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Purity: ≥98%
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.
| Targets |
Natural triterpenoid; Nrf2
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|---|---|
| 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].
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| 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].
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| Cell Assay |
Concentration-dependent effects of AKBA on Gie-3B11-barrier function. The cell layers were treated with AKBA on both cell surfaces for 48 h, beginning 4 days postseeding, before measurements were performed. Results shown represent the mean ± standard error for n = 7 cell layers (for the Rt) or n = 4 cell layers (for the mannitol flux). * indicates P < 0.05, ** indicates P < 0.01, and *** indicates P < 0.001 (one-way ANOVA, Tukey).[1]
Cell layers were treated with 50 μM zinc, 400 μM quercetin, 15 μM retinoic acid, or 2 μM AKBA, as described. (A) Actual immunoblot bands observed for claudins-1, -2, -4, and -5 for the four control cell layers (lanes 1–4) and four micronutrient-treated cell layers (lanes 5–8). (B) Band densities quantitated by the optical densities.[1] |
| References |
[1]. J Agric Food Chem. 2017 Dec 7. doi: 10.1021/acs.jafc.7b04203.
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| Additional Infomation |
3-Acetyl-11-keto-beta-boswellic acid is a triterpenoid.
3-Acetyl-11-keto-beta-boswellic acid has been reported in Boswellia sacra, Boswellia serrata, and Boswellia papyrifera with data available. See also: Indian frankincense (part of). |
| Molecular Formula |
C32H48O5
|
|---|---|
| Molecular Weight |
512.73
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| Exact Mass |
512.35
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| Elemental Analysis |
C, 74.96; H, 9.44; O, 15.60
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| CAS # |
67416-61-9
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| PubChem CID |
11168203
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
600.3±55.0 °C at 760 mmHg
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| Flash Point |
184.4±25.0 °C
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| Vapour Pressure |
0.0±3.7 mmHg at 25°C
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| Index of Refraction |
1.549
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| LogP |
8
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
37
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| Complexity |
1060
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| Defined Atom Stereocenter Count |
11
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| SMILES |
C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC(=O)[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 |
HMMGKOVEOFBCAU-BCDBGHSCSA-N
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| 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
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| 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
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| Synonyms |
3-O-acetyl-11-keto-β-Boswellic acid; 3-acetyl-11-keto-β-Boswellic acid; AKBA; 67416-61-9; 3-acetyl-11-keto-beta-boswellic acid; 3-O-Acetyl-11-keto-beta-Boswellic Acid; AKBA cpd; acetyl-11-ketoboswellic acid; Acetyl-11-keto-beta-boswellic acid; UNII-BS16QT99Q1; Acetylketo-β-boswellic acid
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ≥ 5.2 mg/mL (~10.14 mM)
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|---|---|
| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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 : PEG300 ：Tween 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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (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.
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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT03612986 | Completed | Dietary Supplement: SYALOX® 300 Plus Dietary Supplement: Placebo |
Knee Osteoarthritis | River Pharma S.r.l. | 2018-08-22 | Not Applicable |
| NCT03924596 | Unknown status | Drug: AKBA-Incense (3-acetyl-11-keto-ß-boswellic acid) Drug: Potassium Sodium Hydrogen Citrate |
Renal Stones | Sultan Qaboos University | 2019-09 | Phase 1 Phase 2 |
| NCT04487964 | Completed | Dietary Supplement: Licorice extract | COVID-19 | Egyptian Biomedical Research Network | 2020-01-01 | Not Applicable |
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