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
CAS Number	34730-78-4 N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL405043 Y
ChemSpider	158474 Y
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 Y Key: ROGUIJKVZZROIQ-UHFFFAOYSA-N Y 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). N verify (what is YN ?) 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]