Sarcophine

Base Information

• Chemical Name: Sarcophine
• CAS No.: 55038-27-2
• Molecular Formula: C20H28O3
• Molecular Weight: 316.4345
• DSSTox Substance ID: DTXSID001318397
• Nikkaji Number: J28.555B
• Wikidata: Q76386367
• Metabolomics Workbench ID: 141796
• ChEMBL ID: CHEMBL518855
• Mol file: 55038-27-2.mol

Synonyms:sarcophine

Chemical Property of Sarcophine

Chemical Property:

• Vapor Pressure: 4.15E-09mmHg at 25°C
• Melting Point: 133-133.5℃
• Boiling Point: 472.8°Cat760mmHg
• Flash Point: 203.5°C
• PSA: 38.83000
• Density: 1.08g/cm³
• LogP: 4.63260
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 316.20384475
• Heavy Atom Count: 23
• Complexity: 596

Purity/Quality:

Sarcophine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC2(C(O2)CCC(=CC3C(=C(C(=O)O3)C)CC1)C)C
• Isomeric SMILES: C/C/1=C\CC[C@]2([C@@H](O2)CC/C(=C/[C@H]3C(=C(C(=O)O3)C)CC1)/C)C
• Uses: Sarcophine is an inhibitor of acetylcholine esterase and ATPase.

Technology Process of Sarcophine

There total 2 articles about Sarcophine 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: 85.0%

(2S,7S,8S)-sarcophytoxide (65817-46-1,65877-32-9,69853-45-8,70748-49-1,84984-71-4,111900-27-7,111900-28-8,74841-41-1) → Sarcophine (55038-27-2)

Guidance literature:

With air; In dichloromethane; benzene; Irradiation;

DOI:10.1016/S0040-4039(00)71459-6

Reference yield:

(2S,7S,8S)-sarcophytoxide (65817-46-1,65877-32-9,69853-45-8,70748-49-1,84984-71-4,111900-27-7,111900-28-8,74841-41-1) → (2E,11E)-(6S,8S)-3,8,12,16-Tetramethyl-7,18-dioxa-tricyclo[13.3.0.06,8]octadeca-1(15),2,11,16-tetraene (74740-97-9) + Sarcophine (55038-27-2) + (1E,11E)-(6S,8S)-3-Hydroxy-3,8,12,16-tetramethyl-7,18-dioxa-tricyclo[13.3.0.06,8]octadeca-1,11,15-trien-17-one (137762-26-6,137821-40-0) + (1E,11E)-(6S,8S)-3-Hydroperoxy-3,8,12,16-tetramethyl-7,18-dioxa-tricyclo[13.3.0.06,8]octadeca-1,11,15-trien-17-one (137762-25-5,137821-39-7)

Guidance literature:

With air; In chloroform; for 240h; Ambient temperature;

Reference yield: 30.0%

Sarcophine (55038-27-2) + acetic acid (64-19-7,77671-22-8) → 7β,8α-dihydroxy-deepoxysarcophine (99647-44-6) + 7β-acetoxy-8α-hydroxy-deepoxysarcophine (99647-43-5) + 7β-hydroxy-8α-acetoxy-deepoxysarcophine (99647-42-4) + (8S)-7-oxo-deepoxysarcophine (99647-41-3,99685-17-3)

Guidance literature:

With toluene-4-sulfonic acid; at 10 ℃; for 0.25h; Further byproducts given. Yields of byproduct given;

DOI:10.1016/S0040-4020(01)96472-5

upstream raw materials:

(2S,7S,8S)-sarcophytoxide

Downstream raw materials:

7β,8α-dihydroxy-deepoxysarcophine

7β-hydroxy-Δ⁸⁽¹⁹⁾-deepoxysarcophine

(8S)-7-oxo-deepoxysarcophine

8-methoxy-7-hydroxy-deepoxysarcophine