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Send EmailQuercetin, Pentahydroxy Flavone, Sophoretin, Meletin, 117-39-5
Quercetin / 3,3',4',5,7-Pentahydroxyflavone / Sophoretin
CAS Number: 117-39-5
| Parameter | Detail |
|---|---|
| Product Name | Quercetin |
| Chemical Definition | Quercetin / 3,3',4',5,7-Pentahydroxyflavone |
| CAS Number | 117-39-5 |
| Molecular Type | Flavonoid (plant polyphenol) |
| Molecular Formula | C₁₅H₁₀O₇ |
| Molecular Weight | 302.24 g/mol |
| EC Number (EINECS) | 204-187-1 |
| Appearance | Yellow crystalline powder |
| Odor/Taste | Slightly bitter taste |
| Solubility | Soluble in ethanol and dimethyl sulfoxide (DMSO); low solubility in water |
Quercetin is a naturally occurring flavonoid belonging to the class of plant polyphenols. It is one of the most abundant and widely studied flavonoids found in many fruits, vegetables, leaves, seeds, and grains. Common dietary sources include onions, apples, berries, citrus fruits, green tea, red wine, and buckwheat. Quercetin is well known for its potent antioxidant, anti-inflammatory, antiviral, and immunomodulatory properties. It acts as a free radical scavenger, protecting cells from oxidative stress, and has been studied for its potential role in supporting immune function, cardiovascular health, and reducing inflammation. It is widely used in dietary supplements, functional foods, and cosmetic formulations.
| Type | Name |
|---|---|
| Common Names | Quercetin, Sophoretin, Meletin, Quercetine |
| Chemical Names | 3,3',4',5,7-Pentahydroxyflavone, 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one |
| Glycoside Forms | Quercetin-3-O-rutinoside (Rutin), Quercetin-3-O-glucoside (Isoquercitrin), Quercetin-3-O-galactoside (Hyperoside) |
| Abbreviations | Q, QUE |
| CAS Number | 117-39-5 |
| EC Number | 204-187-1 |
| HS Code | 2932.99 |
Quercetin is a flavonol, a subclass of flavonoids, characterized by a 15-carbon skeleton consisting of two benzene rings (A and B) linked by a heterocyclic pyrone ring (C). It contains five hydroxyl groups (-OH) at positions 3, 5, 7, 3', and 4'.
Structural Formula:
OH
|
O
/ \
/ \
/ \
/ \
OH OH
| |
C C
/ \ / \
/ \ / \
/ \ / \
OH C - C C - OH
\ / \ /
C C - C
| |
OH OH
|
OH
Simplified Representation (Flavonol Backbone):
OH
|
O
/ \
/ \
/ \
/ \
OH OH
| |
C C
/ \ / \
/ \ / \
/ \ / \
OH C = C C - OH
\ / \ /
C C - C
| |
OH OH
|
OH
C₁₅H₁₀O₇
302.24 g/mol
| Feature | Description |
|---|---|
| Flavonoid Class | Flavonol (subclass of flavonoids) |
| Hydroxyl Groups | Five hydroxyl groups (-OH) at positions 3, 5, 7, 3', and 4' |
| Carbon Skeleton | 15-carbon skeleton (C6-C3-C6) |
| Aromatic Rings | Two benzene rings (A and B) |
| Heterocyclic Ring | Pyrone ring (C) |
| Glycoside Formation | Can form glycosides with sugars (rutinose, glucose, galactose) |
| Property | Value |
|---|---|
| Appearance | Yellow crystalline powder |
| Odor/Taste | Slightly bitter taste |
| Molecular Weight | 302.24 g/mol |
| Melting Point | ~316-323°C (decomposes) |
| Solubility in Water | Low solubility (~0.01 mg/mL at 20°C) |
| Solubility in Ethanol | Soluble (~3 mg/mL) |
| Solubility in DMSO | Soluble (~30 mg/mL) |
| Solubility in Acetone | Slightly soluble |
| Solubility in Ether | Slightly soluble |
| pKa Values | pKa1 ~ 6.7 (4'-OH), pKa2 ~ 8.6 (7-OH), pKa3 ~ 10.8 (3-OH) |
| Density | ~1.8 g/cm³ |
| λmax (UV-Vis) | 256 nm, 370 nm |
| Stability | Stable under proper storage conditions; sensitive to light, heat, and oxygen |
| Solvent | Solubility | Conditions |
|---|---|---|
| Water | Low solubility (~0.01 mg/mL) | 20°C |
| Ethanol | Soluble (~3 mg/mL) | 25°C |
| DMSO | Highly soluble (~30 mg/mL) | 25°C |
| Methanol | Soluble | 25°C |
| Acetone | Slightly soluble | 25°C |
| Ether | Slightly soluble | 25°C |
| Chloroform | Slightly soluble | 25°C |
| Alkaline Solutions | Soluble (forms salts) | 25°C |
| Property | Description |
|---|---|
| Chemical Character | Weakly acidic (due to phenolic hydroxyl groups) |
| Antioxidant Activity | Potent free radical scavenger; hydrogen atom donor |
