Ilimaquinone

Base Information

• Chemical Name: Ilimaquinone
• CAS No.: 71678-03-0
• Molecular Formula: C22H30 O4
• Molecular Weight: 358.478
• UNII: 5U0WAN3N8Q
• DSSTox Substance ID: DTXSID90221909
• Nikkaji Number: J18.883B
• Wikidata: Q27138473
• Metabolomics Workbench ID: 123617
• ChEMBL ID: CHEMBL155085
• Mol file: 71678-03-0.mol

Synonyms:ilimaquinone

Chemical Property of Ilimaquinone

Chemical Property:

• Vapor Pressure: 3.66E-11mmHg at 25°C
• Melting Point: 108-110℃ (pentane )
• Boiling Point: 478.4°C at 760 mmHg
• PKA: 2.92±0.50(Predicted)
• Flash Point: 159.9°C
• PSA: 63.60000
• Density: 1.14g/cm³
• LogP: 4.66950
• Storage Temp.: −20°C
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 358.21440943
• Heavy Atom Count: 26
• Complexity: 728

Purity/Quality:

98%Min ^*data from raw suppliers

Ilimaquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2(C(C1(C)CC3=C(C(=O)C=C(C3=O)OC)O)CCCC2=C)C
• Isomeric SMILES: C[C@H]1CC[C@]2([C@H]([C@]1(C)CC3=C(C(=O)C=C(C3=O)OC)O)CCCC2=C)C
• Description: Ilimaquinone is a natural sesquiterpene quinone that has antimicrobial, anti-HIV, anti-mitotic, and anti-inflammatory properties. In mammalian cells, 25 μM ilimaquinone reversibly induces vesiculation of Golgi membranes, blocking the secretory pathway. It inhibits the conversion of S-adenosylhomocysteine (SAH) to homocysteine by SAH hydrolase (IC50 = 40 μM). Ilimaquinone also inhibits DNA polymerase β and dual specificity phosphatase Cdc25B (IC50 = 45.2 and 92 μM, respectively) and, at 10 μM, activates gene expression through hypoxia-inducible factor-1.
• Uses: Biological probe for intracellular communications and vesicle-mediated transport. Ilimaquinone is an ADP-ribosylation factor (ARF) and β-COP to the Golgi membrane inhibitor.

Technology Process of Ilimaquinone

There total 38 articles about Ilimaquinone 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: 78.0%

[1R-(1α,2β,4aβ,8aα)]-3-[(decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl)methyl]-2,5-dimethoxy-2,5-cyclohexadiene-1,4-dione (121994-56-7) → ilimaquinone (71678-03-0)

Guidance literature:

With perchloric acid; In tetrahydrofuran; at 25 ℃; for 4h;

DOI:10.1021/ja027517q

Reference yield: 54.0%

(1R,2S,4aS)-trans-decahydro-1α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,2β,4aβ-trimethyl-5-methylene-naphthalene (213026-18-7) → ilimaquinone (71678-03-0) + [1R-(1α,2β,4aβ,8aα)]-3-[(decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl)methyl]-2,5-dimethoxy-2,5-cyclohexadiene-1,4-dione (121994-56-7) + [1R-(1α,2β,4aβ,8aα)]-3-[(decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl)methyl]-5-hydroxy-2-methoxy-2,5-cyclohexadiene-1,4-dione

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at -7 - 20 ℃; for 11h; pH=0.7 - 1.3;

DOI:10.1021/jo9805192

Reference yield: 44.0%

[1R-(1α,2β,4aβ,8aα)]-3-[(decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl)methyl]-2,5-dimethoxy-2,5-cyclohexadiene-1,4-dione (121994-56-7) → ilimaquinone (71678-03-0) + [1R-(1α,2β,4aβ,8aα)]-3-[(decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl)methyl]-5-hydroxy-2-methoxy-2,5-cyclohexadiene-1,4-dione

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 50h;

DOI:10.1002/ejoc.201700609

upstream raw materials:

2-chloro-5-methoxy-3-(1,2,4a-trimethyl-5-methylene-decahydro-naphthalen-1-ylmethyl)-[1,4]benzoquinone

(1R,2S,4aS)-trans-decahydro-1α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,2β,4aβ-trimethyl-5-methylene-naphthalene

[1R-(1α,2β,4aβ,8aα)]-3-[(decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl)methyl]-2,5-dimethoxy-2,5-cyclohexadiene-1,4-dione

2-(Pyridin-2-ylsulfanyl)-3-((1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalen-1-ylmethyl)-[1,4]benzoquinone

Downstream raw materials:

smenospongine

[1R-(1α,2β,4aβ,8aα)]-3-[(decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl)methyl]-2,5-dimethoxy-2,5-cyclohexadiene-1,4-dione

[1R-(1β,2β,4aβ,8aα)]-3-(1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthyl)methyl-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione

nakijiquinone L

Refernces

• 1、 Ling, Taotao,Poupon, Erwan,Rueden, Erik J.,Kim, Sun H.,Theodorakis, Emmanuel A.. "Unified synthesis of quinone sesquiterpenes based on a radical decarboxylation and quinone addition reaction". . p. 12261 - 12267. Retrieved 2007/10/03.
• 2、 Stahl,Kissau,Mazitschek,Huwe,Furet,Giannis,Waldmann. "Total synthesis and biological evaluation of the nakijiquinones". . p. 11586 - 11593. Retrieved 2007/10/03.