13849-08-6

Basic information

• Product Name: marmesin
• Synonyms: (S)-2,3-Dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one;[S,(+)]-2,3-Dihydro-2α-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one;(S)-Marmesin;(S)-2-(2-Hydroxypropan-2-yl)-2H-furo[3,2-g]chromen-7(3H)-one;marmesin
• CAS NO: 13849-08-6
• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.28
• Mol File: 13849-08-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 189-191℃
• Boiling Point: 434℃
• Flash Point: 168℃
• Appearance: /
• Density: 1.334
• Vapor Pressure: 2.66E-08mmHg at 25°C
• Refractive Index: 1.61
• PKA: 14.34±0.29(Predicted)
• CAS DataBase Reference: marmesin(CAS DataBase Reference)
• NIST Chemistry Reference: marmesin(13849-08-6)
• EPA Substance Registry System: marmesin(13849-08-6)

Safety Data

• Hazardous Substances Data: 13849-08-6(Hazardous Substances Data)

Usage

Description

Marmesin, also known as (+)-Marmesin, is a chemical compound that serves as a precursor in the biosynthesis of psoralen and linear furanocoumarins. It has been demonstrated to possess anti-diabetic potential, making it a promising candidate for pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
Marmesin is used as a precursor in the biosynthesis of psoralen and linear furanocoumarins, which are important compounds in the pharmaceutical industry. Its role in the production of these compounds contributes to its significance in this field.
Used in Anti-diabetic Applications:
Marmesin is used as an anti-diabetic agent due to its demonstrated potential in managing diabetes. It may help in the development of new treatments and therapies for diabetes, offering a promising avenue for further research and development in the medical field.

InChI:InChI=1/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H3

Upstream product

• 495-30-7 (S)-marmesinin 
• 13209-79-5 (-)-prantschimgin 
• 325137-98-2 6-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-(trifluoromethanesulfonyl)chromen-2-one 
• 305-01-1 aesculetin 
• 20126-72-1 (S)-peucedanol 
• 325138-02-1 6-formyl-7-(methoxymethoxy)chromen-2-one 
• 202350-87-6 6-hydroxy-7-(methoxymethoxy)-2H-chromen-2-one 
• 325138-04-3 7-(methoxymethoxy)-6-[(Z)-3-oxo-1-butenyl]chromen-2-one 
• 325137-92-6 7-(methoxymethoxy)-6-[(E)-3-oxo-1-butenyl]chromen-2-one 
• 325137-90-4 6-[(1R,2S)-1,2-epoxy-3-oxobutyl]-7-(methoxymethoxy)chromen-2-one 
• 325137-94-8 7-(methoxymethoxy)-6-(trifluoromethanesulfonyl)chromen-2-one 
• 325137-96-0 6-[(1R,2S)-1,2-epoxy-3-hydroxy-3-methylbutyl]-7-(methoxymethoxy)chromen-2-one 
• 616241-73-7 6-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-(methoxymethoxy)chromen-2-one 
• 125497-23-6 Marmesinin-tetraacetat 

Downstream Products

• 64-19-7 acetic acid 
• 108-46-3 recorcinol 
• 66-97-7 psoralen 
• 53106-45-9 secorin 

Relevant articles and documents

A simple and efficient approach for the preparation of dihydroxanthyletin, xanthyletin, decursinol and marmesin

A simple and efficient approach has been developed for the preparation of coumarin natural products such as dihydroxanthyletin, xanthyletin, decursinol and marmesin starting from commercially available 2,4-dihydroxybenzaldehyde with very good yields. Wittig homologation and Claisen rearrangement are the protocols used to achieve these molecules.

Synthesis of coumarin derivatives and their cytoprotective effects on t-BHP-induced oxidative damage in HepG2 cells

Coumarins are ubiquitous in higher plants and exhibit various biological actions. The aim of this study was to investigate the structure-activity relationships of coumarin derivatives on tert-butyl hydroperoxide (t-BHP)-induced oxidative damage in human hepatoma HepG2 cells. A series of coumarin derivatives were prepared and assessed for their cytoprotective effects. Among these, a caffeoyl acid-conjugated dihydropyranocoumarin derivative, caffeoyllomatin, efficiently protected against cell damage elicited by t-BHP. Our findings suggest that caffeoyllomatin appears to be a potent cytoprotective agent.

Glycosides from the methanol extract of Notopterygium incisum

Five new (15) and twelve known (617) different types of glycosides together with a known sesquiterpene triol (18) were isolated from the methanol extract of the rhizomes of Notopterygium incisum. The new structures were elucidated by means of spectroscopic and chemical methods to be pregn-5-en-3,20(S)-diol-3-O- bis - D-glucopyranosyl-(l2,16) - D-glucopyranoside (1), oleuropeic aldehyde 8-O - D-glucopyranoside (2), 2(R)-(3,4-dimethoxyphenyl)-propane-1,3-diol-1-O - D-glucopyranoside (3), eudesman-3,4,11-triol-11-O - D-glucopyranoside (4), and marmesin-11-O - D-glucopyranosyl-(16) - D-glucopyranoside (5). The absolute configuration of the aglycone in compound 3 was assigned by application of Klyne's rule. Georg Thieme Verlag KG Stuttgart - New York.