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3-Acetyl-beta-boswellic acid

Cat No.:V29985 Purity: ≥98%
3-Acetyl-beta-boswellic acid is a boswellic acid extracted from Boswellia serrata resin.
3-Acetyl-beta-boswellic acid
3-Acetyl-beta-boswellic acid Chemical Structure CAS No.: 5968-70-7
Product category: Disease Research Fields
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
25mg
Other Sizes
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Product Description
3-Acetyl-beta-boswellic acid is a boswellic acid extracted from Boswellia serrata resin.
3-Acetyl-beta-boswellic acid (CAS#: 5968-70-7), also known as 3-O-Acetyl-beta-boswellic acid, is a non-reducing inhibitor of 5-lipoxygenase (5-LO) with antitumor effects. It inhibits synthesis of DNA, RNA, and protein in human leukemia HL-60 cells in a dose-dependent manner with IC50 values ranging from 0.6 to 7.1 μM. The compound exhibits significant pharmacological properties including anti-inflammatory, anti-tumor, and antioxidant effects. It inhibits cell proliferation, decreases DNA synthesis, and inhibits migration, invasion, and colony formation of human glioblastoma cell lines.
Biological Activity I Assay Protocols (From Reference)
Targets
3-Acetyl-beta-boswellic acid targets 5-lipoxygenase (5-LO), functioning as a non-reducing inhibitor. It also targets DNA, RNA, and protein synthesis pathways in cancer cells. The compound increases apoptosis and the activity of caspase 3/7. It inhibits cell proliferation, decreases DNA synthesis, and inhibits the migration, invasion, and colony formation of human glioblastoma cell lines. Its anti-inflammatory effects are mediated through 5-LO inhibition.
ln Vitro
In vitro, 3-Acetyl-beta-boswellic acid inhibits synthesis of DNA, RNA, and protein in human leukemia HL-60 cells with IC50 values ranging from 0.6 to 7.1 μM. It inhibits cell proliferation, decreases DNA synthesis, and inhibits the migration, invasion, and colony formation of human glioblastoma cell lines. The compound increases apoptosis and caspase 3/7 activity. It is a non-reducing inhibitor of 5-lipoxygenase (5-LO). Its anti-tumor and anti-inflammatory activities have been characterized in various cell-based assays.
ln Vivo
In vivo, 3-Acetyl-beta-boswellic acid has antitumor activity. It exhibits anti-inflammatory, anti-tumor, and antioxidant effects. The compound's inhibition of 5-lipoxygenase suggests potential for treating inflammatory diseases. Its anti-tumor effects have been demonstrated in preclinical models. Further in vivo studies are ongoing to fully characterize its therapeutic potential. The compound is typically administered orally or via injection in preclinical studies.
Enzyme Assay
In vitro enzyme assays for 3-Acetyl-beta-boswellic acid involve measuring 5-lipoxygenase (5-LO) inhibition. 5-LO activity is assessed by monitoring the conversion of arachidonic acid to leukotrienes. The compound is added at varying concentrations, and IC50 values are calculated from dose-response curves. For DNA, RNA, and protein synthesis inhibition, HL-60 cells are treated with the compound and incorporation of radiolabeled precursors is measured. Apoptosis is assessed by measuring caspase 3/7 activity. Assays are performed in appropriate buffer systems with positive controls.
Cell Assay
In vitro cell-based assays for 3-Acetyl-beta-boswellic acid are conducted in HL-60 leukemia cells, glioblastoma cell lines, and other cancer cell lines. Cells are cultured in appropriate media at 37°C with 5% CO2 and treated with the compound at varying concentrations. Cell viability is assessed by MTT or CCK-8 assays. DNA, RNA, and protein synthesis are assessed by measuring incorporation of radiolabeled precursors. Apoptosis is evaluated by Annexin V/PI staining and caspase activity assays. Migration and invasion are assessed using Transwell assays. Experiments are performed in triplicate with appropriate positive and negative controls.
Animal Protocol
3-Acetyl-beta-boswellic acid in vivo studies are conducted in animal models of cancer and inflammation. Tumor-bearing mice are treated with the compound via oral administration or injection. Tumor growth is monitored by caliper measurements. Apoptosis in tumors is assessed by TUNEL assay and caspase activity measurement. For anti-inflammatory studies, animal models of inflammation such as carrageenan-induced paw edema are used. Dosing regimens are optimized based on pharmacokinetic data. Animals are monitored for clinical signs. Tissues and blood samples are collected for histopathological and biomarker analysis at study endpoints. Studies are conducted in accordance with institutional animal care guidelines.
ADME/Pharmacokinetics
3-Acetyl-beta-boswellic acid (MW 498.74 g/mol, C32H50O4) is a triterpenoid compound. It is a non-reducing inhibitor of 5-lipoxygenase (5-LO). The compound is soluble in DMSO and other organic solvents. It is stable under recommended storage conditions. 3-Acetyl-beta-boswellic acid is a natural product from Boswellia with anti-inflammatory and anti-tumor activities. Pharmacokinetic parameters such as half-life, bioavailability, and tissue distribution would be determined in species-specific studies.
Toxicity/Toxicokinetics
3-Acetyl-beta-boswellic acid is generally well-tolerated in preclinical studies. The compound is a natural triterpenoid with established safety profiles. Its anti-inflammatory, anti-tumor, and antioxidant effects have been demonstrated with acceptable safety profiles. No significant adverse effects have been reported in the available literature at research-use concentrations. The compound is intended for research use only. Standard safety precautions should be followed when handling. Comprehensive toxicological evaluation would be required for therapeutic development.
References

