Divanillin | CAS#2092-49-1 | biochemical

MedKoo Cat#: 146220 | Name: Divanillin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Divanillin is a naturally occurring dimer of vanillin, typically formed through oxidative coupling. It is known for its antioxidant and antimicrobial properties and is used in research and industry as a flavoring agent, fragrance component, and potential pharmaceutical intermediate. Its mechanism of action primarily involves free radical scavenging due to its phenolic structure, which helps neutralize oxidative species and may inhibit microbial growth by disrupting cellular processes. Ongoing studies also explore its role in polymer chemistry and materials science due to its reactive functional groups.

Chemical Structure

Divanillin

CAS#2092-49-1

Theoretical Analysis

MedKoo Cat#: 146220

Name: Divanillin

CAS#: 2092-49-1

Chemical Formula: C16H14O6

Exact Mass: 302.0790

Molecular Weight: 302.28

Elemental Analysis: C, 63.58; H, 4.67; O, 31.76

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Divanillin; Dehydrovanillin;

IUPAC/Chemical Name

6,6'-dihydroxy-5,5'-dimethoxy-[1,1'-biphenyl]-3,3'-dicarbaldehyde

InChi Key

NSTQUZVZBUTVPY-UHFFFAOYSA-N

InChi Code

1S/C16H14O6/c1-21-13-5-9(7-17)3-11(15(13)19)12-4-10(8-18)6-14(22-2)16(12)20/h3-8,19-20H,1-2H3

