54287-99-9

Usage

Uses

Used in Flavoring Industry:
5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE is used as a flavoring agent for its distinctive sweet, vanilla-like aroma, enhancing the taste and aroma of food and beverages.
Used in Perfumery and Cosmetics Industry:
In the perfumery and cosmetics industry, 5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE is utilized as a fragrance ingredient, contributing to the creation of various scents in perfumes and other cosmetic products.
Used in Pharmaceutical Synthesis:
5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE is used as a precursor in the synthesis of pharmaceuticals, playing a crucial role in the development of new medicinal compounds.
Used in Neuroprotective Applications:
5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE is being studied for its potential neuroprotective properties, with the aim of developing treatments for neurodegenerative diseases.
Used in Antioxidant Applications:
Due to its antioxidant properties, 5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE may be employed in various applications where protection against oxidative stress is required, such as in the food industry to extend shelf life or in cosmetics to protect against environmental damage.

InChI:InChI=1/C12H12O3/c1-12(2)6-5-9-10(15-12)4-3-8(7-13)11(9)14/h3-7,14H,1-2H3

Upstream product

• 32268-30-7 2,4-dihydroxy-3-(3-methyl-2-but-en-1-yl)benzaldehyde 
• 54287-98-8 2-hydroxy-4-((2-methylbut-3-yn-2-yl)oxy)benzaldehyde 
• 31525-67-4 dimethylacetal of 3-methyl-3-hydroxybutyraldehyde 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 163041-67-6 2-hydroxy-3-(3-methylbut-2-en-1-yl)-4-[(tetrahydro-2H-pyran-2-yl)oxy]benzaldehyde 
• 115-18-4 2-methyl-3-buten-2-ol 
• 513-35-9 2-methyl-but-2-ene 
• 115-19-5 2-methyl-but-3-yn-2-ol 

Downstream Products

• 87963-59-5 6-formyl-5-hydroxy-2,2-dimethyl-3-phenylthiochroman 
• 91078-11-4 5-Methoxymethoxy-2,2-dimethyl-3-phenylsulfanyl-chroman-6-carbaldehyde 
• 111492-45-6 3-(5-methoxymethoxy-2,2-dimethyl-2H-benzopyran-6-yl)-1-(2-hydroxy-4-methoxymethoxyphenyl)prop-2-en-1-one 
• 91078-12-5 3-(5-methoxymethoxy-2,2-dimethyl-3-phenylthiochroman-6-yl-)-1-(2-hydroxy-4-methoxymethoxyphenyl)prop-2-en-1-one 
• 31501-55-0 lonchocarpin 
• 63286-36-2 2-(3,4-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-2-(phenylsulfonyl)ethanone 
• 63286-38-4 3-(3,4-dimethoxyphenyl)-8,8-dimethyl-4-oxo-4H,8H-benzo[1,2-b:3,4-b']dipyran 
• 67015-34-3 5,6-dimethoxy-2,2-dimethyl-2H-benzopyran 
• 1435269-72-9 C₂₄H₃₁NO₅ 
• 1435269-79-6 C₂₄H₃₁NO₅ 
• 1435268-77-1 (5,6-dimethoxy-2,2-dimethyl-2H-benzopyran-7-yl)(2-hydroxy-5-methylphenyl)methanone 
• 1435268-96-4 (5,6-dimethoxy-2,2-dimethyl-2H-benzopyran-8-yl)(2-hydroxy-5-methylphenyl)methanone 
• 1435268-74-8 (5,6-dimethoxy-2,2-dimethyl-2H-benzopyran-7-yl)(2-hydroxy-5-methoxyphenyl)methanone 
• 1435268-92-0 (5,6-dimethoxy-2,2-dimethyl-2H-benzopyran-8-yl)(2-hydroxy-5-methoxyphenyl)methanone 

Relevant academic research and scientific papers

A short synthesis of 5-methoxy-2,2-dimethyl-2H-1-benzopyran-6-propanoic acid methyl ester

5-Methoxy-2,2-dimethyl-2H-1-benzopyran-6-propanoic acid methyl ester was prepared in five steps and approximately 20% overall yield from 2,4-dihydroxybenzaldehyde. The two key reactions are the chromenylation between the unchelated hydroxyl group and C-3 of the resbenzaldehyde and the demethoxycarbonylation-alkylation of dimethyl malonate with a quaternary ammonium iodide.

Base-catalyzed condensation of 2-hydroxybenzaldehydes with α,β-unsaturated aldehydes - Scope and limitations

The base-catalyzed condensation of α,β-unsaturated carbonyl compounds with 2-hydroxybenzaldehydes yielding tetrahydroxanthones and dihydrobenzopyrans has been investigated. A novel access to highly functionalized dihydrobenzopyrans via a mild generation of the dienol of senecialdehyde and subsequent conjugated aldol reaction has been reported.

Direct preparation method of 5-hydroxy-2, 2-dimethyl-2H-benzofuran-6-formaldehyde

The invention belongs to the technical field of compound synthesis, and relates to a direct preparation method of 5-hydroxy-2, 2-dimethyl-2H-benzofuran-6-formaldehyde. The preparation method comprisesthe following steps of: (1) dissolving 4-hydroxy-salicylaldehyde, 2-methyl-3-butyne-2-ol and a catalyst in an organic solvent, and carrying out a reflux reaction under the protection of nitrogen until no obvious water is generated; and (2) washing a product obtained after the reaction, collecting an organic phase, and carrying out drying, reduced pressure concentration and column chromatography purification to obtain a faint yellow solid product, namely the 5-hydroxy-2, 2-dimethyl-2H-benzofuran-6-formaldehyde. According to the method, the 2-methyl-3-butyne-2-ol which is low in price and easyto obtain serves as a raw material and reacts with the reaction substrate 4-hydroxy-salicylaldehyde; on the basis of a cascade reaction, the target product is directly obtained through a one-step reaction under the action of the catalyst. The direct preparation method has the advantages of low cost, easy and convenient operation and high production efficiency.

