3,4-Divanillyltetrahydrofuran

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
CAS Number	34730-78-4 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL405043 ;
ChemSpider	158474 ;
PubChem CID	182210;
CompTox Dashboard (EPA)	DTXSID20956217 ;
	InChI 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 Key: ROGUIJKVZZROIQ-UHFFFAOYSA-N ; 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;
	SMILES Oc1ccc(cc1OC)CC3COCC3Cc2cc(OC)c(O)cc2;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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).

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

^ 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. doi:10.1515/znc-1997-11-1218. PMID 9463941.

[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. doi:10.1515/znc-1997-11-1218. PMID 9463941.

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