1200-93-7

Basic information

• Product Name: (+/-)-MELLEIN
• Synonyms: (+/-)-MELLEIN;(±)-3,4-Dihydro-8-hydroxy-3-methyl-2-benzopyran-1-one
• CAS NO: 1200-93-7
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.1846
• Mol File: 1200-93-7.mol

Chemical Properties

• Melting Point: 37-39 °C
• Boiling Point: 392.7±42.0 °C(Predicted)
• Appearance: /
• Density: 1.252±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 9.86±0.40(Predicted)
• CAS DataBase Reference: (+/-)-MELLEIN(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-MELLEIN(1200-93-7)
• EPA Substance Registry System: (+/-)-MELLEIN(1200-93-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 1200-93-7(Hazardous Substances Data)

Usage

Purification Methods

Purify it by recrystallisation from H2O or aqueous EtOH. It has UV: at 247 and 314nm. [Arakawa et al. Justusmax Liebigs Ann Chem 728 152 1969, Blair & Newbold Chem Ind (London) 93 1955, J Chem Soc 2871 1955.] The methyl ether has m 66-67o and UV: 242nm ( 7,400) and 305nm ( 4,600). R(-)-Mellein has m56o(aqueous Me2CO), [] D -102.5o (c 1, CHCl3) and R(+)-mellein has m 56-57o(hexane), [] D +102o (c 1, CHCl3) or [] 25 +88o (c 1, MeOH). [Beilstein 18 III/IV 188, 18/1 V 274.]

Upstream product

• 16281-42-8 8-methoxy-3-methyl-3,4-dihydro-1H-isochromen-1-one 
• 591-20-8 3-Bromophenol 
• 193544-56-8 methyl (S)-(+)-2-(2-tert-butyldimethylsiloxypropyl)-6-methoxybenzoate 
• 193544-57-9 (+)-(3S)-8-methoxy-3-methyl-3,4-dihydro-1H-isochromen-1-one 
• 141315-57-3 (+)-3,4-dihydro-8-hydroxy-3-methyl-7-isocoumarincarboxylic acid 
• 104317-26-2 (R)-1-methyl-3,5-hexadienyl 4-oxo-2-pentenoate 
• 104317-23-9 (R)-4,6-heptadien-2-ol THP ether 
• 49636-38-6 (R)-4,6-heptadien-2-ol 
• 193544-54-6 methyl (R)-(-)-2-(2-tert-butyldimethylsiloxypropyl)-6-methoxybenzoate 
• 2161-90-2 1-methoxy-1,3-cyclohexadiene 
• 579-75-9 2-Methoxybenzoic acid 
• 88105-14-0 (2-methoxyphenyl)-tert-butylamino-methanone 
• 918548-71-7 (2R)-N-tert-butyl-2-(2-hydroxypropyl)-6-methoxybenzamide 
• 126784-47-2 8-hydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-isochromen-1-one 

Downstream Products

• 567-61-3 2-hydroxy-6-methylbenzoic acid 
• 138310-59-5 (1R,3S)-(-)-thysanone 
• 138535-42-9 6-(1-propenyl)salicylic acid 

Relevant articles and documents

Ruthenium-NHC-Diamine Catalyzed Enantioselective Hydrogenation of Isocoumarins

A novel and practical chiral ruthenium-NHC-diamine system is disclosed for the enantioselective hydrogenation of isocoumarins, which provides a new concept to apply (chiral) NHC ligands in asymmetric catalysis. A variety of optically active 3-substituted 3,4-dihydroisocoumarins were obtained in excellent enantioselectivities (up to 99% ee). Moreover, this methodology was utilized in the synthesis of O-methylmellein, mellein, and ochratoxin A.

Synthesis of (-)-mellein, (+)-ramulosin, and related natural products

(-)-Mellein, (+)-ramulosin, (-)-O-methylmellein, (-)-6-hydroxymellein, (-)-6-methoxymellein, and (+)-6-hydroxyramulosin were synthesized as optically active forms using one-pot esterification-Michael addition-aldol reaction of δ-hydroxy-α,β-unsaturated aldehyde and diketene as a key step.

