3-ACETYL-11-KETO-BETA-BOSWELLIC ACID

Iupac 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

CAS No.: 67416-61-9

Molecular Weight：512.72

Modify Date.: 2024-01-29 01:50

Introduction:

Acetyl-11-Keto-β-Boswellic Acid (AKBA) is an active triterpenoid compound from the extract of Boswellia serrate; a novel Nrf2 activator.IC50 value:Target: Nrf2 activatorin vitro: AKBA 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, w

3-Acetyl-11-keto-beta-boswellic acid is a triterpenoid.

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1. Names and Identifiers

: 1.1 Name; 3-ACETYL-11-KETO-BETA-BOSWELLIC ACID; 1.2 Synonyms; (3R,4R,6aR,6bS,8aR,11R,12S,12aR,14bS)-3-(acetyloxy)-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid (3R,4R,6aR,6bS,8aR,11R,12S,12aR,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 (3α)-3-(acetyloxy)-11-oxours-12-en-24-oic acid (3α)-3-Acetoxy-11-oxours-12-en-24-oic acid (3α,5ξ,9ξ)-3-Acetoxy-11-oxours-12-en-24-oic acid 3-ACETYL-11-KETONE-BETA-ACETYLBOSWELLIC ACID 3-Acetyl-11-keto-Β-boswellic Acid 3-O-ACETYL-11-KETO-BETA-BOSWELLIC ACID 3-O-Acetyl-11-keto-Β-boswellic acid 3α-Acetoxy-11-keto-β-boswellic acid ACETYL-11-KETO-B-BOSWELLIC ACID, 3 ACETYL-11-KETO-BETA-BOSWELLIC ACID AKBA AK-BETABA BOSWELLIC ACID, ACETYL KETO Urs-12-en-24-oic acid, 3-(acetyloxy)-11-oxo-, (3α)- Urs-12-en-24-oic acid, 3-(acetyloxy)-11-oxo-, (3α,5ξ,9ξ)-; View all

1.3 CAS No.: 67416-61-9

1.4 CID: 11168203

1.5 EINECS(EC#): 614-060-6

1.6 Molecular Formula: C32H48O5 (isomer)

1.7 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

1.8 InChIkey: HMMGKOVEOFBCAU-BCDBGHSCSA-N

1.9 Canonical Smiles: CC1CCC2(CCC3(C(=CC(=O)C4C3(CCC5C4(CCC(C5(C)C(=O)O)OC(=O)C)C)C)C2C1C)C)C

1.10 Isomers Smiles: C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC(=O)[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@H]([C@]5(C)C(=O)O)OC(=O)C)C)C)[C@@H]2[C@H]1C)C)C

2. Properties

2.1 Density: 1.13

2.1 Melting point: 271℃

2.1 Boiling point: 600.3 °C at 760 mmHg

2.1 Refractive index: 1.549

2.1 Flash Point: 600.3 °C at 760 mmHg

2.1 Precise Quality: 512.35000

2.1 PSA: 80.67000

2.1 logP: 6.83930

2.1 Storage: ?20°C

2.2 Color/Form: Powder

2.3 pKa: 4.28±0.70(Predicted)

2.4 StorageTemp: Sealed in dry,Store in freezer, under -20°C

3. Safety and Handling

3.1 Risk Statements: R36/37/38

3.1 Safety Statements: 26

3.1 RIDADR: NONH for all modes of transport

3.1 WGK Germany: 3

3.1 Specification

The Acetyl-11-keto-beta-boswellic acid is an organic compound with the formula C₃₂H₄₈O₅. The systematic name of this chemical is (3α)-3-(acetyloxy)-11-oxours-12-en-24-oic acid. With the CAS registry number 67416-61-9, it is also named as urs-12-en-24-oic acid, 3-(acetyloxy)-11-oxo-, (3α)-. The product's categories are Miscellaneous Natural Products; Pharmaceuticals. Besides, it should be stored at temperature of -20 °C.

Physical properties about Acetyl-11-keto-beta-boswellic acid are: (1)ACD/LogP: 8.00; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 6.76; (4)ACD/LogD (pH 7.4): 4.97; (5)ACD/BCF (pH 5.5): 40485.62; (6)ACD/BCF (pH 7.4): 663.88; (7)ACD/KOC (pH 5.5): 30680.92; (8)ACD/KOC (pH 7.4): 503.11; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 69.67 Å²; (13)Index of Refraction: 1.549; (14)Molar Refractivity: 143.22 cm³; (15)Molar Volume: 450.1 cm³; (16)Polarizability: 56.77×10^-24cm³; (17)Surface Tension: 45.7 dyne/cm; (18)Density: 1.13 g/cm³; (19)Flash Point: 184.4 °C; (20)Enthalpy of Vaporization: 97.58 kJ/mol; (21)Boiling Point: 600.3 °C at 760 mmHg; (22)Vapour Pressure: 5.85E-16 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@@]1(C)[C@H](OC(=O)C)CC[C@@]3(C)[C@H]1CC[C@]2([C@]5(/C(=C\C(=O)[C@@H]23)[C@@H]4[C@H]([C@@H](CC[C@]4(C)CC5)C)C)C)C
(2)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
(3)InChIKey: HMMGKOVEOFBCAU-BCDBGHSCBM
(4)Std. 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
(5)Std. InChIKey: HMMGKOVEOFBCAU-BCDBGHSCSA-N

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4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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5. NMR Spectrum

13C NMR : Predict

Predict 1H proton NMR

6. Synthesis Route

67416-61-9Total: 1 Synthesis Route

631-69-6 62 Suppliers

17019-92-0 53 Suppliers

5968-70-7 22 Suppliers

108-24-7

67416-61-9 53 Suppliers

Literatures:
WO2006/95355 A1, ; Page/Page column 11-12 ;
Yield: null

7. Precursor and Product

precursor:

17019-92-0

5968-70-7

631-69-6

product :

17019-92-0

8. Other Information

8.0 体外研究: 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.; View all

8.1 体内研究: 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.

8.2 Description: 3-acetyl-11-keto-β-Boswellic acid is a naturally occurring pentacyclic triterpene isolated from the gum resin exudate from the stem of the tree B. serrata (frankincense). It selectively inhibits 5-lipoxygenase (IC₅₀ = 1.5 μM) in an enzyme-directed, nonredox, and noncompetitive manner. 3-acetyl-11-keto-β-Boswellic acid and other members of the boswellic acid family have been studied for potential use in the control of inflammatory diseases, including arthritis and cancer.

8.3 Mesh Entry Terms: 3-O-acetyl-11-keto-boswellic acid

9. Computational chemical data

Molecular Weight: 512.72g/mol
Molecular Formula: C₃₂H₄₈O₅
Compound Is Canonicalized: True
XLogP3-AA: 7.2
Exact Mass: 512.35017463
Monoisotopic Mass: 512.35017463
Complexity: 1060
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 80.7
Heavy Atom Count: 37
Defined Atom Stereocenter Count: 11
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB8OAAAAAAAAAAAAAAAAAAAAAAAAAAwYMGCAAAAAADAAAAAGgAACAAADxSggAICCAAABgCIAqDSCAAAAAAgAAAACAEAAEgAABYAAQACQAAFoAAIAQOIyPCPgAAAAAAAAADAAAYAADAAAAAAAAAAAA==

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11. Realated Product Infomation

17019-92-0 11-KETO-BETA-BOSWELLIC ACID

38-26-6 BOSWELLIC ACID, KETO-

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