1146-04-9

Basic information

• Product Name: illudin M
• Synonyms: illudin M;(3S)-2,3-Dihydro-3α,6β-dihydroxy-2,2,4,6-tetramethylspiro[5H-indene-5,1'-cyclopropan]-7(6H)-one;(3'S,6'R)-2',3'-Dihydro-3',6'-dihydroxy-2',2',4',6'-tetramethylspiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one
• CAS NO: 1146-04-9
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32
• Mol File: 1146-04-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 120-122.5° (Matsumoto); mp 128-130° (McMorris)
• Boiling Point: 452.4°Cat760mmHg
• Flash Point: 241.5°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 4.36E-10mmHg at 25°C
• Refractive Index: 1.593
• PKA: 12.57±0.70(Predicted)
• CAS DataBase Reference: illudin M(CAS DataBase Reference)
• NIST Chemistry Reference: illudin M(1146-04-9)
• EPA Substance Registry System: illudin M(1146-04-9)

Safety Data

• Hazardous Substances Data: 1146-04-9(Hazardous Substances Data)

Usage

Description

Illudin M is a cytotoxic sesquiterpene derived from the fungus Omphalotus illudens and Granulobasidium vellereum. It is known for its alkylating properties, which involve the covalent attachment of an alkyl group to DNA, leading to the inhibition of cell growth or replication. Illudin M has demonstrated cytotoxicity to HL-60 human leukemia cells at concentrations ranging from 6-100 nM. It serves as a base structure for the development of potential anticancer agents with reduced toxicity and enhanced efficacy. Illudin M is closely related to illudin S, which has been the subject of further research.

Uses

Used in Anticancer Applications:
Illudin M is utilized as a cytotoxic agent in the development of potential anticancer drugs. It is particularly effective against various types of cancer due to its ability to alkylate DNA, thereby inhibiting cell growth and replication. The compound has shown promise in the development of less toxic and more effective cancer treatments.
Used in Pharmaceutical Research:
Illudin M serves as a base structure for pharmaceutical research and development. Its alkylating properties and cytotoxic effects make it a valuable compound for the creation of new anticancer agents. Researchers are working on modifying the structure of illudin M to improve its efficacy and reduce potential side effects, with the ultimate goal of developing more effective cancer treatments.
Used in Drug Delivery Systems:
Similar to gallotannin, illudin M can also be incorporated into drug delivery systems to enhance its applications and efficacy against cancer cells. Various organic and metallic nanoparticles can be employed as carriers for illudin M delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes. This approach can potentially increase the effectiveness of illudin M as an anticancer agent and minimize any adverse effects associated with its use.

InChI:InChI=1/C15H20O3/c1-8-10-9(7-13(2,3)12(10)17)11(16)14(4,18)15(8)5-6-15/h7,12,17-18H,5-6H2,1-4H3/t12-,14+/m1/s1

Upstream product

• 127-09-3 sodium acetate 

Downstream Products

• 1075723-53-3 C₂₉H₃₇Cl₂NO₄ 
• 144156-48-9 (R)-4,6,6,8a-Tetramethyl-2,3,6,8a-tetrahydro-indeno[5,6-b]furan-8-one 
• 112953-12-5 Deoxyilludin M 
• 34338-99-3 Dihydroilludin M 
• 28282-65-7 dehydroilludin M 

Relevant articles and documents

Synthesis of [3H]-illudin S, [3H]-acylfulvene, [3H]and[14C]- hydroxymethylacylfulvene (MGI 114)

Tritiated derivatives of the toxic sesquiterpene illudin S (1) have been prepared by fermentation of Omphalotus illudens in the presence of [3H]- sodium acetate. [3H]-illudin S was converted to antitumor [3H]-acylfulvene (4) by treatment with dilute sulfuric acid. Antitumor [14C]- hydroxymethylacylfulvene (5) was best prepared by reacting acylfulvene with [14C]-paraformaldehyde in dilute sulfuric acid.

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