SMILES Code

COC1=C(O)C(=CC(C=O)=C1)C2=CC(C=O)=CC(OC)=C2O

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 302.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Zhang M, Subramaniyan S, Hakkarainen M. Divanillin Cross-Linked Recyclable Cellulose Networks. Macromol Rapid Commun. 2025 Mar 26:e2401094. doi: 10.1002/marc.202401094. Epub ahead of print. PMID: 40135528. 2: Savonnet E, Le Coz C, Grau E, Grelier S, Defoort B, Cramail H. Divanillin- Based Aromatic Amines: Synthesis and Use as Curing Agents for Fully Vanillin- Based Epoxy Thermosets. Front Chem. 2019 Sep 6;7:606. doi: 10.3389/fchem.2019.00606. PMID: 31555641; PMCID: PMC6743216. 3: Garbay G, Giraud L, Gali SM, Hadziioannou G, Grau E, Grelier S, Cloutet E, Cramail H, Brochon C. Divanillin-Based Polyazomethines: Toward Biobased and Metal-Free π-Conjugated Polymers. ACS Omega. 2020 Mar 4;5(10):5176-5181. doi: 10.1021/acsomega.9b04181. PMID: 32201805; PMCID: PMC7081409. 4: Kunkel R, Fath M, Schmiedl D, Schmidt VM, Tübke J. Electroreduction of divanillin to polyvanillin in an electrochemical flow reactor. BMC Chem. 2024 Feb 8;18(1):28. doi: 10.1186/s13065-024-01133-2. PMID: 38331896; PMCID: PMC10854100. 5: Venturini D, de Souza AR, Caracelli I, Morgon NH, da Silva-Filho LC, Ximenes VF. Induction of axial chirality in divanillin by interaction with bovine serum albumin. PLoS One. 2017 Jun 2;12(6):e0178597. doi: 10.1371/journal.pone.0178597. PMID: 28575123; PMCID: PMC5456067. 6: Imer MR, Aldabalde V, Pagola S, Streek JV, Suescun L. Four interpenetrating hydrogen-bonded three-dimensional networks in divanillin. Acta Crystallogr C Struct Chem. 2018 Dec 1;74(Pt 12):1768-1773. doi: 10.1107/S2053229618016200. Epub 2018 Nov 27. PMID: 30516163. 7: Fanjul-Mosteirín N, Odelius K. Covalent Adaptable Networks with Tailorable Material Properties Based on Divanillin Polyimines. Biomacromolecules. 2024 Apr 8;25(4):2348-2357. doi: 10.1021/acs.biomac.3c01224. Epub 2024 Mar 18. PMID: 38499398; PMCID: PMC11005045. 8: Oliveira GSN, Furlaneto CG, Tokuhara CK, Ventura TMO, Pessôa AS, Fakhoury VS, Pagnan AL, Inacio KK, Sanches MLR, Buzalaf MAR, Ximenes VF, Oliveira RC. Exploring the effects of vanillin and divanillin on murine osteosarcoma cells: evaluation of cellular response and proteomic analysis. Nat Prod Res. 2024 Sep 1:1-6. doi: 10.1080/14786419.2024.2398207. Epub ahead of print. PMID: 39219162. 9: Kumar B, Agumba DO, Pham DH, Latif M, Dinesh, Kim HC, Alrobei H, Kim J. Recent Research Progress on Lignin-Derived Resins for Natural Fiber Composite Applications. Polymers (Basel). 2021 Apr 5;13(7):1162. doi: 10.3390/polym13071162. PMID: 33916412; PMCID: PMC8038635. 10: Telatin T, De la Flor S, Montané X, Serra À. Chemically Degradable Vitrimers Based on Divanillin Imine Diepoxy Monomer and Aliphatic Diamines for Enhanced Carbon Fiber Composite Applications. Polymers (Basel). 2024 Sep 29;16(19):2754. doi: 10.3390/polym16192754. PMID: 39408465; PMCID: PMC11479291. 11: Kunkel R, Schmidt VM, Cremers C, Müller D, Schmiedl D, Tübke J. Electrochemical synthesis of biobased polymers and polymer building blocks from vanillin. RSC Adv. 2021 Mar 1;11(15):8970-8985. doi: 10.1039/d1ra00649e. PMID: 35423363; PMCID: PMC8695360. 12: Colpa DI, Lončar N, Schmidt M, Fraaije MW. Creating Oxidase-Peroxidase Fusion Enzymes as a Toolbox for Cascade Reactions. Chembiochem. 2017 Nov 16;18(22):2226-2230. doi: 10.1002/cbic.201700478. Epub 2017 Oct 11. PMID: 28885767; PMCID: PMC5708271. 13: Silva D, Sousa AC, Robalo MP, Martins LO. A wide array of lignin-related phenolics are oxidized by an evolved bacterial dye-decolourising peroxidase. N Biotechnol. 2023 Nov 25;77:176-184. doi: 10.1016/j.nbt.2022.12.003. Epub 2022 Dec 20. PMID: 36563877. 14: Eydelman I, Zehavi N, Feinshtein V, Kumar D, Ben-Shabat S, Sintov AC. Cannabidiol-Loaded Nanoparticles Based on Crosslinked Starch: Anti-Inflammatory Activity and Improved Nose-to-Brain Delivery. Pharmaceutics. 2023 Jun 23;15(7):1803. doi: 10.3390/pharmaceutics15071803. PMID: 37513990; PMCID: PMC10384644. 15: Giraud L, Grelier S, Grau E, Garel L, Hadziioannou G, Kauffmann B, Cloutet É, Cramail H, Brochon C. Synthesis and Characterization of Vanillin-Based π-Conjugated Polyazomethines and Their Oligomer Model Compounds. Molecules. 2022 Jun 28;27(13):4138. doi: 10.3390/molecules27134138. PMID: 35807392; PMCID: PMC9268122. 16: Jantaree P, Lirdprapamongkol K, Kaewsri W, Thongsornkleeb C, Choowongkomon K, Atjanasuppat K, Ruchirawat S, Svasti J. Homodimers of Vanillin and Apocynin Decrease the Metastatic Potential of Human Cancer Cells by Inhibiting the FAK/PI3K/Akt Signaling Pathway. J Agric Food Chem. 2017 Mar 22;65(11):2299-2306. doi: 10.1021/acs.jafc.6b05697. Epub 2017 Mar 8. PMID: 28248106. 17: Saito K, Eisenreich F, Türel T, Tomović Ž. Closed-Loop Recycling of Poly(Imine-Carbonate) Derived from Plastic Waste and Bio-based Resources. Angew Chem Int Ed Engl. 2022 Oct 24;61(43):e202211806. doi: 10.1002/anie.202211806. Epub 2022 Sep 29. PMID: 36074694; PMCID: PMC9828757. 18: Boukis AC, Llevot A, Meier MA. High Glass Transition Temperature Renewable Polymers via Biginelli Multicomponent Polymerization. Macromol Rapid Commun. 2016 Apr;37(7):643-9. doi: 10.1002/marc.201500717. Epub 2016 Jan 22. PMID: 26800511. 19: Yamamoto H, Hoshino T, Uchiyama T. Convenient Preparation and Quantification of 5,5'-Diferulic Acid. Biosci Biotechnol Biochem. 1999;63(2):390-4. doi: 10.1271/bbb.63.390. PMID: 27393064. 20: Saito K, Türel T, Eisenreich F, Tomović Ž. Closed-Loop Recyclable Poly(imine-acetal)s with Dual-Cleavable Bonds for Primary Building Block Recovery. ChemSusChem. 2023 Nov 8;16(21):e202301017. doi: 10.1002/cssc.202301017. Epub 2023 Aug 21. PMID: 37518676.