(+)-alpha-Muurolene

Base Information

• Chemical Name: (+)-alpha-Muurolene
• CAS No.: 17627-24-6
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• DSSTox Substance ID: DTXSID80275971,DTXSID601020738
• Nikkaji Number: J259.747K
• Wikidata: Q63398997
• Mol file: 17627-24-6.mol

Synonyms:a-muuroladiene;(+)-alpha-muurolene;17627-24-6;Naphthalene,1,2,4a,5,6,8a-;B1-Cadinene;.alpha.-Muurolene;(1R,4aR,8aS)-4,7-dimethyl-1-propan-2-yl-1,2,4a,5,6,8a-hexahydronaphthalene;(-)-.alpha.-Muurolene;.alpha.-Muurolene, (-)-;alpha-muuroladiene;DTXSID80275971;CHEBI:192740;Naphthalene, 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S,4aS,8aR)-;QMAYBMKBYCGXDH-QLFBSQMISA-N;DTXSID601020738;31983-22-9;Naphthalene, 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, [1S-(1.alpha.,4a.alpha.,8a.alpha.)]-;Q63398997;1-Isopropyl-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalene, (1S,4aS,8aR)-;rel-(1R,4aR,8aS)-1,2,4a,5,6,8a-Hexahydro-4,7-dimethyl-1-(1-methylethyl)naphthalene

Chemical Property of (+)-alpha-Muurolene

Chemical Property:

• Boiling Point: 271.5±30.0 °C(Predicted)
• PSA: 0.00000
• Density: 0.876±0.06 g/cm3(Predicted)
• LogP: 4.58110
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 293

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2C(CC1)C(=CCC2C(C)C)C
• Isomeric SMILES: CC1=C[C@H]2[C@@H](CC1)C(=CC[C@@H]2C(C)C)C

Technology Process of (+)-alpha-Muurolene

There total 12 articles about (+)-alpha-Muurolene 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: 60.0%

1-mesyloxymethyl-6-methyl-4-(1'-methylethyl)-3,4,4a,7,8,8a-hexahydronaphthalene (82452-14-0,106092-22-2) → (±)-α-cadinene (483-75-0,10208-80-7,13862-36-7,17627-24-6,20085-19-2,23515-88-0,24406-05-1,31983-21-8,31983-22-9,51260-25-4,68000-45-3,82468-90-4)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 3h; Heating;

Reference yield: 45.0%

farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5) → (+)-γ-cadinene (39029-41-9) + α–cadinene (483-75-0,10208-80-7,13862-36-7,17627-24-6,20085-19-2,23515-88-0,24406-05-1,31983-21-8,31983-22-9,51260-25-4,68000-45-3,82468-90-4) + (1R,7S,10S)-4-Methylidene-7-(1-methylethyl)-10-methylbicyclo[4.4.0]dec-5-ene + (1R,7S,10S)-7-(1-Methylethyl)-4,10-dimethylbicyclo[4.4.0]deca-3,5-diene

Guidance literature:

With glycerol; magnesium chloride; In phosphate buffer; at 27 ℃; pH=7.2; Enzyme kinetics;

DOI:10.1016/j.phytochem.2005.06.012

Reference yield: 10.0%

germacrene D (105453-16-5) → (±)-α-cadinene (483-75-0,10208-80-7,13862-36-7,17627-24-6,20085-19-2,23515-88-0,24406-05-1,31983-21-8,31983-22-9,51260-25-4,68000-45-3,82468-90-4) + (±)-δ-cadinene (483-76-1,13061-82-0,16729-01-4,20085-20-5,60305-17-1,73365-79-4) + γ-cadinene (39029-41-9) + γ-muurolene (30021-74-0)

Guidance literature:

With boron trifluoride dimethyl etherate; In diethyl ether; Dimethyl ether; at 0 ℃; for 0.2h; Further byproducts given;

DOI:10.1016/S0031-9422(00)00266-1

upstream raw materials:

γ-muurolene

α-copaene

farnesyl pyrophosphate

germacrene D

Downstream raw materials:

(+)-ε-Cadinen

(4α,4aα,8aα)-decahydro-1,6-bis(methylene)-4-(1-methylethyl)naphthalene

(1R,10S)-7-(1-Methylethyl)-4,10-dimethylbicyclo[4.4.0]deca-4,6-diene

bicyclosesquiphellandrene