Bicyclogermacrene

Base Information

• Chemical Name: Bicyclogermacrene
• CAS No.: 24703-35-3
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• Metabolomics Workbench ID: 168044,168777
• Wikidata: Q27132747
• Mol file: 24703-35-3.mol

Synonyms:Bicyclogermacrene;CHEBI:63709;(1S,2E,6E,10R)-3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-diene;LMPR0103100001;C20175;Q27132747

Chemical Property of Bicyclogermacrene

Chemical Property:

• Vapor Pressure: 0.0132mmHg at 25°C
• Boiling Point: 267.8°Cat760mmHg
• Flash Point: 104.6°C
• Density: 0.861g/cm³
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 304

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CCCC(=CC2C(C2(C)C)CC1)C
• Isomeric SMILES: C/C/1=C\CC/C(=C/[C@H]2[C@H](C2(C)C)CC1)/C

Technology Process of Bicyclogermacrene

There total 2 articles about Bicyclogermacrene 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) → (E)-β-farnesene (18794-84-8) + (-)-α-bisabolol (515-69-5,23089-26-1,23178-88-3,25428-43-7,72059-10-0,72691-24-8,76738-75-5,78148-59-1,123877-54-3,26560-22-5) + (+)-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 magnesium chloride; In aq. buffer; at 30 ℃; for 2h; pH=7.5; enantioselective reaction; Mechanism; Microbiological reaction; Enzymatic reaction;

DOI:10.1042/BJ20140306

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: 57.0%

(+)-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) → spathulenol (6750-60-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform-d1; chloroform; at 25 ℃; for 0.25h; Inert atmosphere;

DOI:10.1002/chem.201403082

upstream raw materials:

farnesyl pyrophosphate

Downstream raw materials:

[1aR-(1aα,7α,7aβ,7bα)]-1a,2,3,5,6,7,7a,7b-octahydro-1,1,4,7-tetramethyl-1H-cycloprop[e]azulene

spathulenol

psiguadial A