Taurin

Base Information

• Chemical Name: Taurin
• CAS No.: 23522-05-6
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• European Community (EC) Number: 607-244-2
• DSSTox Substance ID: DTXSID60946258
• Nikkaji Number: J412.466I
• Wikidata: Q1541127
• Mol file: 23522-05-6.mol

Synonyms:Taurin;Gracilin;Barrelierin;23522-05-6;BRN 4785228;Eudesm-4-en-12-oic acid, 6-hydroxy-1-oxo-, gamma-lactone;3,5,5a,7,8,9b-Hexahydro-3,5a,9-trimethylnaphtho(1,2-b)furan-2,6(3H,4H)-dione (3S-(3alpha,3aalpha,5abeta,9bbeta))-;Naphtho(1,2-b)furan-2,6(3H,4H)-dione, 3,5,5a,7,8,9b-hexahydro-3,5a,9-trimethyl-, (3S-(3alpha,3aalpha,5abeta,9bbeta))-;DTXSID60946258;LS-68584;Q1541127;3,5a,9-trimethyl-3a,5,5a,7,8,9b-hexahydronaphtho[1,2-b]furan-2,6(3H,4H)-dione

Chemical Property of Taurin

Chemical Property:

• Vapor Pressure: 5.74E-07mmHg at 25°C
• Boiling Point: 411.1°Cat760mmHg
• Flash Point: 183.3°C
• PSA: 43.37000
• Density: 1.15g/cm³
• LogP: 2.64360
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 462

Purity/Quality:

99% ^*data from raw suppliers

EUDESM-4-EN-12-OIC ACID, 6-HYDROXY-1-OXO-, GAMMA-LACTONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A reproductive hazard.
• Hazard Codes: A reproductive hazard.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CCC3(C(=O)CCC(=C3C2OC1=O)C)C
• Isomeric SMILES: C[C@H]1[C@@H]2CC[C@]3(C(=O)CCC(=C3[C@H]2OC1=O)C)C
• Uses: Measuring liquids in chemical and biological laboratories.

Technology Process of Taurin

There total 15 articles about Taurin 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: 80.0%

4β-hydroxy-1-oxo-5αH,6,11βH-eudesman-6,13-olide (5090-75-5,60134-11-4,78037-37-3,95723-43-6,97549-52-5) → (+/-)-1-oxo-dihydromagnolialide (23522-05-6,54192-33-5,81124-57-4,95723-42-5,126642-72-6)

Guidance literature:

With pyridine; thionyl chloride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)98812-X

Reference yield:

3-methylcyclohexen-2-one (1193-18-6) → (+/-)-1-oxo-dihydromagnolialide (23522-05-6,54192-33-5,81124-57-4,95723-42-5,126642-72-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 1) LDA, HMPA / 1) THF, -78 deg C: 2) -20 deg C, 2 h

2: hexane / 504 h / Irradiation

3: NaBH₄ / methanol / 1 h / -20 °C

4: 1) HCl, 2) NaIO₄ aq / 1) MeOH, 1 h, RT; 2) H₂O-MeOH, 30 min, 25 deg C

5: 98 percent / triethylamine / dimethylformamide / 2 h / Ambient temperature

6: 80 percent / LiEt₃BH / tetrahydrofuran / 0.25 h / Ambient temperature

7: 96 percent / TsOH / 24 h / Ambient temperature

8: 93 percent / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

9: 97 percent / Amberlite IR 120 / methanol / 24 h / Ambient temperature

10: O₂ / Pt / H₂O / 24 h / 50 °C

11: PCC / CH₂Cl₂ / 2 h / Ambient temperature

12: 80 percent / pyridine, SOCl₂ / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; thionyl chloride; Amberlite IR 120; oxygen; lithium triethylborohydride; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; platinum; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)98812-X

Reference yield:

6-(1'-methylcarbonyl-ethyl)-3-methyl-2-cyclohexenone (83037-73-4) → (+/-)-1-oxo-dihydromagnolialide (23522-05-6,54192-33-5,81124-57-4,95723-42-5,126642-72-6)

Guidance literature:

Multi-step reaction with 11 steps

1: hexane / 504 h / Irradiation

2: NaBH₄ / methanol / 1 h / -20 °C

3: 1) HCl, 2) NaIO₄ aq / 1) MeOH, 1 h, RT; 2) H₂O-MeOH, 30 min, 25 deg C

4: 98 percent / triethylamine / dimethylformamide / 2 h / Ambient temperature

5: 80 percent / LiEt₃BH / tetrahydrofuran / 0.25 h / Ambient temperature

6: 96 percent / TsOH / 24 h / Ambient temperature

7: 93 percent / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

8: 97 percent / Amberlite IR 120 / methanol / 24 h / Ambient temperature

9: O₂ / Pt / H₂O / 24 h / 50 °C

10: PCC / CH₂Cl₂ / 2 h / Ambient temperature

11: 80 percent / pyridine, SOCl₂ / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; thionyl chloride; Amberlite IR 120; oxygen; lithium triethylborohydride; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; platinum; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)98812-X

upstream raw materials:

1-β-hydroxy-6β,7α,11β-H-eudesm-4-en-6,12-olide

1β-hydroxy-5α,6β,7αH-eudesma-4(5),11(13)-dien-12,6-olide

4β-hydroxy-1-oxo-5αH,6,11βH-eudesman-6,13-olide

3-methylcyclohexen-2-one

Downstream raw materials:

(+/-)-dihydromagnolialide

Toluene-4-sulfonic acid (3S,3aS,5aS,6R,9aR,9bS)-9a-hydroxy-3,5a-dimethyl-9-methylene-2-oxo-dodecahydro-naphtho[1,2-b]furan-6-yl ester

C₂₂H₂₈O₆S

Toluene-4-sulfonic acid (3S,3aS,5aR,6R,9bS)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester

Refernces

• 1、 Serkerov, S. V.,Aleskerova, A. N.. "TERPENOIDS OF Artemisia splendens". . p. 173 - 175. Retrieved 1991.