465-92-9

Basic information

• Product Name: MARRUBIIN
• Synonyms: MARRUBIIN;5-[2-(3-furyl)ethyl]decahydro-5-hydroxy-1,4a,6-trimethyl-1,8-naphthalenecarbolactone;MARRUBIIN(P);6β-[2-(3-Furanyl)ethyl]decahydro-6α-hydroxy-2aα,5aβ,7α-trimethyl-2H-naphtho[1,8-bc]furan-2-one;MARRUBIIN(SH);MarrubiuM bitter;Marrubin
• CAS NO: 465-92-9
• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.43
• Product Categories: Di-Terpenoids
• Mol File: 465-92-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 159-162°C
• Boiling Point: 465.2°Cat760mmHg
• Flash Point: 235.2°C
• Appearance: /
• Density: 1.152±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.87E-09mmHg at 25°C
• Refractive Index: 1.537
• PKA: 14.66±0.70(Predicted)
• CAS DataBase Reference: MARRUBIIN(CAS DataBase Reference)
• NIST Chemistry Reference: MARRUBIIN(465-92-9)
• EPA Substance Registry System: MARRUBIIN(465-92-9)

Safety Data

• Statements: 25
• Safety Statements: 1-22-45
• RIDADR: 2811
• Hazardous Substances Data: 465-92-9(Hazardous Substances Data)

Usage

Uses

Marrubiin is an α-glucosidase inhibitor and an analgesic compound.

InChI:InChI=1/C20H28O4/c1-13-11-15-16-18(2,17(21)24-15)7-4-8-19(16,3)20(13,22)9-5-14-6-10-23-12-14/h6,10,12-13,15-16,22H,4-5,7-9,11H2,1-3H3

Upstream product

• 63184-61-2 3-(bromomethyl)furan 
• 7439-95-4 magnesium 
• 101822-35-9 (2-(trimethylsilyl)furan-3-yl)methanol 
• 223419-32-7 3-(bromomethyl)-2-(trimethylsilyl)furan 
• 81719-68-8 (3-furylmethyl)magnesium bromide 

Downstream Products

• 564-12-5 15,16-epoxy-6β,9-dihydroxy-8βH-labda-13(16),14-dien-19-oic acid 

Relevant articles and documents

Total syntheses of marrubiin and related labdane diterpene lactones

Total syntheses of the labdane diterpene lactones marrubiin, marrulibacetal, desertine, marrulibacetal A, marrubasch F, cyllenine C, marrulanic acid, and marrulactone are described. The trans-decalin moiety of these molecules was constructed in a stereoselective manner by a Pauson-Khand reaction, and the resultant cyclopentenone was oxidatively cleaved for formation of the lactone ring. Elongation of the side chain at C9 was achieved by an epoxide-opening reaction with a variety of nucleophiles, and the functional group manipulations completed the syntheses of these natural products. Stereochemistries of desertine could be established by the transformations.