Vescalagin (Oak C-Glucosidic Ellagitannin · Reactive Barrel Tannin)
Compiled from published pharmacological and botanical literature. Not independently verified by Herbuno. Spotted an error or have a correction? Flag it below →
| Compound | Vescalagin |
| Chemical class | Tannin — C-glucosidic ellagitannin (open-chain glucose; NHTP + HHDP units) |
| CAS | 54474-27-2 |
| Primary source | Quercus spp. (oak) and Castanea sativa (chestnut) heartwood; oak leaves |
| Key applications | Barrel-ageing tannin; flavono-ellagitannin precursor; enzyme-inhibition research |
| Claim strength | Moderate (technological); Emerging (bioactivity) |
| Typical form | Oak/chestnut heartwood ellagitannin extract (availability on request) |
| Buy from Herbuno | Availability on request — request bulk pricing → |
Name origin: Vescalagin, like its diastereomer castalagin, derives from the chestnut lineage of names attached to these wood tannins. It is a C-glucosidic ellagitannin: an open-chain glucose core joined by a carbon-carbon bond at C-1 to a nonahydroxyterphenoyl unit, with a hexahydroxydiphenoyl unit completing the structure. Vescalagin and castalagin differ only in the configuration at that C-1 centre, but the difference is functionally significant — vescalagin is much the more reactive of the two. Traditional use: Vescalagin has no medicinal tradition, but it has a central place in the technology of oak barrel ageing, a practice refined in Europe from the seventeenth and eighteenth centuries onward when it was observed that oak, uniquely among woods, improved wine Michel 2020. It is also present in oak leaves and contributes to the durability of oak timber. Research trajectory: Vescalagin and castalagin were the first C-glucosidic ellagitannin monomers isolated from chestnut and oak wood, fifty years ago, and remain the principal ellagitannins quantified in oak and in barrel-aged spirits Michel 2020; the stereochemistry of the pair has since been reinvestigated and revised Quideau (Org Lett). Vescalagin's distinctive chemistry is its reactivity. In young oak leaves it is degraded by an indirect oxidative route: polyphenol oxidase acts on catechin, and the resulting catechin o-quinone then oxidises one of vescalagin's pyrogallol rings to a cyclopentene-1,2-dione product, a mechanism confirmed by detection of the product in the leaves Oxidation of vescalagin. The same C-1 reactivity generates the flavono-ellagitannins, such as acutissimin A, when vescalagin reacts with catechin during wine ageing. Commercial source: Oak or chestnut heartwood ellagitannin extract is available from Herbuno on request.
Evidence for Vescalagin Applications
Principal oak ellagitannin: Vescalagin and castalagin are the main ellagitannin monomers of oak wood, which carries these compounds at up to 10% of heartwood dry weight; they are extracted progressively into wine and spirits during barrel ageing, contributing to colour, astringency, and bitterness, and a validated LC-QQQ method quantifies them through the ageing process Michel 2020. Claim strength: Moderate (technological).
Distinctive reactivity: Vescalagin's C-1 configuration makes it far more prone than castalagin to form carbon-carbon bonds with nucleophiles, and this reactivity generates the flavono-ellagitannins — acutissimin A being formed when vescalagin reacts with the flavan-3-ol catechin. This is the chemical basis of oak-tannin/grape-polyphenol interaction during ageing. Claim strength: Moderate.
Oxidative degradation mechanism: In young oak leaves, vescalagin declines as catechin and procyanidins rise, and the mechanism has been worked out: polyphenol oxidase first oxidises the catechin B-ring, and the resulting catechin o-quinone then oxidises one of vescalagin's pyrogallol rings to give a cyclopenten-1,2-dione product, whose presence in the leaves was confirmed directly Oxidation of vescalagin. This is an elegant demonstration of indirect, coupled oxidation. Claim strength: Moderate.
Stereochemical definition: The stereochemistry of vescalagin and castalagin has been reinvestigated and corrected in the modern literature, definitively establishing the configurations that distinguish the two diastereomers Quideau (Org Lett). Claim strength: Moderate.
Carbohydrase inhibition: Vescalagin has been evaluated among fourteen C-glucosidic ellagitannins, alongside galloylated glucoses, for alpha-glucosidase and alpha-amylase inhibition as potential functional food ingredients with antidiabetic properties; these are in vitro enzyme-inhibition studies rather than clinical evidence Quideau (Org Lett). Claim strength: Emerging.
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Dosage & Formulator Specification
Vescalagin has no established human dosing and is not offered as a purified compound. Like castalagin, its evidence base is predominantly technological rather than nutritional, and the bioactivity data are early-stage in vitro enzyme work that would not support a functional-ingredient position.
The same source distinction applies as for castalagin, and it bears repeating because the genus name invites the error. Vescalagin is an oak and chestnut heartwood ellagitannin. Herbuno's Majuphal product is Quercus infectoria gall extract — gallotannin material dominated by galloylglucoses and gallic acid, chemically distinct from the C-glucosidic heartwood ellagitannins and containing no meaningful vescalagin. Species alone does not determine chemistry; tissue does. Oak or chestnut heartwood ellagitannin extract standardised to C-glucosidic ellagitannins is available from Herbuno on request.
Vescalagin's reactivity is the practical handling issue. It is not a stable, inert tannin: its C-1 position readily forms adducts with nucleophiles including flavan-3-ols, and it is susceptible to coupled oxidation via catechin quinones. In any material containing both vescalagin and catechins — which describes oak-aged wine, and would describe any co-formulation of oak tannin with a flavanol-rich extract — adduct formation and oxidative loss should be anticipated rather than assumed away. This reactivity is central to what oak tannins do in wine, but it is a stability liability in a formulated product.
This monograph documents vescalagin as a formulator reference within the HerbIQ index, connecting it to castalagin (its diastereomer), the galloylglucoses, and the wider ellagitannin group covered elsewhere.
Frequently Asked Questions — Vescalagin
What is vescalagin?
Vescalagin is a C-glucosidic ellagitannin of oak and chestnut wood and the C-1 diastereomer of castalagin. Together the two are the principal ellagitannin monomers of oak heartwood and the main tannins extracted into wine and spirits during barrel ageing.
How does vescalagin differ from castalagin?
They are diastereomers, differing only in the configuration at C-1 of the open-chain glucose core. That single stereochemical difference makes vescalagin the more reactive of the pair: its C-1 position readily forms carbon-carbon bonds with nucleophiles, which is how the flavono-ellagitannins such as acutissimin A arise from reaction with catechin.
Can I source vescalagin from Herbuno?
Oak or chestnut heartwood ellagitannin extract standardised to C-glucosidic ellagitannins is available on request. Herbuno's Majuphal (Quercus infectoria gall) product is gallotannin material, not heartwood ellagitannin, and does not deliver vescalagin.
Is vescalagin stable?
It is chemically reactive rather than inert. In young oak leaves, vescalagin is degraded through a polyphenol-oxidase-mediated route: the oxidase acts on catechin, and the resulting catechin o-quinone oxidises one of vescalagin's pyrogallol rings. Its reactivity toward nucleophiles at C-1 also drives adduct formation during wine ageing.
Related compounds: Castalagin, Galloylglucose, Catechin, Ellagic Acid
Claim-strength scale – High = multiple human RCTs; Moderate = limited trials or strong preclinical convergence; Emerging = early-stage lab or animal data.
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