19314-92-2

Basic information

• Product Name: 6-Hydroxymellein
• Synonyms: 3,4-Dihydro-6,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one
• CAS NO: 19314-92-2
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• Mol File: 19314-92-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 209-211 °C
• Boiling Point: 472.3±34.0 °C(Predicted)
• Appearance: /
• Density: 1.380±0.06 g/cm3(Predicted)
• PKA: 8.11±0.40(Predicted)
• CAS DataBase Reference: 6-Hydroxymellein(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Hydroxymellein(19314-92-2)
• EPA Substance Registry System: 6-Hydroxymellein(19314-92-2)

Safety Data

• Hazardous Substances Data: 19314-92-2(Hazardous Substances Data)

Usage

Description

6-Hydroxymellein, also known as 6,8-dihydroxy-3-methylisochroman-1-one, is an organic compound that serves as an intermediate in the total synthesis of 6,8-dimethoxy-3-methylisocoumarin, a fungal metabolite precursor. It is characterized by its unique chemical structure and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
6-Hydroxymellein is used as an intermediate in the synthesis of 6,8-dimethoxy-3-methylisocoumarin, a fungal metabolite precursor. 6-Hydroxymellein has potential applications in the development of pharmaceuticals, particularly those targeting fungal infections or other related conditions.
Used in Chemical Research:
6-Hydroxymellein is utilized as a research compound in the field of organic chemistry, where it can be studied for its properties, reactions, and potential applications in the synthesis of other organic compounds.
Used in Fungal Metabolite Studies:
As an intermediate in the synthesis of 6,8-dimethoxy-3-methylisocoumarin, 6-Hydroxymellein plays a role in the study of fungal metabolites and their potential applications in various industries, such as pharmaceuticals, agriculture, and environmental management.

Upstream product

• 77844-97-4 3,4-dihydro-6,8-dimethoxy-3-methyl-1H-2-benzopyran-1-one 
• 2524-37-0 ethyl orselinate 
• 57749-86-7 ethyl 2,4-dimethoxy-6-methylbenzoate 
• 82218-06-2 6,8-dimethoxy-1H-2-benzopyran-1,3(4H)-dione 
• 18110-66-2 6,8‐dimethoxy‐3‐methylisocoumarin 
• 4778-99-8 2-carboxymethyl-4,6-dimethoxy-benzoic acid 
• 3686-57-5 2,4-dimethoxy-6-methylbenzoic acid 
• 83375-20-6 2,4-dimethoxy-6-(methoxycarbonylmethyl)benzoic acid 
• 82218-07-3 4-carboxy-6,8-dimethoxy-3-methylisocoumarin 
• 61227-52-9 5,7-dimethoxy-2-methylindan-1-one 
• 61227-55-2 4,6-dimethoxy-2-methylinden-3-yl trifluoroacetate 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 122333-94-2 3-(3,5-dimethoxyphenyl)-2-methylpropanoic acid 
• 122333-93-1 3-(3,5-dimethoxyphenyl)-2-methylpropenoic acid 

Downstream Products

• 6803-02-7 6-methoxymellein 
• 582-46-7 (+)-terrein 

Related news

Free CoA as activator of 6-Hydroxymellein (cas 19314-92-2) synthase, a multifunctional polyketide biosynthetic enzyme in carrot08/11/2019

The activity of 6-hydroxymellein (6HM) synthase, a multifunctional polyketide biosynthetic enzyme in carrot, was appreciably inhibited in the presence of ATP: citrate lyase, a CoA-scavenging enzyme. Catalytic rate of the synthase markedly decreased when deuterium-labeled NADPH was employed in th...detailed

Activation of acyl condensation reaction of monomeric 6-Hydroxymellein (cas 19314-92-2) synthase, a multifunctional polyketide biosynthetic enzyme, by free coenzyme A08/10/2019

6-Hydroxymellein (6HM) synthase is a multifunctional polyketide enzyme induced in carrot cells, whose fully active homodimer catalyzes condensation of acyl-CoAs and the NADPH-dependent ketoreduction of the enzyme-bound intermediate. 6HM-forming activity of the synthase was markedly decreased whe...detailed

Role of reducing co-factors in catalytic reactions of 6-Hydroxymellein (cas 19314-92-2) synthase, a multifunctional polyketide biosynthetic enzyme in carrot cells08/09/2019

