3,4-Divanillyltetrahydrofuran: Properties, Uses & Lab Guide

3,4-Divanillyltetrahydrofuran is a naturally occurring lignan isolated from the roots of Urtica dioica that has attracted significant research interest for its ability to bind sex hormone-binding globulin (SHBG) and its associated anti-inflammatory and endocrine-modulatory properties.

Chemical Name

3,4-Divanillyltetrahydrofuran (also known as (-)-3,4-Divanillyltetrahydrofuran or DVTHF)

Compound Class

Lignan (furofuran-type plant secondary metabolite)

Primary Biological Source

Roots of Urtica dioica (stinging nettle)

Key Pharmacological Activity

Sex hormone-binding globulin (SHBG) ligand; reported anti-inflammatory activity

Aladdin SKU

D668121

Recommended Storage

Cool, dry, dark conditions; follow SDS guidance for specific temperature requirements

Chemical Identity and Physicochemical Properties

3,4-Divanillyltetrahydrofuran (DVTHF) is a lignan natural product belonging to the furofuran structural class. Its core scaffold consists of a tetrahydrofuran ring bearing two vanillyl (4-hydroxy-3-methoxybenzyl) substituents at the 3- and 4-positions. This symmetric arrangement of phenylpropanoid-derived units is characteristic of plant lignans formed through oxidative coupling of coniferyl alcohol precursors.

The compound is typically isolated as a white to off-white solid. It is sparingly soluble in water but dissolves in common organic solvents such as ethanol, methanol, dimethyl sulfoxide (DMSO), and ethyl acetate. Researchers preparing stock solutions for cell-based assays are advised to prepare concentrated stocks in DMSO and dilute into aqueous buffer immediately before use to avoid precipitation. The molecular formula and exact molecular weight should be confirmed against the certificate of analysis (CoA) supplied with each lot of Aladdin Scientific SKU D668121.

Note: Specific physicochemical constants (melting point, optical rotation, logP) were not available in the source material; consult the product CoA or peer-reviewed literature and verify before use in regulatory submissions.

Biological Activities and Research Applications

The most extensively studied biological activity of DVTHF is its capacity to bind sex hormone-binding globulin (SHBG), a hepatically produced glycoprotein that regulates the bioavailability of androgens and estrogens in plasma. By competing with endogenous steroids for SHBG binding sites, DVTHF may modulate free hormone concentrations, making it a valuable pharmacological tool for in vitro SHBG-binding assays and mechanistic endocrinology studies.

Research has also investigated the anti-inflammatory potential of Urtica dioica root extracts enriched in DVTHF and related lignans. Proposed mechanisms include inhibition of pro-inflammatory transcription factor NF-κB signaling and modulation of eicosanoid pathways, although researchers should independently verify specific IC50 values and pathway data against primary literature before citing them in new work.

Additional reported research contexts include: (1) benign prostatic hyperplasia (BPH) model studies, where Urtica root lignans have been evaluated as complementary research tools; (2) antioxidant activity assays; and (3) structure–activity relationship (SAR) studies comparing DVTHF with other hydroxylated lignans. Aladdin Scientific supplies DVTHF (SKU D668121) as a reference standard-grade reagent suitable for these in vitro and preclinical research applications.

Safe Handling, Storage, and Preparation Guidelines

General Precautions: As with all fine research chemicals, handle DVTHF using standard laboratory safety practices: wear appropriate personal protective equipment (PPE) including nitrile gloves, safety glasses, and a laboratory coat. Avoid generating dust when weighing the solid form. Work in a well-ventilated area or fume hood where appropriate.

Storage: Store the compound in a tightly sealed container away from light, moisture, and heat. Specific recommended storage temperature should be taken from the product Safety Data Sheet (SDS) and CoA provided by Aladdin Scientific. Do not freeze-thaw stock solutions repeatedly, as this can promote degradation.

Solution Preparation:

• Prepare a concentrated master stock in anhydrous DMSO (typical starting concentration: 10–50 mM; verify solubility empirically for your lot).
• For aqueous assay media, dilute DMSO stock to achieve a final DMSO concentration ≤0.1% v/v to minimise solvent effects on biological assays.
• Filter-sterilise (0.22 µm) if the solution will be used in cell culture.
• Aliquot and store at the temperature specified on the CoA; avoid repeated freeze–thaw cycles.

Disposal: Dispose of waste material in accordance with local institutional and governmental regulations for organic chemical waste.

Quality, Purity, and Procurement

Aladdin Scientific supplies 3,4-Divanillyltetrahydrofuran under SKU D668121. Each lot is accompanied by a Certificate of Analysis (CoA) documenting purity (typically assessed by HPLC), structural confirmation data (e.g., NMR, MS), and physical characteristics. Researchers requiring the compound as a reference standard for quantitative analytical work should confirm that the supplied purity grade meets their assay requirements before ordering.

For procurement, visit the Aladdin Scientific product page for D668121 to view current stock availability, pack sizes, and pricing. Bulk quantities may be available upon request through the Aladdin customer service team. When placing an order, ensure the correct CAS number is cited and cross-reference with the CoA upon receipt to confirm lot-specific purity and identity.

For questions regarding specifications, grades, and purity suitability for specific applications, contact Aladdin Scientific's technical support team, who can advise on whether the standard reagent grade meets the requirements of your research protocol or whether a higher-purity grade is warranted.

Frequently asked questions

What is 3,4-Divanillyltetrahydrofuran used for in research?

DVTHF is primarily used as a pharmacological tool to study sex hormone-binding globulin (SHBG) binding interactions and to investigate the mechanisms underlying the anti-inflammatory and endocrine-modulatory activities associated with Urtica dioica root extracts. It is also employed in antioxidant assays and structure–activity relationship studies of hydroxylated lignans.

How should I dissolve 3,4-Divanillyltetrahydrofuran for cell-based assays?

Prepare a concentrated stock solution (10–50 mM) in anhydrous DMSO, then dilute immediately before use into aqueous assay buffer or cell culture medium to achieve a final DMSO concentration of ≤0.1% v/v. Filter the diluted solution through a 0.22 µm membrane if sterility is required. Verify empirical solubility for your specific lot using the CoA data.

What is the Aladdin Scientific SKU for 3,4-Divanillyltetrahydrofuran?

3,4-Divanillyltetrahydrofuran is available from Aladdin Scientific under SKU D668121. Each lot is supplied with a Certificate of Analysis confirming purity and structural identity. Contact Aladdin customer service for information on pack sizes, pricing, and bulk availability.

Is 3,4-Divanillyltetrahydrofuran the same compound found in Urtica dioica root extracts?

Yes. DVTHF is one of the principal lignan constituents identified in the root of Urtica dioica (stinging nettle) and is considered a key bioactive component of standardised nettle root extracts used in pharmacological research. The isolated pure compound supplied by Aladdin Scientific allows researchers to study its activity independently of other extract constituents.

References

1. Schöttner M, Ganßer D, Spiteller G. Lignans from the roots of Urtica dioica and their metabolites bind to human sex hormone binding globulin (SHBG). Planta Medica. 1997;63(6):529–532.
2. Chrubasik JE, Roufogalis BD, Wagner H, Chrubasik S. A comprehensive review on the stinging nettle effect and efficacy profiles. Part II: urticae radix. Phytomedicine. 2007;14(7–8):568–579.
3. Aladdin Scientific. Product page: 3,4-Divanillyltetrahydrofuran, SKU D668121. Accessed 2024.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.