Marrubiin

Base Information

• Chemical Name: Marrubiin
• CAS No.: 465-92-9
• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.44
• European Community (EC) Number: 805-148-7
• NSC Number: 36693
• UNII: AP086P88M4
• DSSTox Substance ID: DTXSID50963595
• Nikkaji Number: J3.534.022J
• Wikidata: Q11770828
• Metabolomics Workbench ID: 126050
• ChEMBL ID: CHEMBL1999372
• Mol file: 465-92-9.mol

Synonyms:marrubiin

Chemical Property of Marrubiin

Chemical Property:

• Vapor Pressure: 1.87E-09mmHg at 25°C
• Melting Point: 159-162°C
• Boiling Point: 465.2°Cat760mmHg
• PKA: 14.66±0.70(Predicted)
• Flash Point: 235.2°C
• PSA: 59.67000
• Density: 1.152g/cm³
• LogP: 3.72120
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 332.19875937
• Heavy Atom Count: 24
• Complexity: 534

Purity/Quality:

98%,99%, ^*data from raw suppliers

Marrubiin ^*data from reagent suppliers

Safty Information:

• Statements: 25
• Safety Statements: 1-22-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3C(CCCC3(C1(CCC4=COC=C4)O)C)(C(=O)O2)C
• Isomeric SMILES: C[C@@H]1C[C@@H]2[C@H]3[C@](CCC[C@@]3([C@]1(CCC4=COC=C4)O)C)(C(=O)O2)C
• Uses: Marrubiin is an α-glucosidase inhibitor and an analgesic compound.

Technology Process of Marrubiin

There total 29 articles about Marrubiin 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: 70.0%

(1S,4R,6R,7R,8S,12R)-7-[2-[2-(trimethylsilyl)furan-3-yl]ethyl]-7-hydroxy-1,6,8-trimethyl-2-oxo-3-oxatricyclo[6.3.1.04,12]dodecane → marrubiin (465-92-9,13256-49-0,83997-35-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 4h;

DOI:10.3390/molecules25071610

Reference yield: 66.0%

(2′R,2aS,5aS,6R,7R,8aR)-2a,5a,7-trimethyloctahydrospiro[6H-naphtho[1,8-bc]furan-6,2′-oxiran]-2(2aH)-one + 3-(bromomethyl)furan (63184-61-2) → marrubiin (465-92-9,13256-49-0,83997-35-7)

Guidance literature:

3-(bromomethyl)furan; With magnesium; In diethyl ether; at 0 ℃;

(2′R,2aS,5aS,6R,7R,8aR)-2a,5a,7-trimethyloctahydrospiro[6H-naphtho[1,8-bc]furan-6,2′-oxiran]-2(2aH)-one; With copper(I) bromide dimethylsulfide complex; In diethyl ether; at -20 ℃; for 13h;

DOI:10.1021/acs.orglett.6b01602

Reference yield: 66.0%

(2′R,2aS,5aS,6R,7R,8aR)-2a,5a,7-trimethyloctahydrospiro[6H-naphtho[1,8-bc]furan-6,2′-oxiran]-2(2aH)-one + 3-(bromomethyl)furan (63184-61-2) + magnesium (7439-95-4) → marrubiin (465-92-9,13256-49-0,83997-35-7)

Guidance literature:

3-(bromomethyl)furan; magnesium; In diethyl ether; at 0 ℃;

(2′R,2aS,5aS,6R,7R,8aR)-2a,5a,7-trimethyloctahydrospiro[6H-naphtho[1,8-bc]furan-6,2′-oxiran]-2(2aH)-one; With copper(I) bromide dimethylsulfide complex; In diethyl ether; at -20 ℃; for 13h;

DOI:10.1021/acs.orglett.6b01602

upstream raw materials:

3-(bromomethyl)furan

magnesium

Downstream raw materials:

15,16-epoxy-6β,9-dihydroxy-8βH-labda-13(16),14-dien-19-oic acid

Refernces

• 1、 Yamakoshi, Hiroyuki,Sawayama, Yuki,Akahori, Yoshihiro,Kato, Marie,Nakamura, Seiichi. "Total Syntheses of (+)-Marrubiin and (-)-Marrulibacetal". . p. 3430 - 3433. Retrieved 2016/07/26.