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3-O-Acetyl-11-keto-beta-boswellic acid

CAS# 67416-61-9

3-O-Acetyl-11-keto-beta-boswellic acid

Catalog No. BCN1381----Order now to get a substantial discount!

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3-O-Acetyl-11-keto-beta-boswellic acid: 5mg $127 In Stock
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Quality Control of 3-O-Acetyl-11-keto-beta-boswellic acid

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Chemical structure

3-O-Acetyl-11-keto-beta-boswellic acid

3D structure

Chemical Properties of 3-O-Acetyl-11-keto-beta-boswellic acid

Cas No. 67416-61-9 SDF Download SDF
PubChem ID 11168203 Appearance White powder
Formula C32H48O5 M.Wt 512.72
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms AKBA; 11-keto-β-Boswellic acid acetate
Solubility DMSO : ≥ 5.2 mg/mL (10.14 mM)
*"≥" means soluble, but saturation unknown.
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
SMILES CC1CCC2(CCC3(C(=CC(=O)C4C3(CCC5C4(CCC(C5(C)C(=O)O)OC(=O)C)C)C)C2C1C)C)C
Standard InChIKey HMMGKOVEOFBCAU-BCDBGHSCSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 3-O-Acetyl-11-keto-beta-boswellic acid

The herbs of Boswellia carterii Birdw.

Biological Activity of 3-O-Acetyl-11-keto-beta-boswellic acid

Description3-O-Acetyl-11-keto-beta-boswellic acid inhibits 5-lipoxygenase product formation with an IC(50) of 1.5 m muM.
In vitro

Safety and Toxicological Evaluation of a Novel, Standardized 3-O-Acetyl-11-keto-beta-Boswellic Acid (AKBA)-Enriched Boswellia serrata Extract (5-Loxin(R)).[Pubmed: 20021046]

Toxicol Mech Methods. 2006;16(4):199-226.

The novel anti-inflammatory properties of the gum resin derived from Boswellia serrata, also known as Salai guggal in Ayurvedic medicine, are well recognized and highly recommended for human consumption. The active constituents of the gum resin are boswellic acids (BAs). Among the BAs, 3-O-Acetyl-11-keto-beta-boswellic acid potently inhibits 5-lipoxygenase product formation with an IC(50) of 1.5 m muM.
CONCLUSIONS:
We developed a novel Boswellia serrata extract (5-Loxin(R)) enriched with 30% 3-O-Acetyl-11-keto-beta-boswellic acid (US Patent 2004/0073060A1).

Comparative pharmacokinetic study of two boswellic acids in normal and arthritic rat plasma after oral administration of Boswellia serrata extract or Huo Luo Xiao Ling Dan by LC-MS.[Pubmed: 24806456]

Biomed Chromatogr. 2014 Oct;28(10):1402-8.

11-keto-β-boswellic acid and 3-O-Acetyl-11-keto-beta-boswellic acid following oral administration of HLXLD or Boswellia serrata extract alone in normal and arthritic rats.
METHODS AND RESULTS:
An LC-MS method was developed and validated for the determination of 11-keto-β-boswellic acid and 3-O-Acetyl-11-keto-beta-boswellic acid in the comparative pharmacokinetic study. The results showed that there were significant differences in pharmacokinetic parameters between normal and arthritic groups. Interestingly, the absorptions of two boswellic acids were significantly higher in HLXLD than Boswellia serrata extract alone, indicating the synergistic effect of other herbal ingredients in HLXLD.
CONCLUSIONS:
This comparative pharmacokinetic study provided direct evidence supporting the notion that the efficacy of a complex mixture such as HLXLD is better than that of single components in treating human diseases.

3-O-Acetyl-11-keto-beta-boswellic acid Dilution Calculator

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Preparing Stock Solutions of 3-O-Acetyl-11-keto-beta-boswellic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.9504 mL 9.7519 mL 19.5038 mL 39.0076 mL 48.7596 mL
5 mM 0.3901 mL 1.9504 mL 3.9008 mL 7.8015 mL 9.7519 mL
10 mM 0.195 mL 0.9752 mL 1.9504 mL 3.9008 mL 4.876 mL
50 mM 0.039 mL 0.195 mL 0.3901 mL 0.7802 mL 0.9752 mL
100 mM 0.0195 mL 0.0975 mL 0.195 mL 0.3901 mL 0.4876 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 3-O-Acetyl-11-keto-beta-boswellic acid

Comparative pharmacokinetic study of two boswellic acids in normal and arthritic rat plasma after oral administration of Boswellia serrata extract or Huo Luo Xiao Ling Dan by LC-MS.[Pubmed:24806456]

Biomed Chromatogr. 2014 Oct;28(10):1402-8.

