332900-03-5

Basic information

• Product Name: [⁽¹³⁾CO]-1-[2,4,-bis(benzyloxy)-6-hydroxyphenyl]ethanone
• Synonyms: [⁽¹³⁾CO]-1-[2,4,-bis(benzyloxy)-6-hydroxyphenyl]ethanone
• CAS NO: 332900-03-5
• Molecular Weight: 349.387
• Mol File: 332900-03-5.mol

Chemical Properties

• CAS DataBase Reference: [⁽¹³⁾CO]-1-[2,4,-bis(benzyloxy)-6-hydroxyphenyl]ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: [⁽¹³⁾CO]-1-[2,4,-bis(benzyloxy)-6-hydroxyphenyl]ethanone(332900-03-5)
• EPA Substance Registry System: [⁽¹³⁾CO]-1-[2,4,-bis(benzyloxy)-6-hydroxyphenyl]ethanone(332900-03-5)

Safety Data

• Hazardous Substances Data: 332900-03-5(Hazardous Substances Data)

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 1256496-52-2 1-[¹³C]-2',4',6'-trihydroxyacetophenone 
• 100-44-7 benzyl chloride 
• 59434-20-7 1,3,5-tri-O-benzylphloroglucinol 
• 332900-02-4 [⁽¹³⁾CO]-1-[2,4,6-tris(benzyloxy)phenyl]ethanone 

Downstream Products

• 1256496-59-9 (E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(3',4'-bis(benzyloxy)phenyl)prop-2-⁽¹³⁾C-en-1-[⁽¹³⁾C]-one 
• 1256496-63-5 (E)-[1-⁽¹³⁾C,3-⁽¹³⁾C]-(3,5-bis(benzyloxy)-2-(3-(3',4'-bis(benzyloxy)phenyl)allyl)phenoxy)(tert-butyldimethyl)silane 
• 1256496-65-7 (1S,2S)-[1-⁽¹³⁾C,3-⁽¹³⁾C]-3-(2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl)-1-(3',4'-bis(benzyloxy)phenyl)propane-1,2-diol 
• 1357910-94-1 C₄₂⁽¹³⁾C₂H₃₈O₇ 
• 1256496-71-5 5,7,3',4'-tetra-O-benzyl-[2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3S)-catechin 
• 1256496-74-8 [2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3S)-catechin 
• 1256496-78-2 (2R)-[2-⁽¹³⁾C,4-⁽¹³⁾C]-5,7-bis(benzyloxy)-2-(3',4'-bis(benzyloxy)chroman)-3-one 
• 1256496-81-7 5,7,3',4'-tetra-O-benzyl-[2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3R)-epicatechin 
• 1256496-83-9 [2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3R)-epicatechin 
• 357409-17-7 C₆₁⁽¹³⁾CH₅₂O₁₃ 
• 357409-16-6 C₆₁⁽¹³⁾CH₅₂O₁₃ 
• 357409-18-8 C₄₂⁽¹³⁾CH₃₈O₆ 
• 357409-21-3 (-)-[4-⁽¹³⁾C]catechin 
• 357409-20-2 C₄₂⁽¹³⁾CH₃₈O₆ 

Relevant articles and documents

Synthesis of [2-13C, 4-13C]-(2R,3S)-catechin and [2-13C, 4-13C]-(2R,3R)-epicatechin

The first synthesis of doubly labeled, [2-13C, 4- 13C]-(2R,3S)-catechin 15 and [2-13C, 4- 13C]-(2R,3R)-epicatechin 18 starting from labeled 2-hydroxy-4, 6-bis(benzyloxy)acetophenone 3 and labeled 3, 4-bis(benzyloxy)-benzaldehyde 7 are described. Copyright

Gram-scale production and applications of optically pure 13C-labelled (+)-catechin and (-)-epicatechin

In this paper gram-scale asymmetric total syntheses of pure (+)-4-[13C]catechin (1) and (-)-4-[13C]epicatechin (2) are described. Labelling was introduced through acylation of a phloroglucinol derivative 4 by 1-[13C]acetic acid, after activation by TFAA. Condensation of the resulting C6-C2 acetophenone building block 6 with a C1-C6 benzaldehyde unit 9 provided the C6-C3-C6 flavonoid skeleton, with benzyl ethers as phenol protecting groups. Asymmetry was introduced by an inexpensive and very efficient resolution process, performed at the penultimate step towards naturally occurring flavan-3-ols, by using tartaric acid derivatives. Both enantiomers of 4-[13C]catechin were obtained with a high level of enantiomeric purity, especially (+)-1 of the natural series. The other enantiomer (-)-1 was a valuable precursor of natural (-)-4-[13C]epicatechin by epimerisation at C-2. These two natural flavanols are thus obtained for the first time in large quantities in optically pure form as labelled compounds and will be useful tools for biological studies using NMR or isotopic mass spectrometry in forthcoming experiments.

Total synthesis of isotopically labelled flavonoids. Part 3: 13C-labelled (-)-procyanidin B3 from 1-[13C]-acetic acid

The regioselectively 13C-labelled (-)-procyanidin B3 was prepared in eight steps from 1-[13C]-acetic acid.