CID 5725

Base Information

• Chemical Name: CID 5725
• CAS No.: 471-05-6
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.339
• European Community (EC) Number: 687-304-2
• Wikidata: Q105008984,Q105008985,Q105008991
• Mol file: 471-05-6.mol

Synonyms:zerumbone

Chemical Property of CID 5725

Chemical Property:

• Vapor Pressure: 0.000295mmHg at 25°C
• Melting Point: 67-69℃
• Refractive Index: 1.468
• Boiling Point: 321.611 °C at 760 mmHg
• Flash Point: 133.945 °C
• PSA: 17.07000
• Density: 0.888 g/cm³
• LogP: 4.21440
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 218.167065321
• Heavy Atom Count: 16
• Complexity: 354

Purity/Quality:

98%,99%, ^*data from raw suppliers

Zerumbone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 43-50
• Safety Statements: 36/37-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC(C=CC(=O)C(=CCC1)C)(C)C
• Description: Zerumbone (471-05-6) is a natural sesquiterpene ketone isolated from Zingiber sp. Potentiates TRAIL-induced apoptosis via upregulation of death receptor DR4 and DR5 expression. Zerumbone induces apoptosis in T-acute lymphoblastic leukemia cells but has no cytotoxic effect on normal cells. Cell permeable.
• Uses: Zerumbone has been used:for liquid chromatography with mass spectrometry (LC-MS-MS) to investigate its potential application in the preventiontreatment of esophageal squamous cell carcinomas (ESCC)

Technology Process of CID 5725

There total 16 articles about CID 5725 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: 92.0%

(2RS,3RS)-[6E,10E]-3-(dimethylamino)-2,6,9,9-tetramethylcycloundec-6,10-dien-1-one → zerumbone (14790-72-8,14790-73-9,14985-60-5,46478-82-4,471-05-6)

Guidance literature:

(2RS,3RS)-[6E,10E]-3-(dimethylamino)-2,6,9,9-tetramethylcycloundec-6,10-dien-1-one; With 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; at 0 ℃; for 2h;

With sodium carbonate; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(03)00667-7

Reference yield: 80.0%

zerumbol (17678-70-5) → zerumbone (14790-72-8,14790-73-9,14985-60-5,46478-82-4,471-05-6)

Guidance literature:

With manganese(IV) oxide;

DOI:10.1246/cl.1981.717

Reference yield: 55.0%

→ zerumbone (14790-72-8,14790-73-9,14985-60-5,46478-82-4,471-05-6) + 2,6,9,9,13,17,20,20-octamethyl-2,6,10,13,17,21-cyclodocosahexaene-1,12-dione (116187-49-6)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; at 60 ℃; for 16h;

DOI:10.1248/cpb.35.4039

upstream raw materials:

Zerumbol

zerumbol

(2Z,4E,8E)-(S)-2,6,6,9-Tetramethyl-cycloundeca-2,4,8-trienol

(1S,2S)-1,2-epoxyhumulene

Downstream raw materials:

(E)-1,6,6,9-Tetramethyl-4,13-dioxa-tricyclo[10.1.0.0^3,5]tridec-8-en-2-one

(4Z,7E)-1,5,9,9-Tetramethyl-12-oxa-bicyclo[9.1.0]dodeca-4,7-dien-6-one

zerumbone epoxide

zerumbonaminone

Refernces

• 1、 Okamoto, Sho,Yu, Fengnian,Harada, Hisashi,Okajima, Toshihide,Hattan, Jun-Ichiro,Misawa, Norihiko,Utsumi, Ryutaro. "A short-chain dehydrogenase involved in terpene metabolism from Zingiber zerumbet". experimental part. p. 2892 - 2900. Retrieved 2012/04/11.
• 2、 Kodama,Shiobara,Sumitomo,Mitani,Ueno. "Synthesis of macrocyclic terpenoids by intramolecular cyclization. XI. Total synthesis of zerumbone". . p. 4039 - 4042,4039-4042. Retrieved 2007/10/02.