1,5-dihydroxy-2-(hydroxymethyl)-2,5,7-trimethylspiro[1H-indene-6,1'-cyclopropane]-4-one

Base Information

• Chemical Name: 1,5-dihydroxy-2-(hydroxymethyl)-2,5,7-trimethylspiro[1H-indene-6,1'-cyclopropane]-4-one
• CAS No.: 1149-99-1
• Molecular Formula: C15H20 O4
• Molecular Weight: 264.321
• NSC Number: 626369
• Wikidata: Q103818292
• Mol file: 1149-99-1.mol

Synonyms:NSC626369;1,5-dihydroxy-2-(hydroxymethyl)-2,5,7-trimethylspiro[1H-indene-6,1'-cyclopropane]-4-one;NSC-626369;Neuro_000256;NCI60_008311;Lampterol;UNII-EWJ0GY2H7X;(-)-Illudin S;1,5-dihydroxy-2-(hydroxymethyl)-2,5,7-trimethyl-spiro[1H-indene-6,1'-cyclopropane]-4-one;Spiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one, 2',3'-dihydro-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-

Chemical Property of 1,5-dihydroxy-2-(hydroxymethyl)-2,5,7-trimethylspiro[1H-indene-6,1'-cyclopropane]-4-one

Chemical Property:

• Vapor Pressure: 1.61E-12mmHg at 25°C
• Melting Point: 124-126℃
• Refractive Index: 1.4300 (estimate)
• Boiling Point: 509.6°Cat760mmHg
• Flash Point: 276.1°C
• PSA: 77.76000
• Density: 1.34g/cm³
• LogP: 0.71630
• Storage Temp.: -20°C, Inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 264.13615911
• Heavy Atom Count: 19
• Complexity: 540

Purity/Quality:

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

IlludinS ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C(C(C=C2C(=O)C(C13CC3)(C)O)(C)CO)O
• Description: Illudins are fungal sesquiterpenes that, through their unique DNA alkylating actions, have anticancer potential. Illudin S is a cytotoxic illudin that is converted, intracellularly, to metabolites that cause a complete block of cell cycling at the G1-S phase interface, particularly in myeloid and T-lymphocyte leukemia cells (IC50 = 6-11 nM). T-lymphocyte leukemia CEM cells that are resistant to doxorubicin , epipodophyllotoxins, and 1-β-D-arabinofuranosylcytosine display only 2-fold increased resistance to illudin S. Illudin S metabolites induce DNA damage that is not repaired by the processes that counter conventional DNA alkylating agents.
• Uses: Illudin S is potent antitumor sesquiterpene, first isolated from the fungus, Clitocybe illudens, in 1963. Illudin S is metabolically activated to reactive intermediates that bind DNA. The DNA damage appears to differ from that of other reactive metabolites. Importantly, illudin S exhibits in vitro and in vivo potency against multi-drug resistant tumours. Illudin S is a potent antitumor sesquiterpene.

Technology Process of 1,5-dihydroxy-2-(hydroxymethyl)-2,5,7-trimethylspiro[1H-indene-6,1'-cyclopropane]-4-one

There total 2 articles about 1,5-dihydroxy-2-(hydroxymethyl)-2,5,7-trimethylspiro[1H-indene-6,1'-cyclopropane]-4-one 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: 65.0%

((2'S,3'R,6'R)-3'-acetoxy-6'-hydroxy-2',4',6'-trimethyl-7'-oxo-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-inden]-2'-yl)methyl acetate (1099-42-9) → illudin S (1149-99-1) + (2'S,3'R,6'R)-6'-hydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-7'-oxo-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-inden]-3'-yl acetate

Guidance literature:

With ammonia; In methanol; at 40 ℃;

Reference yield:

sodium acetate (127-09-3) → illudin M (1146-04-9) + dehydroilludin M (28282-65-7) + illudin S (1149-99-1)

Guidance literature:

With Omphalotus illudens strain 4435; In ethanol; water; for 504h;

DOI:10.1002/(SICI)1099-1344(199804)41:4<279::AID-JLCR86>3.0.CO;2-J

Reference yield: 40.0%

illudin S (1149-99-1) → (R)-6’-hydroxy-2’,4’,6’-trimethylspiro[cyclopropane-1,5’-inden]-7’(6’H)-one (33781-60-1,125392-76-9)

Guidance literature:

With sulfuric acid; In water; at 25 ℃; for 21h;

DOI:10.1021/tx200401u

upstream raw materials:

sodium acetate

((2'S,3'R,6'R)-3'-acetoxy-6'-hydroxy-2',4',6'-trimethyl-7'-oxo-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-inden]-2'-yl)methyl acetate

Downstream raw materials:

Dihydroilludin S

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

[14C]-Irofulven

((2'S,3'R,6'R)-3',6'-dihydroxy-2',4',6'-trimethyl-7'-oxo-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-inden]-2'-yl)methyl 3,5-dinitrobenzoate

Refernces

• 1、 McMorris, Trevor C.,Yu, Jian,Herman, David M.,Kelner, Michael J.,Dawe, Robin,Minamida, Akira. "Synthesis of [3H]-illudin S, [3H]-acylfulvene, [3H]and[14C]- hydroxymethylacylfulvene (MGI 114)". . p. 279 - 285. Retrieved 2007/10/03.