(3alpha)-3-(acetyloxy)-11-oxours-12-en-24-oic acid
(3alpha)-3-(acetyloxy)-11-oxours-12-en-24-oic acid
CAS: 67416-61-9
Molecular Formula: C32H48O5
(3alpha)-3-(acetyloxy)-11-oxours-12-en-24-oic acid - Names and Identifiers
| Name | (3alpha)-3-(acetyloxy)-11-oxours-12-en-24-oic acid |
| Synonyms | AKBA AK-BETABA BOSWELLIC ACID, ACETYL KETO ACETYL-11-KETO-B-BOSWELLIC ACID, 3 ACETYL-11-KETO-BETA-BOSWELLIC ACID Acetyl-11-keto-beta-boswellic acid 3-ACETYL-11-KETO-BETA-BOSWELLIC ACID 3-Acetyl-11-keto-beta-boswellic acid 3-O-ACETYL-11-KETO-BETA-BOSWELLIC ACID (3α)-3-Acetoxy-11-oxours-12-en-24-oic acid 3-ACETYL-11-KETONE-BETA-ACETYLBOSWELLIC ACID (3α)-3-(acetyloxy)-11-oxours-12-en-24-oic acid (3alpha)-3-(acetyloxy)-11-oxours-12-en-24-oic acid urs-12-en-24-oic acid, 3-(acetyloxy)-11-oxo-, (3α)- |
| CAS | 67416-61-9 |
| InChI | InChI=1/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 |
(3alpha)-3-(acetyloxy)-11-oxours-12-en-24-oic acid - Physico-chemical Properties
| Molecular Formula | C32H48O5 |
| Molar Mass | 512.73 |
| Density | 1.13±0.1 g/cm3(Predicted) |
| Melting Point | 271℃ |
| Boling Point | 600.3±55.0 °C(Predicted) |
| Specific Rotation(α) | (c, 4.2 in CHCl3)+87.3 |
| Flash Point | 184.4°C |
| Solubility | DMSO : ≥ 5.2 mg/mL (10.14 mM) |
| Vapor Presure | 5.85E-16mmHg at 25°C |
| Appearance | White to off-white (Solid) |
| Color | White to Off-White |
| pKa | 4.28±0.70(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.549 |
| MDL | MFCD03788777 |
| In vitro study | AKBA (Acetyl-11-keto-β-boswellic acid) significantly reduced infarct volumes and apoptotic cells, and also increased neurologic scores by elevating the Nrf2 and HO-1 expression in brain tissues in middle cerebral artery occlusion (MCAO) rats at 48 hours post reperfusion. In primary cultured neurons, AKBA increased the Nrf2 and HO-1 expression, which provided protection against OGD-induced oxidative insult. Additionally, AKBA treatment increased Nrf2 binding activity to antioxidant-response elements (ARE). AKBA (Acetyl-11-keto-β-boswellic acid) significantly inhibited human colon adenocarcinoma growth, showing arrest of the cell cycle in G1-phase and induction of apoptosis. AKBA (Acetyl-11-keto-β-boswellic acid) triggered significant lipolysis in 3T3-L1 adipocytes as shown by reduced neutral lipids in cytosol and increased free fatty acids in culture medium. Increased lipolysis by AKBA was accompanied by up-regulation of lipolytic enzymes, adipocyte triglyceride lipase (ATGL) and hormone sensitive lipase (HSL), and a decreased expression of lipid droplet stability regulator perilipin. In addition, AKBA (Acetyl-11-keto-β-boswellic acid) treatment reduced phenotypic markers of mature adipocyte aP2, adiponectin and glut-4 in mature adipocytes. |
| In vivo study | AKBA (Acetyl-11-keto-β-boswellic acid) significantly prevented the formation of intestinal adenomatous polyps without toxicity to mice. AKBA's activity both in the prevention of small intestinal and colonic polyps was more potently than aspirin. Histopathologic examination revealed that AKBA's effect, that is the reduction of polyp size and degree of dysplasia, was more prominent in larger sized polyps, especially those originating in colon. AKBA (Acetyl-11-keto-β-boswellic acid) administration in mice effectively delayed the growth of HT-29 xenografts without signs of toxicity. The activity of AKBA was more potent than that of aspirin. AKBA (Acetyl-11-keto-β-boswellic acid) exhibited anti-cancer activity in vitro and in vivo. With oral application in mice, AKBA significantly inhibited SGC-7901 and MKN-45 xenografts without toxicity. |
(3alpha)-3-(acetyloxy)-11-oxours-12-en-24-oic acid - Risk and Safety
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| HS Code | 2918300000 |
(3alpha)-3-(acetyloxy)-11-oxours-12-en-24-oic acid - Reference
| Reference Show more | 1. Ruixue Chen, Guijuan Zhang, Yi Ma, Fengjie Bie, Hongxia Fan, Min Ma, "Pharmacodynamics and Medicinal Chemistry of an External Chinese Herbal Formula for Mammary Precancerous Lesions", Evidence-Based Complementary and Alternative Medicine, vol. 2017, Articl |
