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Abietic acid

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Abietic acid is a naturally occurring organic compound. It is a resin acid found in the oleoresin of pine trees. Abietic acid is commonly used as a base material in various industrial applications, such as the production of surfactants, adhesives, and coatings.

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Lab products found in correlation

Ethyl acetate, by Merck Group (2 mentions) Chrysin, by Carl Roth (2 mentions) Hexane, by Carl Roth (2 mentions) Linoleic acid, by Carl Roth (2 mentions) Apigenin, by Merck Group (2 mentions) Methanol, by Avantor (2 mentions) Hplc grade acetonitrile, by Avantor (2 mentions) Chloroform d1, by Avantor (2 mentions) Barnstead micropure system, by Thermo Fisher Scientific (2 mentions) Pinocembrin 7 methyl ether, by Carl Roth (2 mentions) Formic acid, by Honeywell (2 mentions) Ethyl acetate, by Carl Roth (2 mentions) Temozolomide tmz, by Merck Group (2 mentions) Dspe peg2000, by Avanti Polar Lipids (2 mentions) Methanol, by Merck Group (2 mentions) Ethanol, by Merck Group (2 mentions) Milli q plus system, by Merck Group (1 mentions) Epi catechin, by Serva Electrophoresis (1 mentions) Catechin, by Merck Group (1 mentions) Acetonitrile, by Merck Group (1 mentions)

14 protocols using abietic acid

1

Lipid-based Temozolomide Nanoformulation

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N-(carbonyl-methoxypolyethylene glycol-2000)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine, sodium salt) (DSPE-PEG2000, Avanti polar lipids), L-α-phosphatidylcholine (PC, Soy, 95%, Avanti polar lipids, Alabaster, AL, USA), cholesterol (Ch, Sigma Grade, ≥99%), abietic acid (Aldrich, Saint Louis, MO, USA), temozolomide (TMZ, Sigma, Saint Louis, MO, USA, ≥98%), abietic acid (Sigma, ~75%), Abies sibirica Ledeb. resin (Ab. Sibirica, Altaivita, 99%).
Pashirova T.N., Nemtarev A.V., Buzyurova D.N., Shaihutdinova Z.M., Dimukhametov M.N., Babaev V.M., Voloshina A.D, & Mironov V.F. (2023). Terpenes-Modified Lipid Nanosystems for Temozolomide, Improving Cytotoxicity against Glioblastoma Human Cancer Cells In Vitro. Nanomaterials, 14(1), 55.
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2

Isolation and Characterization of Phenolic Compounds

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Methanol, chloroform, dichloromethane, ethyl acetate, formic acid, and n-hexane were purchased from POCh (Gliwice, Poland). Acetonitrile was purchased from Merck (Darmstadt, Germany). Water for HPLC experiments was prepared using the Milli-Q Plus system (Millipore, Billerica, MA, USA) (18.2 MΩ cm). All solvents used for chromatography were of gradient grade. Cyclolariciresinol, 7-hydroxylariciresinol (I), 7-hydroxylariciresinol (II), 7-hydroxymatairesinol, lariciresinol, matairesinol, nortrachelogenin, pinoresinol, secoisolariciresinol, and todolactol were isolated in our laboratory. Myricetin, dihydroquercetin (taxifolin), and epi-catechin were purchased from Serva (Heidelberg, Germany). Abietic acid and catechin were purchased from Sigma-Aldrich Chemie GmbH (Steinheim, Germany).
Patyra A., Dudek M.K, & Kiss A.K. (2022). LC-DAD–ESI-MS/MS and NMR Analysis of Conifer Wood Specialized Metabolites. Cells, 11(20), 3332.
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3

Multifunctional Polymeric Materials Synthesis

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Abietic acid (85%), maleic anhydride, N,N-dimethyla-minoethylamine (DAEA), propargyl alcohol, triethylamine (TEA), p-toluene sulfonic acid (PTSA), bromoethane, α-bromoisobutyryl bromide (BIBB), (3-aminopropyl)triethoxysilane (APTES), sodium bicarbonate, calcium chloride, 3-chloroprapanol, sodium azide, methacryloyl chloride, copper(I) bromide, N,N,N′,N′,N″-pentame-thyldiethylenetriamine (PMDETA), sulfuric acid, hydrogen peroxide, ethyl acetate, copper sulfate pentahydrate, and sodium ascorbate were purchased from Sigma-Aldrich, VWR, or Fisher Scientific and used as received. According to procedures reported in literature, (3-azidopropyl)trimethoxysilane (AzPTMS),42 bromotriethylorthosilicate (BrTEOS),43 (link) and 3-azidopropyl methacrylate44 (link) were prepared. QA containing resin acid derived compound 1 was synthesized, following our recent report.41 Acetic acid, dichloromethane (DCM), ethyl acetate, ethanol, hexane, diethyl ether, methanol, toluene, tetrahydrofuran (THF), and N,N-dimethylformamide (DMF) were obtained as ACS grade solvents. Standard protocols were followed to dry solvents or reagents. All other chemicals used for biological assays will be mentioned in the respective sections.
Ganewatta M.S., Miller K.P., Singleton S.P., Mehrpouya-Bahrami P., Chen Y.P., Yan Y., Nagarkatti M., Nagarkatti P., Decho A.W, & Tang C. (2015). Antibacterial and Biofilm-Disrupting Coatings from Resin Acid-Derived Materials. Biomacromolecules, 16(10), 3336-3344.
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4

