11-Hydroxy-9-methyl-3-oxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one

Base Information

• Chemical Name: 11-Hydroxy-9-methyl-3-oxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one
• CAS No.: 133613-71-5
• Molecular Formula: C11H14O3
• Molecular Weight: 194.23
• DSSTox Substance ID: DTXSID90395194
• Wikidata: Q82195123
• Mol file: 133613-71-5.mol

Synonyms:galiellalactone

Chemical Property of 11-Hydroxy-9-methyl-3-oxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one

Chemical Property:

• Boiling Point: 400.7±38.0 °C(Predicted)
• PKA: 12.48±0.40(Predicted)
• PSA: 46.53000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 1.01910
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 194.094294304
• Heavy Atom Count: 14
• Complexity: 333

Purity/Quality:

97% ^*data from raw suppliers

Galiellalactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2CCC3C2(C(=C1)C(=O)O3)O
• Description: Galiellalactone is a fungal metabolite isolated from the ascomycetes G. rufa strain A75-86 and A111-95 that inhibits IL-6-mediated JAK/STAT signal transduction in HepG2 cells with an IC50 value of 0.25-0.5 μM. The selectivity of this compound is achieved by its ability to block the binding of activated STAT3 dimers to their DNA binding sites without affecting phosphorylation of the STAT3 transcription factor. At 10-50 μM, galiellalactone exhibits dose-dependent growth inhibitory effects on prostate cancer stem cell-like cells expressing active STAT3, suggesting it may be a useful therapeutic approach to control JAK/STAT signaling.
• Uses: Galiellalactone was originally isolated from Galiella rufa as a plant growth regulator. Recently it was shown to inhibit IL-6 induced SEAP expression with IC50 values of 250-500 nM, blocking the binding of the activated Stat3 dimers to their DNA binding sites without inhibiting the tyrosine and serine phosphorylation of the Stat3 transcription factor. Galiellalactone is a STAT3 inhibitor; active in vivo. Galiellalactone is also a promising compound for the development of future prostate cancer drugs.

Technology Process of 11-Hydroxy-9-methyl-3-oxatricyclo[5.3.1.04,11]undec-1(10)-en-2-one

There total 12 articles about 11-Hydroxy-9-methyl-3-oxatricyclo[5.3.1.04,11]undec-1(10)-en-2-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: 90.0%

(R)-5-(but-3-enyl)-3-(E)-(1-propenyl)-5H-furan-2-one (408311-40-0) → (4R,5aS,7aS,7bR)-5,5a,6,7,7a,7b-hexahydro-7b-hydroxy-4-methyl-indeno[1,7-bc]furan-2(4H)-one (133613-71-5)

Guidance literature:

With Galiella rufa mycelium; sodium chloride; In methanol; water; at 24 ℃;

DOI:10.1016/S0040-4020(02)00134-5

Reference yield: 76.0%

(2aR,2a1S,4aR,5S,6R)-2a1,5-dihydroxy-6-methyl-2a1,3,4,4a,5,6-hexahydroindeno[1,7-bc]furan-1(2aH)-one → (4R,5aS,7aS,7bR)-5,5a,6,7,7a,7b-hexahydro-7b-hydroxy-4-methyl-indeno[1,7-bc]furan-2(4H)-one (133613-71-5)

Guidance literature:

(2aR,2a1S,4aR,5S,6R)-2a1,5-dihydroxy-6-methyl-2a1,3,4,4a,5,6-hexahydroindeno[1,7-bc]furan-1(2aH)-one; With pyridine; pentafluorophenoxythiocarbonyl chloride; In dichloromethane; at 20 ℃; for 3h;

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In dichloromethane; toluene; at 80 - 100 ℃; for 1h; stereoselective reaction;

DOI:10.1021/acs.joc.5b02121

Reference yield: 55.0%

(1aS,3aR,5S,7aS)-5-Methyl-1a,2,3,3a,4,5-hexahydro-1-oxa-cyclopropa[c]indene-7-carboxylic acid methyl ester (477959-81-2) → (4R,5aS,7aS,7bR)-5,5a,6,7,7a,7b-hexahydro-7b-hydroxy-4-methyl-indeno[1,7-bc]furan-2(4H)-one (133613-71-5)

Guidance literature:

(1aS,3aR,5S,7aS)-5-Methyl-1a,2,3,3a,4,5-hexahydro-1-oxa-cyclopropa[c]indene-7-carboxylic acid methyl ester; With lithium hydroxide; In tetrahydrofuran; water;

With sulfuric acid; at 40 ℃;

DOI:10.7164/antibiotics.55.663

upstream raw materials:

(R)-5-(but-3-enyl)-3-(E)-(1-propenyl)-5H-furan-2-one

(1aS,3aR,5S,7aS)-5-Methyl-1a,2,3,3a,4,5-hexahydro-1-oxa-cyclopropa[c]indene-7-carboxylic acid methyl ester

(6S,7aR)-6-Methyl-2,6,7,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

Trifluoro-methanesulfonic acid (6S,7aR)-6-methyl-2,6,7,7a-tetrahydro-1H-inden-4-yl ester

Downstream raw materials:

C₁₇H₁₇NO₃

2aβ,3-dihydrogaliellalactone

benzoic acid 6-methyl-1-oxo-2a,3,4,4a,5,6-hexahydro-1H-2-oxa-cyclopenta[cd]inden-7b-yl ester

Refernces

• 1、 Johansson, Martin,K?pcke, B?rbel,Anke, Heidrun,Sterner, Olov. "Synthesis of (-)-pregaliellalactone, conversion of (-)-pregaliellalactone to (-)-galiellalactone by mycelia of Galiella rufa". . p. 2523 - 2528. Retrieved 2002.
• 2、 Johansson, Martin,Sterner, Olov. "Synthesis of (-)-galiellalactone". . p. 663 - 665. Retrieved 2007/10/03.