Germacrene a

Base Information

• Chemical Name: Germacrene a
• CAS No.: 28028-64-0
• Molecular Formula: C15H24
• Molecular Weight: 204.356
• DSSTox Substance ID: DTXSID301027123
• Nikkaji Number: J1.049.582B
• Wikipedia: Germacrene
• Wikidata: Q27104477
• Metabolomics Workbench ID: 28252
• Mol file: 28028-64-0.mol

Synonyms:germacrene A

Chemical Property of Germacrene a

Chemical Property:

• Vapor Pressure: 0.013mmHg at 25°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 278

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(=CCC(CC1)C(=C)C)C
• Isomeric SMILES: C/C/1=C\CC/C(=C/C[C@@H](CC1)C(=C)C)/C
• Recent ClinicalTrials: Effect of Creatine+HMB and Creatine+GAA Supplementation in Presarcopenic and Sarcopenic Individuals

Technology Process of Germacrene a

There total 8 articles about Germacrene a 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) → (S)-(-)-germacrene A (28028-64-0,28387-44-2,69460-21-5,69460-22-6,69609-31-0,69609-33-2,69686-13-1,69686-14-2,75023-40-4,83509-17-5) + 4,5-di-epi-aristolochene (123408-96-8) + (-)-valencene (724783-68-0)

Guidance literature:

With aristolochene synthase from Penicillium roqueforti; magnesium chloride; In various solvent(s); at 30 ℃; for 0.166667h; pH=7.5; Further Variations:; var. reagents; Enzyme kinetics; Product distribution;

DOI:10.1021/ja0499593

Reference yield:

farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5) → (2S,4aR,8aR)-4a,8-dimethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene (123123-37-5) + (S)-(-)-germacrene A (28028-64-0,28387-44-2,69460-21-5,69460-22-6,69609-31-0,69609-33-2,69686-13-1,69686-14-2,75023-40-4,83509-17-5) + 4,5-di-epi-aristolochene (123408-96-8) + (-)-valencene (724783-68-0)

Guidance literature:

With tris-buffer; Y₉₂F mutant aristolone synthase; 2-hydroxyethanethiol; magnesium chloride; In water; glycerol; at 30 ℃; for 1h; pH=7.5; Further Variations:; Reagents; reaction time; Product distribution;

DOI:10.1021/ja020762p

Reference yield:

farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5) → (S)-(-)-germacrene A (28028-64-0,28387-44-2,69460-21-5,69460-22-6,69609-31-0,69609-33-2,69686-13-1,69686-14-2,75023-40-4,83509-17-5) + 4,5-di-epi-aristolochene (123408-96-8)

Guidance literature:

With P_. roqueforti aristolochene synthase; 2-hydroxyethanethiol; magnesium chloride; In glycerol; at 30 ℃; Concentration; Reagent/catalyst; Kinetics; Tris buffer; Enzymatic reaction;

DOI:10.1039/c1ob06184d

upstream raw materials:

(E,Z)-farnesyl diphosphate

farnesyl pyrophosphate

Downstream raw materials:

germacra-1⁽¹⁰⁾,4,11⁽¹³⁾-trien-12-al

germacra-1⁽¹⁰⁾,4,11⁽¹³⁾-trien-12-ol

germacra-1⁽¹⁰⁾,4,11⁽¹³⁾-trien-12-oic acid

β-elemene

Refernces

• 1、 Faraldos, Juan A.,Gonzalez, Veronica,Senske, Michael,Allemann, Rudolf K.. "Templating effects in aristolochene synthase catalysis: Elimination versus cyclisation". supporting information; experimental part. p. 6920 - 6923. Retrieved 2011/11/04.
• 2、 Felicetti, Brunella,Cane, David E.. "Aristolochene synthase: Mechanistic analysis of active site residues by site-directed mutagenesis". . p. 7212 - 7221. Retrieved 2007/10/03.