beta-Boswellic acid

Base Information

• Chemical Name: beta-Boswellic acid
• CAS No.: 631-69-6
• Molecular Formula: C30H48O3
• Molecular Weight: 456.709
• Hs Code.: 2918199090
• UNII: B252M1YO2V
• DSSTox Substance ID: DTXSID2057578
• Nikkaji Number: J6.895K
• Wikidata: Q27274271
• Metabolomics Workbench ID: 72193
• ChEMBL ID: CHEMBL267225
• Mol file: 631-69-6.mol

Synonyms:beta-boswellic acid;boswellic acid

Chemical Property of beta-Boswellic acid

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 1.11E-14mmHg at 25°C
• Melting Point: 130-135°C
• Refractive Index: 1.555
• Boiling Point: 556 °C at 760 mmHg
• PKA: 4.50±0.70(Predicted)
• Flash Point: 304.1 °C
• PSA: 57.53000
• Density: 1.09 g/cm³
• LogP: 7.08950
• Storage Temp.: -20?C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 8.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 456.36034539
• Heavy Atom Count: 33
• Complexity: 878

Purity/Quality:

95%-98% ^*data from raw suppliers

Beta-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)O)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)O)C)C)[C@@H]2[C@H]1C)C)C
• Description: β-Boswellic acid is a pentacyclic triterpene originally isolated from Boswellia that has diverse bioactivities. It inhibits 5-lipoxygenase (5-LO) with an IC50 value of approximately 5 μM but is less potent than its derivative 3-acetyl-11-keto-β-boswellic acid . It inhibits cell proliferation in HL-60 cells with IC50 values of 3.7, 7.1, and 6.3 μM for DNA, RNA, and protein synthesis, respectively. In human umbilical vein endothelial cells (HUVECs) transiently deprived of oxygen and glucose, β-boswellic acid increases nitric oxide and increases phosphorylation of enzyme nitric oxide synthase (eNOS). It also increases calcium mobilization in platelets at concentrations ≥3 μM and induces platelet aggregation (EC50 = 8 μM).
• Uses: The principal constitutents of frankincense (olibanum). A specific, nonredox inhibitor of 5-lipoxygenase used to treat inflammation.

Technology Process of beta-Boswellic acid

There total 4 articles about 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: 93.0%

3-O-acetyl-β-boswellic acid (5968-70-7) → beta-boswellic acid (631-69-6)

Guidance literature:

With sodium hydroxide; In ethanol; at 25 ℃; for 12h;

DOI:10.1080/14786419.2018.1564295

Reference yield: 87.0%

11-keto-β-boswellic acid → beta-boswellic acid (631-69-6)

Guidance literature:

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

DOI:10.1080/14786419.2018.1564295

Reference yield:

→ β-boswellic acid (631-69-6,3877-93-8)

Guidance literature:

Aus Acetat III, Verseifg.;

upstream raw materials:

3-O-acetyl-β-boswellic acid

Downstream raw materials:

3-O-acetyl-β-boswellic acid

Refernces

• 1、 Balu, Devipriya,Poomani, Kumaradhas,Nagabushanam, Kalyanam,Balasubramanium, Sridhar,Ramanujam, Rajendran,Muhammed, Majeed. "Synthesis and structural proof of a potent 5-lipoxygenase inhibitor". experimental part. p. 697 - 702. Retrieved 2011/11/30.