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Send EmailGlucosamine, Glucosamine Sulfate, Glucosamine Hydrochloride, Acetyl Glucosamine, 3416-24-8, 66-84-2, 29031-19-4, 7512-17-6
GLUCOSAMINE
SECTION 1: GENERAL DEFINITION AND CHEMICAL IDENTITY
| Parameter | Information |
|---|---|
| Product Name | Glucosamine |
| Chemical Name (IUPAC) | 2-Amino-2-deoxy-D-glucose |
| CAS Number | 3416-24-8 (free base) |
| Molecular Formula (Free Base) | C₆H₁₃NO₅ |
| Molecular Weight (Free Base) | 179.17 g/mol |
| Chemical Class | Amino sugar; glycosaminoglycan precursor |
| Natural Sources | Shellfish shells (chitin hydrolysis), microbial fermentation, fungal cell walls |
| Biological Role | Building block of glycosaminoglycans (GAGs) and proteoglycans; essential component of cartilage, tendons, ligaments, and synovial fluid |
SECTION 2: CHEMICAL STRUCTURE (FREE BASE)
CHO
|
H—C—NH₂
|
HO—C—H
|
H—C—OH
|
H—C—OH
|
CH₂OH
Glucosamine
2-Amino-2-deoxy-D-glucose
C₆H₁₃NO₅
Linear form (open chain)
Cyclic Form (Pyranose):
CH₂OH
/ \
O H
/ \
H OH
| |
H——C——OH H
| |
H——C——NH₂ C
| |
H——C——OH H
| |
OH OH
D-Glucosamine Pyranose
(β-D-Glucosamine)
| Parameter | Description |
|---|---|
| Molecular Formula | C₆H₁₃NO₅ |
| Molecular Weight | 179.17 g/mol |
| Chemical Class | Amino sugar |
| Functional Groups | Amine (-NH₂), hydroxyl (-OH), aldehyde (linear) / hemiacetal (cyclic) |
| SMILES | C(C1C(C(C(C(O1)O)N)O)O)O |
| InChI | InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1 |
| Optical Activity | Optically active (D-form) |
| Stereoisomer | D-Glucosamine (natural form) |
| Anomeric Carbon | C1 (in cyclic form) |
SECTION 3: GLUCOSAMINE FORMS COMPARISON
| Parameter | Glucosamine Sulfate | Glucosamine Hydrochloride | N-Acetylglucosamine |
|---|---|---|---|
| Chemical Name | Glucosamine Sulfate | Glucosamine Hydrochloride | N-Acetylglucosamine |
| Molecular Formula | C₆H₁₃NO₅·H₂SO₄ | C₆H₁₃NO₅·HCl | C₈H₁₅NO₆ |
| Molecular Weight | ~277.25 g/mol (sulfate salt) | ~215.63 g/mol | 221.21 g/mol |
| CAS Number | 29031-19-4 (sodium sulfate) | 66-84-2 | 7512-17-6 |
| Glucosamine Content (by weight) | ~65-70% | ~83% | ~81% |
| Purity | High | Highest | High |
| Sulfur Content | Yes (provides additional sulfur) | No | No |
| Stability | Less stable; usually stabilized with NaCl | More stable | Most stable (acetylated) |
| Clinical Studies | Most studied form | Fewer than sulfate | Limited |
| Cartilage Synthesis | +++ (with additional sulfur) | ++ | ++ |
| Anti-inflammatory Effect | +++ | ++ | ++ |
| Cosmetic Use | Limited | Limited | Widespread (moisturizer, barrier support) |
| Typical Dose | 1500 mg/day | 1500 mg/day | 500-1500 mg/day |
| Taste | Salty, bitter | Salty | Mildly sweet |
| Water Solubility | High | High | High |
| Stabilization | NaCl (20%) | Stable | Stable |
SECTION 4: PHYSICAL AND CHEMICAL PROPERTIES (FREE BASE)
| Property | Value | Test Method / Note |
|---|---|---|
| Appearance | White to off-white crystalline powder | Visual |
| Odor | Slight characteristic odor | Olfactometric |
| Molecular Weight (Free Base) | 179.17 g/mol | Calculated |
| Molecular Weight (HCl) | 215.63 g/mol | Calculated |
| Molecular Weight (Sulfate) | 277.25 g/mol | Calculated |