Organocatalytic Aerobic Oxidation of Benzylic sp3 C-H Bonds of Ethers and Alkylarenes Promoted by a Recyclable TEMPO Catalyst

An entirely metal-free catalyst system consisting of an easily prepared recyclable new TEMPO derived sulfonic salt catalyst, and mineral acids (NaNO2 and HCl) has been developed for selective aerobic oxidation of structurally diverse benzylic sp3 C-H bonds of ethers and alkylarenes. The mild reaction conditions allow for the generation of synthetically and biologically valued isochromanones and xanthones from readily accessible alkyl aromatic precursors in good yields.

Addition of lithiated tertiary aromatic amides to epoxides and aziridines: Asymmetric synthesis of (S)-(+)-mellein

Addition of ortholithiated or laterally lithiated amides to epoxides or aziridines provides, in some cases stereoselectively, products which may cyclise to yield benzopyranones in good enantiomeric excess. Georg Thieme Verlag Stuttgart.

Synthesis of pseudodeflectusin and ustusorane C: Structural revision of aspergione A and B

The syntheses of racemic and optically active pseudodeflectusin and ustusorane C are described. The 1H-and 13C-NMR data for our synthetic pseudodeflectusin and ustusorane C were identical to those of the corresponding natural product

CHIRAL SYNTHESIS OF (R)-(-)-MELLEIN AND (3R,4aS)-(+)-RAMULOSIN

By employing an intramolecular Diels-Alder reaction as the key-step, (R)-(-)-mellein 1a (a metabolite of Aspergillus melleus) and (3R,4aS)-(+)-ramulosin 2 (a metabolite of Pestalotia ramulosa) were synthesised from ethyl(R)-3-hydroxybutanoate 3a.

Synthesis of (R)-mellein by a partially reducing iterative polyketide synthase

Mellein and the related 3,4-dihydroisocoumarins are a family of natural products with interesting biological properties. The mechanisms of dihydroisocoumarin biosynthesis remain largely speculative today. Here we report the synthesis of mellein by a partially reducing iterative polyketide synthase (PR-PKS) as a pentaketide product. Remarkably, despite the head-to-tail homology shared with several fungal and bacterial PR-PKSs, the mellein synthase exhibits a distinct keto reduction pattern in the synthesis of the pentaketide. We present evidence to show that the ketoreductase (KR) domain alone is able to recognize and differentiate the polyketide intermediates, which provides a mechanistic explanation for the programmed keto reduction in these PR-PKSs.

Synthesis and absolute configuration of (+)-pseudodeflectusin: Structural revision of aspergione B

We report herein the total synthesis and determination of the absolute configuration of (+)-pseudodeflectusin. The total synthesis of (+)-pseudodeflectusin starting from o-anisic aid was achieved in 11 total steps with an overall yield of 2.0%. The 1

Isocoumarin derivative as well as preparation method and medical application thereof

The invention belongs to the technical field of chemical medicines, and relates to an isocoumarin compound of general formula (I) and a preparation method and medical application, of the isocoumarin compound in preparation of medicines for treating and mo

Discovery, synthesis, biological evaluation and molecular docking study of (R)-5-methylmellein and its analogs as selective monoamine oxidase A inhibitors

(R)-5-Methylmellein (5-MM), the major ingredient in the fermented mycelia of the medicinal fungus Xylaria nigripes (called Wuling Shen in Chinese)? was found to be a selective inhibitor against monoamine oxidase A (MAO-A) and might play an important role in the clinical usage of this edible fungus as an anti-depressive traditional Chinese medicine (TCM). Based on the discovery and hypothesis, a variety of (R)-5-MM analogs were synthesized and evaluated in vitro against two monoamine oxidase isoforms (MAO-A and MAO-B). Most synthetic analogs showed selective inhibition of MAO-A with IC50 values ranging from 0.06 to 29 μM, and compound 13aR is the most potent analog with high selectivity (IC50, MAO-A: 0.06 μM; MAO-B: >50 μM). Interestingly, the enzyme kinetics study of 13aR indicated that this ligand seemed to bind in the MAO-A active site according to so-called “tight-binding inhibition” mode. The molecular docking study of 13aR was thereafter performed in order to rationalize the obtained biological results.