beta-Amyrin

Base Information

• Chemical Name: beta-Amyrin
• CAS No.: 559-70-6
• Molecular Formula: C30H50O
• Molecular Weight: 426.726
• European Community (EC) Number: 209-204-6
• UNII: KM8353IPSO
• DSSTox Substance ID: DTXSID201025005
• Nikkaji Number: J6.490D
• Wikipedia: Amyrin
• Wikidata: Q27108621
• Metabolomics Workbench ID: 28753
• ChEMBL ID: CHEMBL455098
• Mol file: 559-70-6.mol

Synonyms:beta-amyrin

Chemical Property of beta-Amyrin

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 187-190 °C
• Refractive Index: 1.4910 (estimate)
• Boiling Point: 490.669 °C at 760 mmHg
• PKA: 15.18±0.70(Predicted)
• Flash Point: 217.7°C
• PSA: 20.23000
• Density: 1.014 g/cm³
• LogP: 8.16890
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 9.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 426.386166214
• Heavy Atom Count: 31
• Complexity: 790

Purity/Quality:

≥98% ^*data from raw suppliers

β-Amyrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 22
• Safety Statements: 22-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C)C
• Isomeric SMILES: C[C@@]12CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]1CC(CC2)(C)C)C
• Uses: nociceptive

Technology Process of beta-Amyrin

There total 65 articles about beta-Amyrin 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: 97.0%

(3β)-3-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-olean-12-en (129511-76-8) → beta-amyrin (559-70-6)

Guidance literature:

With zinc; In acetic acid; at 20 - 40 ℃; for 4h; Reagent/catalyst; Solvent;

DOI:10.3390/molecules23071552

Reference yield: 94.0%

β-amyrin acetate (1616-93-9,33055-28-6,64200-19-7) → beta-amyrin (559-70-6)

Guidance literature:

With ethylenediamine; In methanol; for 0.0666667h; Microwave irradiation;

DOI:10.1080/10286020.2010.507545

Reference yield: 77.0%

(3S,4R,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-3-Hydroxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde (195156-15-1) → beta-amyrin (559-70-6)

Guidance literature:

(3S,4R,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-3-Hydroxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde; With hydrazine hydrate; In ethanol; diethylene glycol; for 1h; Heating; Huang-Minlon reduction;

With potassium hydroxide; for 2h; Heating;

DOI:10.1016/j.bmc.2005.04.074

upstream raw materials:

β-amyrin palmitate

sodium ethanolate

β-amyrin acetate

β-amyrone

Downstream raw materials:

β-amyrin acetate

β-amyrin acetate

oleana-2,12-diene

1,2,7-trimethylnaphthalene

Refernces

10.1021/jo01017a002

The research explores novel rearrangement reactions of pentacyclic triterpenes, aiming to develop a general approach for synthesizing naturally occurring triterpenes like friedelin from α- and β-amyrin. The study investigates oxidative rearrangements, such as the conversion of β-amyrin to taraxerene derivatives through photooxidation and chemical reactions involving hydrogen peroxide and acids. Key chemicals include α- and β-amyrin, chromic acid, lithium aluminum hydride, and various reagents like peracetic acid and osmium tetroxide. The research concludes that specific oxidative conditions can drive rearrangements to less stable carbon skeletons, providing a method for synthesizing complex triterpenes. This approach involves coupling rearrangement steps with exothermic reactions, such as electrophilic addition to carbon-carbon double bonds, to overcome thermodynamic barriers and achieve desired triterpene structures.