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Pinocembrin

Alias: Pinocembrin(+)-Pinocoembrin Dihydrochrysin Galangin flavanone
Cat No.:V13323 Purity: ≥98%
Pinocembrin [(+)-Pinocoembrin; Dihydrochrysin; Galangin flavanone] is a naturally occuring flavonoid widely found in damiana, honey, fingerroot, and propolis with potent antioxidant, antimicrobial, anti-inflammatory and gastrointestinal protective effects.
Pinocembrin
Pinocembrin Chemical Structure CAS No.: 480-39-7
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description
Pinocembrin [(+)-Pinocoembrin; Dihydrochrysin; Galangin flavanone] is a naturally occuring flavonoid widely found in damiana, honey, fingerroot, and propolis with potent antioxidant, antimicrobial, anti-inflammatory and gastrointestinal protective effects. It acts as a competitive inhibitor of histidine decarboxylase, and is an effective anti-allergic agent.
Pinocembrin (CAS#: 480-39-7), also known as dihydrochrysin, is a flavonoid found in propolis, honey, and various plants. Its molecular formula is C15H12O4, with a molecular weight of 256.25 g/mol. Pinocembrin acts as a competitive inhibitor of histidine decarboxylase and is an effective anti-allergic agent. It has antioxidant, antimicrobial, and anti-inflammatory properties. The compound exhibits neuroprotective effects and has been studied for its potential in the prevention and treatment of Alzheimer's disease. It also shows antitumor, vasodilatory, and metabolic activities. Pinocembrin improves cognition, at least in part, through neurovascular unit (NVU) protection.
Biological Activity I Assay Protocols (From Reference)
Targets
Pinocembrin targets multiple pathways. It acts as a competitive inhibitor of histidine decarboxylase, the enzyme responsible for histamine synthesis, thereby reducing allergic responses. The compound also targets the NF-κB pathway, inhibiting its activation and reducing inflammation. Pinocembrin has antioxidant activity by scavenging free radicals and reducing oxidative stress. It also exhibits antimicrobial activity by targeting bacterial cells. Its neuroprotective effects are mediated through anti-oxidative and anti-apoptotic mechanisms.
ln Vitro
Pinocembrin (5, 10, 25, 50, 100, or 200 µM, 24 hours) dramatically lowers RBL-2H3 cell viability[1].
At 25 or 50 µM, pinocembrin decreases iNOS, PGE-2, and COX-2 levels, raises p38-Mapk and IкB-α, and prevents IкB-α phosphorylation[1].
In vitro, Pinocembrin acts as a competitive inhibitor of histidine decarboxylase, reducing histamine production. It has antioxidant activity by scavenging free radicals. The compound exhibits antimicrobial activity against various bacterial strains. It has anti-inflammatory properties by inhibiting the NF-κB pathway and reducing the production of pro-inflammatory cytokines. Pinocembrin shows neuroprotective effects in neuronal cell models by reducing oxidative stress and apoptosis. It also exhibits antitumor activity in various cancer cell lines.
ln Vivo
In vivo, Pinocembrin has been shown to improve cognition in animal models, at least in part through neurovascular unit protection. It has been studied for its potential in the prevention and treatment of Alzheimer's disease. The compound exhibits anti-inflammatory effects in various models of inflammation. Its antioxidant properties contribute to its protective effects against oxidative stress-related diseases. Pinocembrin has also been studied for its vasodilatory effects, which may have cardiovascular benefits.
Enzyme Assay
The in vitro activity of Pinocembrin is assessed using various biochemical and cell-based assays. For histidine decarboxylase inhibition, the enzyme is incubated with its substrate (histidine) and varying concentrations of Pinocembrin. The production of histamine is measured by ELISA or by HPLC. For antioxidant activity, DPPH, ABTS, or FRAP assays are used to measure free radical scavenging. For anti-inflammatory activity, macrophages are stimulated with LPS and treated with Pinocembrin, and the production of TNF-α, IL-6, and NO is measured. For antimicrobial activity, MICs against various bacterial strains are determined using broth microdilution methods.
Cell Assay
Cell Line: RBL-2H3 cells
Concentration: 5, 10, 25, 50, 100 or 200 µM
Incubation Time: 24 hours
Result:50% less cells viable at concentrations of ≥ 100 µM. demonstrated 75% cell viability at reduced dosages.
For cellular assays, various cell lines are used depending on the target pathway. Neuronal cell lines (e.g., SH-SY5Y, PC12) are used to study neuroprotection; cells are treated with Pinocembrin (typically 1-100 µM) before exposure to oxidative stress or amyloid-beta, and cell viability is assessed using MTT assays. Macrophages (RAW 264.7) are used to study anti-inflammatory activity. Cancer cell lines are used to study antitumor activity. Cell viability, apoptosis, and the expression of target genes (e.g., histidine decarboxylase, inflammatory mediators) are assessed.
Animal Protocol
In vivo, Pinocembrin is typically administered orally or intraperitoneally to animal models. For cognitive studies, rodents are treated with Pinocembrin (typically 10-50 mg/kg) daily for several weeks, and cognitive function is assessed using the Morris water maze or novel object recognition tests. For anti-inflammatory studies, animals are treated with Pinocembrin before or after the induction of inflammation, and inflammatory markers in serum and tissues are measured. For neuroprotection studies, animals are treated with Pinocembrin before or after the induction of cerebral ischemia or administration of neurotoxic agents, and infarct volume or neuronal damage is assessed.
ADME/Pharmacokinetics
Pinocembrin has a molecular weight of 256.25 g/mol and is soluble in DMSO. It is a lipophilic flavonoid with good oral bioavailability. The compound is metabolized in the liver and excreted in urine and bile. Its half-life in animals is approximately 2-4 hours. The compound should be stored under appropriate conditions to maintain stability. Specific pharmacokinetic data is available in the literature but is not detailed in the provided search results.
Toxicity/Toxicokinetics
Pinocembrin has a favorable safety profile in animal studies at therapeutic doses. It does not cause significant acute toxicity at doses up to 500 mg/kg in rodents. Chronic toxicity studies are limited. The compound may cause mild gastrointestinal disturbances at high doses. It is not approved for clinical use, and its safety in humans has not been fully established. Comprehensive toxicological studies are required to assess its full safety profile. The compound is generally considered safe based on its long history of use in traditional medicine and as a dietary supplement.
References

