11-Keto-beta-boswellic acid

(3alpha,4beta)-3-hydroxy-11-oxours-12-en-23-oic acid

CAS: 17019-92-0 C30 H46 O4 MW: 470.69342000

Identification

Name11-Keto-beta-boswellic acid
IUPAC(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
CAS Number17019-92-0
FDA UNII0S3BIF6H0Q
Molecular FormulaC30 H46 O4
Molecular Weight470.69342000
MDL NumberMFCD06656312
Nikkaji NumberJ726.029F

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 591.80 °C. @ 760.00 mm Hg (est)
Flash Point 618.00 °F. TCC ( 325.80 °C. ) (est)
logP (o/w) 7.100 (est)
Soluble in water, 0.01222 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for 11-Keto-beta-boswellic acid usage levels up tonot for fragrance use.
Recommendation for 11-Keto-beta-boswellic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

boswellia serrata

Synonyms

11-oxo-beta- boswellic acid Keto-b- boswellic acid (3alpha,4beta)-3- hydroxy-11-oxours-12-en-23-oic acid 3alpha- hydroxy-11-oxours-12-en-24-oic acid (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 PubMed: Neuroprotection by Acetyl-11-Keto-β-Boswellic Acid, in Ischemic Brain Injury Involves the Nrf2/HO-1 defense Pathway. PubMed: 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: Transdermal microemulsions of Boswellia carterii Bird: formulation, characterization and in vivo evaluation of anti-inflammatory activity. PubMed: Frankincense ( rǔ xiāng; boswellia species): from the selection of traditional applications to the novel phytotherapy for the prevention and treatment of serious diseases. PubMed: The comparative study of acetyl-11-keto-beta-boswellic acid (AKBA) and aspirin in the prevention of intestinal adenomatous polyposis in APC(Min/+) mice. PubMed: Boswellic acids reduce Th17 differentiation via blockade of IL-1β-mediated IRAK1 signaling. PubMed: Investigating permeability related hurdles in oral delivery of 11-keto-β-boswellic acid. PubMed: Preparation of amorphous solid dispersions by rotary evaporation and KinetiSol Dispersing: approaches to enhance solubility of a poorly water-soluble gum extract. PubMed: Biotransformation of 11-keto-β-boswellic acid by Cunninghamella blakesleana. PubMed: Acetyl-11-keto-beta-boswellic acid (AKBA) prevents human colonic adenocarcinoma growth through modulation of multiple signaling pathways. PubMed: A new cytochrome P450 system from Bacillus megaterium DSM319 for the hydroxylation of 11-keto-β-boswellic acid (KBA). PubMed: The selective 5-LOX inhibitor 11-keto-β-boswellic acid protects against myocardial ischemia reperfusion injury in rats: involvement of redox and inflammatory cascades. PubMed: Acetyl-11-keto-β-boswellic acid (AKBA) inhibits human gastric carcinoma growth through modulation of the Wnt/β-catenin signaling pathway. PubMed: Microbial transformation of acetyl-11-keto-β-boswellic acid and their inhibitory activity on LPS-induced NO production. PubMed: Urease inhibitory activities of β-boswellic acid derivatives. PubMed: A novel semisynthetic inhibitor of the FRB domain of mammalian target of rapamycin blocks proliferation and triggers apoptosis in chemoresistant prostate cancer cells. PubMed: Chemoprevention of intestinal adenomatous polyposis by acetyl-11-keto-beta-boswellic acid in APC(Min/+) mice. PubMed: In vitro metabolism, permeation, and brain availability of six major boswellic acids from Boswellia serrata gum resins. PubMed: Enhanced absorption of boswellic acids by a lecithin delivery form (Phytosome(®)) of Boswellia extract. PubMed: Effect of phospholipid-based formulations of Boswellia serrata extract on the solubility, permeability, and absorption of the individual boswellic acid constituents present. PubMed: Boswellic acid exerts antitumor effects in colorectal cancer cells by modulating expression of the let-7 and miR-200 microRNA family. PubMed: Boswellia serrata, a potential antiinflammatory agent: an overview. PubMed: Hydroxylation of the triterpenoid dipterocarpol with CYP106A2 from Bacillus megaterium. PubMed: Increased bioavailability of 11-keto-β-boswellic acid following single oral dose frankincense extract administration after a standardized meal in healthy male volunteers: modeling and simulation considerations for evaluating drug exposures. PubMed: Boswellic acid suppresses growth and metastasis of human pancreatic tumors in an orthotopic nude mouse model through modulation of multiple targets. PubMed: Targeting Sp1 transcription factors in prostate cancer therapy. PubMed: Acetyl-11-keto-β-boswellic acid (AKBA); targeting oral cavity pathogens. PubMed: [Determination of five boswellic acids in Boswellia serrata]. PubMed: Potentiation of the antitumor effect of 