6′-O-Benzoylpaeoniflorin

6′-O-Benzoylpaeoniflorin at a Glance

6′-O-Benzoylpaeoniflorin — usually shortened to benzoylpaeoniflorin — is a minor monoterpene glycoside of peony root (Paeonia lactiflora and the related tree peony, P. × suffruticosa). Structurally it is the parent glycoside paeoniflorin carrying a benzoyl ester on the 6′ position of its glucose. That single acyl group is the whole story of the molecule: it is what distinguishes benzoylpaeoniflorin from paeoniflorin, and it is what separates it from the galloyl esters of the same peony series — 6′-O-galloylpaeoniflorin, 6′-O-galloylalbiflorin and 3′-O-galloylpaeoniflorin — which carry a galloyl (trihydroxybenzoyl) group instead.

The molecule surfaces in two strands of the peony literature. In a screen of peony-root constituents for androgen-receptor activity, benzoylpaeoniflorin acted as a weak AR antagonist ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}. Separately, it was flagged as one of the major active constituents behind peony’s antiplatelet and anticoagulant activity ^{2Reference 2Koo YK et al. · 2010Platelet anti-aggregatory and blood anti-coagulant effects of compounds isolated from Paeonia lactiflora and Paeonia suffruticosaView study →}. Both findings are in-vitro, on the isolated compound — there is no human data on benzoylpaeoniflorin itself.

This is a thin molecule. The honest posture is that benzoylpaeoniflorin is a real, named peony constituent with a couple of specific in-vitro signals, not an established active in its own right.

The Benzoyl Ester of Paeoniflorin

The point of this molecule is its acylation, so it is worth separating clearly from its relatives.

• Parent — paeoniflorin. The pharmacopoeial marker of white peony root; the unacylated glycoside. In the androgen screen, paeoniflorin and albiflorin showed no AR binding at all ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}.
• This compound — 6′-O-benzoylpaeoniflorin. Paeoniflorin with a benzoyl group (C₆H₅–CO–) esterified at the 6′-hydroxyl of the glucose. The acyl group confers the modest AR affinity and the antiplatelet activity that the bare parent lacks ^{1,2Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →Reference 2Koo YK et al. · 2010Platelet anti-aggregatory and blood anti-coagulant effects of compounds isolated from Paeonia lactiflora and Paeonia suffruticosaView study →}.
• The galloyl cousins. 6′-O-galloylpaeoniflorin, 6′-O-galloylalbiflorin and 3′-O-galloylpaeoniflorin carry a galloyl (3,4,5-trihydroxybenzoyl) group. The extra phenolic hydroxyls matter: in the same study the galloyl ester 6′-O-galloylalbiflorin was a strong AR binder (IC₅₀ ≈ 33.7 µg/mL), whereas benzoylpaeoniflorin — bearing only a plain benzoyl, no hydroxyls — was among the weak compounds ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}.

The takeaway is a small structure–activity lesson: on this monoterpene-glycoside scaffold, adding an acyl group switches on activity that the parent doesn’t have, and a hydroxyl-rich galloyl group does so far more potently than a plain benzoyl one.

Note also a near-namesake to avoid confusing: benzoyloxypaeoniflorin is a different peony compound (an additional hydroxyl on the paeoniflorin core), reported alongside benzoylpaeoniflorin as a separate antiplatelet constituent ^{2Reference 2Koo YK et al. · 2010Platelet anti-aggregatory and blood anti-coagulant effects of compounds isolated from Paeonia lactiflora and Paeonia suffruticosaView study →}. And CP-25 (paeoniflorin-6′-O-benzene sulfonate) is a synthetic sulfonate derivative of paeoniflorin — not this natural benzoyl ester.

What It's Used For

The evidence is narrow: two isolated-compound in-vitro reports, no animal outcome studies and no human data. Read the per-row basis before drawing any conclusion.

Evidence by IndicationStrength of support · Beta

Support is an experimental score — weighted by study type (human > animal > in vitro) and volume. A beta, not a validated metric. Both rows here rest on single in-vitro isolate reports, so the scores are deliberately low.

01Antiplatelet & Anticoagulant (Circulation)Shaky24%One in-vitro study naming it a major active constituent for platelet/coagulation inhibition ^{2Reference 2Koo YK et al. · 2010Platelet anti-aggregatory and blood anti-coagulant effects of compounds isolated from Paeonia lactiflora and Paeonia suffruticosaView study →}

02Androgen Modulation (AR Antagonism)Shaky18%One in-vitro screen; weak AR binding (galloyl relatives stronger) ^{1Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →}

Mechanisms

The load-bearing point is structural: activity here is a property of the acyl group, not the paeoniflorin core, and the plain benzoyl ester is consistently the weaker relative next to the galloyl esters.

Pharmacokinetics

No pharmacokinetic study of benzoylpaeoniflorin exists — absorption, bioavailability, metabolism and half-life are all uncharacterised for this molecule. The relevant caution comes from its parent: paeoniflorin is a large, polar monoterpene glycoside with notoriously poor oral bioavailability (single-digit percent), and there is no reason to expect a still-larger benzoyl ester to be absorbed better. This directly undercuts the in-vitro antiplatelet and AR findings above — a compound that barely enters the circulation intact after oral peony intake cannot be assumed to reach platelets or the androgen receptor at the concentrations used in the assays. Whether it is hydrolysed to paeoniflorin (or to benzoic acid) in the gut is not documented here.

