Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside

Name: Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside
Brand: MedChemExpress
SKU: HY-N5084
Rating: 4.5 (0 reviews)

Cat. No.: HY-N5084 Pureté: 98.92%: Fiche technique
COA

SDS
Instruction de manipulation
FAQs
Technical Support

Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside is a TRPV1 antagonist and HDAC7 inhibitor. Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside blocks TRPV1-mediated calcium influx, suppresses phosphorylation of p65, IκBα, p38, JNK, and ERK1/2, inhibiting NF-κB and MAPK signaling cascades. Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside reduces production and gene expression of pro-inflammatory cytokines IL-1β, IL-6, and TNF-α. Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside exhibits potent analgesic activity, elevates thermal pain threshold and mechanical pain threshold in murine models. Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside restores CD8⁺ T cell infiltration into bladder cancer tumors and improves bladder cancer immunotherapy efficacy. Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside can be used for the researches of painand bladder cancer.

Nos produits utilisent uniquement pour la recherche. Nous ne vendons pas aux patients.

Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside Chemical Structure

CAS No. : 205370-59-8

Size	Stock	Quantité
Solution
10 mM * 1 mL in Ethanol	En stock	Estimated Time of Arrival: December 31
Solid
1 mg	En stock	Estimated Time of Arrival: December 31
5 mg	En stock	Estimated Time of Arrival: December 31
10 mg	En stock	Estimated Time of Arrival: December 31
25 mg	En stock	Estimated Time of Arrival: December 31
50 mg	Obtenir un devis
100 mg	Obtenir un devis

or Bulk Inquiry

* Veuillez sélectionner la quantité avant d'ajouter des articles.

This product is a controlled substance and not for sale in your territory.

Avis client

Based on 1 Customer Validation

Recommandations en vedette

•Related Screening Libraries:

•Related Small Molecules:

•Related Proteins:

Voir tous les produits spécifiques à Isoform TRP Channel:

Voir toutes les isoformes

TRPA1 TRPC3 TRPC4 TRPC5 TRPC6 TRPC7 TRPM8 TRPM2 TRPM3 TRPM4 TRPM7 TRPML1 TRPML2 TRPML3 TRPV1 TRPV2 TRPV3 TRPV4 TRPV6

Voir tous les produits spécifiques à Isoform HDAC:

Voir toutes les isoformes

HDAC HDAC1 HDAC2 HDAC3 HDAC4 HDAC5 HDAC6 HDAC7 HDAC8 HDAC9 HDAC10 HDAC11 HD1 HD2

Voir tous les produits spécifiques à Isoform p38 MAPK:

Voir toutes les isoformes

p38 MAPK Akt1 p38α p38β MAPK13 p38δ p38γ

Voir tous les produits spécifiques à Isoform JNK:

Voir toutes les isoformes

JNK1 JNK2 JNK3 JNK

Voir tous les produits spécifiques à Isoform ERK:

Voir toutes les isoformes

ERK ERK1 ERK2 ERK5 ERK8

Voir tous les produits spécifiques à Isoform NF-κB:

Voir toutes les isoformes

NF-κB NF-κB1/p50 RelA/p65 RelB c-Rel

Voir tous les produits spécifiques à Isoform TNF Receptor:

Voir toutes les isoformes

TNFRSF1A/CD120a TNFRSF3/CD18 TNFRSF4 TNFRSF5/CD40 TNFRSF6/Fas/CD95 TNFRSF7/CD27 TNFRSF8/CD30 TNFRSF9/4-1BB/CD137 TNFRSF10B/DR5/CD262 TNFRSF12A/TWEAK TNFRSF16/NGF Receptor/CD271 TNFRSF18/GITR/CD357

Voir tous les produits spécifiques à Isoform Interleukin Related:

Voir toutes les isoformes

IL-1 IL-2 IL-3 IL-4 IL-5 IL-6 IL-8 IL-10 IL-12 IL-13 IL-15 IL-17 IL-23 IL-7 IL-33 IL-22 IL-18

Activité biologique
Pureté et documentation
Références
Avis client

Description

IC₅₀ & Target^[1]

