| 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 |
| CAS Number: | 17019-92-0 |  3D/inchi
|
| FDA UNII: | 0S3BIF6H0Q |
| Nikkaji Web: | J726.029F |
| MDL: | MFCD06656312 |
| XlogP3-AA: | 7.20 (est) |
| Molecular Weight: | 470.69342000 |
| Formula: | C30 H46 O4 |
| BioActivity Summary: | listing |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| |
| Hazards identification |
| |
| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
| |
| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
|
Not determined
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| Dermal Toxicity: |
|
Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for 11-Keto-beta-boswellic acid usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for 11-Keto-beta-boswellic acid flavor usage levels up to: |
| | not for flavor use.
|
Safety References:
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :9847548 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| (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 |
| Chemidplus:0017019920 |
References:
| | (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 |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 17019-92-0 |
| Pubchem (cid): | 9847548 |
| Pubchem (sid): | 163639709 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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 |
Articles:
| 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. |
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