3-ACETYL-11-KETO-beta-BOSWELLIC ACID

Base Information

• Chemical Name: 3-ACETYL-11-KETO-beta-BOSWELLIC ACID
• CAS No.: 67416-61-9
• Deprecated CAS: 187945-03-5
• Molecular Formula: C32H48O5
• Molecular Weight: 512.73
• Hs Code.: 2918300000
• European Community (EC) Number: 614-060-6
• UNII: BS16QT99Q1
• DSSTox Substance ID: DTXSID601303401
• Nikkaji Number: J38.478J
• Wikidata: Q27274850
• Metabolomics Workbench ID: 128478
• ChEMBL ID: CHEMBL237111
• Mol file: 67416-61-9.mol

Synonyms:3-O-acetyl-11-keto-boswellic acid;acetyl-11-keto-beta-boswellic acid;acetyl-11-keto-boswellic acid;acetyl-11-ketoboswellic acid;AcKBA;AKBA cpd

Chemical Property of 3-ACETYL-11-KETO-beta-BOSWELLIC ACID

Chemical Property:

• Vapor Pressure: 5.85E-16mmHg at 25°C
• Melting Point: 271℃
• Refractive Index: 1.549
• Boiling Point: 600.3 °C at 760 mmHg
• PKA: 4.28±0.70(Predicted)
• Flash Point: 184.4 °C
• PSA: 80.67000
• Density: 1.13 g/cm³
• LogP: 6.83930
• Storage Temp.: −20°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 512.35017463
• Heavy Atom Count: 37
• Complexity: 1060

Purity/Quality:

≥98% ^*data from raw suppliers

3-Acetyl-11-keto-β-boswellic Acid ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(CCC3(C(=CC(=O)C4C3(CCC5C4(CCC(C5(C)C(=O)O)OC(=O)C)C)C)C2C1C)C)C
• Isomeric 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
• 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.
• Uses: 3-Acetyl-11-keto-β-boswellic Acid (AKBA), be used in the place of the non-steroidal anti-inflammatory drug. AKBA, also inhibits human gastric carcinoma growth through modulation of the Wnt/β-catenin signaling pathway. It can be used as an anticancer agent.

Technology Process of 3-ACETYL-11-KETO-beta-BOSWELLIC ACID

There total 2 articles about 3-ACETYL-11-KETO-beta-BOSWELLIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

β-boswellic acid (631-69-6,3877-93-8) + 11-keto-β-boswellic acid (17019-92-0) + 3-O-acetyl-β-boswellic acid (5968-70-7) + acetic anhydride (108-24-7) → acetyl-11-keto-beta-boswellic acid (67416-61-9)

Guidance literature:

β-boswellic acid; 11-keto-β-boswellic acid; 3-O-acetyl-β-boswellic acid; acetic anhydride; With pyridine; at 20 - 65 ℃; for 3h;

With chromium(VI) oxide; acetic anhydride; In acetic acid; at 40 ℃; for 2h; Product distribution / selectivity;

Reference yield:

→ acetyl-11-keto-beta-boswellic acid (67416-61-9)

Guidance literature:

Aus Saeure VII mit Ac2O/Py.;

Reference yield:

acetyl-11-keto-beta-boswellic acid (67416-61-9) → 11-keto-β-boswellic acid (17019-92-0)

Guidance literature:

With methanol; potassium hydroxide; water;

upstream raw materials:

β-boswellic acid

11-keto-β-boswellic acid

3-O-acetyl-β-boswellic acid

acetic anhydride

Downstream raw materials:

11-keto-β-boswellic acid

Refernces