(3alpha)-3-(acetyloxy)-11-oxours-12-en-24-oic acid - Reference Information
| Plant Source: | frankincense |
| Overview | 11-carbonyl-β-acetylmastic acid (acetyl-11-keto-β-bosulic acid,AKBA) can significantly inhibit the formation of 5-lipoxygenase (5-LO), thus play a strong anti-inflammatory and antioxidant effect, followed by the tumor, diseases such as ulcers and Immune Regulation show good therapeutic prospects. AKBA can inhibit the activation of NF-κB induced by TNF-α, thereby inhibiting the activation of matrix metalloproteinases, and play a protective role in blood vessels. Similar compounds of glycyrrhizic acid and Asiatic acid have been reported, based on their good antioxidant effect, vascular remodeling can be effectively inhibited and reversed by regulating the expression of different cytokines in vivo. It is an important active ingredient in Xihuang pills. figure: Xihuang pill preparation |
| identification and content determination of 11-carbonyl-β-acetyl mastic acid in Xihuang pills | method: thin layer chromatography (TLC) and high performance liquid chromatography (HPLC) were used to develop a method for the determination of 11-carbonyl-β-acetyl mastic acid in Xihuang pills. The content of 11-carbonyl-β-acetyl mastic acid was determined by HPLC. The lowest content of 11-carbonyl-β-acetyl mastic acid was 0.27%, and the highest content was 1.05%. The thin layer chromatography and high performance liquid chromatography can be used for qualitative and quantitative determination of 11-carbonyl-β-acetyl mastic acid in Xihuang pills, it can be used as a useful supplement for the microscopic identification of frankincense in the current legal inspection standard of Xihuang pills. |
| pharmacological application | carbonyl-β-acetylmastic acid (AKBA) is one of the main medicinal components of mastic extract. A certain mass concentration of AKBA for HL-60 cells can be observed in cell apoptosis of morphological changes, DNA gel electrophoresis appeared characteristic of apoptosis of small DNA degradation fragments, the early apoptosis rate was up to 39.49% and the total apoptosis rate was up to 99.9% by flow cytometry in a time-and dose-dependent manner. Therefore, AK-BA can induce HL-60 cell apoptosis in a dose-and time-dependent manner. As a monomer component of frankincense, KBA has a strong effect on inducing apoptosis of leukemia cells, and its effect is dose and time dependent. It has a good clinical application prospect in the treatment of acute myeloid leukemia. |
| references | [1] Wang alcohol, Xia Lei, Song Zhiqian, etc. Content analysis of five kinds of frankincense acids in frankincense [J]. Chinese Journal of Traditional Chinese Medicine, 2011,36( 10)1330-1332 [2] Cui Rui, Zhou Jinyun. Research progress on the chemistry and pharmacology of frankincense [J]. Chinese Pharmaceutical Journal, 2003, 38(6): 407-410 |
| biological activity | AKBA (acetyl-11-keto-β-bosulic acid) is an active compound extracted from frankincense, is a novel activator of Nrf2. |
| Use | for content determination/identification/pharmacological experiments |
Last Update：2024-04-09 21:54:55
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View History
(3alpha)-3-(acetyloxy)-11-oxours-12-en-24-oic acid
3-(Benzyloxy)-4-nitrobenzenecarboxylic acid
2-[(E)-2-(3-nitrophenyl)vinyl]quinoline
7-Bromo-3,4-dihydro-1,5-naphthyridin-2(1H)-one
297149-93-0
Phenol, 2-(1H-benzotriazol-1-ylmethyl)-6-(1,1-dimethylethyl)-4-methyl-
1-methyl-4-(2-oxazolin-2-ylamino)indazole
(1R,2S,5R)-2-(5-Amino-1,2,4-oxadiazol-3-yl)-7- oxo-1,6-diazabicyclo[3.2.1]oct-6-yl hydrogen sulfate
Lomitapide Mesylate
55000-33-4
3-(Benzyloxy)-4-nitrobenzenecarboxylic acid
2-[(E)-2-(3-nitrophenyl)vinyl]quinoline
7-Bromo-3,4-dihydro-1,5-naphthyridin-2(1H)-one
297149-93-0
Phenol, 2-(1H-benzotriazol-1-ylmethyl)-6-(1,1-dimethylethyl)-4-methyl-
1-methyl-4-(2-oxazolin-2-ylamino)indazole
(1R,2S,5R)-2-(5-Amino-1,2,4-oxadiazol-3-yl)-7- oxo-1,6-diazabicyclo[3.2.1]oct-6-yl hydrogen sulfate
Lomitapide Mesylate
55000-33-4