27973-72-4

Basic information

• Product Name: pederin
• Synonyms: pederin
• CAS NO: 27973-72-4
• Molecular Formula: C₂₅H₄₅NO₉
• Molecular Weight: 503.629
• Mol File: 27973-72-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 112-112.5°
• Boiling Point: 636°Cat760mmHg
• Flash Point: 338.5°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 7.48E-19mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: pederin(CAS DataBase Reference)
• NIST Chemistry Reference: pederin(27973-72-4)
• EPA Substance Registry System: pederin(27973-72-4)

Safety Data

• Hazardous Substances Data: 27973-72-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A polyketide and carboxamide produced by a (Pseudomonas) bacterial endosymbiont of certain rove beetles (genus Paederus). Pederin is the agent responsible for the vesicant effects (linear or Paederus dermatitis) when the beetle is crushed against the skin. It is a powerful inhibitor of protein biosynthesis and mitosis and a potent antitumour agent.

Enzyme inhibitor

pederine and paederine, from the blister beetle Paederus fuscipes inhibits eukaryotic protein biosynthesis and mitosis, even at concentrations of 2–3 nM. 1. Carrasco, Battaner & Vazquez Meth. Enzymol. 30, 282. 2. Jiménez Trends Biochem. Sci

InChI:InChI=1/C25H45NO9/c1-14-12-25(33-9,35-16(3)15(14)2)21(28)22(29)26-23(32-8)18-11-19(27)24(4,5)20(34-18)10-17(31-7)13-30-6/h15-21,23,27-28H,1,10-13H2,2-9H3,(H,26,29)

Upstream product

• 111194-21-9 (+/-)-pederin dibenzoate 
• 85279-96-5 methyl benzoylpedimidate 
• 73787-23-2 (+)-benzoylpedamide 
• 73787-26-5 (+)-acetylpederic acid 
• 1750-73-8 2,2-dimethyl-3-oxo-butanal 
• 956117-45-6 (S)-2-chloro-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-oxoethyl benzoate 
• 175085-05-9 (S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid 
• 1271737-46-2 C₃₈H₆₃NO₁₀Si 
• 1271737-45-1 (2S,4R,6R)-6-((S)-2,3-dimethoxypropyl)-5,5-dimethyl-4-((triethylsilyl)oxy)tetrahydro-2H-pyran-2-carbonitrile 
• 1271737-42-8 (2S,4R,6R)-1-methoxy-5,5-dimethyl-6-((triethylsilyl)oxy)non-8-ene-2,4-diol 
• 1271737-44-0 (2S,4R,6R)-6-((S)-2-hydroxy-3-methoxypropyl)-5,5-dimethyl-4-((triethylsilyl)oxy)tetrahydro-2H-pyran-2-carbonitrile 
• 869964-37-4 (4S)-4-triethylsilanyloxy-3,3-dimethylhept-6-en-2-one 
• 869964-24-9 (4S)-4-hydroxy-3,3-dimethylhept-6-en-2-one 
• 956117-56-9 C₄₁H₆₉NO₁₂Si₂ 

Downstream Products

• 123483-10-3 (+)-dibenzoylpederin 

Relevant articles and documents

A new stereocontrolled synthesis of (+)-pederine. Unusual conformation around C-10-C-11 bond in pederine derivatives

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PEDERIN AND PSYMBERIN AGENTS

Compounds that include a pederin, psymberin or pederin/psymberin chimera scaffold. The pederin scaffold includes a substituent at the C10 and/or C13 position that may include a linker that may be conjugated to a targeting moiety. The psymberin scaffold in

Total synthesis of pederin and analogues

A ten-step program: The potent cytotoxin pederin and several analogues have been prepared through an efficient route that proceeds in ten steps (longest linear sequence) from isobutyraldehyde. The key transformation is a multicomponent N-acylaminal construction (see scheme) that allows for late-stage fragment coupling and diversification.

Pederin: The metallated dihydropyran approach. Stereoselective reduction of N-acylimidates via rhodium-catalysed hydroboration

A synthesis of the insect toxin pederin (1) based upon the union of metallated dihydropyran 8 with the oxamate ester derivative 9 is described. Noteworthy features include (a) a new method for the construction of metallated dihydropyrans which tolerates h