3,4-Divanillyltetrahydrofuran

3,4-Divanillyltetrahydrofuran is a lignan found in an Urtica dioica (stinging nettle) subspecies. This same compound may also be found in other lignan-containing plant sources such as Linum usitatissimum (flax seed).

3,4-Divanillyltetrahydrofuran
Names
IUPAC name
3,3′-Dimethoxy-9,9′-epoxylignane-4,4′-diol
Systematic IUPAC name
4,4′-[Oxolane-3,4-diylbis(methylene)]bis(2-methoxyphenol)
Other names
3,4-Divanilyltetrahydrofuran; α,α'-(Tetrahydro-3,4-furandiyl)dicreosol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C20H24O5/c1-23-19-9-13(3-5-17(19)21)7-15-11-25-12-16(15)8-14-4-6-18(22)20(10-14)24-2/h3-6,9-10,15-16,21-22H,7-8,11-12H2,1-2H3 checkY
    Key: ROGUIJKVZZROIQ-UHFFFAOYSA-N checkY
  • InChI=1/C20H24O5/c1-23-19-9-13(3-5-17(19)21)7-15-11-25-12-16(15)8-14-4-6-18(22)20(10-14)24-2/h3-6,9-10,15-16,21-22H,7-8,11-12H2,1-2H3
    Key: ROGUIJKVZZROIQ-UHFFFAOYAP
  • Oc1ccc(cc1OC)CC3COCC3Cc2cc(OC)c(O)cc2
Properties
C20H24O5
Molar mass 344.40 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

The compound has been found to occupy binding sites of sex hormone-binding globulin (SHBG), thereby reducing the ability of SHBG to bind additional steroid hormones such as estrogens and androgens, mostly testosterone and estradiol. Certain extracts of stinging nettle are therefore used by some bodybuilders in an effort to increase free testosterone.[1]

References
  1. Schöttner M; Gansser D; Spiteller G. (1997). "Interaction of lignans with human sex hormone binding globulin (SHBG)". Z Naturforsch C. 52 (11–12): 834–43. PMID 9463941.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.