| Metal Chelation | Chelates metal ions (Fe²⁺, Cu²⁺, Zn²⁺) |
| Autoxidation | Undergoes autoxidation in alkaline solutions |
| Complex Formation | Forms complexes with metal ions |
| Glycosylation | Reacts with sugars to form glycosides |
| Incompatible Materials | Strong oxidizers, strong bases, light, heat, oxygen |
Quercetin (OH) + R• → Quercetin (O•) + RH
Quercetin + Fe²⁺ → Quercetin-Fe²⁺ Complex
Quercetin + O₂ (alkaline) → Degradation Products (oxidation products)
Quercetin + Rutinose → Quercetin-3-O-rutinoside (Rutin)
| Source | Quercetin Content | Description |
|---|---|---|
| Onions | High | Rich in quercetin-3,4'-diglucoside |
| Apples | Moderate | Contains quercetin glycosides in the peel |
| Berries | High | Blueberries, cranberries, blackberries |
| Citrus Fruits | Moderate | Oranges, grapefruits, lemons |
| Green Tea | Moderate | Contains quercetin glycosides |
| Red Wine | Moderate | Rich in quercetin from grape skins |
| Buckwheat | High | Rich in rutin (quercetin-3-O-rutinoside) |
| Ginkgo Biloba | Moderate | Contains quercetin glycosides |
Quercetin is primarily produced by extraction from plant materials or by hydrolysis of quercetin glycosides (rutin).
| Stage | Process | Description |
|---|---|---|
| 1 | Raw Material Preparation | Plant material (e.g., onion skins, buckwheat) is dried and ground. |
| 2 | Extraction | Plant material is extracted with organic solvents (ethanol, methanol, acetone) or water. |
| 3 | Concentration | The extract is concentrated under vacuum. |
| 4 | Precipitation | Quercetin is precipitated from the concentrated extract. |
| 5 | Purification | The precipitate is purified by recrystallization or chromatography. |
| 6 | Drying | The purified product is dried to obtain final quercetin powder. |
| Stage | Process | Description |
|---|---|---|
| 1 | Raw Material | Rutin (quercetin-3-O-rutinoside) from buckwheat or other plant sources. |
| 2 | Hydrolysis | Rutin is hydrolyzed with acid (HCl) or enzymes to release quercetin. |
| 3 | Precipitation | Quercetin is precipitated from the hydrolysate. |
| 4 | Purification | The product is purified by recrystallization. |
| 5 | Drying | The purified product is dried to obtain final quercetin powder. |
| Property | Description |
|---|---|
| Antioxidant Activity | Potent free radical scavenger; protects cells from oxidative stress |
| Anti-inflammatory Activity | Inhibits pro-inflammatory cytokines (IL-1β, TNF-α); inhibits COX-2 and iNOS expression |
| Antiviral Activity | Inhibits viral replication (influenza, SARS-CoV-2, hepatitis C) |
| Immunomodulation | Modulates immune response; supports immune function |
| Cardioprotective Effects | Reduces oxidative stress; improves endothelial function |
| Bioavailability | Low oral bioavailability (~2%); extensively metabolized |
| Metabolism | Extensively metabolized in the liver and intestine to glucuronides and sulfates |
| Distribution | Widely distributed in tissues; crosses the blood-brain barrier |
| Excretion | Primarily excreted in urine and bile |
| Effect | Mechanism |
|---|---|
| Antioxidant Effect | Direct free radical scavenging (hydrogen atom donor); upregulates endogenous antioxidant enzymes (SOD, CAT, GPx); chelates pro-oxidant metal ions (Fe²⁺, Cu²⁺) |
| Anti-inflammatory Effect | Inhibits NF-κB and MAPK pathways; reduces expression of COX-2, iNOS, and pro-inflammatory cytokines (IL-1β, TNF-α, IL-6) |
| Antiviral Effect | Inhibits viral entry and replication; interferes with viral proteases and polymerases |
| Immune Modulation | Modulates T-cell and B-cell responses; supports antibody production |
| Cardioprotective Effect | Reduces LDL oxidation; improves endothelial function; reduces platelet aggregation |
| Cellular Signaling | Activates AMPK and SIRT1; modulates PI3K/Akt and Nrf2 pathways |
| Application | Description |
|---|---|
| Tablet Form | Compressed tablets for oral consumption. |
| Capsule Form | Powder or granule-filled capsules. |
| Powder Form | Bulk powder for reconstitution or addition to foods/beverages. |