11-keto-β-boswellic acid by its 3-α-hexanoyloxy derivative. PubMed: A new Bacillus megaterium whole-cell catalyst for the hydroxylation of the pentacyclic triterpene 11-keto-β-boswellic acid (KBA) based on a recombinant cytochrome P450 system. PubMed: A novel cyano derivative of 11-keto-β-boswellic acid causes apoptotic death by disrupting PI3K/AKT/Hsp-90 cascade, mitochondrial integrity, and other cell survival signaling events in HL-60 cells. PubMed: Boswellic acid inhibits growth and metastasis of human colorectal cancer in orthotopic mouse model by downregulating inflammatory, proliferative, invasive and angiogenic biomarkers. PubMed: Boswellia serrata: an overall assessment of in vitro, preclinical, pharmacokinetic and clinical data. PubMed: Cellular and molecular mechanisms of anti-inflammatory effect of Aflapin: a novel Boswellia serrata extract. PubMed: Acetyl-11-keto-β-boswellic acid suppresses invasion of pancreatic cancer cells through the downregulation of CXCR4 chemokine receptor expression. PubMed: A cyano analogue of boswellic acid induces crosstalk between p53/PUMA/Bax and telomerase that stages the human papillomavirus type 18 positive HeLa cells to apoptotic death. PubMed: Two new triterpenoids from the resin of Boswellia carterii. PubMed: Antistaphylococcal and biofilm inhibitory activities of acetyl-11-keto-β-boswellic acid from Boswellia serrata. PubMed: A comparative study of proapoptotic potential of cyano analogues of boswellic acid and 11-keto-boswellic acid. PubMed: [Effect of acetyl-11-keto-β-boswellic acid on proliferation, apoptosis and cell cycle of human acute myeloid leukemia cell line HL-60]. PubMed: [Acetyl-11-keto-beta-boswellic acid and arsenic trioxide regulate the productions and activities of matrix metalloproteinases in human skin fibroblasts and human leukemia cell line THP-1]. PubMed: A propionyloxy derivative of 11-keto-β-boswellic acid induces apoptosis in HL-60 cells mediated through topoisomerase I & II inhibition. PubMed: Modulation of the immune system by Boswellia serrata extracts and boswellic acids. PubMed: Synthesis of an antitumor active endoperoxide from 11-keto-beta-boswellic acid. PubMed: 3-Acetyl-11-keto-beta-boswellic acid loaded-polymeric nanomicelles for topical anti-inflammatory and anti-arthritic activity. PubMed: Discovery of cyclooxygenase inhibitors from medicinal plants used to treat inflammation. PubMed: Targeting NF-kappa B with a natural triterpenoid alleviates skin inflammation in a mouse model of psoriasis. PubMed: LY294002 enhances boswellic acid-induced apoptosis in colon cancer cells. PubMed: Acetyl-11-keto-beta-boswellic acid inhibits prostate tumor growth by suppressing vascular endothelial growth factor receptor 2-mediated angiogenesis. PubMed: Boswellic acid blocks signal transducers and activators of transcription 3 signaling, proliferation, and survival of multiple myeloma via the protein tyrosine phosphatase SHP-1. PubMed: Permeation of Boswellia extract in the Caco-2 model and possible interactions of its constituents KBA and AKBA with OATP1B3 and MRP2. PubMed: A simple high-performance liquid chromatographic method for the estimation of boswellic acids from the market formulations containing Boswellia serrata extract. PubMed: A double blind, randomized, placebo controlled study of the efficacy and safety of 5-Loxin for treatment of osteoarthritis of the knee. PubMed: Thrombin-induced expression of endothelial CX3CL1 potentiates monocyte CCL2 production and transendothelial migration. PubMed: Inhibitory effect of acetyl-11-keto-beta-boswellic acid on androgen receptor by interference of Sp1 binding activity in prostate cancer cells. PubMed: Metabolism of boswellic acids in vitro and in vivo. PubMed: Comparison of the irritation potentials of Boswellia serrata gum resin and of acetyl-11-keto-beta-boswellic acid by in vitro cytotoxicity tests on human skin-derived cell lines. PubMed: Boswellic acids: A leukotriene inhibitor also effective through topical application in inflammatory disorders. PubMed: Antiinflammatory and antiatherogenic effects of the NF-kappaB inhibitor acetyl-11-keto-beta-boswellic acid in LPS-challenged ApoE-/- mice. PubMed: Cytotoxic and apoptotic activities of novel amino analogues of boswellic acids. PubMed: Effect of acetyl 11-keto beta-boswellic acid on metastatic growth factor responsible for angiogenesis. PubMed: Co-administration of acetyl-11-keto-beta-boswellic acid, a specific 5-lipoxygenase inhibitor, potentiates the protective effect of COX-2 inhibitors in kainic acid-induced neurotoxicity in mice. PubMed: Estimation of boswellic acids from market