1256496-52-2Relevant academic research and scientific papers
Total synthesis of [13C]2-, [13C]3-, and [13C]5-isotopomers of xanthohumol, the principal prenylflavonoid from hops
Ellinwood, Duncan C.,El-Mansy, Mohamed F.,Plagmann, Layhna S.,Stevens, Jan F.,Maier, Claudia S.,Gombart, Adrian F.,Blakemore, Paul R.
, p. 639 - 648 (2017)
Xanthohumol [(E)-6′-methoxy-3′-(3-methylbuten-2-yl)-2′,4′,4″-trihydroxychalcone], he principal prenylated flavonoid from hops, has a complex bioactivity profile, and 13C-labeled isotopomers of this compound are of potential use as molecular probes and as analytical standards to study metabolism and mode of action. 1,3-[13C]2-Xanthohumol was prepared by an adaptation of the total synthesis of Khupse and Erhardt in 7 steps and 5.7% overall yield from phloroglucinol by a route incorporating a cascade Claisen-Cope rearrangement to install the 3′-prenyl moiety from a 5′-prenyl aryl ether and an aldol condensation between 1-[13C]-2′,4′-bis(benzyloxymethyloxy)-6′-methoxy-3′-(3-methylbuten-2-yl)acetophenone and 1′-[13C]-4-(methoxymethyloxy)benzaldehyde. The 13C-atom in the methyl ketone was derived from 1-[13C]-acetyl chloride while that in the aryl aldehyde was derived from [13C]-iodomethane. Tri- and penta-13C-labeled xanthohumols were similarly prepared by applying minor modifications to the route.
Synthesis of [2-13C, 4-13C]-(2R,3S)-catechin and [2-13C, 4-13C]-(2R,3R)-epicatechin
Sharma, Pradeep K.,He, Min,Romanczyk Jr., Leo J.,Schroeter, Hagen
experimental part, p. 605 - 612 (2011/08/21)
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