Clinical Trials

There are no clinical trials of benzoylpaeoniflorin — as an isolated compound it has not been tested in humans. All human evidence for peony belongs to the whole root or to the standardised extract total glucosides of paeony (TGP), within which benzoylpaeoniflorin is a minor component, not the studied active.

Last checked: July 2026.

Isolate vs. Plant Studies

Unusually, both of this molecule’s findings are on the isolated compound — the AR screen and the platelet/coagulation survey both purified benzoylpaeoniflorin (and its relatives) and tested them individually ^{1,2Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →Reference 2Koo YK et al. · 2010Platelet anti-aggregatory and blood anti-coagulant effects of compounds isolated from Paeonia lactiflora and Paeonia suffruticosaView study →}. That removes the “was it really this molecule?” ambiguity at the assay bench, but it does not make the compound a validated active: the studies are in-vitro, at concentrations that its likely poor oral absorption may never reach in vivo, and neither has an animal or human follow-up. The whole-plant human evidence for peony is a separate track — trials of TGP and of peony–licorice combinations — where benzoylpaeoniflorin is only one minor constituent among many and is never the thing being measured.

Prevalence in Nature

Benzoylpaeoniflorin is a minor, characteristic monoterpene glycoside of the genus Paeonia. It is reported from white peony root (Radix Paeoniae Alba, P. lactiflora with the bark removed), from red peony root (unprocessed P. lactiflora / P. veitchii), and from tree-peony (moutan) bark (P. × suffruticosa) — the same source set as the parent paeoniflorin and the galloyl esters ^{1,2Reference 1Washida K et al. · 2009Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, JapanView study →Reference 2Koo YK et al. · 2010Platelet anti-aggregatory and blood anti-coagulant effects of compounds isolated from Paeonia lactiflora and Paeonia suffruticosaView study →}. It occurs at low levels well below paeoniflorin, which the Chinese Pharmacopoeia sets at a minimum of ≥1.6% of dried white peony root; a separate quantified figure for benzoylpaeoniflorin is not established here (logged in the gaps tracker). It is not known outside Paeonia.

Discovery & Synthesis

Benzoylpaeoniflorin (CAS 38642-49-8, molecular formula C₃₀H₃₂O₁₂) was characterised as one of the acylated members of the paeoniflorin monoterpene-glycoside series isolated from peony root; a precise first-isolation attribution is not well documented here and is left for a later pass. Its structure is unambiguous — the 6′-O-benzoyl ester of paeoniflorin — which is also how it is most simply obtained: as a natural extraction product from Paeonia roots, typically as a minor fraction separated during the isolation of paeoniflorin and its galloyl esters. No dedicated total synthesis is recorded here; semi-synthetically it would correspond to selective 6′-O-benzoylation of paeoniflorin, but no such preparative route is cited in the sources used. There is no commercial-scale manufacture — it is available only as an analytical reference standard.

Patents: not yet researched.

Toxicity & Safety

Benzoylpaeoniflorin carries a low flag. It is a minor constituent of peony root, a herb with a long record of traditional use and a generally benign safety profile for its standardised extract; there is no toxicology specific to the isolated compound — no genotoxicity, repeat-dose or reproductive dataset for benzoylpaeoniflorin exists in the sources used here. Its two reported activities (a weak in-vitro AR antagonism and an in-vitro antiplatelet/anticoagulant effect) are theoretical considerations rather than demonstrated clinical risks, and both are undercut by the likely poor oral bioavailability of this class.

Safety at a Glance

✅ Low / no toxicity

• Minor constituent of a well-tolerated herb. Occurs at low levels in peony root, whose standardised extract has a long, benign use record.
• No isolate toxicology. No genotoxicity, repeat-dose or reproductive data exist for the pure compound; absence of data is not evidence of safety.
• Theoretical antiplatelet signal. An in-vitro platelet/coagulation-inhibiting effect ^{2Reference 2Koo YK et al. · 2010Platelet anti-aggregatory and blood anti-coagulant effects of compounds isolated from Paeonia lactiflora and Paeonia suffruticosaView study →} is a plausibility to note around bleeding risk or anticoagulant use, not a demonstrated clinical interaction — and its poor expected absorption argues against systemic relevance.

No reproductive-toxicity data exist for isolated benzoylpaeoniflorin. Pregnancy and lactation decisions belong to the peony herb page and to any product page, where actual intake is decided — not to this molecule-level entry.

Dosage

There is no dose for benzoylpaeoniflorin. It has never been given to humans as an isolated compound, and no research dose exists. Real-world exposure is entirely indirect — as a minor constituent of peony-root preparations (decoctions, tinctures) and of the standardised extract total glucosides of paeony (TGP), which is dosed and studied as a whole extract standardised to paeoniflorin, not to this benzoyl ester. Any figure here would be invented. These points describe how the compound is encountered in research and in herbal use, and are not a personal recommendation.

References

1. Washida K, Itoh Y, Iwashita T, et al. (2009). Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in Nara prefecture, Japan. Chemical & Pharmaceutical Bulletin. https://pubmed.ncbi.nlm.nih.gov/19721258/
2. Koo YK, Kim JM, Koo JY, et al. (2010). Platelet anti-aggregatory and blood anti-coagulant effects of compounds isolated from Paeonia lactiflora and Paeonia suffruticosa. Pharmazie. https://pubmed.ncbi.nlm.nih.gov/20824965/