| Liquid Form | Pre-dissolved liquid formulations. |
| Combination Products | Often combined with vitamin C, vitamin E, bromelain, or zinc. |
| Application | Description |
|---|---|
| Immune Support Products | Fortified foods and beverages targeting immune health. |
| Sports Nutrition | Products for athletes to support immune function and reduce oxidative stress. |
| Geriatric Nutrition | Products targeting age-related health conditions. |
| Application | Description |
|---|---|
| Anti-aging Products | Used for its antioxidant and free radical scavenging properties. |
| Skin Care | Used in creams, serums, and lotions to protect skin from oxidative damage. |
| Sun Protection | Used in sunscreens for its photoprotective properties. |
| Application | Description |
|---|---|
| Pharmaceutical Intermediate | Used in the synthesis of pharmaceutical compounds. |
| Cell Culture | Used in cell culture studies as a standard antioxidant. |
| Research | Used in antioxidant, anti-inflammatory, and antiviral research. |
| Property | Quercetin | Rutin (Quercetin-3-O-rutinoside) |
|---|---|---|
| Structure | Aglycone (without sugar) | Glycoside (with rutinose sugar) |
| Solubility in Water | Low solubility | Higher solubility |
| Bioavailability | Low (~2%) | Even lower |
| Absorption | Absorbed in the small intestine | Hydrolyzed by gut microbiota |
| Metabolism | Extensively metabolized | Extensively metabolized |
| Antioxidant Activity | Potent | Moderate |
| Stability | Less stable | More stable |
| Substance / Environment | Compatibility | Description |
|---|---|---|
| Water | LIMITED | Low solubility; may form suspensions. |
| Ethanol | COMPATIBLE | Soluble; suitable for formulations. |
| DMSO | COMPATIBLE | Highly soluble; suitable for research. |
| Alkaline Solutions | LIMITED | Soluble but may undergo autoxidation. |
| Oxidizers | INCOMPATIBLE | May cause degradation. |
| Reducing Agents | COMPATIBLE | Generally compatible. |
| Light | LIMITED | UV light accelerates degradation. |
| Heat | LIMITED | High temperature accelerates degradation. |
| Air / Oxygen | LIMITED | Oxidation may occur; store under inert atmosphere. |
| Parameter | Value |
|---|---|
| Acute Oral Toxicity (LD50, Rat) | > 5000 mg/kg (low toxicity) |
| Acute Dermal Toxicity | Low |
| Acute Inhalation Toxicity | Low risk; may cause mild respiratory irritation. |
| Skin Irritation | Mild irritant in powder form. |
| Eye Irritation | May cause mild eye irritation. |
| Skin Sensitization | Not classified as a sensitizer. |
| Mutagenicity | Negative. |
| Carcinogenicity | Not classified as a carcinogen. |
| Reproductive Toxicity | Not classified as a reproductive toxin. |
| Target Organs | No specific target organs identified. |
| High Dose Effects | May cause gastrointestinal discomfort (nausea, vomiting, diarrhea). |
| Drug Interactions | May interact with anticoagulants, antiplatelet drugs, and certain medications metabolized by CYP450 enzymes. |
GHS Classification (Generally Not Classified as Hazardous):
| Hazard Class | Category | H-Statement |
|---|---|---|
| Not classified as hazardous | - | - |
Signal Word: None (not classified as hazardous)
Hazard Pictograms: None
Hazard Statements (H-Codes): None
Safety Phrases (Historically):
| Code | Statement |
|---|---|
| S22 | Do not breathe dust. |
| S24/25 | Avoid contact with skin and eyes. |
| S26 | In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| Code | Statement |
|---|---|
| P261 | Avoid breathing dust/fume/gas/mist/vapors/spray. |
| P264 | Wash hands thoroughly after handling. |
| P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
| P305+P351+P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present. |
| P337+P313 | If eye irritation persists: Get medical advice/attention. |
| P501 | Dispose of contents/container in accordance with local regulations. |
| Route of Exposure | Action to Be Taken |
|---|---|
| Inhalation | Move to fresh air. If respiratory irritation persists, seek medical attention. |
