Alloaromadendrene

Base Information

• Chemical Name: Alloaromadendrene
• CAS No.: 25246-27-9
• Molecular Formula: C15H24
• Molecular Weight: 204.356
• Hs Code.: 2902909090
• European Community (EC) Number: 866-284-0
• Metabolomics Workbench ID: 178148
• Wikidata: Q105120419
• Mol file: 25246-27-9.mol

Synonyms:alloaromadendrene

Chemical Property of Alloaromadendrene

Chemical Property:

• Vapor Pressure: 0.0226mmHg at 25°C
• Refractive Index: n20/D 1.501
• Boiling Point: 258.1°Cat760mmHg
• Flash Point: 106.5°C
• PSA: 0.00000
• Density: 0.93g/cm³
• LogP: 4.27090
• Storage Temp.: 2-8°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 299

Purity/Quality:

99% ^*data from raw suppliers

(–)-Alloaromadendrene ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2C1C3C(C3(C)C)CCC2=C
• Isomeric SMILES: C[C@@H]1CC[C@H]2[C@H]1[C@H]3[C@H](C3(C)C)CCC2=C

Technology Process of Alloaromadendrene

There total 5 articles about Alloaromadendrene 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:

farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5) → 4α-hydroxygermacra-1(10),5-diene (207221-31-6) + alloaromadendrene (25246-27-9) + germacrene D (23986-74-5) + (+)-bicyclogermacrene (41437-00-7,67650-49-1,67650-90-2,79951-53-4,100762-45-6,100762-46-7,100762-48-9,100762-49-0,133005-43-3,24703-35-3)

Guidance literature:

With recombinant (His)8-tagged Medicago truncatula MtTPS₅ sesquiterpene synthase Y₅₂₆F mutant; water; magnesium chloride; In pentane; at 30 ℃; for 1.5h; pH=7.5; optical yield given as %ee; stereospecific reaction; Mechanism; aq. buffer; Enzymatic reaction;

DOI:10.1021/jo100917c

Reference yield:

methyl triphenylphosphonium bromide (27200-84-6) + (-)-apoaromadendrone (6790-66-5,14682-45-2,14917-87-4,95977-69-8,97275-30-4,97950-12-4,99147-41-8) → (+)-aromadendrene (489-39-4,552-01-2,14682-34-9,14682-39-4,14682-40-7,14682-42-9,25246-27-9,55721-09-0,72747-25-2,74036-37-6,97950-10-2,109119-91-7,125133-80-4,146389-60-8)

Guidance literature:

With dimsylsodium; Yield given. Multistep reaction; 1) dimethyl sulfoxide, r.t., 30 min., 2) ether, r.t., 2 h;

DOI:10.1016/S0040-4020(01)87904-7

Reference yield:

(-)-apoaromadendrone (6790-66-5,14682-45-2,14917-87-4,95977-69-8,97275-30-4,97950-12-4,99147-41-8) → (-)-alloaromadendrene (489-39-4,552-01-2,14682-34-9,14682-39-4,14682-40-7,14682-42-9,25246-27-9,55721-09-0,72747-25-2,74036-37-6,97950-10-2,109119-91-7,125133-80-4,146389-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / Et₃N / dimethylformamide / 48 h / Heating

2: 99 percent / Et₃N / methanol / 4 h / -20 °C

With triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)88765-2

upstream raw materials:

farnesyl pyrophosphate

methyl triphenylphosphonium bromide

(-)-apoaromadendrone

(-)-alloaromadendrone

Downstream raw materials:

spathulenol

(+)-11β-hydroxy-apoaromadendrone

[1R-(1α,3aβ,4α,7β)]-1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-azulene

ledol

Refernces

• 1、 Gijsen, Harrie J. M.,Wijnberg, Joannes B. P. A.,Stork, Gerrit A.,De Groot, Aede,De Waard, Maarten A.,Van Nistelrooy, Johannes G. M.. "The synthesis of mono- and dihydroxy aromadendrane sesquiterpenes, starting from natural (+)-aromadendrene-III". . p. 2465 - 2476. Retrieved 2007/10/02.