rac-Irofulven

Base Information

• Chemical Name: rac-Irofulven
• CAS No.: 187277-46-9
• Molecular Formula: C15H18O3
• Molecular Weight: 246.30162
• DSSTox Substance ID: DTXSID80397208,DTXSID70870055
• Mol file: 187277-46-9.mol

Synonyms:rac-Irofulven;187277-46-9;5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one;(5'S)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one;(+/-)-Hydroxymethylacylfulvene;SCHEMBL12201226;DTXSID70870055;DTXSID80397208;FT-0670418;FT-0670419;MGI 114;HMAF;6-Hydroxymethylacylfulvene;J-012052;6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-6',7'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one;6'-Hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'H)-one

Chemical Property of rac-Irofulven

Chemical Property:

• Boiling Point: 501.0±45.0 °C(Predicted)
• PKA: 12.48±0.70(Predicted)
• PSA: 57.53000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 1.66560
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 246.125594432
• Heavy Atom Count: 18
• Complexity: 558

Purity/Quality:

95% ^*data from raw suppliers

rac-Irofulven ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(C3(CC3)C(C(=O)C2=C1)(C)O)C)CO
• Uses: rac-Irofulven is a semi-synthetic antitumor agent derived from Illudin S. Inhibits DNA synthesis and induces apoptosis in tumor cells. Antineoplastic.

Technology Process of rac-Irofulven

There total 6 articles about rac-Irofulven 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: 73.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (R)-6’-hydroxy-2’,4’,6’-trimethylspiro[cyclopropane-1,5’-inden]-7’(6’H)-one (33781-60-1,125392-76-9) → [14C]-Irofulven (158440-71-2,187277-46-9)

Guidance literature:

With sulfuric acid;

DOI:10.1039/a607077i

Reference yield: 70.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + acylfulvene (33781-60-1) → (+/-)-hydroxymethylacylfulvene (187277-46-9)

Guidance literature:

With sulfuric acid; In acetone; for 20h; Ambient temperature;

DOI:10.1039/a607077i

Reference yield: 41.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (S)-6’-hydroxy-2’,4’,6’-trimethylspiro[cyclopropane-1,5’-inden]-7’(6’H)-one → (+)-irofulven (187277-46-9)

Guidance literature:

formaldehyd; With sulfuric acid; In water; at 90 ℃; for 0.5h;

(S)-6’-hydroxy-2’,4’,6’-trimethylspiro[cyclopropane-1,5’-inden]-7’(6’H)-one; In water; acetone; at 20 ℃; for 72h;

upstream raw materials:

formaldehyd

(R)-6’-hydroxy-2’,4’,6’-trimethylspiro[cyclopropane-1,5’-inden]-7’(6’H)-one

illudin S

acylfulvene

Downstream raw materials:

6-ethyl-2,5,7-trimethyl-1-methylene-1H-inden-4-ol