109741-38-0

Basic information

• Product Name: Murraol
• Synonyms: Murraol
• CAS NO: 109741-38-0
• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.28514
• Mol File: 109741-38-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Murraol(CAS DataBase Reference)
• NIST Chemistry Reference: Murraol(109741-38-0)
• EPA Substance Registry System: Murraol(109741-38-0)

Safety Data

• Hazardous Substances Data: 109741-38-0(Hazardous Substances Data)

Usage

General Description

Murraol is a naturally occurring chemical compound found in the essential oil of the Australian shrub Eremophila murrayana. It is classified as a monoterpene and is known for its pleasant aroma reminiscent of eucalyptus and mint. Murraol has been studied for its potential medicinal properties, including its antimicrobial and anti-inflammatory effects. It has also been used in traditional Indigenous Australian medicine for its supposed healing properties. Research on murraol is ongoing, and it is being explored for its potential applications in pharmaceuticals, aromatherapy, and other industries.

Upstream product

• 484-12-8 osthole 
• 5673-37-0 7-methoxy-8-(2',3'-dihydroxy-3'-methylbutyl)coumarin 
• 65763-01-1 7-methoxy-8-iodo-2H-chromen-2-one 
• 115-18-4 2-methyl-3-buten-2-ol 
• 65763-04-4 8-(3-hydroxy-3-methylbut-1-yn-1-yl)-7-methoxy-2H-chromen-2-one 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 121994-13-6 peroxymurraol 

Downstream Products

• 114032-24-5 8-Naphthoherniarin 

Related news

Synthesis of the natural coumarins, Murraol (cas 109741-38-0) (CM-c2), trans-dehydroosthol and swietenocoumarin G07/22/2019

The coumarin CM-c2, from Cnidium monnieri, 7-methoxy-8-(3-hydroxy-3-methylbut-1-enyl) coumarin, has been synthesized by palladium acetate-catalysed condensation of 7-methoxy-8-iodocoumarin with 2-methylbut-3-en-2-ol. Its stereochemistry follows from its conversion to trans-dehydroosthol. The ide...detailed

Relevant articles and documents

SYNTHESIS OF THE NATURAL COUMARINS, MURRAOL (CM-c2), TRANS-DEHYDROOSTHOL AND SWIETENOCOUMARIN G

The coumarin CM-c2 from Cnidium monnieri, 7-methoxy-8-(3-hydroxy-3-methylbut-1-enyl)coumarin, has been synthesized by palladium acetate-catalysed condensation of 7-methoxy-8-iodocoumarin with 2-methylbut-3-en-2-ol.Its stereochemistry follows from its conversion to trans-dehydroosthol.The identity of CM-c2 and murraol has been established.Swietenocoumarin G has been prepared similarly from bergaptol. - Keywords: Cnidium monnieri; Umbelliferae; fruit; coumarin syntheses; CM-c2; murraol; trans-dehydroosthol; swietenocoumarin G.Keywords: Cnidium monnieri; Umbelliferae; fruit; coumarin synthese; CM-c2; murraol; trans-dehydroosthol; swietenocoumarin G.

Half-Sandwich Ruthenium Carbene Complexes Link trans-Hydrogenation and gem-Hydrogenation of Internal Alkynes

The hydrogenation of internal alkynes with [Cp?Ru]-based catalysts is distinguished by an unorthodox stereochemical course in that E-alkenes are formed by trans-delivery of the two H atoms of H2. A combined experimental and computational study now provides a comprehensive mechanistic picture: a metallacyclopropene (??2-vinyl complex) is primarily formed, which either evolves into the E-alkene via a concerted process or reacts to give a half-sandwich ruthenium carbene; in this case, one of the C atoms of the starting alkyne is converted into a methylene group. This transformation represents a formal gem-hydrogenation of a ?€-bond, which has hardly any precedent. The barriers for trans-hydrogenation and gem-hydrogenation are similar: whereas DFT predicts a preference for trans-hydrogenation, CCSD(T) finds gem-hydrogenation slightly more facile. The carbene, once formed, will bind a second H2 molecule and evolve to the desired E-alkene, a positional alkene isomer or the corresponding alkane; this associative pathway explains why double bond isomerization and over-reduction compete with trans-hydrogenation. The computed scenario concurs with para-hydrogen-induced polarization transfer (PHIP) NMR data, which confirm direct trans-delivery of H2, the formation of carbene intermediates by gem-hydrogenation, and their evolution into product and side products alike. Propargylic aOR (R = H, Me) groups exert a strong directing and stabilizing effect, such that several carbene intermediates could be isolated and characterized by X-ray diffraction. The gathered information spurred significant preparative advances: specifically, highly selective trans-hydrogenations of propargylic alcohols are reported, which are compatible with many other reducible functional groups. Moreover, the ability to generate metal carbenes by gem-hydrogenation paved the way for noncanonical hydrogenative cyclopropanations, ring expansions, and cycloadditions.

Natural Product Chemistry, 118. - Synthesis of the Coumarins 6- and 8-Naphthoherniarin, Dehydrogeijerin, and Murraol

The Pd/Cu-catalysed reaction of 6-bromo-7-methoxycoumarin (1) with 2-methyl-3-butyn-2-ol yields 1,2-dehydrosuberenol (2).By Lindlar reduction, water elimination, Diels-Alder reaction with 2-methoxy-p-benzoquinone (6), and dehydrogenation with 6-naphthoherniarin (9), a novel coumarin from Ruta graveolens is synthesized.Dehydrogeijerin (8) is available by Schuster-Meyer rearrangement of 2.By Heck vinylation 8-iodo-7-methoxycoumarin (11) is transferred into murraol (12).By water elimination from 12, Diels-Alder reaction with 6 and aromatisation 8-naphthoherniarin (14) is available.