Germacrene B

Base Information

• Chemical Name: Germacrene B
• CAS No.: 15423-57-1
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• UNII: ML9S6L9M3X
• ChEMBL ID: CHEMBL448125
• Metabolomics Workbench ID: 28256
• Nikkaji Number: J16.137C
• Wikidata: Q27106722
• Mol file: 15423-57-1.mol

Synonyms:Germacrene B;(E,E)-germacrene B;(1E,4E)-germacrene B;Germacra-1(10),4,7(11)-triene;15423-57-1;CHEBI:5337;(1E,5E)-1,5-dimethyl-8-propan-2-ylidenecyclodeca-1,5-diene;Germacra-1(10),4,7(11)-triene, (E,E)-;(1E,5E)-1,5-dimethyl-8-(propan-2-ylidene)cyclodeca-1,5-diene;1,5-Cyclodecadiene, 1,5-dimethyl-8-(1-methylethylidene)-, (1E,5E)-;trans,trans-germacrene B;ML9S6L9M3X;1,5-Cyclodecadiene, 1,5-dimethyl-8-(1-methylethylidene)-, (E,E)-;(E,E)-germacra-1(10),4,7(11)-triene;(1E,4E)-germacra-1(10),4,7(11)-triene;1,5-Dimethyl-8-(1-methylethylidene)-1,5-cyclodecadiene;(1E,5E)-8-isopropylidene-1,5-dimethylcyclodeca-1,5-diene;CHEMBL448125;GXEGJTGWYVZSNR-LBJJKJHXSA-N;GXEGJTGWYVZSNR-SJRHNVSNSA-N;LMPR0103090007;NS00121785;C09672;Q27106722;1,5-Dimethyl-8-(1-methylethylidene)-1,5-cyclodecadiene #;(E,E)-1,5-Dimethyl-8-(1-methylethylidene)-1,5-cyclodecadiene;(1E,5E)-1,5-DIMETHYL-8-(1-METHYLETHYLIDENE)-1,5-CYCLODECADIENE

Chemical Property of Germacrene B

Chemical Property:

• Vapor Pressure: 0.00435mmHg at 25°C
• Boiling Point: 287.2°C at 760 mmHg
• Flash Point: 115.6°C
• PSA: 0.00000
• Density: 0.844g/cm³
• LogP: 5.17950
• 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: 296

Purity/Quality:

99.90% ^*data from raw suppliers

GermacreneB ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(=CCC(=C(C)C)CC1)C
• Isomeric SMILES: C/C/1=C\CC/C(=C/CC(=C(C)C)CC1)/C
• Uses: Germacrene B is a sesquiterpene and an essential oil component found in a variety of plants, and has been shown to have functional antioxidant, antiradical and antimicrobial properties.

Technology Process of Germacrene B

There total 15 articles about Germacrene B 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: 82.0%

2,2-dibromopropane (594-16-1) + (E,E)-4,8-dimethyl-3,7-cyclodecadien-1-one (250207-21-7) → germacrene B (15423-57-1,17091-09-7,32663-54-0,69460-23-7,69609-32-1)

Guidance literature:

With chromium chloride; samarium; samarium diiodide; In tetrahydrofuran; at 20 ℃; for 0.5h;

Reference yield:

(1Z,7E)-4-Isopropylidene-7-methyl-cyclodeca-1,7-dienecarbaldehyde (196401-57-7) → germacrene B (15423-57-1,17091-09-7,32663-54-0,69460-23-7,69609-32-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Red-Al / toluene / 0.25 h / -78 °C

2: 1.) N,N,N',N'-tetramethylethylenediamine, BuLi, 2.) TMPDCl, 3.) Li, EtNH₂ / 1) THF, hexane, 78 deg C, 15 min; 2) THF, hexane, -78 deg C, 5 min, rt, 1 h; 3) THF, hexane, 0 deg C, 25 min

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; TMPDCl; lithium; ethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene;

DOI:10.1021/jo970901z

Reference yield:

Farnesol (106-28-5) → germacrene B (15423-57-1,17091-09-7,32663-54-0,69460-23-7,69609-32-1)

Guidance literature:

Multi-step reaction with 10 steps

1: Ph₃P; CCl₄ / 1 h / Heating

2: m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 0 °C

3: 72 percent / HIO₄*2H₂O / tetrahydrofuran; diethyl ether / 1 h / 0 °C

4: KCN*18-crown-6 / 12 h / 4 °C

5: PhCH₂NMe₃F / H₂O; tetrahydrofuran / 2 h / 20 °C

6: p-TsOH / benzene / 3 h / 0 °C

7: 48 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / 70 °C

8: pyridinium p-toluenesulfonate / methanol / 6 h / 40 °C

9: NaOH / H₂O; diethyl ether / 0.05 h

10: 82 percent / Sm; SmI₂; CrCl₃ / tetrahydrofuran / 0.5 h / 20 °C

With tetrachloromethane; chromium chloride; sodium hydroxide; samarium; samarium diiodide; (K-18-crown-6 ether) cyanide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; trimethyl(benzyl)ammonium fluoride; toluene-4-sulfonic acid; periodic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; benzene; 1: Chlorination / 2: Epoxidation / 3: Oxidation / 4: Addition / 5: Hydrolysis / 6: Etherification / 7: Cyclization / 8: Deetherification / 9: Hydrolysis / 10: Alkylation;

upstream raw materials:

(3E,7E)-3,7-dimethyl-10-(1-methylethylidene)-3,7-cyclodecanedien-1-ol

((1Z,7E)-4-Isopropylidene-7-methyl-cyclodeca-1,7-dienyl)-methanol

2,2-dibromopropane

(E,E)-4,8-dimethyl-3,7-cyclodecadien-1-one

Downstream raw materials:

(4aR,8aS)-4a-methyl-1-methylene-7-(propan-2-ylidene)decahydronaphthalene

(4aR,8aR)-5,8a-dimethyl-3-propan-2-ylidene-1,2,4,4a,7,8-hexahydronaphthalene

selina-3,7(11)-diene

rac-eudesm-7⁽¹¹⁾-en-4-ol

Refernces

• 1、 Muto, Shin-Etsu,Nishimura, Yutaka,Mori, Kenji. "Pheromone synthesis, CXCVI. Synthesis of germacrene-B and its extension to the synthesis of (±)-9-methylgermacrene-B, the racemate of the male- produced sex pheromone of the sandfly Lutzomyia longipalpis from Lapinha, Brazil". . p. 2159 - 2165. Retrieved 2007/10/03.
• 2、 Piet, Dennis P.,Schrijvers, Robert,Franssen, Maurice C. R.,De Groot, Aede. "Biotransformation of germacrane epoxides by Cichorium intybus". . p. 6303 - 6314. Retrieved 2007/10/02.