Strigol

Base Information

• Chemical Name: Strigol
• CAS No.: 11017-56-4
• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.38
• UNII: 7I81Q4NS29
• ChEMBL ID: CHEMBL2270918
• DSSTox Substance ID: DTXSID8074449
• Metabolomics Workbench ID: 53451
• Nikkaji Number: J465.547H
• Wikidata: Q27108346
• Mol file: 11017-56-4.mol

Synonyms:(+)-orobanchyl acetate;(+)-strigol;strigol

Chemical Property of Strigol

Chemical Property:

• Vapor Pressure: 2.85E-19mmHg at 25°C
• Boiling Point: 643.4°Cat760mmHg
• Flash Point: 235.6°C
• Density: 1.34g/cm³
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 346.14163842
• Heavy Atom Count: 25
• Complexity: 741

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(OC1=O)OC=C2C3CC4=C(C3OC2=O)C(CCC4O)(C)C
• Isomeric SMILES: CC1=C[C@@H](OC1=O)O/C=C/2\[C@H]3CC4=C([C@H]3OC2=O)C(CC[C@@H]4O)(C)C

Technology Process of Strigol

There total 22 articles about Strigol 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: 70.0%

(3aRS)-8,8-dimethyl-3-((SR,E)-4-methyl-5-oxo-2,5-dihydro-furan-2-yloxymethylene)-(3ar,8bc)-3,3a,4,5,6,7,8,8b-octahydro-indeno<1,2-b>furan-2-one (139540-45-7,139628-05-0) → (3aR*,5R*,8bS*,2'R*)-3-[(E)-2',5'-Dihydro-4'-methyl-5'-oxo-2'-furanyloxymethylene]-5-hydroxy-8,8-dimethyl-3,3a,4,5,6,7,8,8b-octahydroindeno[1,2-b]furan-2-one (11017-56-4,51820-11-2,52389-58-9,52389-59-0,56993-70-5,56993-71-6,98049-12-8,133645-87-1)

Guidance literature:

With selenium(IV) oxide; In 1,4-dioxane; at 80 ℃; for 5h;

DOI:10.1055/s-2000-8230

Reference yield: 70.0%

(+/-)-5-deoxy-strigol (139540-45-7,139628-05-0) → (+/-)-5-epi-strigol (11017-56-4,51820-11-2,52389-58-9,52389-59-0,56993-70-5,56993-71-6,98049-12-8,133645-87-1)

Guidance literature:

With selenium(IV) oxide; In 1,4-dioxane; at 80 ℃; for 5h;

DOI:10.1055/s-2000-8230

Reference yield: 35.0%

2-bromo-4-methyl-2H-furan-5-one (59488-94-7) + Methyl formate (107-31-3) + ((1SR,2RS,4RS)-1,4-dihydroxy-7,7-dimethyl-2,3,4,5,6,7-hexahydroinden-2-yl)-9,1-lactone (51820-15-6) → (3aR*,5R*,8bS*,2'R*)-3-[(E)-2',5'-Dihydro-4'-methyl-5'-oxo-2'-furanyloxymethylene]-5-hydroxy-8,8-dimethyl-3,3a,4,5,6,7,8,8b-octahydroindeno[1,2-b]furan-2-one (11017-56-4,51820-11-2,52389-58-9,52389-59-0,56993-70-5,56993-71-6,98049-12-8,133645-87-1) + (+/-)-5-epi-strigol (11017-56-4,51820-11-2,52389-58-9,52389-59-0,56993-70-5,56993-71-6,98049-12-8,133645-87-1)

Guidance literature:

Methyl formate; ((1SR,2RS,4RS)-1,4-dihydroxy-7,7-dimethyl-2,3,4,5,6,7-hexahydroinden-2-yl)-9,1-lactone; With sodium hydride;

2-bromo-4-methyl-2H-furan-5-one;

DOI:10.1055/s-2000-8230

upstream raw materials:

(3aR*,5S*,8bS*,2'R*)-3-[(E)-2',5'-Dihydro-4'-methyl-5'-oxo-2'-furanyloxymethylene]-5-hydroxy-8,8-dimethyl-3,3a,4,5,6,7,8,8b-octahydroindeno[1,2-b]furan-2-one

2-bromo-4-methyl-2H-furan-5-one

Methyl formate

(+/-)-(3aR*,5S*,8bS*)-5-hydroxy-8,8-dimethyl-3,3a,4,5,6,7,8,8b-octahydroindeno[1,2-b]furan-2-one