82864-24-2

Basic information

• Product Name: (3S,4S)-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol
• CAS NO: 82864-24-2
• Molecular Formula: C₁₂H₁₆O₄
• Molecular Weight: 224.253
• Mol File: 82864-24-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 340.6°C at 760 mmHg
• Flash Point: 159.8°C
• Density: 1.22g/cm³
• Vapor Pressure: 3.28E-05mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: (3S,4S)-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol(82864-24-2)
• EPA Substance Registry System: (3S,4S)-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol(82864-24-2)

Safety Data

• Hazardous Substances Data: 82864-24-2(Hazardous Substances Data)

Usage

Description

(3S,4S)-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol, a dihydrochalcone flavonoid compound with the molecular formula C12H16O4, is commonly found in plant-based foods. It is recognized for its antioxidant properties and has potential applications in various industries, including pharmaceuticals and cosmetics. (3S,4S)-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol has been studied for its potential use in skincare products and as a natural alternative to synthetic antioxidants. Furthermore, research indicates that it may possess anti-inflammatory and anti-cancer properties, making it a promising candidate for further investigation in medicinal chemistry.

Uses

Used in Pharmaceutical Applications:
(3S,4S)-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol is used as a potential therapeutic agent for its anti-inflammatory and anti-cancer properties. It is being investigated for its ability to modulate various signaling pathways associated with inflammation and cancer, which could lead to the development of novel treatments for these conditions.
Used in Cosmetic Applications:
In the cosmetics industry, (3S,4S)-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol is used as an ingredient in skincare products for its antioxidant properties. Its natural origin and potential benefits for skin health make it an attractive alternative to synthetic antioxidants, which could help in formulating more effective and safer skincare products.
Used in Food Industry:
(3S,4S)-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol is used as a natural antioxidant in the food industry to extend the shelf life of products and maintain their quality. Its presence in plant-based foods and its antioxidant capabilities make it a suitable candidate for enhancing the nutritional value and preserving the freshness of various food items.

Upstream product

• 82833-93-0 3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4S)-3-bromo-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 82833-91-8 (2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3R,4R)-3-[2-(2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 17598-02-6 2,2 dimethyl 7 methoxychromene 
• 180469-92-5 (-)-(3S,4S)-3,4-Epoxy-7-methoxy-2,2-dimethylchromane 
• 73385-38-3 (+/-)-trans-3-Bromo-7-methoxy-2,2-dimethylchraman-4-ol 
• 82833-92-9 (3R,4S)-3-Bromo-7-methoxy-2,2-dimethyl-chroman-4-ol 
• 82833-93-0 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4S)-3-bromo-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 13229-63-5 cis-3,4-dihydroxy-7-methoxy-2,2-dimethylchroman 
• 73385-36-1 cis-4-(3-chlorobenzoyloxy)-3-hydroxy-7-methoxy-2,2-dimethylchroman 
• 87894-88-0 (+/-)-3-acetoxy-7-methoxy-2,2-dimethylchroman-4-one 
• 343829-23-2 3-Chloro-benzoic acid 3-hydroxy-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 54874-21-4 7-methoxy-2,2-dimethylchroman-4-ol 
• 20321-73-7 7-methoxy-2,2-dimethyl-4-chromanone 
• 73385-36-1 trans-4-(3-chlorobenzoyloxy)-3-hydroxy-7-methoxy-2,2-dimethylchroman 

Downstream Products

• 83686-07-1 C₃₀H₃₄N₂O₆ 
• 82833-91-8 (2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3R,4R)-3-[2-(2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 82833-91-8 (2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3S,4S)-3-[2-(2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 82833-91-8 (2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3R,4S)-3-[2-(2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 82833-91-8 (2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3S,4R)-3-[2-(2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 82864-23-1 (+)-(3R,4R)-cis-7-Methoxy-2,2-dimethylchromane-3,4-diol 
• 82864-22-0 (-)-(3R,4S)-trans-7-Methoxy-2,2-dimethylchromane-3,4-diol 
• 82864-21-9 (+)-(3S,4R)-trans-7-Methoxy-2,2-dimethylchromane-3,4-diol 
• 83686-04-8 C₃₀H₃₄N₂O₆ 

Relevant articles and documents

OsO4?streptavidin: A tunable hybrid catalyst for the enantioselective cis-dihydroxylation of olefins

Taking control: Selective catalysts for olefin dihydroxylation have been generated by the combination of apo-streptavidin and OsO4. Site-directed mutagenesis allows improvement of enantioselectivity and even inversion of enantiopreference in certain cases. Notably allyl phenyl sulfide and cis-β-methylstyrene were converted with unprecedented enantiomeric excess.

Synthesis of models of metabolites: Oxidation of variously substituted chromenes including acronycine, by a porphyrin catalytic system

The influence of chemical neighbouring on oxidation of substituted 2,2-dimethylchromenes derivatives 5-8 by a biomimetic catalytic system was first studied. It was then applied to acronycine an anti-cancer drug in order to obtain in one single step oxidized products resulting from the reactivity of the 1,2-double bond in the pyranic D-ring. These 2,2-dimethylchromenes constitute the structural moiety responsible for the activity of acronycine. This oxidation showed the sensitivity of the ethylenic bond, leading to the formation of the corresponding epoxides, diols and/or ketoalcohol. In the case of 5-dimethylamino-2,2-dimethylchromene 8, the double bond was not sensitive to oxidation, but the N-methyl groups reacted to lead to the formamide derivative 16 and an imino-alcohol 17. This methodology applied to acronycine molecule 1, allowed to obtain in one step, two oxidized compounds, a trans-diol 3 and a ketoalcohol 4 under preparative conditions.

Osmium-Catalyzed Asymmetric Dihydroxylation of Cyclic Cis-Disubstituted Olefins

A new class of cis-disubstituted olefins has been found to give good enantioselectivities in the asymmetric dihydroxylation reaction using the standard PHAL and PYR ligands, all the olefins are conjugated, and the reacting double bond is endocyclic in a 5