[1]. In vitro metabolism, permeation, and brain availability of six major boswellic acids from Boswellia serrata gum resins. Fitoterapia. 2013 Jan;84:99-106.

Additional Infomation
It has been reported that frankincense (Boswellia sacra) and saw-tooth frankincense (Boswellia serrata) contain 3-acetyl-β-boswellic acid, and relevant data are available for reference.
3-Acetyl-beta-boswellic acid (3-O-Acetyl-beta-boswellic acid) is a non-reducing inhibitor of 5-lipoxygenase (5-LO) with antitumor effects. It inhibits DNA, RNA, and protein synthesis in HL-60 cells with IC50 values of 0.6-7.1 μM. The compound inhibits glioblastoma cell proliferation, migration, invasion, and colony formation, and increases apoptosis and caspase 3/7 activity. It exhibits anti-inflammatory, anti-tumor, and antioxidant effects. All applications are limited to non-human research use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C32H50O4
Molecular Weight
498.7370
Exact Mass
498.37
CAS #
5968-70-7
PubChem CID
11386458
Appearance
White to off-white solid powder
Density
1.1±0.1 g/cm3
Boiling Point
566.8±50.0 °C at 760 mmHg
Melting Point
157-161ºC
Flash Point
171.4±23.6 °C
Vapour Pressure
0.0±3.3 mmHg at 25°C
Index of Refraction
1.544
LogP
10.27
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Heavy Atom Count
36
Complexity
985
Defined Atom Stereocenter Count
11
SMILES
C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@H]([C@]5(C)C(=O)O)OC(=O)C)C)C)[C@@H]2[C@H]1C)C)C
InChi Key
YJBVHJIKNLBFDX-MQURJEHKSA-N
InChi Code
InChI=1S/C32H50O4/c1-19-11-14-28(4)17-18-30(6)22(26(28)20(19)2)9-10-23-29(5)15-13-25(36-21(3)33)32(8,27(34)35)24(29)12-16-31(23,30)7/h9,19-20,23-26H,10-18H2,1-8H3,(H,34,35)/t19-,20+,23-,24-,25-,26+,28-,29-,30-,31-,32-/m1/s1
Chemical Name
(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-3-acetyloxy-4,6a,6b,8a,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-4-carboxylic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.0051 mL 10.0253 mL 20.0505 mL
5 mM 0.4010 mL 2.0051 mL 4.0101 mL
10 mM 0.2005 mL 1.0025 mL 2.0051 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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