Imidazo ring PAR4 antagonist and medical applications thereof

The invention relates to an imidazo ring compound represented by formula (I) or formula (II), or a pharmaceutically acceptable salt or ester or solvate thereof. The compound disclosed by the inventioncan be used for preparing medicines for preventing or treating thromboembolic diseases.

Novel Hypoxia-Inducible Factor 1α (HIF-1α) Inhibitors for Angiogenesis-Related Ocular Diseases: Discovery of a Novel Scaffold via Ring-Truncation Strategy

Ocular diseases featuring pathologic neovascularization are the leading cause of blindness, and anti-VEGF agents have been conventionally used to treat these diseases. Recently, regulating factors upstream of VEGF, such as HIF-1α, have emerged as a desirable therapeutic approach because the use of anti-VEGF agents is currently being reconsidered due to the VEGF action as a trophic factor. Here, we report a novel scaffold discovered through the complete structure-activity relationship of ring-truncated deguelin analogs in HIF-1α inhibition. Interestingly, analog 6i possessing a 2-fluorobenzene moiety instead of a dimethoxybenzene moiety exhibited excellent HIF-1α inhibitory activity, with an IC50 value of 100 nM. In particular, the further ring-truncated analog 34f, which showed enhanced HIF-1α inhibitory activity compared to analog 2 previously reported by us, inhibited in vitro angiogenesis and effectively suppressed hypoxia-mediated retinal neovascularization. Importantly, the heteroatom-substituted benzene ring as a key structural feature of analog 34f was identified as a novel scaffold for HIF-1α inhibitors that can be used in lieu of a chromene ring.

Synthetic method of antitumor deguelin broken-ring structure and amino acid derivatives

The invention discloses a synthetic method of antitumor deguelin broken-ring structure and amino acid derivative. The antitumor deguelin broken-ring structure and amino acid derivative has a following structural formula, wherein R is side-chain groups of amino acid; the synthetic method includes: 1), condensing 3-methylcrotonaldehyde and 2,4-2-hydroxybenzaldehyde under alkali catalysis condition; 2), methylating a product of step 1) with a methylation reagent under alkali catalysis condition; 3), subjecting a product of step 2) to reductive amination with amino acid to obtain a final product. The application of the deguelin broken-ring structure and amino acid derivative in the preparation of antitumor drugs is also disclosed. Deguelin is structurally modified with amino acid to synthesize a drug that has the advantages of high efficiency, low toxicity, targeting property and the like, the drug is highly water-soluble and low toxic and side effect and provides significant inhibitory action for the proliferation of tumor cells, particularly the proliferation of lung cancer cells.

Alkyne Carbonyl Metathesis As a Means to Make 4-Acyl Chromenes: Syntheses of (±)-Deguelin and (±)-Munduserone

A highly convergent synthetic approach to rotenoid natural products is described. Successful pairing of two building blocks for Sonogashira cross-coupling and intramolecular alkyne carbonyl metathesis allows ready access to 4-acylchromene, a key substruct

NOVEL COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT

The present invention relates to a compound inhibiting Hsp90 and a pharmaceutical composition comprising the same as an active ingredient. The compounds represented by formula 1 and formula 2 of the present invention suppress the expression of Hsp90 so that they can inhibit the accumulation of HIF-1α, the Hsp90 client protein, and also efficiently inhibit the activation of VEGF. In addition, these compounds display low cytotoxicity, so that they can be effectively used as an active ingredient of an anti-cancer agent, a diabetic retinopathy treating agent, and an anti-arthritic agent.

NOVEL COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT

The present invention relates to a novel compound inhibiting Hsp 90 and to a pharmaceutical composition including same as an active ingredient. Compounds of formula 1 and formula 2 according to the present invention inhibit the accumulation of HIF-1α protein, which is an Hsp90 client protein, by suppressing Hsp90 expression, and effectively inhibit the activity of vascular endothelial growth factor (VEGF). Furthermore, said compounds have low cytotoxicity and can thus be used as an active ingredient for the treatment of diabetic retinopathy and arthritis.

Multidimensional optimization of promising antitumor xanthone derivatives

A promising antitumor xanthone derivative was optimized following a multidimensional approach that involved the synthesis of 17 analogues, the study of their lipophilicity and solubility, and the evaluation of their growth inhibitory activity on four human tumor cell lines. A new synthetic route for the hit xanthone derivative was also developed and applied for the synthesis of its analogues. Among the used cell lines, the HL-60 showed to be in general more sensitive to the compounds tested, with the most potent compound having a GI50 of 5.1 μM, lower than the hit compound. Lipophilicity was evaluated by the partition coefficient (Kp) of a solute between buffer and two membrane models, namely liposomes and micelles. The compounds showed a log Kp between 3 and 5 and the two membrane models showed a good correlation (r2 = 0.916) between each other. Studies concerning relationship between solubility and structure were developed for the hit compound and 5 of its analogues.