19012-99-8

Basic information

• Product Name: 2,2-dimethyl-2H-chromen-6-ol
• CAS NO: 19012-99-8
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.2118
• Mol File: 19012-99-8.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 307.8°C at 760 mmHg
• Flash Point: 139.6°C
• Density: 1.119g/cm³
• Vapor Pressure: 0.000391mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: 2,2-dimethyl-2H-chromen-6-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-dimethyl-2H-chromen-6-ol(19012-99-8)
• EPA Substance Registry System: 2,2-dimethyl-2H-chromen-6-ol(19012-99-8)

Safety Data

• Hazardous Substances Data: 19012-99-8(Hazardous Substances Data)

Usage

General Description

2,2-dimethyl-2H-chromen-6-ol, also known as esculetin, is a naturally occurring coumarin derivative with a chemical structure consisting of a chromen-6-ol core substituted with two methyl groups at the 2 position. It is commonly found in various plants, particularly in the bark of the horse chestnut tree and in the seeds of the celery plant. Esculetin has been studied for its potential pharmacological properties, including anti-inflammatory, antioxidant, anti-cancer, and anti-coagulant effects. It has also been investigated for its role in skin protection and wound healing. Additionally, esculetin has been used in traditional medicine for its potential health benefits, although further research is needed to fully understand its mechanisms of action and potential clinical applications.

Upstream product

• 5594-02-5 2-(3-methyl-2-buten-1-yl)-2,5-cyclohexadiene-1,4-dione 
• 556-82-1 3-methyl-2-buten-1-ol 
• 106-51-4 p-benzoquinone 
• 67-56-1 methanol 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 31366-85-5 6-hydroxy-2,2-dimethyl-chroman-4-one 
• 123-31-9 hydroquinone 
• 115-18-4 2-methyl-3-buten-2-ol 
• 132681-24-4 4-[(1,1-dimethyl-2-propynyl)oxy]phenol 
• 5919-91-5 prenylhydroquinone 
• 23030-43-5 2,5-dihydroxy-1-iodobenzene 
• 31366-88-8 6-hydroxy-2,2-dimethylchroman-4-ol 
• 93767-23-8 1-(2',5'-dihydroxyphenyl)-1-oxo-3-methylbutane-3-ol 

Relevant articles and documents

Structure-activity relationship studies on thiaplidiaquinones A and B as novel inhibitors of Plasmodium falciparum and farnesyltransferase

Marine meroterpenoids, thiaplidiaquinones A and B and their respective non-natural dioxothiazine regioisomers have been shown to inhibit mammalian and protozoal farnesyltransferase (FTase) with the regioisomers exhibiting activity in the nanomolar range. In order to explore the structure-activity relationship (SAR) of this class of marine natural products, analogues of thiaplidiaquinones A and B and their regioisomers were synthesised, with variation in the number of isoprene units present in their side chains to afford prenyl and farnesyl analogues. The previously reported geranyl series of compounds were found to be the most potent FTase inhibitors closely followed by the novel farnesyl series. The prenyl series exhibited the most potent anti-plasmodial activity but the series was also the most cytotoxic. Overall, the farnesyl series exhibited moderate anti-plasmodial activity with one analogue, 14 also exhibiting low cytotoxicity, identifying it as a scaffold worthy of further exploration.

Photoinduced Irreversible Intramolecular Proton Transfer of Arnebinones B, D, and E: The Case of Photoenolization at the p-Benzoquinone-CH2/CH-πSystem

Arnebinones B, E, and D (1-3) have been found to be sensitive to light, generating complex and diverse proton transfer products when triggered by light. A unique two-step irreversible intramolecular proton transfer of 1 produced five scalemic mixtures, of

Bio-inspired dimerisation of prenylated quinones directed towards the synthesis of the meroterpenoid natural products, the scabellones

Stirring 2-geranyl-6-methoxy-1,4-hydroquinone in pyridine/O2 or 2-geranyl-6-methoxy-1,4-benzoquinone in pyridine/N2 affords the dimeric meroterpenoid natural products, scabellones A-C in modest to low yields and also identifies 2-methoxy-6-(4-methylpent-3-en-1-yl)-1,4-naphthoquinone (scabellone E) as a new natural product. The corresponding reaction of the des-methoxy analogue, 2-geranyl-1,4-benzoquinone in degassed pyridine for three days afforded the natural product cordiachromene A (15% yield) and 6-(4-methylpent-3-en-1-yl)-1,4-naphthoquinone (12%), the latter being a likely biosynthetic precursor to the marine meroterpenoid alkaloids, conicaquinones A and B.