(1R,4Z,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

Base Information

• Chemical Name: (1R,4Z,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
• CAS No.: 15503-86-3
• Molecular Formula: C₁₈H₂₅NO₇
• Molecular Weight: 367.399
• European Community (EC) Number: 805-145-0
• Mol file: 15503-86-3.mol

Synonyms:isatidine;RET-NO;retrorsine N-oxide

Chemical Property of (1R,4Z,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

Chemical Property:

• Melting Point: 145°C
• Refractive Index: 1.5100 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: 11.96±0.40(Predicted)
• Flash Point: °C
• PSA: 122.49000
• Density: g/cm³
• LogP: 0.13660
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 367.16310214
• Heavy Atom Count: 26
• Complexity: 673

Purity/Quality:

99% ^*data from raw suppliers

RetrorsineN-Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1CC(C(C(=O)OCC2=CC[N+]3(C2C(CC3)OC1=O)[O-])(CO)O)C
• Isomeric SMILES: C/C=C\1/C[C@@H]([C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(CO)O)C
• Description: This hepatotoxic alkaloid occurs in certain Senecio species and was first isolated from S. isatideus D.C. It occurs abundantly in S. retrorsus D.C. and S. scleratus Schw. The alkaloid crystallizes in rhombic prisms as the dihydrate and has [α]27D . 8.25° (H 20). It is soluble in MeOH, hot EtOH and hot H20 but virtually insoluble in Et 20, Me2CO or CHCl 3. On reduction it absorbs 4 molecules of H2 to give hexahydrodeoxyisatidine which melts at l15-l20°C and then remelts at l83-4°C following an intermediate solidification. This compound gives a hydrochloride, m.p. 218°C (dec.); [α]20D - 52.5° (H20) and may be hydrolyzed with Ba(OHh to give a basic product, tetrahydroisatinecine, CSH1703N, m.p. l74.5°C; [α]20D - 88° (H 20). The alkaloid itself, on hydrolysis with Ba(OHh yields isatinecine and two acid products, isatinecic acid and the monolactone, the latter almost certainly being formed by the action of the base upon the acid.

Technology Process of (1R,4Z,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

There total 1 articles about (1R,4Z,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione 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:

retrorsine (480-54-6) → retrorsine N-oxide (15503-86-3,117020-54-9)

Guidance literature:

With ethanol; dihydrogen peroxide;

upstream raw materials:

retrorsine