alpha-Bergamotene

Base Information

• Chemical Name: alpha-Bergamotene
• CAS No.: 17699-05-7
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• European Community (EC) Number: 241-702-9
• DSSTox Substance ID: DTXSID90864411
• Nikkaji Number: J1.526.550G,J1.526.551E,J38.585I
• Wikidata: Q27132146
• Mol file: 17699-05-7.mol

Synonyms:alpha-bergamotene;cis-alpha-bergamotene;trans-alpha-bergamotene

Chemical Property of alpha-Bergamotene

Chemical Property:

• Vapor Pressure: 0.021mmHg at 25°C
• Boiling Point: 259.5°Cat760mmHg
• Flash Point: 100.6°C
• PSA: 0.00000
• Density: 0.881g/cm³
• LogP: 4.72520
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 304

Purity/Quality:

99% ^*data from raw suppliers

2,6-DIMETHYL-6-(4-METHYL-3-PENTENYL)BICYCLO[3.1.1]HEPT-2-ENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC2CC1C2(C)CCC=C(C)C

Technology Process of alpha-Bergamotene

There total 4 articles about alpha-Bergamotene 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: 55.0%

→ trans-α-bergamotene (13474-59-4,14087-02-6,17699-05-7,17829-53-7,18252-46-5,23971-87-1,35334-58-8,64727-43-1)

Guidance literature:

With hydrogen iodide; In benzene; for 1h;

DOI:10.1021/jo00254a017

Reference yield: 54.0%

β-trans-bergamotene (55123-21-2) → trans-α-bergamotene (13474-59-4,14087-02-6,17699-05-7,17829-53-7,18252-46-5,23971-87-1,35334-58-8,64727-43-1)

Guidance literature:

With hydrogen iodide; In benzene; for 2.5h;

DOI:10.1021/jo00254a017

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) + racemic zingiberene (38738-45-3) + 7‐epi‐sesquithujene (159407-35-9) + sesquisabinene B (1431636-59-7) + (S)-1-methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene (495-61-4) + (+/-)-β-curcumene (72345-84-7) + (+)-(2S,6S,7S)-sesquithujene (1309585-05-4) + [E]-γ-bisabolene (53585-13-0) + trans‐α‐bergamotene (13474-59-4,14087-02-6,17699-05-7,17829-53-7,18252-46-5,35334-58-8,64727-43-1,23971-87-1) + γ-curcumene (451-55-8) + sesquisabinene A + (R)-(-)-trans-nerolidol (142-50-7,1119-38-6,2211-29-2,3790-78-1,7212-44-4,17430-12-5,35944-21-9,40716-66-3,53991-23-4,77171-59-6,132958-73-7,77551-75-8) + trans-α-bergamotene (13474-59-4,14087-02-6,17699-05-7,17829-53-7,18252-46-5,23971-87-1,35334-58-8,64727-43-1)

Guidance literature:

With sodium tungstate; recombinant terpene synthases TPS₄-B₇₃ from Zea mays; sodium fluoride; magnesium chloride; In pentane; at 30 ℃; for 0.333333h; pH=7; Reagent/catalyst; Inert atmosphere; Enzymatic reaction;

DOI:10.1039/c4cc10395e

upstream raw materials:

farnesyl pyrophosphate

β-trans-bergamotene

Refernces

• 1、 Snider, Barry B.,Beal, Richard B.. "Total Synthesis of Sesquiterpenes via Intramolecular Ketene Cycloadditions: Isocomene and α-cis- and α-trans-Bergamotenes, an Approach to Seychellene". . p. 4508 - 4515. Retrieved 2007/10/02.