TRPV1

HDAC7

ERK1

ERK2

IL-1β

IL-6

In Vitro

Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside (100 ns) forms a more stable complex with human TRPV1 than capsazepine, with a binding free energy of -117.696 kJ/mol^[1].
Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside (1-10 μM; 1 h) inhibits Capsaicin (HY-10448)-induced calcium influx in human TRPV1-expressing HEK293 cells^[1].
Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside (6.25-100 μM; 24 h) is non-toxic to RAW264.7 macrophage cells at concentrations up to 100 μM after 24 h treatment^[1].
Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside (2.5-10 μM; 1 h) inhibits TNF-α-induced inflammatory gene expression in RAW264.7 macrophage cells^[1].
Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside (10 μM; 1 h pre-incubation before TNF-α stimulation, 1 h) inhibits TNF-α-induced activation of the NF-κB and MAPK signaling pathways in RAW264.7 macrophage cells at 10 μM, an effect that is attenuated by capsaicin co-treatment, suggesting TRPV1-mediated activity^[1].
Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside (Compound PINO) (3.13 µM-0.38 nM) binds to recombinant human HDAC7 protein with a K_d of 76.7 nM^[2].
Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside (10-200 µM; 48 h) specifically inhibits HDAC activity in HDAC7-overexpressing T24 and MB49 bladder cancer cells, with no significant effect on other HDAC subtypes or their non-histone substrates^[2].
Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside (10-200 µM) activates the SRSF7-CCL5 pathway in T24 and UMUC3 bladder cancer cells by increasing SRSF7 acetylation and expression, and upregulating CCL5 expression^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Real Time qPCR^[1]

Cell Line:	TNF-α-stimulated RAW264.7 macrophage cells
Concentration:	2.5 μM; 5 μM; 10 μM
Incubation Time:	1 h (pre-incubated before TNF-α stimulation)
Result:	Reduced TNF-α-induced mRNA expression of IL-1β, IL-6, IL-18, COX-2, TGF-β, and TNF-α in RAW264.7 cells.

Western Blot Analysis^[1]

Cell Line:	TNF-α-stimulated RAW264.7 macrophage cells
Concentration:	10 μM (pre-incubated before TNF-α stimulation); 10 μM (co-incubated with 10 μM Capsaicin)
Incubation Time:	1 h (pre-incubated before TNF-α stimulation); 1 h (co-incubated with 10 μM Capsaicin)
Result:	Reduced TNF-α-induced phosphorylation of p65, IκBα, p38, JNK, and ERK1/2 in RAW264.7 cells. Had its suppression of NF-κB activation and phosphorylation of p38 and ERK1/2 attenuated by co-treatment with 10 μM capsaicin. Reduced TRPV1 protein levels in RAW264.7 cells.

In Vivo

Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside (20 mg/kg; i.p.; single dose) exhibits potent analgesic activity in a Mus musculus mouse model of Acetic acid (HY-Y0319)-induced acute inflammatory pain^[1].
Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside (20 mg/kg; i.p.; single dose) increases the thermal pain threshold in mice, as demonstrated by prolonged tail-flick latency in the hot water tail-flick test^[1].
Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside (10-20 mg/kg; i.p.; single dose) exhibits dose-dependent analgesic activity in a mouse model of CFA (HY-153808)-induced chronic inflammatory pain, with the 20 mg/kg dose significantly increasing the mechanical withdrawal threshold and exerts anti-inflammatory effects in a mouse model of CFA-induced chronic inflammatory pain, reducing serum levels of IL-1β, IL-6, and TNF-α^[1].
Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside (20 mg/kg; i.p.; single dose) effectively alleviates both thermal and mechanical bone cancer pain in mice, restoring mechanical withdrawal threshold to near pre-inoculation levels^[1].
Pinocembrin 7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-β-D-glucoside (Compound PINO) (50 µg/g; i.p.; daily for 2 weeks) enhances BCa sensitivity to anti-PD1 immunotherapy by increasing CD8⁺ T cell tumor infiltration and reducing tumor growth^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	C57BL/6J with Acetic acid (HY-Y0319)-induced acute inflammatory pain (male)^[1]
Dosage:	20 mg/kg
Administration:	i.p.; single dose (1 hour prior to Acetic acid challenge)
Result:	Reduced the number of acetic acid-induced abdominal stretches more pronouncedly than Capsazepine (HY-15640) (20 mg/kg).

Animal Model:	C57BL/6J with CFA (HY-153808)-induced chronic inflammatory pain (male)^[1]
Dosage:	10 mg/kg; 15 mg/kg; 20 mg/kg
Administration:	i.p.; single dose (7 days post-CFA injection; 20 mg/kg also as standalone treatment without CFA)
Result:	Increased the mechanical withdrawal threshold significantly compared to the CFA-induced vehicle group at 20 mg/kg. Did not produce a significant effect at 10 mg/kg or 15 mg/kg. Did not alter the mechanical withdrawal threshold compared to the non-CFA control group at 20 mg/kg standalone treatment. Reduced serum levels of pro-inflammatory cytokines IL-1β, IL-6, and TNF-α compared to the CFA-induced vehicle group. Reduced DRG mRNA expression of pro-inflammatory cytokines (IL-1β, IL-6, IL-18, COX-2, IFN-γ, TNF-α) and Ca2+ signaling-related genes (PKA, PKC, P2X3, CAMK2A, CAMK2B) compared to the CFA-induced vehicle group.

