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| | 11-KETO-BETA-BOSWELLIC ACID Basic information |
| | 11-KETO-BETA-BOSWELLIC ACID Chemical Properties |
| Melting point | 190～192℃ | | Boiling point | 591.8±50.0 °C(Predicted) | | density | 1.14±0.1 g/cm3(Predicted) | | storage temp. | 4°C, protect from light | | solubility | ≤5mg/ml in ethanol;25mg/ml in DMSO;25mg/ml in dimethyl formamide | | form | Solid | | pka | 4.46±0.70(Predicted) | | color | White | | Water Solubility | insoluble in water | | Major Application | food and beverages | | InChIKey | YIMHGPSYDOGBPI-IQQSWPBXSA-N | | SMILES | C12C(=O)C=C3C4[C@@H](C)[C@@H](CC[C@]4(C)CC[C@@]3(C)[C@]1(C)CCC1[C@@](C)(C(=O)O)[C@]([H])(O)CC[C@]21C)C |&1:6,8,11,15,17,22,27,32,r| | | LogP | 7.100 (est) |
| WGK Germany | 3 | | HS Code | 29189900 | | Storage Class | 11 - Combustible Solids |
| | 11-KETO-BETA-BOSWELLIC ACID Usage And Synthesis |
| Uses | A constitutent of frankincense (olibanum) with anti-inflammatory properties. It has been shown to trigger apoptosis via a pathway dependent on caspase-8 activation but independent on Fas/Fas ligand interaction in colon cancer HT-29 cells. | | Biological Activity | 37.9 μm: blocks a2780 (cis-platin resistant ovarian cancer cells) [1].11-keto-β-boswellic acid, known as kba, is a naturally occurring pentacyclic triterpene isolated from the gum resin of the tree boswellia serrata. kba is non-redox, specific leukotriene synthesis inhibitors through the inhibition of 5-lipoxygenase (5-lox) which has anti-arthritic and anti-inflammatory activities. 5-lox catalyzes essential fatty acids substrates into leukotrienes and a variety of other biologically active products. kba is a novel activator of nuclear factor erythroid-2-related factor 2 (nrf2), which protects against cerebral ischemic injury. | | in vitro | kba, concentration dependently, decreased the formation of leukotriene b4 and the synthesis of all 5-lox products from endogenous arachidonic acid in rat peritoneal neutrophils. in contrast, kba exerted no remarkable effects on the 12-lipoxygenase and cyclooxygenase activities. [2]. | | in vivo | adult male sprague–dawley rats were injected kab intraperitoneally at a dose of 25 mg/kg for 48 hours. kab remarkably decreased infarct volumes as well as apoptotic cells at 1 h, and then increased neurologic scores when applied 48 h. moreover, posttreatment with kba induced the decrease of malondialdehyde levels and the increase of protein nrf2 and heme oxygenase-1 expression in brain tissues, indicating that the nrf2/ho-1 pathway was involved in the neuroprotection of kba against oxidative stress-induced ischemic injury [3]. | | IC 50 | 35.8 μm: inhibits mcf-7 (human breast adenocarcinoma) [1]. | | references | [1]. csuk, r., barthel-niesen, a., barthel, a., schffer, r., & al-harrasi, a. 11-keto-boswellic acid derived amides and monodesmosidic saponins induce apoptosis in breast and cervical cancers cells. european journal of medicinal chemistry. 2015; 100: 98-105.
[2]. safayhi, h., mack, t. h. o. m. a. s., sabieraj, j. o. a. c. h. i. m., anazodo, m. i., subramanian, l. r., & ammon, h. p. boswellic acids: novel, specific, nonredox inhibitors of 5-lipoxygenase. journal of pharmacology and experimental therapeutics. 1992; 261(3):1143-1146.
[3]. ding, y., chen, m., wang, m., li, y., & wen, a. posttreatment with 11-keto-β-boswellic acid ameliorates cerebral ischemia–reperfusion injury: nrf2/ho-1 pathway as a potential mechanism. molecular neurobiology. 2014; 52(3): 1430-1439. |
| | 11-KETO-BETA-BOSWELLIC ACID Preparation Products And Raw materials |
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