methoxybenzoic acid (10 g, 59.49 mmol) in EtOH (400 mL) was added. To the above solution 600 mg (6.11 mmol) of cone. H2SO4 was added. The mixture was then stirred at reflux temperature for 48 h. The solution was rotary evaporated. Water (100 mL) was then added to the residue and a greenish oily compound separates out. The greenish oil was then separated and then dried in vacuo to 11.45 g (98 %) of ethyl 4-hydroxy-3- methoxybenzoate. (0284) 1H NMR (400 MHz, Chloroform-d) delta 7.62 (dd, J = 8.5, 2.1 Hz, 1H), 7.53 (d, J = 1.8 Hz, 1H), 6.91 (d, J = 8.6 Hz, 1H), 4.33 (q, J = 7.1 Hz, 2H), 3.91 (s, 3H), 1.36 (t, J = 7.3 Hz, 3H). HPLC-MS: Expected: 197 (MH+); Found: 197
With sulfuric acid; for 10h;Reflux; 4-Hydroxy-3-methoxybenzoic acid (20 g, 119 mmol) in ethanol (50 mL) was treated with concentrated sulfuric acid (3 mL) under reflux for 10 h. The solvent was evaporated until no longer liquid outflow. Water (20 mL) was added, extracting by adding respectively 30 mL ethyl acetate. After washing the organic phase with saturated NaCl solution (40 mL), drying it with anhydrous Na2SO4 and evaporating the solvent under reduced pressure. Crude product were purified by column chromatography, product 2 appeared.
With hydrogenchloride; at 60℃; for 14h; [0573j To a solution of 4-hydroxy-3-methoxybenzoic acid (6-A) (5 g, 29.7 mmol) in EtOH (20 mL) was added HC1. The mixture was stirred for 60C for 14 h. The reaction was concentrated to afford crude ethyl 4-hydroxy-3-methoxybenzoate (6-B) (4.6 g, 79% yield).
With sulfuric acid; In water; for 6h;Reflux; General procedure: Hydrazides (30-58) were synthesized by one pot conventionalmethod24 Benzoic acid or its derivative (10 mmol) was dissolvedin ethanol (20 mL). Sulfuric acid (3 N, 2 mL) was added and thereaction contents were refluxed for six hours. The reaction wasmonitored with TLC. After the completion of the reaction, the reactionmixture was neutralized by adding solid NaHCO3, and filteredto remove excess of NaHCO3. In the neutralized reaction mixture which contains ethyl ester, hydrazine monohydrate (1.5 mL,3 mmol) was added and refluxed for 3-6 h to complete the reaction.Ethanol and unreacted hydrazine were removed by distillationupto 1/3 volume. The reaction contents were cooled, filteredand recrystallized from methanol to obtain the desired hydrazidecrystals (see Supporting information).

  • 2
  • [ 121-34-6 ]
  • [ 75-03-6 ]
  • [ 617-05-0 ]
  • 3
  • [ 121-34-6 ]
  • [ 78-39-7 ]
  • [ 617-05-0 ]
  • 4
  • [ 121-34-6 ]
  • [ 617-05-0 ]
YieldReaction ConditionsOperation in experiment
A. Esterification of 3-methoxy-4-hydroxybenzoic Acid to Yield ethyl-3-methoxy-4-hydroxybenzoate.
(i) Estenrfication of 3-methoxy-4-hydroxybenzoic acid to Yield ethyl-3-methoxy-4-hydroxybenzoate.
(i) Esterification of 3-methoxy-4-hydroxybenzoic acid to yield ethyl-3-methoxy-4-hydroxybenzoate.
A. Esterification of 3-methoxy-4-hydroxybenzoic acid to yield ethyl-3-methoxy-4-hydroxybenzoate.
A. Esterification of 3-methoxy-4-hydroxybenzoic Acid to Yield Ethyl-3-methoxy-4-hydroxybenzoate.
A. Esterification of 3-methoxy-4-hydroxybenzoic Acid to Yield ethyl-3-methoxy-4-hydroxybenzoate.
With sulfuric acid; In ethanol; dichloromethane; A. Esterification of 3-methoxy-4-hydroxybenzoic acid to yield ethyl-3-methoxy-4-hydroxybenzoate A solution of 100 g of 3-methoxy-4-hydroxybenzoic acid and 17 g of concentrated sulfuric acid in 300 mL of absolute ethanol was heated at reflux overnight. The mixture was concentrated and the residue poured into water. Methylene chloride was added and the solution washed successively with water, dilute sodium bicarbonate and water, then dried and concentrated. Yield: 118 g
A. Esterification of 3-methoxy-4-hydroxybenzoic acid to yield ethyl-3-methoxy-4-hydroxybenzoate.

  • 5
  • [ 121-34-6 ]
  • ethyl 4-hydroxy-3-methoxybenzoate (ethyl vanillate) [ No CAS ]
  • [ 617-05-0 ]
YieldReaction ConditionsOperation in experiment
80% With sulfuric acid; sodium hydrogencarbonate; mercury; In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; EXAMPLE 2 Preparation of ethyl 4-hydroxy-3-methoxybenzoate (ethyl vanillate) 50 g of vanillic acid and 250 ml of methanol were introduced into a reactor. 40 ml of sulfuric acid was introduced dropwise using a dropping funnel; cooling was carried out if the alcohol boiled. The mixture was refluxed for 2 hours with stirring. The mixture was cooled to room temperature, poured into 100 ml of ice water, and the alcohol was evaporated off under reduced pressure. The aqueous phase was extracted three times with ethyl ether. The combined organic phases were washed with a saturated solution of sodium bicarbonate until the pH was neutral, then washed once with water to eliminate the salts. The organic phase was dried over magnesium sulfate and evaporated under reduced pressure (200 mm of mercury=2.6600 Pa) to obtain the crude ester. The ethyl ester was distilled at 132 C. under a reduced pressure of 2 mm of mercury (266 PA), then crystallized from petroleum ether (40-60 C. fraction) to provide ethyl vanillate having a purity of more than 97% at a yield of 80%. The ethyl vanillate has a spicy vanilla scent.
  • 7
  • [ 121-34-6 ]
  • [ 19387-91-8 ]
  • C8H13N3O4S*C8H8O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; for 1.66667h; General procedure: The TN salts/molecular salts was preparedby grinding an equimolar mixture containing 200mg (1 mmol) of TN and 1mmol of correspondingcarboxylic acids/PTSA wetted with few drops of waterwas manually grounded in an agate mortar for 100minutes until a dried powder was obtained.
  • 8
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  • [ 65-85-0 ]
  • [ 498-02-2 ]
  • [ 98-89-5 ]
  • [ 99-96-7 ]
  • 9
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  • 10
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  • [ 498-02-2 ]
  • 11
  • [ 9005-53-2 ]
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  • [ 121-34-6 ]
  • [ 306-08-1 ]
  • [ 104-87-0 ]
  • [ 123-08-0 ]
  • [ 121-33-5 ]
  • [ 65-85-0 ]
  • [ 620-23-5 ]
  • [ 99-04-7 ]
  • [ 99-96-7 ]
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