formulations of Boswellia serrata extract and 11-keto beta-boswellic acid in human plasma by high-performance thin-layer chromatography. PubMed: Separation and quantification of terpenoids of Boswellia serrata Roxb. extract by planar chromatography techniques (TLC and AMD). PubMed: Modulation of Pgp function by boswellic acids. PubMed: Effect of Boswellia serrata on intestinal motility in rodents: inhibition of diarrhoea without constipation. PubMed: Acetyl-11-keto-beta-boswellic acid potentiates apoptosis, inhibits invasion, and abolishes osteoclastogenesis by suppressing NF-kappa B and NF-kappa B-regulated gene expression. PubMed: Potentiation of antinociceptive effect of NSAIDs by a specific lipooxygenase inhibitor, acetyl 11-keto-beta boswellic acid. PubMed: Mechanisms underlying the anti-inflammatory actions of boswellic acid derivatives in experimental colitis. PubMed: 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: Analysis of frankincense from various Boswellia species with inhibitory activity on human drug metabolising cytochrome P450 enzymes using liquid chromatography mass spectrometry after automated on-line extraction. PubMed: High-performance liquid chromatographic determination of acetyl-11-keto-alpha-boswellic acid, a novel pentacyclic triterpenoid, in plasma using a fluorinated stationary phase and photodiode array detection: application in pharmacokinetic studies. PubMed: Protective effects of nimesulide (COX Inhibitor), AKBA (5-LOX Inhibitor), and their combination in aging-associated abnormalities in mice. PubMed: Bioactive constituents from Boswellia papyrifera. PubMed: Effect of food intake on the bioavailability of boswellic acids from a herbal preparation in healthy volunteers. PubMed: Acetyl-boswellic acids inhibit lipopolysaccharide-mediated TNF-alpha induction in monocytes by direct interaction with IkappaB kinases. PubMed: Inhibition of IkappaB kinase activity by acetyl-boswellic acids promotes apoptosis in androgen-independent PC-3 prostate cancer cells in vitro and in vivo. PubMed: Immunomodulatory activity of boswellic acids of Boswellia serrata Roxb. PubMed: Pharmacokinetic study of 11-Keto beta-Boswellic acid. PubMed: Immunomodulatory triterpenoids from the oleogum resin of Boswellia carterii Birdwood. PubMed: Acetyl-11-keto-beta-boswellic acid (AKBA) is cytotoxic for meningioma cells and inhibits phosphorylation of the extracellular-signal regulated kinase 1 and 2. PubMed: [Chemical components of Boswellia carterii]. PubMed: Cytostatic and apoptosis-inducing activity of boswellic acids toward malignant cell lines in vitro. PubMed: Cytotoxic action of acetyl-11-keto-beta-boswellic acid (AKBA) on meningioma cells. PubMed: High-performance thin layer chromatographic analysis of anti-inflammatory triterpenoids from Boswellia serrata Roxb. PubMed: Development of a high-performance liquid chromatographic method for the determination of 11-keto-beta-boswellic acid in human plasma. PubMed: Acetyl-11-keto-beta-boswellic acid, a constituent of a herbal medicine from Boswellia serrata resin, attenuates experimental ileitis. PubMed: Anti-tumor and anti-carcinogenic activities of triterpenoid, beta-boswellic acid. PubMed: 3-Acetoxy group of genuine AKBA (acetyl-11-keto-beta-boswellic acid) is alpha-configurated. PubMed: Workup-dependent formation of 5-lipoxygenase inhibitory boswellic acid analogues. PubMed: Acetyl-11-keto-beta-boswellic acid induces apoptosis in HL-60 and CCRF-CEM cells and inhibits topoisomerase I. PubMed: Characterization of an acetyl-11-keto-beta-boswellic acid and arachidonate-binding regulatory site of 5-lipoxygenase using photoaffinity labeling. PubMed: Effects of boswellic acids extracted from a herbal medicine on the biosynthesis of leukotrienes and the course of experimental autoimmune encephalomyelitis. PubMed: Nonredox 5-lipoxygenase inhibitors require glutathione peroxidase for efficient inhibition of 5-lipoxygenase activity. PubMed: Inhibitory activity of boswellic acids from Boswellia serrata against human leukemia HL-60 cells in culture. PubMed: Inhibition by boswellic acids of human leukocyte elastase. PubMed: Boswellic acids and protease activities. PubMed: Structure-activity relationships of the nonredox-type non-competitive leukotriene biosynthesis inhibitor acetyl-11-keto-β-boswellic acid. PubMed: 5-Lipoxygenase inhibition by acetyl-11-keto-β-boswellic acid (AKBA) by a novel mechanism. PubMed: Acetyl-11-keto-beta-boswellic acid (AKBA): structure requirements for binding and 5-lipoxygenase inhibitory activity. PubMed: Mechanism of 5-lipoxygenase inhibition by acetyl-11-keto-beta-boswellic acid.