6-[8-(3,4-Dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraenyl]-4-methoxy-5-methylpyran-2-one

Base Information

• Chemical Name: 6-[8-(3,4-Dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraenyl]-4-methoxy-5-methylpyran-2-one
• CAS No.: 25425-12-1
• Molecular Formula: C₂₃H₃₀O₆
• Molecular Weight: 402.488
• Hs Code.: 29322090
• European Community (EC) Number: 636-737-5
• Wikipedia: Citreoviridin
• Wikidata: Q104169659,Q105131060
• Mol file: 25425-12-1.mol

Synonyms:citreoviridin

Chemical Property of 6-[8-(3,4-Dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraenyl]-4-methoxy-5-methylpyran-2-one

Chemical Property:

• Vapor Pressure: 3.97E-16mmHg at 25°C
• Melting Point: 107-111℃
• Refractive Index: 1.4593 (estimate)
• Boiling Point: 585.1°Cat760mmHg
• PKA: 13.67±0.70(Predicted)
• Flash Point: 197.7°C
• PSA: 89.13000
• Density: 1.18g/cm³
• LogP: 3.31800
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 402.20423867
• Heavy Atom Count: 29
• Complexity: 828

Purity/Quality:

99% ^*data from raw suppliers

Citreoviridin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 63-23/24/25-36/37/38
• Safety Statements: 22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(O1)(C)C=C(C)C=CC=CC=CC2=C(C(=CC(=O)O2)OC)C)O)(C)O
• Uses: Citreoviridin is the dominant analogue of a family of tetraene mycotoxins with potent neurotoxic effects, produced by several species of Aspergillus and Penicillium. Citreoviridin inhibits mitochondrial ATPase and is a causative agent of cardiac beriberi. Citreoviridin is a mycotoxin isolated from several Penicillium species that has been shown to inhibit the mitochondrial ATP synthetase system. It inhibits soluble ATPase (KD = 4.1 μM), ADP-stimulated respiration in isolated rat liver mitochondria (KD = 0.15 μM), and ATP-driven reduction of NAD+ by succinate (KD = 2 μM). Citreoviridin has been used to target ectopic ATPase activity in cancer cells in order to modulate the metabolic activity associated with tumorigenesis.[Cayman Chemical]

Technology Process of 6-[8-(3,4-Dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraenyl]-4-methoxy-5-methylpyran-2-one

There total 10 articles about 6-[8-(3,4-Dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraenyl]-4-methoxy-5-methylpyran-2-one 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: 95.0%

6-{(1E,3E,5E,7E)-8-[(2S,3S,4S,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4,5-trimethyl-tetrahydro-furan-2-yl]-7-methyl-octa-1,3,5,7-tetraenyl}-4-methoxy-5-methyl-pyran-2-one → (-)-citreoviridin (25425-12-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.333333h;

DOI:10.1021/jo00025a042

Reference yield: 35.0%

6-<(1E,3E,5E,7E)-8-<(2S,3R,4S,5R)-3-(tert-butyldimethylsiloxy)tetrahydro-4-hydroxy-2,4,5-trimethyl-2-furyl>-7-methyl-1,3,5,7-octatetraenyl>-4-methoxy-5-methyl-2H-pyran-2-one (111905-16-9) → (-)-citreoviridin (25425-12-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h; in red light;

DOI:10.1021/ja00210a026

Reference yield: 16.0%

(2E,4E,6E)-6-methyl-7-<(2S,3R,4R,5R)-tetrahydro-3,4-dihydroxy-2,4,5-trimethyl-2-furyl>-2,4,6-heptatrienal (111957-25-6) + dimethyl <(4-methoxy-5-methyl-2-oxo-2H-pyran-6-yl)methyl>phosphonate (111905-08-9) → (-)-citreoviridin (25425-12-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; -78 deg C then 23 deg C;

DOI:10.1021/ja00210a026

upstream raw materials:

(2E,4E,6E)-6-methyl-7-<(2S,3R,4R,5R)-tetrahydro-3,4-dihydroxy-2,4,5-trimethyl-2-furyl>-2,4,6-heptatrienal

dimethyl <(4-methoxy-5-methyl-2-oxo-2H-pyran-6-yl)methyl>phosphonate

6-<(1E,3E,5E,7E)-8-<(2S,3R,4S,5R)-3-(tert-butyldimethylsiloxy)tetrahydro-4-hydroxy-2,4,5-trimethyl-2-furyl>-7-methyl-1,3,5,7-octatetraenyl>-4-methoxy-5-methyl-2H-pyran-2-one

4-methoxy-5.6-dimethyl-2H-pyran-2-one

Downstream raw materials:

(+)-citreoviral

isocitreoviridinol

epicitreoviridinol

epiisocitreoviridinol

Refernces

• 1、 Nishiyama,Shizuri,Yamamura. "Total synthesis and the absolute configuration of citreoviral and citreoviridin". . p. 231 - 234. Retrieved 2007/10/02.