alpha-Amyrin

Base Information

• Chemical Name: alpha-Amyrin
• CAS No.: 638-95-9
• Molecular Formula: C30H50 O
• Molecular Weight: 426.726
• European Community (EC) Number: 211-352-1
• UNII: 30ZAG40J8N
• DSSTox Substance ID: DTXSID701025612
• Nikkaji Number: J6.928K
• Wikidata: Q2501558
• Metabolomics Workbench ID: 28757
• ChEMBL ID: CHEMBL455357
• Mol file: 638-95-9.mol

Synonyms:alpha-amyrenol;alpha-amyrin;amyrin, (3alpha)-isomer;viminalol

Chemical Property of alpha-Amyrin

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 188 C
• Refractive Index: 1.4910 (estimate)
• Boiling Point: 243 C
• PKA: 15.18±0.70(Predicted)
• Flash Point: 218.6oC
• PSA: 20.23000
• Density: 0.9600 (rough estimate)
• LogP: 8.02480
• XLogP3: 9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 426.386166214
• Heavy Atom Count: 31
• Complexity: 779

Purity/Quality:

98% ^*data from raw suppliers

α-Amyrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): UN NO.
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)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](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C)C
• General Description: Alpha-Amyrin is a pentacyclic triterpene alcohol, also known by various synonyms such as Urs-12-en-3β-ol, Viminalol, and NSC 114787. It serves as a key precursor in the synthesis of complex triterpenes, including friedelin, through oxidative rearrangements. Studies highlight its role in reactions involving chromic acid, hydrogen peroxide, and other reagents, which can transform it into less stable carbon skeletons, enabling the production of diverse triterpene derivatives. These processes often leverage exothermic steps, such as electrophilic additions, to overcome thermodynamic challenges and achieve structural modifications.

Technology Process of alpha-Amyrin

There total 34 articles about alpha-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: 99.0%

urs-12-en-3β-yl acetate (863-76-3,101915-52-0,22395-84-2) → α-amyrin (638-95-9)

Guidance literature:

With potassium hydroxide; In methanol; Reflux;

DOI:10.1002/ardp.201700178

Reference yield: 94.0%

(3β)-3-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-urs-12-en → α-amyrin (638-95-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 14h; Reagent/catalyst; Solvent;

DOI:10.3390/molecules23071552

Reference yield:

methanol (67-56-1) + 3β-12-ursen-3-yl docosanoate → behenic acid methyl ester (929-77-1) + α-amyrin (638-95-9)

Guidance literature:

With potassium hydroxide;

upstream raw materials:

urs-12-en-3-one

aluminum isopropoxide

sodium ethanolate

isopropyl alcohol

Downstream raw materials:

α-amyrin stearate

1,2,7-trimethylnaphthalene

α-Amyrinmethylether

3-cinnamoyloxy-urs-12-ene

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.