Animal Model:	C57BL/6 with bladder cancer(5-week-old female)^[2]
Dosage:	50 µg/g
Administration:	i.p.; daily for 2 weeks
Result:	Inhibited bladder cancer proliferation in vivo. Showed significantly greater therapeutic efficacy when combined with anti-PD1 antibody than anti-PD1 alone, including reduced tumor volume and tumor weight. Increased CD8 + T cell tumor infiltration to levels significantly higher than in the single-agent anti-PD1 group.

Masse moléculaire

872.69

Formule

C₄₂H₃₂O₂₁

CAS No.

205370-59-8

Appearance

Solid

Color

White to off-white

SMILES

O=C1C[C@@H](C2=CC=CC=C2)OC3=CC(O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](COC5=O)O4)OC(C6=CC(O)=C(O)C(O)=C6C7=C(O)C(O)=C(O)C=C75)=O)OC(C8=CC(O)=C(O)C(O)=C8)=O)O)=CC(O)=C13

Structure Classification

Initial Source

Livraison

Room temperature in continental US; may vary elsewhere.

Stockage

4°C, sealed storage, away from moisture and light

*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)

Solvant et solubilité

In Vitro:

Ethanol : 25 mg/mL (28.65 mM; Need ultrasonic)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	1.1459 mL	5.7294 mL	11.4588 mL
5 mM	0.2292 mL	1.1459 mL	2.2918 mL
10 mM	0.1146 mL	0.5729 mL	1.1459 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Calculateur de molarité
Calculateur de dilution

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)

Volume _(start)

Concentration _(final)

Volume _(final)

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% EtOH 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 1.25 mg/mL (1.43 mM); Clear solution

This protocol yields a clear solution of ≥ 1.25 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL EtOH stock solution (12.5 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Protocol 2

Add each solvent one by one: 10% EtOH 90% Corn Oil
Solubility: ≥ 1.25 mg/mL (1.43 mM); Clear solution

This protocol yields a clear solution of ≥ 1.25 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Taking 1 mL working solution as an example, add 100 μL EtOH stock solution (12.5 mg/mL) to 900 μL Corn oil, and mix evenly.

For the following dissolution methods, please prepare the working solution directly. It is recommended to prepare fresh solutions and use them promptly within a short period of time.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 45% PEG300 5% Tween-80 50% Saline
Solubility: 4 mg/mL (4.58 mM); Clear solution; Need ultrasonic
Protocol 2

Add each solvent one by one: 17% Solutol HS-15 in Saline
Solubility: 5 mg/mL (5.73 mM); Clear solution; Need ultrasonic

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Calculation results:

Working solution concentration: mg/mL

Pureté et documentation

Purity: 98.92%

Select Batch:

Fiche technique (292 KB) SDS (252 KB)

COA (261 KB) HNMR (233 KB) CNMR (236 KB) LCMS (104 KB)

Instruction de manipulation (2659 KB)

Références

[1]. Chen H, et al. Identification and evaluation of a pinocembrin analog as a TRPV1 inhibitor with analgesic properties in murine pain models. Front Pharmacol. 2025;16:1585181. Published 2025 Jun 10.

[2]. Lv J, et al. Histone deacetylase HDAC7 restricts CD8 + T cell tumor infiltration and limits immunotherapy sensitivity in bladder cancer: reversal by pinocembrin. J Exp Clin Cancer Res. 2025;44(1):324. Published 2025 Dec 24. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

Ethanol	1 mM	1.1459 mL	5.7294 mL	11.4588 mL	28.6471 mL
	5 mM	0.2292 mL	1.1459 mL	2.2918 mL	5.7294 mL
	10 mM	0.1146 mL	0.5729 mL	1.1459 mL	2.8647 mL
	15 mM	0.0764 mL	0.3820 mL	0.7639 mL	1.9098 mL
	20 mM	0.0573 mL	0.2865 mL	0.5729 mL	1.4324 mL
	25 mM	0.0458 mL	0.2292 mL	0.4584 mL	1.1459 mL