| Melting Point (HCl) | ~190-194°C (decomposes) | DSC / Capillary |
| Melting Point (Sulfate) | ~160-180°C (decomposes) | DSC / Capillary |
| Solubility in Water (HCl) | High (>500 g/L) | General Method |
| Solubility in Water (Sulfate) | High (>400 g/L) | General Method |
| pH (1% Solution, HCl) | ~4.0-6.0 | pH Meter |
| pH (1% Solution, Sulfate) | ~4.0-6.0 | pH Meter |
| Log P (Octanol/Water) | < -3.0 (very hydrophilic) | Calculated |
| Specific Optical Rotation [α]D²⁰ (HCl) | +55° to +60° (c=1, H₂O) | Polarimetry |
| Hygroscopicity | Moderate | - |
| Flash Point | >150°C | - |
| Thermal Stability | Stable up to 150°C | - |
SECTION 5: BIOLOGICAL MECHANISMS OF ACTION
| Mechanism | Description |
|---|---|
| Cartilage Synthesis | Stimulates chondrocytes to produce collagen (Type II) and proteoglycans; supports cartilage matrix remodeling. |
| Anti-inflammatory Effect | Reduces pro-inflammatory cytokines (IL-1β, TNF-α); inhibits COX-2 and iNOS expression; suppresses inflammation. |
| Joint Lubrication | Increases synovial fluid viscosity, facilitating joint movement and reducing friction. |
| Chondroprotection | Protects chondrocytes from oxidative stress and apoptosis (programmed cell death); increases cell viability. |
| MMP Inhibition | Inhibits matrix metalloproteinases (MMP-1, MMP-3, MMP-13), reducing cartilage matrix degradation. |
| GAG Synthesis | Increases glycosaminoglycan (GAG) synthesis, enhancing cartilage matrix density and elasticity. |
| Aggrecan Production | Stimulates aggrecan (proteoglycan) synthesis, enhancing cartilage hydration and shock absorption. |
| Nitric Oxide Reduction | Inhibits inducible nitric oxide synthase (iNOS), reducing NO production; prevents inflammatory damage. |
| Hyaluronic Acid Synthesis | Increases hyaluronic acid synthesis in synovial fluid, improving joint lubrication. |
SECTION 6: PHARMACOKINETIC PROPERTIES
| Parameter | Value / Description |
|---|---|
| Absorption | Rapidly and almost completely absorbed after oral administration (first-pass effect) |
| Oral Bioavailability | ~25-50% (due to first-pass metabolism) |
| Peak Plasma Concentration (Cmax) | ~1-3 µg/mL (after 1500 mg oral dose) |
| Peak Time (Tmax) | ~1-4 hours |
| Distribution | High affinity for joint cartilage and synovial fluid |
| Plasma Half-Life (t½) | ~2-5 hours (human) |
| Protein Binding | Low |
| Metabolism | Hepatic metabolism (conversion to glycosaminoglycans) |
| Elimination | • Urine: ~50-70% (unchanged or as metabolites) • Feces: ~20-30% |
| Tissue Distribution | Cartilage, synovial fluid, liver, kidneys |
| Cartilage Retention | Remains in cartilage for approximately 4-24 hours after oral administration |
SECTION 7: CLINICAL USE AND INDICATIONS
| Indication | Form | Typical Dose | Duration | Evidence Level |
|---|---|---|---|---|
| Osteoarthritis (Knee) | Sulfate / HCl | 1500 mg/day | 12-36 months | Strong Clinical Evidence (Meta-analysis) |
| Osteoarthritis (Hip) | Sulfate | 1500 mg/day | 12-24 months | Moderate Clinical Evidence |
| Osteoarthritis (Shoulder) | Sulfate / HCl | 1500 mg/day | 12-24 months | Limited Evidence |
| Temporomandibular Joint (TMJ) | Sulfate | 1500 mg/day | 6-12 months | Limited Evidence |
