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D-9200 (R,S)-2,3-Dihydrodaidzein, >99%

D-9200PR

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M.W. 256.25

C₁₅H₁₂O₄

Storage: Store at or below -20 ºC. Solubility: Soluble in DMSO, methanol, or ethanol. Disposal: A

Human urinary metabolite of daidzein. Heinonen, S., et al. "Identification of isoflavone metabolites dihydrodaidzein, dihydrogenistein, 6'-OH-O-dma, and cis-4-OH-equol in human urine by gas chromatography-mass spectrometry using authentic reference compounds." Anal. Biochem. 274: 211-219 (1999).

This product is a racemic mixture of the R- and S-enantiomers. As of this writing, we are not aware of any studies establishing the stereochemistry of the human urinary metabolite form of dihydrodaidzein. This is an important point; the natural metabolite is likely to be a single stereoisomer with different biological properties from the racemic mixture.

The Heinonen et al. article makes many references to the "enol tautomer" of dihydrodaidzein. Although is it not always obvious from the wording in their descriptions, a careful reading indicates that all references in this article to the "enol tautomer" of dihydrodaidzein refer to a silylated derivative of this compound. The trimethylsilyl ether of the enol is indeed an isolatable compound, whereas the free, unsilylated enol form is in dynamic equilibrium with the keto form and cannot be isolated separately.

We have found that dihydrodaidzein is somewhat unstable in air; it partially oxidizes to form daidzein if left at room temperature for a few days, even if kept in the dark as a dry powder. Storage in solid form at -20 ºC under nitrogen is recommended. Solutions are expected to be even more susceptible to oxidation than the solid, so they should be freshly prepared and used as quickly as possible.

NOTE: Although there are one or two exceptions, we generally do not carry products that are unstable and not easily maintained at 98-99+% purity under ordinary handling conditions. At present, dihydrodaidzein is not in stock, and we are working to solve production problems for this compound related to its stability.

Sold for laboratory or manufacturing purposes only; not for human, veterinary, food, or household use.

(R, S)-2,3-Dihydrodaidzein