Noreugenin

Base Information

• Chemical Name: Noreugenin
• CAS No.: 1013-69-0
• Molecular Formula: C10H8O4
• Molecular Weight: 192.171
• Hs Code.: 2914400090
• UNII: M0KFC1Q5JC
• DSSTox Substance ID: DTXSID80143828
• Nikkaji Number: J12.482F
• Wikidata: Q27135833
• Metabolomics Workbench ID: 65021
• ChEMBL ID: CHEMBL507707
• Mol file: 1013-69-0.mol

Synonyms:Noreugenin;1013-69-0;5,7-Dihydroxy-2-methyl-4H-chromen-4-one;5,7-Dihydroxy-2-methylchromone;5,7-dihydroxy-2-methylchromen-4-one;4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-methyl-;5,7-Dihydroxy-2-methyl-4H-1-benzopyran-4-one;2-Methyl-5,7-dihydroxychromone;UNII-M0KFC1Q5JC;M0KFC1Q5JC;5,7-Dihydroxy-2-methylchromome;CHEBI:67375;4H-1-Benzopyran-4-one,5,7-dihydroxy-2-methyl-;Chromone, 5,7-dihydroxy-2-methyl-;MFCD03001435;dihydroxymethylchromone;SCHEMBL168822;2-Methyl-5,7-dihydroxychromon;CHEMBL507707;DTXSID80143828;HY-N3029;AKOS006277487;DIHYDROXY METHYLCHROMONE [INCI];5,7-dihydroxy-2-methyl-chromen-4-one;5,7-dihydroxy-2-methylbenzopyran-4-one;AS-78622;SY310866;CS-0023039;FT-0775292;5,7-Dihydroxy-2-methyl-4H-chromen-4-one #;C20462;A897187;Q27135833

Chemical Property of Noreugenin

Chemical Property:

• Vapor Pressure: 8.59E-07mmHg at 25°C
• Melting Point: 279 °C
• Refractive Index: 1.651
• Boiling Point: 394.6 °C at 760 mmHg
• PKA: 6.58±0.40(Predicted)
• Flash Point: 164 °C
• PSA: 70.67000
• Density: 1.456 g/cm³
• LogP: 1.51260
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 192.04225873
• Heavy Atom Count: 14
• Complexity: 284

Purity/Quality:

99.3% ^*data from raw suppliers

Noreugenin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C2=C(C=C(C=C2O1)O)O

Technology Process of Noreugenin

There total 19 articles about Noreugenin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.6%

3-Acetyl-5,7-bis(acetyloxy)-2-methyl-4H-1-benzopyran-4-one (1162-81-8) → eugenin (1013-69-0)

Guidance literature:

With sodium carbonate; for 2h; Reagent/catalyst; Reflux;

Reference yield: 66.7%

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) + acetic anhydride (108-24-7) → eugenin (1013-69-0)

Guidance literature:

2,4,6-trihydroxyacetophenone; acetic anhydride; With sodium acetate; for 2h; Reflux;

With sodium carbonate; In water; for 3h; Reflux;

Reference yield: 59.0%

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) + sodium acetate (127-09-3) → eugenin (1013-69-0)

Guidance literature:

2,4,6-trihydroxyacetophenone; sodium acetate; With acetic anhydride; at 180 ℃; for 0.666667h; Microwave irradiation;

With potassium carbonate; In water; for 2h; Reflux;

DOI:10.1021/jo902117e

upstream raw materials:

eugenin

1-Methyl-3-(2',4',6'-trimethoxyphenyl)propan-1,3-dione

3-acetyl-5,7-dihydroxy-2-methyl-chromen-4-one

2,4,6-trihydroxyacetophenone

Downstream raw materials:

eugenin

5-hydroxy-2-methyl-7-(toluene-4-sulfonyloxy)-chromen-4-one

2-methyl-5,7-bis-(toluene-4-sulfonyloxy)-chromen-4-one

eugenitin

Refernces

Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus

10.1016/j.carres.2010.07.029

The research primarily focuses on the synthesis and widespread occurrence of monoterpenoid esters, cuniloside B and cypellocarpin C, in the Eucalyptus genus. Experiments involved the synthesis of these esters along with related natural products using reactants such as D-glucopyranose, (+)-(R)-oleuropeic acid, noreugenin, and various glycosides. The synthesis processes were optimized using different conditions and reagents, including phase transfer glycosylation, deacetylation with sodium methoxide, and acylation using HBTU–NMM–DMAP. The experiments also encompassed the extraction and analysis of leaf samples from 28 diverse eucalypt species, utilizing techniques like LC-ESIMS, NMR, and IR spectroscopy for compound identification and quantification. The study revealed that cuniloside B is present in all examined species, while cypellocarpin C is found in most, suggesting their potential roles in essential oil biosynthesis or mobilization.

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