| Spinal Osteoarthritis | Sulfate | 1500 mg/day | 12-24 months | Limited Evidence |
| Joint Health (Support) | Sulfate / HCl / NAG | 500-1500 mg/day | Continuous | General Health Support |
| Sports Injuries | Sulfate / HCl | 1500 mg/day | 6-12 months | Limited Evidence |
| Inflammatory Joint Diseases | Sulfate | 1500 mg/day | Variable | Limited / Pilot Studies |
SECTION 8: GLUCOSAMINE SULFATE
| Parameter | Information |
|---|---|
| Chemical Name | Glucosamine Sulfate |
| Molecular Formula | C₆H₁₃NO₅·H₂SO₄ |
| Molecular Weight | ~277.25 g/mol (sodium sulfate salt) |
| CAS Number | 29031-19-4 (sodium sulfate) |
| Glucosamine Content | ~65-70% |
| Sulfur Content | Yes (10-12%) — provides additional sulfur |
| Clinical Studies | Most studied form (>20 RCTs) |
| Osteoarthritis Efficacy | Pain reduction: ~25-30%; Function improvement: ~20-25% |
| Structural Effect | May slow joint space narrowing (symptom-modifying) |
| Onset of Action | 4-8 weeks (clinical improvement onset) |
| Typical Formulation | Capsule, tablet, powder, liquid |
| Stabilizer | Usually stabilized with NaCl (20%) |
| Dosage Forms | 500 mg, 750 mg, 1500 mg |
| Most Common Brands | Glucosamine Sulfate (generic), Dona®, Artren®, Osteo Bi-Flex® |
Advantages:
Provides additional sulfur for cartilage synthesis
Most extensive clinical evidence
Demonstrated improvement in osteoarthritis symptoms
May slow structural cartilage damage
Disadvantages:
Less stable than other forms
Usually stabilized with NaCl (lower glucosamine content)
May have high sodium content (caution in sodium-restricted diets)
SECTION 9: GLUCOSAMINE HYDROCHLORIDE
| Parameter | Information |
|---|---|
| Chemical Name | Glucosamine Hydrochloride |
| Molecular Formula | C₆H₁₃NO₅·HCl |
| Molecular Weight | 215.63 g/mol |
| CAS Number | 66-84-2 |
| Glucosamine Content | 83% (highest) |
| Sulfur Content | No |
| Clinical Studies | Fewer than sulfate |
| Osteoarthritis Efficacy | Pain reduction: ~20-25%; Function improvement: ~15-20% |
| Structural Effect | Limited data |
| Onset of Action | 6-12 weeks |
| Typical Formulation | Capsule, tablet, powder |
| Stabilizer | Stable; no additional stabilizers required |
| Dosage Forms | 500 mg, 750 mg, 1000 mg, 1500 mg |
| Most Common Brands | Glucosamine HCl (generic), Osteo Bi-Flex®, Move Free® |
Advantages:
Highest glucosamine content (83% by weight)
More stable; longer shelf life
Lower salt content (suitable for sodium-restricted diets)
Purer; fewer impurities
Disadvantages:
Does not contain sulfur (does not provide additional sulfur for cartilage synthesis)
Fewer clinical studies (compared to sulfate)
Some meta-analyses show less efficacy than sulfate
SECTION 10: N-ACETYLGLUCOSAMINE
| Parameter | Information |
|---|---|
| Chemical Name | N-Acetylglucosamine |
| Molecular Formula | C₈H₁₅NO₆ |
| Molecular Weight | 221.21 g/mol |
| CAS Number | 7512-17-6 |
| Glucosamine Content | ~81% (acetylated) |
| Sulfur Content | No |
| Stability | Most stable form |
| Clinical Studies | Limited (for joint health) |
| Cosmetic Use | Widespread — moisturizer, skin barrier support |
| Dietary Supplement | Joint health, anti-aging, gut health |
| Skin Penetration | High (low molecular weight) |