| Skin Contact | Wash with plenty of soap and water. Remove contaminated clothing. If irritation persists, consult a physician. |
| Eye Contact | Rinse thoroughly with plenty of water for at least 15 minutes. Remove contact lenses. If irritation persists, seek medical attention. |
| Ingestion | Rinse mouth with water. Drink plenty of water. Do not induce vomiting. If large amount is swallowed, seek medical attention. |
| General Note | If symptoms persist, always consult a healthcare facility. |
| Parameter | Information |
|---|---|
| Fire Hazard | Not flammable; may decompose at high temperatures. |
| Hazards During Fire | Thermal decomposition produces toxic fumes including carbon monoxide, carbon dioxide. |
| Suitable Extinguishing Media | Water spray, CO₂, dry chemical powder, alcohol-resistant foam. |
| Special Protective Equipment | Self-contained breathing apparatus (SCBA), full protective clothing. |
| Special Precautions | Prevent fire-fighting water from entering the environment. |
| Parameter | Information |
|---|---|
| Personal Protection | Dust mask, protective goggles, gloves, coverall. |
| Ventilation | Increase ventilation; use local exhaust in confined spaces. |
| Containment | Cover spilled area to prevent dust dispersion. |
| Cleaning Methods | Collect dry using vacuum or careful sweeping. Avoid washing with water (product is insoluble and may spread). |
| Environmental Precautions | Prevent entry into drains, sewers, and water bodies. |
| Waste Disposal | Dispose of in accordance with local regulations. |
| Parameter | Information |
|---|---|
| Storage Conditions | Store in a cool, dry, and well-ventilated area at room temperature (15-25°C). |
| Container Requirements | Keep tightly closed in original packaging. Protect from light, heat, and oxygen. |
| Materials to Avoid | Strong oxidizers, strong bases, light, heat, oxygen. |
| Shelf Life | 24 months (under proper storage conditions). |
| Stability Note | Sensitive to light, heat, and oxygen. Store under inert atmosphere for long-term storage. |
| Packaging Options | 1 kg, 5 kg, 10 kg, 25 kg bags or drums. |
| Packaging Type | Quantity | Material |
|---|---|---|
| Polyethylene bag + outer bag | 1 – 5 kg | PE / Paper |
| Fiber drum | 10 – 25 kg | Cardboard / Plastic |
| Plastic drum | 25 kg | HDPE |
| Big-Bag | 500 – 1000 kg | Polypropylene |
| Parameter | Information |
|---|---|
| UN Number | Not applicable (not classified as dangerous goods). |
| Hazard Class | Not classified as hazardous for transport. |
| Packing Group | Not applicable. |
| ADR/RID | Not classified as dangerous goods. |
| IMDG Code | Not classified as dangerous goods. |
| IATA (Air) | Not classified as dangerous goods. |
| Marine Pollutant | No. |
| Transport Temperature | Ambient temperature; protect from light and moisture. |
| Region / Authority | Status |
|---|---|
| European Union | Approved as a dietary supplement ingredient. |
| USA (FDA) | Approved as a dietary supplement (DSHEA). |
| Turkey | Approved as a dietary supplement; regulated by Turkish Food Codex. |
| EFSA | Health claims related to antioxidant and immune support are under evaluation. |
| Canada (NHP) | Licensed as a Natural Health Product. |
| Australia (TGA) | Listed as a complementary medicine ingredient. |
| Sector | Suitability | Description |
|---|---|---|
| Dietary Supplements | HIGH | Tablets, capsules, powders, and liquids for antioxidant and immune support. |
| Functional Foods | MEDIUM | Fortified foods and beverages targeting immune health and oxidative stress. |
| Cosmetics | HIGH | Anti-aging, skin care, and sun protection products. |
| Pharmaceuticals | LOW | Used as an intermediate in drug synthesis and research. |
| Compound | Description |
|---|---|
| Rutin | Quercetin-3-O-rutinoside; more water-soluble; found in buckwheat. |
| Isoquercitrin | Quercetin-3-O-glucoside; more bioavailable than rutin. |
| Hyperoside | Quercetin-3-O-galactoside; found in St. John's wort. |
| Quercitrin | Quercetin-3-O-rhamnoside; found in many plants. |
