Picrotin, analytical standard

Base Information

• Chemical Name: Picrotin, analytical standard
• CAS No.: 21416-53-5
• Molecular Formula: C₁₅H₁₈O₇
• Molecular Weight: 310.304
• NSC Number: 129536
• Wikidata: Q105247508
• ChEMBL ID: CHEMBL1881068
• Mol file: 21416-53-5.mol

Synonyms:Picrotin, analytical standard;MLS002707384;NSC129536;Picrotin (VAN);SMR001306771;NSC 129536;NSC-129536;Picrotin (from Anamirta cocculus seed);BRN 5302552;NCGC00017246-02;AI3-41570;MLS002207223;CHEMBL1881068;BDBM81474;CHEBI:181758;1-Hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione;NSC_5311359;NCGC00181138-01;CAS_124-87-8;LS-109757;FT-0630472;Picrotin, European Pharmacopoeia (EP) Reference Standard;3,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-, (1a.alpha.,2a.beta.,3.beta.,6.beta.,6a.beta.,8aS*,8b.beta.,9R*)-;3,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-, [1aR-(1a.alpha.,2a.beta.,3.beta.,6.beta.,6a.beta.,8aS*,8b.beta.,9S*)]-

Chemical Property of Picrotin, analytical standard

Chemical Property:

• Vapor Pressure: 1.12E-16mmHg at 25°C
• Melting Point: 256-258°C
• Boiling Point: 595.8°C at 760 mmHg
• PKA: 13.28±0.60(Predicted)
• Flash Point: 228.9°C
• PSA: 105.59000
• Density: 1.59
• LogP: -0.86720
• Storage Temp.: 2-8°C
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 310.10525291
• Heavy Atom Count: 22
• Complexity: 644

Purity/Quality:

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

Picrotin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12C3C4C(C(C1(CC5C2(O5)C(=O)O3)O)C(=O)O4)C(C)(C)O
• Description: Picrotin is a natural picrotoxane that antagonizes glycine receptors (GlyRs; IC50s = 57 and 117 μM for α1 and α2 homodimeric GlyRs, respectively). It also inhibits α3 homodimeric GlyRs. Picrotin is inactive in inhibiting γ-aminobutyric acid (GABA) type A and type C receptors. Picrotin occurs in the natural plant-derived poison picrotoxin , equimolar with picrotoxinin.
• Uses: GABAa receptor antagonist

Technology Process of Picrotin, analytical standard

There total 16 articles about Picrotin, analytical standard 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: 88.0%

13-(Phenylseleno)picrotin (119619-32-8,119678-64-7) → picrotin (21416-53-5)

Guidance literature:

With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile); In toluene; at 100 ℃; for 0.5h;

DOI:10.1021/ja00192a035

Reference yield: 84.0%

picrotoxinin (17617-45-7) → picrotin (21416-53-5)

Guidance literature:

With phenylsilane; oxygen; cobalt acetylacetonate; In isopropyl alcohol; at 23 ℃; for 2h;

DOI:10.1021/jacs.0c05042

Reference yield:

(2aS)-2a,3c-epoxy-9syn-((Ξ)-α,β-epoxy-isopropyl)-4a-hydroxy-8b-methyl-(2ar,4ac,8ac,8bc)-octahydro-1,7-dioxa-5c,8c-methano-cyclopent[cd]azulene-2,6-dione (58281-91-7,119678-62-5,119678-63-6) → picrotin (21416-53-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / NaBH₄, AcOH / ethanol / 0.5 h / Ambient temperature

2: 88 percent / tributyltin hydride / AIBN / toluene / 0.5 h / 100 °C

With sodium tetrahydroborate; tri-n-butyl-tin hydride; acetic acid; 2,2'-azobis(isobutyronitrile); In ethanol; toluene;

DOI:10.1021/ja00192a035

upstream raw materials:

(2aS)-2a,3c-epoxy-4a-hydroxy-9syn-(α-hydroxy-isopropyl)-8b-methyl-(2ar,4ac,8ac,8bc)-octahydro-1,7-dioxa-5c,8c-methano-cyclopent[cd]azulene-2,6-dione; compound with picrotoxinin

13-(Phenylseleno)picrotin

picrotin bis trifluoroacetate

picrotoxinin

Refernces

• 1、 Burdge, Hannah E.,Crossley, Steven W. M.,Lambrecht, Michael J.,Shenvi, Ryan A.,Tong, Guanghu. "Synthesis of (-)-Picrotoxinin by Late-Stage Strong Bond Activation". supporting information. . Retrieved 2020/07/08.