Tutin

Base Information

• Chemical Name: Tutin
• CAS No.: 2571-22-4
• Molecular Formula: C₁₅H₁₈O₆
• Molecular Weight: 294.304
• European Community (EC) Number: 808-861-1
• UNII: B69P754702
• DSSTox Substance ID: DTXSID30180400
• Nikkaji Number: J9.962G
• Wikipedia: Tutin_(toxin)
• Wikidata: Q7856945
• Metabolomics Workbench ID: 156528
• ChEMBL ID: CHEMBL297057
• Mol file: 2571-22-4.mol

Synonyms:2a,3a-epoxy-3a,4a,5,6,7,7a-hexahydro-3a alpha,6 beta,7 beta-trihydroxy-5 alpha-isopropyl-7a alpha- methylspiro(indan-1,2'-oxirane) gamma-lactone;tutin

Chemical Property of Tutin

Chemical Property:

• Melting Point: 204 - 205 °C (hexane)
• Refractive Index: 1.4359 (estimate)
• Boiling Point: 356.07°C (rough estimate)
• PKA: 12.83±0.70(Predicted)
• Flash Point: 212.6oC
• PSA: 91.82000
• Density: 1.1975 (rough estimate)
• LogP: -0.61780
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 294.11033829
• Heavy Atom Count: 21
• Complexity: 603

Purity/Quality:

CoriariaLactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1C2C(C3(C4(CO4)C5C(C3(C1C(=O)O2)O)O5)C)O
• Isomeric SMILES: CC(=C)[C@@H]1[C@@H]2[C@H]([C@]3([C@@]4(CO4)[C@H]5[C@@H]([C@]3([C@H]1C(=O)O2)O)O5)C)O
• Uses: Coriaria Lactone can be used in biological study for effects of tutin and its derivatives on GAD and GABA-T in Pseudelatia separata tested as novel active ingredients for pest control. It is also utilized in agricultural use for anti-feedant activities and effects of tutin and its derivatives on mythimna separata and its physiological parameters.

Technology Process of Tutin

There total 13 articles about Tutin 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: 99.0%

2,2,2-trichloroethoxycarbonyl α-bromotutin (93178-02-0,112136-61-5) → tutin (17617-47-9,2571-22-4,79029-98-4)

Guidance literature:

With ammonium chloride; zinc; In ethanol; for 1.5h; Heating;

DOI:10.1016/S0040-4039(01)91191-8 DOI:10.1016/S0040-4020(01)88159-X

Reference yield:

C15H20Br2O3 (90123-12-9) → tutin (17617-47-9,2571-22-4,79029-98-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 96 percent / pyridine; acetonitrile / 0.67 h / 0 °C

2: 76 percent / potassium superoxide, dicyclohexyl-18-crown-6 / dimethylsulfoxide; dimethylformamide / 0.25 h / 0 °C

3: 57 percent / Pb(OAc)4 / benzene / 7 h / Heating

4: 1) CaH₂; 2) Bu₄NBr, CaH₂ / 1) MeCN, RT, 30 min; 2) MeCN, 40 deg C, 4 h

5: 99 percent / Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

6: 90 percent / K₂CO₃ / methanol / 3.5 h / 0 °C

7: 99 percent / pyridine / 1.5 h / Ambient temperature

8: 43 percent / Na₂HPO₄*12H₂O, CF₃CO₃H / CH₂Cl₂ / 20 h / 35 °C

9: 73 percent / RuCl₃*H₂O, NaIO₄, phosphate buffer (pH 6.9) / CCl₄; acetonitrile / 24 h / 40 °C

10: 99 percent / Zn, NH₄Cl / ethanol / 1.5 h / Heating

With lead(IV) acetate; perhydrodibenzo-18-crown-6; ruthenium trichloride; potassium superoxide; sodium periodate; disodium hydrogenphosphate; phosphate buffer; calcium hydride; trifluoroacetyl peroxide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; potassium carbonate; ammonium chloride; zinc; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4020(01)88159-X

Reference yield:

C21H34Br2O3Si (110673-51-3) → tutin (17617-47-9,2571-22-4,79029-98-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 76 percent / potassium superoxide, dicyclohexyl-18-crown-6 / dimethylsulfoxide; dimethylformamide / 0.25 h / 0 °C

2: 57 percent / Pb(OAc)4 / benzene / 7 h / Heating

3: 1) CaH₂; 2) Bu₄NBr, CaH₂ / 1) MeCN, RT, 30 min; 2) MeCN, 40 deg C, 4 h

4: 99 percent / Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

5: 90 percent / K₂CO₃ / methanol / 3.5 h / 0 °C

6: 99 percent / pyridine / 1.5 h / Ambient temperature

7: 43 percent / Na₂HPO₄*12H₂O, CF₃CO₃H / CH₂Cl₂ / 20 h / 35 °C

8: 73 percent / RuCl₃*H₂O, NaIO₄, phosphate buffer (pH 6.9) / CCl₄; acetonitrile / 24 h / 40 °C

9: 99 percent / Zn, NH₄Cl / ethanol / 1.5 h / Heating

With lead(IV) acetate; perhydrodibenzo-18-crown-6; ruthenium trichloride; potassium superoxide; sodium periodate; disodium hydrogenphosphate; phosphate buffer; calcium hydride; trifluoroacetyl peroxide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; potassium carbonate; ammonium chloride; zinc; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4020(01)88159-X

upstream raw materials:

2,2,2-trichloroethoxycarbonyl α-bromotutin

C₁₅H₂₀Br₂O₃

C₁₇H₂₁BrO₅

C₂₁H₃₄Br₂O₃Si

Refernces

• 1、 Wakamatsu, Kazumasa,Kigoshi, Hideo,Niiyama, Kenji,Niwa, Haruki,Yamada, Kiyoyuki. "STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-TUTIN, A TOXIC SESQUITERPENE OF PICROTOXANE-TYPE". . p. 3873 - 3874. Retrieved 2007/10/02.