Huo Luo Xiao Ling Dan (HLXLD), a Chinese herbal formula composed of 11 different herbs, has been used traditionally for the treatment of arthritis and other chronic inflammatory diseases. However, the pharmacokinetic profile of its anti-inflammatory bioactive compounds has not been elucidated. Boswellic acids are the bioactive compounds with potent anti-inflammatory activity isolated from Boswellia serrate which is one of the 11 herbs of HLXLD. The objective of the study was to compare the pharmacokinetics of the two bioactive bowsellic acids: 11-keto-beta-boswellic acid and 3-O-acetyl-11-keto-beta-boswellic following oral administration of HLXLD or Boswellia serrata extract alone in normal and arthritic rats. An LC-MS method was developed and validated for the determination of 11-keto-beta-boswellic acid and 3-O-acetyl-11-keto-beta-boswellic in the comparative pharmacokinetic study. The results showed that there were significant differences in pharmacokinetic parameters between normal and arthritic groups. Interestingly, the absorptions of two boswellic acids were significantly higher in HLXLD than Boswellia serrata extract alone, indicating the synergistic effect of other herbal ingredients in HLXLD. This comparative pharmacokinetic study provided direct evidence supporting the notion that the efficacy of a complex mixture such as HLXLD is better than that of single components in treating human diseases.

Safety and Toxicological Evaluation of a Novel, Standardized 3-O-Acetyl-11-keto-beta-Boswellic Acid (AKBA)-Enriched Boswellia serrata Extract (5-Loxin(R)).[Pubmed:20021046]

Toxicol Mech Methods. 2006;16(4):199-226.

The novel anti-inflammatory properties of the gum resin derived from Boswellia serrata, also known as Salai guggal in Ayurvedic medicine, are well recognized and highly recommended for human consumption. The active constituents of the gum resin are boswellic acids (BAs). Among the BAs, AKBA potently inhibits 5-lipoxygenase product formation with an IC(50) of 1.5 m muM. We developed a novel Boswellia serrata extract (5-Loxin(R)) enriched with 30% AKBA (US Patent 2004/0073060A1). The genetic basis of the anti-inflammatory effects of 5-Loxin(R) was explored in a system of TNFalpha-induced gene expression in human microvascular endothelial cells. 5-Loxin(R) significantly prevented the TNFalpha-induced expression of matrix metalloproteinases and adhesion molecules (ICAM-1 and VCAM-1), and inducible expression of the mediators of apoptosis. With such interesting findings, we planned to determine the broad-spectrum safety of 5-Loxin(R). Acute oral, acute dermal, primary skin and eye irritation, and dose-dependent 90-day subchronic toxicity studies were conducted. In safety studies, acute oral LD(50) of 5-Loxin(R) was found to be greater than 5,000 mg/kg in both male and female Sprague-Dawley rats. No changes in body weight or adverse effects were observed following necropsy. Acute dermal LD(50) of 5-Loxin(R) was found to be >2,000 mg/kg. Primary skin irritation test was conducted with 5-Loxin(R) on New Zealand Albino rabbits and 5-Loxin(R) was classified as nonirritating. Primary eye irritation test was conducted with 5-Loxin on rabbits and 5-Loxin(R) was classified as mildly irritating to the eye. A dose-dependent 90-day subchronic toxicity study demonstrated no significant changes in selected organ weights individually and as percentages of body and brain weights. 5-Loxin(R) supplementation did not cause changes in hepatic DNA fragmentation on 30, 60, or 90 days of treatment. Hematology, clinical chemistry, and histopathological evaluations did not show any adverse effects in all organs tested. Taken together, these results demonstrate the broad spectrum safety of 5-Loxin(R).

Description

AKBA (Acetyl-11-keto-β-boswellic acid) is an active triterpenoid compound from the extract of Boswellia serrate and a novel Nrf2 activator.

Keywords:

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