6-Hydroxymellein (6HM) synthase, a multifunctional polyketide biosynthetic enzyme in carrot cells, is capable of catalyzing the acyl-CoA condensation and the ketoreduction in the presence of the nucleotide reducing co-factors. Although free CoA at high concentrations functioned as the activator ...detailed

Transacylase-like structure and its role in substrate channeling of 6-Hydroxymellein (cas 19314-92-2) synthase, a multifunctional polyketide biosynthetic enzyme in carrot cell extracts08/08/2019

6-Hydroxymellein synthase, a multifunctional polyketide biosynthetic enzyme of carrot, lost the binding ability toward its co-substrates, acetyl- and malonyl-CoAs, by the treatment with the blocking reagents for serine-OH. In contrast, the enzyme retained the binding ability even when the two SH...detailed

Unusual arrangement of catalytic domains in head-to-tail associated homodimer of 6-Hydroxymellein (cas 19314-92-2) synthase, a multifunctional polyketide biosynthetic enzyme08/07/2019

6-Hydroxymellein synthase, a multifunctional polyketide synthetic enzyme in carrot, is organized as a homodimer, and the activity of the synthase was appreciably inhibited upon the specific alkylation of cysteine- and cysteamine-SHs at the reaction center with iodoacetoamide and chloroacetyl-CoA...detailed

6-Hydroxymellein (cas 19314-92-2) synthetase as a multifunctional enzyme complex in elicitor-treated carrot root extract08/06/2019

Synthetic activity of a polyketide compound 6-hydroxymellein was induced in elicitor-treated carrot root tissues. The activity was significantly inhibited by an antiserum raised against the acyl carrier protein (ACP) of fatty acid synthetase, suggesting that the enzyme(s) for 6-hydroxymellein sy...detailed

Toxicity of 6-methoxymellein and 6-Hydroxymellein (cas 19314-92-2) to the producing carrot cells08/05/2019

6-Methoxymellein (6-MM) is the carrot phytoalexin and 6-hydroxymellein (6-HM) its immediate biosynthetic precursor. 6-MM is more toxic than 6-HM to the producing carrot cells, as demonstrated by the differential toxicity of these two dihydroisocoumarins to either colony forming units in solid me...detailed

Dimer as the active form of a polyketide biosynthetic enzyme 6-Hydroxymellein (cas 19314-92-2) synthase08/04/2019

Activity of 6-hydroxymellein synthase, an inducible polyketide biosynthetic enzyme in carrot cell extracts, was appreciably inhibited in the presence of molar levels of NaCl or (NH4)2SO4. However, the salt-induced inhibition of the synthase activity was reversible, and was almost fully restored ...detailed

Interaction between cerulenin and 6-Hydroxymellein (cas 19314-92-2) synthase in carrot cell extracts08/03/2019

Activity of 6-hydroxymellein synthase, an induced polyketide synthetic enzyme in carrot cell extract, was not inhibited by cerulenin which is known as a potent inhibitor for fatty acid synthases and biosynthetic enzymes of various polyketide compounds. However, when 6-hydroxymellein synthase was...detailed

Induction of 6-methoxymellein 6-Hydroxymellein (cas 19314-92-2) production in carrot cells08/02/2019

6-Methoxymellein, a phytoalexin of carrot, and 6-hydroxymellein, its presumed biosynthetic precursor, were isolated from carrot root slices infected with Sclerotium rolfsii and Fusarium solani. Elicitation of both 6-methoxymellein and 6-hydroxymellein synthesis was achieved also in carrot cell s...detailed

Relevant articles and documents

Direct isocoumarin synthesis through LDA-promoted addition of acetaldehyde on orsellinate. An abrupt synthesis of 6-hydroxymellein, a fungal phytotoxin

The LDA-promoted addition of acetaldehyde on orsellinate gives (±) 6-hydroxymellein, a fungal phytotoxin, with a 51% yield.

Synthesis of Chlorinated Isocoumarin Derivatives

Syhtheses of 5-chloro-, 7-chloro-, and 5,7-dichloro-isocoumarin derivatives, including the fungal metabolites 5-chloro-3,4-dihydro-8-hydroxy-6-methoxy-3-methylisocoumarin (3), 7-chloro-3,4-dihydro-8-hydroxy-6-methoxy-3-methylisocoumarin (2), and 5,7-dichl