AKBA (Acetyl-11-keto-β-boswellic acid)

Alias: 3-O-acetyl-11-keto-β-Boswellic acid 3-acetyl-11-keto-β-Boswellic acid Acetylketo-β-boswellic acid
Cat No.:V10619 Purity: ≥98%
AKBA,an active triterpenoid isolated from Boswellia serrate,is an antiangiogenic and neuroprotective agent as well asa novel Nrf2 activator.
AKBA (Acetyl-11-keto-β-boswellic acid) Chemical Structure CAS No.: 67416-61-9
Product category: Lipoxygenase
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

AKBA, an active triterpenoid isolated from Boswellia serrate, is an antiangiogenic and neuroprotective agent as well as a novel Nrf2 activator. It reduces the impact of proliferative retinopathies, protecting neurons against ischemic injury involving the Nrf2/HO-1 pathway. It selectively inhibits 5-lipoxygenase (IC50 = 1.5 µM) in an enzyme-directed, nonredox, and noncompetitive manner.2 3-acetyl-11-keto-β-Boswellic acid and other members of the boswellic acid family have been studied for potential use in the control of inflammatory diseases, including arthritis and cancer.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
AKBA (Acetyl-11-keto-β-boswellic Acid) Significantly Reduces Infarct Volume and Improves Cellularity and Increases Neurological Score via Nrf2 and HO-1 Expression in 48-Hour Middle Cerebral Artery Occlusion (MCAO) Brain Tissue Reperfusion Recovery. In primary cultured neurons, AKBA increased the expression of Nrf2 and HO-1, thereby preventing OGD-induced oxidative damage. In addition, AKBA therapy improves the binding activity of Nrf2 to the antioxidant response element (ARE) [1]. AKBA (11-methyl-β-boswellic acid) strongly suppresses the development of human adrenal cancer cells, demonstrating cell cycle activation in the G1 phase and causing cellular inflammation [3]. AKBA (11-oneki-beta-boswellic acid) causes substantial lipolysis in 3T3-L1 adipocytes, as demonstrated by a decrease in cytoplasm neutral sodium and an increase in carotene in the intermediates. Increased lipolysis by AKBA is accompanied by upregulation of adipose lipase, adipocyte triglyceride lipase (ATGL) and adipose lipase (HSL), and decreased expression of the lipid droplet stability regulator perilipin. In addition, AKBA (Acetyl-11-keto-β-boswellic) Acid) treatment reduced the phenotypic markers of mature adipocytes aP2, adiponectin, and glut-4 in mature adipocytes [5].
ln Vivo
AKBA (acetyl-11-keto-beta-boswellic acid) strongly reduced intestinal adenomatous polyps without harm in mice. AKBA is more active than aspirin in preventing the growth of tiny intestinal and respiratory polyps. Histopathological investigation suggests that the effect of AKBA, i.e. reducing polyp size and degree of atypical repair, is more noticeable in polyps of larger size, especially those originating from intermittent polyps [1]. AKBA successfully inhibited the growth of HT-29 xenografts in mice without harm. AKBA is more active than aspirin [3]. AKBA demonstrates antitumor action both in vitro and in vivo. Through sidewall application in mice, AKBA significantly decreased SGC-7901 and MKN-45 xenografts without toxicity [4].
References
: J Agric Food Chem. 2017 Dec 7. doi: 10.1021/acs.jafc.7b04203.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C32H48O5
Molecular Weight
512.73
Exact Mass
512.35
CAS #
67416-61-9
SMILES
O=C([C@@]([C@]1([H])CC[C@@]2(C)[C@]3(C)CC[C@@]4(C)CC[C@@H](C)[C@H](C)[C@@]4([H])C3=C5)(C)[C@H](OC(C)=O)CC[C@]1(C)[C@@]2([H])C5=O)O
InChi Key
HMMGKOVEOFBCAU-BCDBGHSCSA-N
InChi Code
InChI=1S/C32H48O5/c1-18-9-12-28(4)15-16-30(6)21(25(28)19(18)2)17-22(34)26-29(5)13-11-24(37-20(3)33)32(8,27(35)36)23(29)10-14-31(26,30)7/h17-19,23-26H,9-16H2,1-8H3,(H,35,36)/t18-,19+,23-,24-,25+,26-,28-,29+,30-,31-,32-/m1/s1
Chemical Name
(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-acetyloxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-4-carboxylic acid
Synonyms
3-O-acetyl-11-keto-β-Boswellic acid 3-acetyl-11-keto-β-Boswellic acid Acetylketo-β-boswellic acid
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

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)
DMSO : ≥ 5.2 mg/mL (~10.14 mM)
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 1.9503 mL 9.7517 mL 19.5034 mL
5 mM 0.3901 mL 1.9503 mL 3.9007 mL
10 mM 0.1950 mL 0.9752 mL 1.9503 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:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • 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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