3-Acetyl-beta-boswellic acid

Base Information

• Chemical Name: 3-Acetyl-beta-boswellic acid
• CAS No.: 5968-70-7
• Molecular Formula: C32H50O4
• Molecular Weight: 498.747
• European Community (EC) Number: 611-863-3
• UNII: 5M3483EOU5
• ChEMBL ID: CHEMBL236906
• DSSTox Substance ID: DTXSID7057579
• Metabolomics Workbench ID: 128474
• Nikkaji Number: J38.465H
• Wikidata: Q27262544
• Mol file: 5968-70-7.mol

Synonyms:3-O-acetyl-beta-boswellic acid;acetyl-beta-boswellic acid

Chemical Property of 3-Acetyl-beta-boswellic acid

Chemical Property:

• Vapor Pressure: 2.51E-14mmHg at 25°C
• Melting Point: 157-161℃
• Refractive Index: 1.543
• Boiling Point: 566.8 °C at 760 mmHg
• PKA: 4.32±0.70(Predicted)
• Flash Point: 171.4 °C
• PSA: 63.60000
• Density: 1.09 g/cm³
• LogP: 7.66030
• Storage Temp.: -20°C Freezer
• Solubility.: Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Very Sligh
• XLogP3: 8.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 498.37091007
• Heavy Atom Count: 36
• Complexity: 985

Purity/Quality:

98% ^*data from raw suppliers

3-O-Acetyl-β-boswellic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(CCC3(C(=CCC4C3(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[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
• Uses: Boswellic acids are pentacyclic triterpenes first isolated from the resin of Boswellia plants. They have anti-inflammatory and anti-arthritic actions in mice. β-acetyl-Boswellic acid is a non-reducing inhibitor of 5-lipoxygenase (5-LO) that shows selectivity for 5-LO over 12-LO or COX. When studied as a 1:1 mixture with α-acetyl-boswellic acid, it inhibits topoisomerase II activity and arrests cell cycling or induces apoptosis in cancer cells.[Cayman Chemical]

Technology Process of 3-Acetyl-beta-boswellic acid

There total 6 articles about 3-Acetyl-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: 95.0%

beta-boswellic acid (631-69-6) + acetic anhydride (108-24-7) → 3-O-acetyl-β-boswellic acid (5968-70-7)

Guidance literature:

With dmap; In dichloromethane;

DOI:10.1016/j.bmcl.2015.11.035

Reference yield: 89.0%

beta-boswellic acid (631-69-6) + acetyl chloride (75-36-5) → 3-O-acetyl-β-boswellic acid (5968-70-7)

Guidance literature:

With pyridine; dmap; at 25 ℃; for 6h;

DOI:10.1080/14786419.2018.1564295

Reference yield: 87.0%

3-O-acetyl-11-keto-β-boswellic acid (8050-07-5) → 3-O-acetyl-β-boswellic acid (5968-70-7)

Guidance literature:

With platinum(IV) oxide; hydrogen; acetic acid; at 25 ℃; for 12h; under 63756.4 Torr;

DOI:10.1080/14786419.2018.1564295

upstream raw materials:

beta-boswellic acid

acetic anhydride

3-O-acetyl-11-keto-β-boswellic acid

acetyl chloride

Downstream raw materials:

beta-boswellic acid

acetyl-11-keto-beta-boswellic acid

3α-acetyl-β-boswellic acid methyl ester

Refernces

• 1、 Shamraiz, Umair,Hussain, Hidayat,Ur Rehman, Najeeb,Al-Shidhani, Sulaiman,Saeed, Aasim,Khan, Husain Yar,Khan, Ajmal,Fischer, Lucie,Csuk, René,Badshah, Amin,Al-Rawahi, Ahmed,Hussain, Javid,Al-Harrasi, Ahmed. "Synthesis of new boswellic acid derivatives as potential antiproliferative agents". . p. 1845 - 1852. Retrieved 2020.
• 2、 Sharma, Simmi,Gupta, Shilpa,Khajuria, Vidushi,Bhagat, Asha,Ahmed, Zabeer,Shah, Bhahwal Ali. "Analogues of boswellic acids as inhibitors of pro-inflammatory cytokines TNF-α and IL-6". supporting information. p. 695 - 698. Retrieved 2016/01/09.
• 3、 Kumar, Ajay,Shah, Bhahwal A.,Singh, Samar,Hamid, Abid,Singh, Shashank K.,Sethi, Vijay K.,Saxena, Ajit K.,Singh, Jaswant,Taneja, Subhash C.. "Acyl derivatives of boswellic acids as inhibitors of NF-κB and STATs". supporting information; experimental part. p. 431 - 435. Retrieved 2012/03/11.