| Dihydroquercetin | Taxifolin; reduced form of quercetin. |
| Property | Value |
|---|---|
| CAS Number | 117-39-5 |
| Molecular Formula | C₁₅H₁₀O₇ |
| Molecular Weight | 302.24 g/mol |
| Appearance | Yellow crystalline powder |
| Odor/Taste | Slightly bitter |
| Melting Point | ~316-323°C (decomposes) |
| Solubility in Water | Low (~0.01 mg/mL at 20°C) |
| Solubility in Ethanol | Soluble (~3 mg/mL) |
| Solubility in DMSO | Highly soluble (~30 mg/mL) |
| λmax (UV-Vis) | 256 nm, 370 nm |
| Main Uses | Dietary supplements, cosmetics, functional foods |
| Shelf Life | 24 months |
| UN Number | Not applicable |
| pKa Values | 6.7, 8.6, 10.8 |
CRITICAL NOTICES:
Poor Bioavailability: Quercetin has very low oral bioavailability (~2%) due to poor aqueous solubility, extensive first-pass metabolism, and rapid elimination. Formulation strategies such as liposomal delivery, phospholipid complexes (phytosomes), cyclodextrin complexes, or co-administration with piperine (black pepper extract) may be used to enhance bioavailability.
Light and Oxygen Sensitivity: Quercetin is sensitive to light, heat, and oxygen. Exposure may cause degradation and loss of potency. Store in light-resistant containers and under inert atmosphere for long-term storage.
Low Water Solubility: Quercetin has very low water solubility, which can limit its absorption and application in aqueous formulations. Use of solubilizers, surfactants, or nanoparticle formulations may be required for certain applications.
Drug Interactions: Quercetin may interact with anticoagulant and antiplatelet drugs (warfarin, aspirin, clopidogrel) and medications metabolized by CYP450 enzymes (e.g., cyclosporine, calcium channel blockers). Use under medical supervision when taking these medications.
High Dose Effects: High doses ( > 1 g/day) may cause gastrointestinal discomfort (nausea, vomiting, diarrhea). It is recommended to start with lower doses and gradually increase.
Pregnancy and Lactation: Limited safety data; use during pregnancy and lactation should be under medical supervision.
Color Stability: Quercetin imparts a yellow color to formulations. This color may change upon exposure to light and heat. Consider the visual impact on final products.
Source Variability: Quercetin content in natural extracts may vary significantly. Standardized extracts with specified quercetin content should be used for consistent quality.
BEST PRACTICE RECOMMENDATIONS:
Storage: Store in a cool, dry, and well-ventilated area at room temperature (15-25°C). Keep containers tightly closed. Protect from light, heat, and oxygen. Use inert atmosphere (nitrogen) for long-term storage.
Personnel Protection: Use protective gloves, goggles, and dust mask. Ensure adequate ventilation.
Dosage Control: Recommended daily dose for health benefits: 500-1000 mg (as quercetin aglycone or glycosides). Follow specific product recommendations.
Formulation Considerations: For aqueous formulations, consider using quercetin glycosides (rutin, isoquercitrin) or solubilized forms. For supplements, consider bioavailability-enhancing strategies (phytosomes, cyclodextrins, piperine).
Quality Assurance: Verify product source, purity, and quercetin content. Test for heavy metals, microbial contamination, and solvents.
Color Management: Consider the yellow color of quercetin in final product formulations. Use opaque packaging to protect from light.
Waste Management: Dispose of waste in accordance with local regulations.
LEGAL DISCLAIMER:
The information provided in this document is based on our current knowledge and experience and is presented in good faith; however, as all conditions of use are beyond our control, it does not constitute a binding specification or warranty. This Technical Data Sheet is for informational purposes only. Users are obligated to test the suitability of the product for their own applications. For complete safety, storage, handling, transport, waste, and regulatory compliance information, the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier must be consulted.