Sinactine

Base Information

• Chemical Name: Sinactine
• CAS No.: 38853-67-7
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.391
• DSSTox Substance ID: DTXSID50959635
• Nikkaji Number: J1.238.127A,J1.238.128J,J11.691B
• Wikidata: Q27155305
• ChEMBL ID: CHEMBL5200898
• Mol file: 38853-67-7.mol

Synonyms:Tetrahydroepiberberine;Sinactine;38853-67-7;Sinactin;(+-)-Sinactine;Epiberberine, tetrahydro-;Tetrahydroepiberberine, Sinactine;12H-Benzo(a)-1,3-benzodioxolo(4,5-g)quinolizine, 6,6a,11,14-tetrahydro-8,9-dimethoxy-;16,17-dimethoxy-5,7-dioxa-1-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaene;6,6a,11,14-Tetrahydro-8,9-dimethoxy-12H-benzo(a)-1,3-benzodioxolo(4,5-g)quinolizine;522-96-3;SCHEMBL2742533;CHEMBL5200898;CHEBI:81368;DTXSID50959635;HY-N3035;AKOS025149078;MS-25169;CS-0023054;C17898;E80730;Q27155305;(13R)-6,6a,11,14-Tetrahydro-8,9-dimethoxy-12H-benzo[a]-1,3-benzodioxolo[4,5-g]quinolizine;(13S)-6,6a,11,14-Tetrahydro-8,9-dimethoxy-12H-benzo[a]-1,3-benzodioxolo[4,5-g]quinolizine;8,9-Dimethoxy-6,11,12,14-tetrahydro-2H,6aH-[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinoline

Chemical Property of Sinactine

Chemical Property:

• Appearance/Colour: yellow solid
• Melting Point: 170 - 172 °C (methanol),183 - 184 °C (ethanol)
• PSA: 40.16000
• Density: 1.33±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 3.02590
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 339.14705815
• Heavy Atom Count: 25
• Complexity: 488

Purity/Quality:

≥98% ^*data from raw suppliers

Tetrahydroepiberberine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C5=C(C=C4)OCO5)OC
• Uses: Tetrahydroepiberberine is an isoquinoline alkaloid displaying antioxidant and antibacterial activity.

Technology Process of Sinactine

There total 2 articles about Sinactine 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:

2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine (63375-81-5) → sinactine (522-96-3,22554-51-4,38853-67-7,82051-55-6)

Guidance literature:

Multi-step reaction with 6 steps

2: lithium aluminum hydride

3: triethylamine

4: stannic chloride / CH₂Cl₂ / 0 °C

5: 80 percent / Raney Ni / ethanol / Heating

6: 1) POCl₃, 2) NaBH₄

With sodium tetrahydroborate; lithium aluminium tetrahydride; tin(IV) chloride; nickel; triethylamine; trichlorophosphate; In ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)96135-5

Reference yield:

2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine (63375-81-5) → sinactine (522-96-3,22554-51-4,38853-67-7,82051-55-6)

Guidance literature:

Multi-step reaction with 7 steps

1: CH₂Cl₂ / 24 h / 20 °C

2: LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

3: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

4: SnCl₄ / CH₂Cl₂ / 1 h / 0 °C

5: 80 percent / Raney Ni / ethanol / 2 h / Heating

6: POCl₃; K₂CO₃ / acetonitrile / 0.67 h / 60 °C

7: NaBH₄ / methanol / 1 h / Heating

With sodium tetrahydroborate; lithium aluminium tetrahydride; tin(IV) chloride; nickel; potassium carbonate; triethylamine; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile; 1: Condensation / 2: Reduction / 3: Acylation / 4: Cyclization / 5: desulfurization; debromination / 6: Bischler-Napieralski reaction / 7: Reduction;

DOI:10.1248/cpb.48.399

Reference yield:

sinactine (522-96-3,22554-51-4,38853-67-7,82051-55-6) → cryptopine (482-74-6)

Guidance literature:

Multi-step reaction with 4 steps

1: PhCO₃H / CHCl₃

2: K₂CrO₄ / H₂O

4: methanol

With potassium chromate; Perbenzoic acid; In methanol; chloroform; water;

DOI:10.1039/jr9630002497

upstream raw materials:

2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine

Downstream raw materials:

cryptopine

Refernces

• 1、 Yasuda, Shingo,Hirasawa, Taeko,Hanaoka, Miyoji. "A NEW AND CONVENIENT SYNTHESIS OF PROTOBERBERINE ALKALOIDS: (+/-)-TETRAHYDROPALMATINE, (+/-)-SINACTINE, (+/-)-CANADINE AND-)-STYLOPINE". . p. 2399 - 2402. Retrieved 2007/10/02.