54287-99-9

Basic information

• Product Name: 5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE
• Synonyms: 5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE;5-hydroxy-2,2-dimethylchromene-6-carbaldehyde
• CAS NO: 54287-99-9
• Molecular Formula: C₁₂H₁₂O₃
• Molecular Weight: 204.22188
• Mol File: 54287-99-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: 70-71 °C(Solv: heptane (142-82-5))
• Boiling Point: 309.965°C at 760 mmHg
• Flash Point: 117.82°C
• Appearance: /
• Density: 1.208g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.76±0.40(Predicted)
• CAS DataBase Reference: 5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE(54287-99-9)
• EPA Substance Registry System: 5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE(54287-99-9)

Safety Data

• Hazardous Substances Data: 54287-99-9(Hazardous Substances Data)

Usage

General Description

5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE, also known as homovanillin, is a chemical compound with the molecular formula C11H12O3. It is a natural product found in the vanilla bean plant and is commonly used as a flavoring agent in food and beverages. Homovanillin has a sweet, vanilla-like aroma and is often used in perfumes and cosmetics. It has been studied for its potential antioxidant and neuroprotective properties, and may have applications in the treatment of neurodegenerative diseases. Additionally, homovanillin has been used as a precursor in the synthesis of pharmaceuticals and other organic compounds.

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

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

Downstream Products

• 523-59-1 seseline 
• 850417-23-1 5-benzoyloxy-2,2-dimethyl-6-formyl-2H-1-benzopyran 
• 31501-55-0 lonchocarpin 
• 51589-67-4 (E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 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 
• 91078-12-5 3-(5-methoxymethoxy-2,2-dimethyl-3-phenylthiochroman-6-yl-)-1-(2-hydroxy-4-methoxymethoxyphenyl)prop-2-en-1-one 
• 111492-45-6 3-(5-methoxymethoxy-2,2-dimethyl-2H-benzopyran-6-yl)-1-(2-hydroxy-4-methoxymethoxyphenyl)prop-2-en-1-one 
• 91078-11-4 5-Methoxymethoxy-2,2-dimethyl-3-phenylsulfanyl-chroman-6-carbaldehyde 
• 87963-59-5 6-formyl-5-hydroxy-2,2-dimethyl-3-phenylthiochroman 

Relevant articles and documents

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.

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.

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.

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.