Germacrene D

Base Information

• Chemical Name: Germacrene D
• CAS No.: 23986-74-5
• Molecular Formula: C15H24
• Molecular Weight: 204.356
• Hs Code.: 2902199090
• European Community (EC) Number: 639-624-9
• UNII: V2I9ATG34E
• DSSTox Substance ID: DTXSID70881247
• Nikkaji Number: J17.213H
• Wikidata: Q27121450
• Metabolomics Workbench ID: 57180
• Mol file: 23986-74-5.mol

Synonyms:germacrene D;germacrene D, (S-(E,E))-isomer

Chemical Property of Germacrene D

Chemical Property:

• Vapor Pressure: 0.00673mmHg at 25°C
• Boiling Point: 279.7°C at 760 mmHg
• Flash Point: 111.9°C
• PSA: 0.00000
• Density: 0.85g/cm³
• LogP: 4.89130
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• 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: 266

Purity/Quality:

99%, ^*data from raw suppliers

GermacreneD(~90%)(StabilizedwithHydroquinone) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(=C)C=CC(CC1)C(C)C
• Isomeric SMILES: C/C/1=C\CCC(=C)/C=C/[C@@H](CC1)C(C)C
• Uses: Germacrene D is a plant-derived insect repellant used in the design of analogs of olifactory ligands. It is present in the extraction of essential oils from plants.

Technology Process of Germacrene D

There total 15 articles about Germacrene D 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: 91.1%

Farnesol (106-28-5) → germacrene D (23986-74-5)

Guidance literature:

With sodium carbonate; magnesium chloride; In terpene synthase buffer; at 25 ℃; for 18h; pH=10; Enzymatic reaction;

DOI:10.1002/cbic.200900671

Reference yield: 84.3%

Farnesol (106-28-5) → delta-cadinene (483-76-1,13061-82-0,16729-01-4,20085-20-5,60305-17-1,73365-79-4) + germacrene D (23986-74-5)

Guidance literature:

With sodium acetate; magnesium chloride; In terpene synthase buffer; at 25 ℃; for 18h; pH=5; Enzymatic reaction;

DOI:10.1002/cbic.200900671

Reference yield: 10.7%

Farnesol (106-28-5) → β-cubebene + cubebol + delta-cadinene (483-76-1,13061-82-0,16729-01-4,20085-20-5,60305-17-1,73365-79-4) + germacrene D (23986-74-5) + β-copaene

Guidance literature:

With potassium chloride; In terpene synthase buffer; at 25 ℃; for 18h; pH=8; Enzymatic reaction;

DOI:10.1002/cbic.200900671

upstream raw materials:

farnesyl pyrophosphate

(2E,6E)-<1,1-²H2>-farnesyl diphosphate

Farnesol

3-methyl-2-buten-1-ol

Downstream raw materials:

Germacran

γ-muurolene

(1S,3aS,3bR,6aS,6bR)-1-Isopropyl-3a-methyl-6-methylene-decahydro-cyclobutadicyclopentene

α-bourbonene

Refernces

• 1、 Touchet, Sabrina,Chamberlain, Keith,Woodcock, Christine M.,Miller, David J.,Birkett, Michael A.,Pickett, John A.,Allemann, Rudolf K.. "Novel olfactory ligands via terpene synthases". . p. 7550 - 7553. Retrieved 2015.
• 2、 Allemann, Rudolf K.,Benton, Jennifer C. R.,Dunbabin, Alice,Johnson, Luke A.,Mart, Robert J.. "Modular Chemoenzymatic Synthesis of Terpenes and their Analogues". . p. 8486 - 8490. Retrieved 2020/03/30.