Extraction and Isolation of Natural Compounds

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Solvents for different steps in analyses were partially denatured ethanol (AustrAlco, Spillern, Austria) for extraction, hexane, ethyl acetate (both Carl Roth, Karlsruhe, Baden-Württemberg, Germany) and methanol (VWR, Radnor, PA, USA) for open column chromatography and TLC, chloroform-d1 (VWR) and pyridine-d5 (Armar, Döttingen, Aargau, Switzerland) for NMR.
HPLC mobile phases consisted of ultrapure water prepared from deionized water with a Barnstead MicroPure system (Thermo Fisher Scientific, Waltham, MA, USA), HPLC-grade acetonitrile (VWR) and formic acid for LC-MS (Honeywell, Charlotte, NC, USA).
Reference substances were abietic acid contributed by the Department of Pharmaceutical Chemistry, University of Graz, Austria, apigenin (Sigma-Aldrich, St. Louis, MO, USA), chrysin, pinocembrin-7-methyl ether (pinostrobin), linoleic acid (all Carl Roth) and oleic acid (Fluka, Buchs, St. Gallen, Switzerland).
Alperth F., Schneebauer A., Kunert O, & Bucar F. (2023). Phytochemical Analysis of Pinus cembra Heartwood—UHPLC-DAD-ESI-MSn with Focus on Flavonoids, Stilbenes, Bibenzyls and Improved HPLC Separation. Plants, 12(19), 3388.
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5

Extraction and Isolation of Natural Compounds

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Solvents for different steps in analyses were partially denatured ethanol (AustrAlco, Spillern, Austria) for extraction, hexane, ethyl acetate (both Carl Roth, Karlsruhe, Baden-Württemberg, Germany) and methanol (VWR, Radnor, PA, USA) for open column chromatography and TLC, chloroform-d1 (VWR) and pyridine-d5 (Armar, Döttingen, Aargau, Switzerland) for NMR.
HPLC mobile phases consisted of ultrapure water prepared from deionized water with a Barnstead MicroPure system (Thermo Fisher Scientific, Waltham, MA, USA), HPLC-grade acetonitrile (VWR) and formic acid for LC-MS (Honeywell, Charlotte, NC, USA).
Reference substances were abietic acid contributed by the Department of Pharmaceutical Chemistry, University of Graz, Austria, apigenin (Sigma-Aldrich, St. Louis, MO, USA), chrysin, pinocembrin-7-methyl ether (pinostrobin), linoleic acid (all Carl Roth) and oleic acid (Fluka, Buchs, St. Gallen, Switzerland).
Alperth F., Schneebauer A., Kunert O, & Bucar F. (2023). Phytochemical Analysis of Pinus cembra Heartwood—UHPLC-DAD-ESI-MSn with Focus on Flavonoids, Stilbenes, Bibenzyls and Improved HPLC Separation. Plants, 12(19), 3388.
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6

Nanoliposomal Encapsulation of Leelamine and Abietic Acid

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Leelamine hydrochloride (Tocris Biosciences, Ellisville, MO) was encapsulated into a nanoliposome (called Nanolipolee-007) prepared by combining egg L-α-Phosphatidylcholine (ePC) and 1,2-Dipalmitoyl-sn-Glycero-3-Phosphoethanolamine-N-[Methoxy(Polyethylene glycol)-2000] ammonium salt (DPPE-PEG-2000) in chloroform at 80:20 mol% and a final lipid concentration of 25 mg/mL in buffer solution (Avanti Polar Lipids Inc- Alabaster, AL). The same lipid formulation was found to load Abietic acid (Sigma Chemical Co. St. Louis, MO) and an empty control nanoliposome was also made. 7.5 mg of leelamine hydrochloride and/or Abietic acid (in methanol) was added to 1.0 mL of nanoliposome solution resulting in a 22.6 mM concentration. Mixture was then dried under nitrogen gas and resuspended in 0.9% saline at 60°C. Following rehydration, the mixture was sonicated at 60°C for 30 minutes followed by extrusion at 60°C through a 100-nm polycarbonate membrane using Avanti Mini Extruder (Avanti Polar Lipids Inc- Alabaster, AL). The particle size and charge characteristics were determined using a Malvern Zetasizer (Malvern Instruments, UK)
Gowda R., Madhunapantula S.V., Sharma A., Kuzu O.F, & Robertson G.P. (2014). Nanolipolee-007, a novel nanoparticle based drug containing leelamine for the treatment of melanoma. Molecular cancer therapeutics, 13(10), 2328-2340.
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7

