(3S,4R,6aR,6bS,8aR,11R,12S,14bS)-3-hydroxy-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

Base Information

• Chemical Name: (3S,4R,6aR,6bS,8aR,11R,12S,14bS)-3-hydroxy-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.: 17019-92-0
• Molecular Formula: C30H46O4
• Molecular Weight: 470.693
• Hs Code.: 29189900
• European Community (EC) Number: 605-571-5
• Metabolomics Workbench ID: 72161
• Mol file: 17019-92-0.mol

Synonyms:11-keto-beta-boswellic acid;11-keto-boswellic acid

Chemical Property of (3S,4R,6aR,6bS,8aR,11R,12S,14bS)-3-hydroxy-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

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 190～192℃
• Refractive Index: 1.561
• Boiling Point: 591.839 °C at 760 mmHg
• PKA: 4.46±0.70(Predicted)
• Flash Point: 325.767 °C
• PSA: 74.60000
• Density: 1.141 g/cm³
• LogP: 6.26850
• Solubility.: ≤5mg/ml in ethanol;25mg/ml in DMSO;25mg/ml in dimethyl formamide
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 470.33960994
• Heavy Atom Count: 34
• Complexity: 954

Purity/Quality:

95%-98% ^*data from raw suppliers

11-Keto 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(=CC(=O)C4C3(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(=O)C4[C@]3(CCC5[C@@]4(CC[C@@H]([C@]5(C)C(=O)O)O)C)C)C2[C@H]1C)C)C
• Uses: A constitutent of frankincense (olibanum) with anti-inflammatory properties. It has been shown to trigger apoptosis via a pathway dependent on caspase-8 activation but independent on Fas/Fas ligand interaction in colon cancer HT-29 cells.

Technology Process of (3S,4R,6aR,6bS,8aR,11R,12S,14bS)-3-hydroxy-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

There total 2 articles about (3S,4R,6aR,6bS,8aR,11R,12S,14bS)-3-hydroxy-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 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:

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

Guidance literature:

With methanol; potassium hydroxide; water;

Reference yield:

→ 11-keto-β-boswellic acid (17019-92-0)

Guidance literature:

Aus Saeure I mit NBS/CaCO3 in wss. Dioxan;

Reference yield: 91.0%

3,4-dimethoxycinnamic acid (2316-26-9) + 11-keto-β-boswellic acid (17019-92-0) → 3-O-(3',4'-dimethoxycinnamoyl)-11-keto-β-boswellic acid

Guidance literature:

With dicyclohexyl-carbodiimide; dmap; In dichloromethane; at 0 - 20 ℃; for 2h;

upstream raw materials:

acetyl-11-keto-beta-boswellic acid

Downstream raw materials:

acetyl-11-keto-beta-boswellic acid

Refernces