Penniclavine

Base Information

• Chemical Name: Penniclavine
• CAS No.: 519-13-1
• Molecular Formula: C16H18N2O2
• Molecular Weight: 270.33
• UNII: 28Z5OY3SFA
• DSSTox Substance ID: DTXSID301020153
• Nikkaji Number: J13.978E
• Wikipedia: Penniclavine
• Wikidata: Q15633929
• Mol file: 519-13-1.mol

Synonyms:Penniclavine;Penniclavin;519-13-1;UNII-28Z5OY3SFA;28Z5OY3SFA;9,10-Didehydro-8-hydroxy-6-methylergoline-8beta-methanol;Ergoline-8beta-methanol, 9,10-didehydro-8-hydroxy-6-methyl-;DTXSID301020153;J13.978E;Q15633929;9,10-DIDEHYDRO-8.ALPHA.-HYDROXY-6-METHYLERGOLINE-8-METHANOL;Ergoline-8-methanol, 9,10-didehydro-8-hydroxy-6-methyl-, (8alpha)-;ERGOLINE-8.BETA.-METHANOL, 9,10-DIDEHYDRO-8-HYDROXY-6-METHYL-;(6aR,9S)-9-(hydroxymethyl)-7-methyl-4,6,6a,8-tetrahydroindolo[4,3-fg]quinolin-9-ol;ERGOLINE-8-METHANOL, 9,10-DIDEHYDRO-8-HYDROXY-6-METHYL-, (8.ALPHA.)-

Chemical Property of Penniclavine

Chemical Property:

• Vapor Pressure: 3.45E-11mmHg at 25°C
• Boiling Point: 509.1°C at 760 mmHg
• Flash Point: 261.7°C
• PSA: 59.49000
• Density: 1.4g/cm³
• LogP: 1.08270
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 270.136827821
• Heavy Atom Count: 20
• Complexity: 438

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)(CO)O
• Isomeric SMILES: CN1C[C@@](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)(CO)O

Technology Process of Penniclavine

There total 5 articles about Penniclavine 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: 9.2%

lysergol (602-85-7) → (2R,3S,4S,5R)-2,5-Bis-hydroxymethyl-2-((6aR,9R)-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-furan-3,4-diol + Penniclavin (519-13-1)

Guidance literature:

With succinic acid; DL-5-fluorotryptophan; Sucrose; In water; at 24 ℃; for 1296h; Claviceps purpurea 88-EP-47;

Reference yield: 9.2%

lysergol (602-85-7) + Sucrose (57-50-1) → (2R,3S,4S,5R)-2,5-Bis-hydroxymethyl-2-((6aR,9R)-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-furan-3,4-diol + Penniclavin (519-13-1)

Guidance literature:

With succinic acid; DL-5-fluorotryptophan; In water; at 24 ℃; for 1296h; Claviceps purpurea 88-EP-47;

Reference yield:

→ Penniclavin (519-13-1)

Guidance literature:

With potassium dichromate; sulfuric acid;

upstream raw materials:

lysergol

Sucrose

Refernces

• 1、 Kren, V.,Svatos, A.,Valsar, T.,Havlicek, V.,Sedmera, P.,et al.. "Fructosylation of ergot alkaloids by submerged cultures of Claviceps purpurea inhibited in alkaloid production". . p. 652 - 659. Retrieved 2007/10/02.