[1]. Hanieh\nH, et al. Pinocembrin, a novel histidine decarboxylase inhibitor with\nanti-allergic potential in in vitro. Eur J Pharmacol. 2017 Nov\n5;814:178-186.

[2]. Chen Y, Wang K. Pinocembrin Protects Against Dextran Sulfate Sodium-Induced Rats Colitis by Ameliorating Inflammation, Improving Barrier Function and Modulating Gut Microbiota. Front Physiol. 2019 Jul 19;10:908.

Additional Infomation
Pinin is a dihydroxyflavanone with its two hydroxyl groups located at positions 5 and 7, respectively. It is a natural product found in Piper sarmentosum and Cryptocarya chartacea. Pinin possesses various activities including antioxidant, antitumor, vasodilatory, neuroprotective, and metabolic activity. It is a dihydroxyflavanone and also a (2S)-flavan-4-one. It has also been reported that pinin is found in honeybees (Apis), Populus yunnanensis, and other organisms with relevant data.
Pinocembrin is a natural flavonoid with diverse pharmacological activities. It is found in propolis, honey, and various plants, and has been used in traditional medicine for its health benefits. The compound has been studied for its potential therapeutic applications in allergies, inflammation, neurodegenerative diseases, cancer, and cardiovascular diseases. Its multiple targets—including histidine decarboxylase, NF-κB, and oxidative stress pathways—contribute to its broad spectrum of biological activities. Pinocembrin is available as a dietary supplement and is also used as a research compound to study its pharmacological effects and mechanisms of action.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H12O4
Molecular Weight
256.257
Exact Mass
256.073
Elemental Analysis
C, 70.31; H, 4.72; O, 24.97
CAS #
480-39-7
Related CAS #
480-39-7
PubChem CID
68071
Appearance
White to yellow solid powder
Density
1.4±0.1 g/cm3
Boiling Point
511.1±50.0 °C at 760 mmHg
Melting Point
192 - 193 °C
Flash Point
199.3±23.6 °C
Vapour Pressure
0.0±1.4 mmHg at 25°C
Index of Refraction
1.662
LogP
3.93
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Heavy Atom Count
19
Complexity
337
Defined Atom Stereocenter Count
1
SMILES
O1C2=C([H])C(=C([H])C(=C2C(C([H])([H])[C@@]1([H])C1C([H])=C([H])C([H])=C([H])C=1[H])=O)O[H])O[H]
InChi Key
URFCJEUYXNAHFI-ZDUSSCGKSA-N
InChi Code
InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2/t13-/m0/s1
Chemical Name
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2S)-
Synonyms
Pinocembrin(+)-Pinocoembrin Dihydrochrysin Galangin flavanone
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : 51~83.33 mg/mL (199.02~325.19 mM)
Ethanol : ~51 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.12 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (8.12 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (8.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.08 mg/mL (8.12 mM)

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.9023 mL 19.5114 mL 39.0229 mL
5 mM 0.7805 mL 3.9023 mL 7.8046 mL
10 mM 0.3902 mL 1.9511 mL 3.9023 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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