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11-Keto-beta-boswellic acid (11-Keto-β-boswellic acid), a pentacyclic triterpenic acid of the oleogum resin, is a natural product isolated from the bark of the Boswellia serrate tree, popularly known as Indian Frankincense. The main reason that 11-Keto-beta-boswellic acid has anti-inflammatory properties is because it prevents the production of 5-lipoxygenase, leukotriene, nuclear factor-kappa B (NF-κB), and tumor necrosis factor alpha.
| Targets |
NF-κB; 5-LOX
|
|---|---|
| ln Vitro |
11-keto-beta-boswellic acid inhibits DPP-4 activity with an IC50 of 1.65 μM[2]. Inhibiting 4-inhibitor pyridine-stimulated amino acid trough release in hippocampal nerve terminals, 11-keto-beta-boswellic acid (10 minutes) (IC50: 31 μM) [3].
|
| ln Vivo |
In streptozotocin-induced diabetic signaling, 11-Keto-beta-boswellic acid (1–10 mg/kg, applied topically for 21 days) exhibits antidiabetic activity [2]. The excitotoxicity caused by kainic acid (15 mg/kg, i.p.) is prevented by boswellic acid (10 or 50 mg/kg, i.p.) [3].
|
| Animal Protocol |
Animal/Disease Models: Streptozotocin-induced diabetic rats [2]
Doses: 1-10 mg/kg Route of Administration: Orally for 21 days Experimental Results: diminished blood glucose levels. Reduce serum SGPT, SGOT, ALP and serum creatinine levels. Serum MDA levels diminished and serum SOD levels increased. |
| References | |
| Additional Infomation |
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 |
C30H46O4
|
|---|---|
| Molecular Weight |
470.6838
|
| Exact Mass |
470.34
|
| CAS # |
17019-92-0
|
| Related CAS # |
17019-92-0
|
| PubChem CID |
9847548
|
| Appearance |
White to off-white solid
|
| Density |
1.14g/cm3
|
| Boiling Point |
591.8ºC at 760mmHg
|
| Melting Point |
190 - 191 °C
|
| Flash Point |
325.8ºC
|
| Vapour Pressure |
0mmHg at 25°C
|
| Index of Refraction |
1.561
|
| LogP |
6.268
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
34
|
| Complexity |
954
|
| Defined Atom Stereocenter Count |
11
|
| SMILES |
O([H])C1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])C([H])([C@]1(C(=O)O[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@]1(C([H])([H])[H])C2([H])C(C([H])=C2C3([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]12C([H])([H])[H])=O
|
| InChi Key |
YIMHGPSYDOGBPI-YZCVQEKWSA-N
|
| InChi Code |
InChI=1S/C30H46O4/c1-17-8-11-26(3)14-15-28(5)19(23(26)18(17)2)16-20(31)24-27(4)12-10-22(32)30(7,25(33)34)21(27)9-13-29(24,28)6/h16-18,21-24,32H,8-15H2,1-7H3,(H,33,34)/t17-,18+,21-,22-,23+,24-,26-,27+,28-,29-,30-/m1/s1
|
| Chemical Name |
(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-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 |
11-Keto-beta-boswellic acid; 11-Keto-β-boswellic 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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO: ~100 mg/mL (~212.5 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.31 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (5.31 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (5.31 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1246 mL | 10.6229 mL | 21.2459 mL | |
| 5 mM | 0.4249 mL | 2.1246 mL | 4.2492 mL | |
| 10 mM | 0.2125 mL | 1.0623 mL | 2.1246 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.
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