Tanacetin

Base Information

• Chemical Name: Tanacetin
• CAS No.: 1401-54-3
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• UNII: 3JZ8COC2DK
• DSSTox Substance ID: DTXSID201112028
• Nikkaji Number: J9.857D
• Wikidata: Q27257350
• Mol file: 1401-54-3.mol

Synonyms:Tanacetin;1401-54-3;UNII-3JZ8COC2DK;3JZ8COC2DK;Naphtho(1,2-b)furan-2(3H)-one, decahydro-6,9a-dihydroxy-5a-methyl-3,9-bis(methylene)-, (3aS,5aS,6R,9aR,9bS)-;Naphtho(1,2-b)furan-2(3H)-one, decahydro-6,9a-dihydroxy-5a-methyl-3,9-bis(methylene)-, (3as-(3aalpha,5abeta,6beta,9aalpha,9bbeta))-;(3aS,5aS,6R,9aR,9bS)-6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one;TANACETIN [MI];CHEBI:173151;DTXSID201112028;NS00094028;Q27257350;(3aS,5aS,6R,9aR,9bS)-6,9a-dihydroxy-5a-methyl-3,9-dimethylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzouran-2-one;(3aS,5aS,6R,9aR,9bS)-Decahydro-6,9a-dihydroxy-5a-methyl-3,9-bis(methylene)naphtho[1,2-b]furan-2(3H)-one;NAPHTHO(1,2-B)FURAN-2(3H)-ONE, DECAHYDRO-6,9A-DIHYDROXY-5A-METHYL-3,9-BIS(METHYLENE)-, (3AS-(3A.ALPHA.,5A.BETA.,6.BETA.,9A.ALPHA.,9B.BETA.))-

Chemical Property of Tanacetin

Chemical Property:

• Melting Point: 205°
• PSA: 66.76000
• LogP: 1.32630
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 264.13615911
• Heavy Atom Count: 19
• Complexity: 483

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1(C(=C)CCC2O)O)OC(=O)C3=C
• Isomeric SMILES: C[C@@]12CC[C@@H]3[C@@H]([C@]1(C(=C)CC[C@H]2O)O)OC(=O)C3=C

Technology Process of Tanacetin

There total 3 articles about Tanacetin 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:

1β-hydroxy-5α-hydroperoxy-6β,7αH-eudesma-4(15),11(13)dien-12,6-olide (85847-67-2) → tanacetin (1401-54-3)

Guidance literature:

With triphenylphosphine; In acetone; for 0.5h;

Reference yield:

costunolide (553-21-9) → tanacetin (1401-54-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) m-ClC₆H₄O₃H, 2.) SOCl₂

2: 106 mg / oxygen, methylene blue / ethanol / 7 h / Irradiation

3: 40 mg / triphenylphosphine / acetone / 0.5 h

With thionyl chloride; oxygen; methylene blue; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In ethanol; acetone;

Reference yield:

1β-hydroxy-5α,6β,7αH-eudesma-4(5),11(13)-dien-12,6-olide (95782-68-6,125356-46-9,72145-13-2) → tanacetin (1401-54-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 106 mg / oxygen, methylene blue / ethanol / 7 h / Irradiation

2: 40 mg / triphenylphosphine / acetone / 0.5 h

With oxygen; methylene blue; triphenylphosphine; In ethanol; acetone;

upstream raw materials:

1β-hydroxy-5α-hydroperoxy-6β,7αH-eudesma-4(15),11(13)dien-12,6-olide

costunolide

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

Downstream raw materials:

artemin