3,4-Divanillyltetrahydrofuran

3,4-Divanillyltetrahydrofuran

IUPAC name 4,4’-(Tetrahydrofuran-3,4-diyldimethanediyl)bis(2-methoxyphenol)
Other names 3,4-Divanilyltetrahydrofuran; α,α'-(Tetrahydro-3,4-furandiyl)dicreosol
Identifiers
CAS number	34730-78-4^N
PubChem	182210
ChemSpider	158474^Y
ChEMBL	CHEMBL405043^Y
Jmol-3D images	Image 1
SMILES Oc1ccc(cc1OC)CC3COCC3Cc2cc(OC)c(O)cc2
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
Properties
Molecular formula	C₂₀H₂₄O₅
Molar mass	344.40 g/mol
Exact mass	344.162374 u
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

3,4-Divanillyltetrahydrofuran is a lignan found in a 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. PMID 9463941.