Synthesis and Characterization of Surfactant Formulations

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Polyethylene glycol sorbitan monooleate (Tween 80, Sigma Aldrich, Saint Louis, MO, USA, ≥99%), oleic acid (Alfa Aesar, Ward Hill, MA, USA, 99%), Carbopol® 940 (Acros Organics, Geel, Belgium), abietic acid (Sigma Aldrich, Saint Louis, MO, USA, ~75%), 2,2′-azobis(2-methylpropionamidine) dihydrochloride (AAPH) and luminol were obtained from Stanchem Sp. z o.o. Przedsiębiorstwo Chemiczne. Reagents were used as received without further purification. The carbamate surfactant CB-16(Bu) was synthesized according to the method described in [38 (link)].
Mirgorodskaya A., Kushnazarova R., Pavlov R., Valeeva F., Lenina O., Bushmeleva K., Kuryashov D., Vyshtakalyuk A., Gaynanova G., Petrov K, & Zakharova L. (2022). Supramolecular Tools to Improve Wound Healing and Antioxidant Properties of Abietic Acid: Biocompatible Microemulsions and Emulgels. Molecules, 27(19), 6447.
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8

Fabrication of Doxorubicin-Loaded Polymer Nanoparticles

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Hydroxypropylcellulose (HPC, molecular weight (Mw) 100,000, Polydispersity Index (PDI) = 1.09), bovine serum albumin (BSA), abietic acid (AA), and 4-toluene sulfonyl chloride (TOS-Cl) were bought from Sigma-Aldrich Co., LLC (St. Louis, MO, USA). Doxorubicin hydrochloride (DOX) was purchased from the Aladdin Chemical Reagents Company. Hydrochloric acid, petroleum ether, dimethylacetamide, and other chemical reagents were used without any further purification.
Chen Y., Wang X., Huang Y., Kuang P., Wang Y., Liu Y., Yin W., Zan J., Liu Y., Yin C, & Fan Q. (2021). In Situ-Forming Cellulose/Albumin-Based Injectable Hydrogels for Localized Antitumor Therapy. Polymers, 13(23), 4221.
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9

Abietic Acid Modulates Macrophage Viability and Inflammation

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RAW264.7 (SC-6003, ATCC) was cultured in DMEM medium (11965092, Gbico, Grand Island, NY, USA) plus with 10% fetal bovine serum (FBS) (10099141, Gbico) at 37°C with 5% CO2. For
the effect of abietic acid (00010, Sigma, St. Louis, MO, USA) (AA) treatment on the viability of RAW264.7 cells test, different concentration of AA (20, 40, 80, 160 and 320
µmol/l) were added into the cell culture medium of RAW264.7 cells, and then continue to culture for 26 h. For the effect of AA treatment on the secretion of inflammation
mediators, different concentration of AA (20, 40 and 80 µmol/l) were added into the cell culture medium of RAW264.7 cells to culture for 2 h, and then 1
µg/ml LPS were added into the cell culture medium of RAW264.7 cells to continue to culture for 24 h.
Fang H., Chen J., Luo J., Hu J., Wang D., Lv L, & Zhang W. (2022). Abietic acid attenuates sepsis-induced lung injury by inhibiting nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) pathway to inhibit M1 macrophage polarization. Experimental Animals, 71(4), 481-490.
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10

Antioxidant Potential Evaluation

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All reagents used were analytical grade. Ethyl acetate, 2,2-di(4-tert-octylphenyl)-1-picrylhydrazyl (DPPH·) free radical, gallic acid (97%), caffeic acid (98%), rosmarinic acid (≥98%), and abietic acid (≥75%), were obtained from Sigma-Aldrich (Castle Hill, Australia). Acetic acid, ethanol, methanol, were from Merck (Darmstadt, Germany), and anisaldehyde was from ACROS organics (Fair Lawn, NJ, USA). Milli-Q (Millipore) water was used to prepare all aqueous solutions.
Agatonovic-Kustrin S., Balyklova K.S., Gegechkori V, & Morton D.W. (2021). HPTLC and ATR/FTIR Characterization of Antioxidants in Different Rosemary Extracts. Molecules, 26(19), 6064.
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