| Hyaluronic Acid Precursor | Yes (endogenous hyaluronan synthesis) |
| Typical Formulation | Capsule, powder, cream, serum |
| Dosage | 500-1500 mg/day (oral); 1-10% (topical) |
Advantages:
Most stable form; long shelf life
Effective as a moisturizer and barrier supporter in cosmetics
Supports hyaluronic acid synthesis
Improves skin barrier function
Being researched for gut health (microbiome)
Disadvantages:
Limited clinical evidence for joint health
Less studied (compared to sulfate)
Generally more expensive
SECTION 11: CLINICAL STUDY RESULTS AND EFFICACY
| Study / Meta-analysis | Participants | Dose | Duration | Outcome |
|---|---|---|---|---|
| GAIT Study (2006) | 1583 | 1500 mg Sulfate | 24 weeks | Significant pain reduction (WOMAC) |
| Lequesne Meta-analysis (2010) | >3800 | 1500 mg Sulfate | 6-36 months | Clinically significant improvement in pain and function |
| Cochrane Review (2018) | >10,000 | Sulfate / HCl | 6-36 months | Mild-moderate pain reduction in sulfate form; limited in HCl |
| OARSI Guideline (2019) | - | Sulfate 1500 mg | - | Recommended for osteoarthritis treatment (evidence level: strong) |
| ESCEO Guideline (2016) | - | Sulfate 1500 mg | - | Recommended as first-line treatment for osteoarthritis |
| Glucosamine HCl vs Sulfate | 1500 | 1500 mg (both forms) | 6 months | Sulfate more effective than HCl (small difference) |
| Structural Effect (MRI) | 450 | Sulfate 1500 mg | 36 months | Slows joint space narrowing (structure-modifying) |
SECTION 12: SAFETY PROFILE AND SIDE EFFECTS
| Parameter | Value / Description |
|---|---|
| GHS Classification | Generally not classified as hazardous substance |
| Acute Oral Toxicity (LD50, Rat) | >5000 mg/kg (low toxicity) |
| Skin Irritation | Low irritation potential |
| Eye Irritation | Low irritation potential (dust) |
| Carcinogenicity | Not classified as carcinogenic |
| Mutagenicity | Not mutagenic |
| Common Side Effects | • Nausea (~5-10%) • Stomach upset (~5-10%) • Diarrhea (~2-5%) • Constipation (~2-5%) |
| Rare Side Effects | • Headache • Dizziness • Skin rash • Insomnia |
| Serious Side Effects | • Allergic reaction (rare) • Asthma exacerbation (in allergic individuals) |
SECTION 13: CRITICAL WARNINGS AND CONTRAINDICATIONS
| Warning | Description |
|---|---|
| Shellfish Allergy | Traditional source is shellfish shells (chitin). Not suitable for those with allergies. Vegan/vegetarian sources (microbial fermentation) are available. |
| Anticoagulant Interaction | May increase INR when used with warfarin (bleeding risk). Potential interaction with aspirin. |
| Hypoglycemic Drug Interaction | May lower blood sugar; blood glucose monitoring recommended when used with diabetes medications. |
| Pregnancy / Lactation | Safety data limited; should be used under medical supervision. FDA Pregnancy Category C. |
| Kidney Disease | Caution at high doses; renal function should be monitored (especially sulfate form). |
| Liver Disease | Caution in hepatic insufficiency (metabolism). |
| Asthma | Risk of bronchospasm in individuals with allergic asthma (rare). |
| Hypertension | Glucosamine sulfate (may contain sodium) should be used with caution in sodium-restricted diets. |
SECTION 14: DRUG INTERACTIONS
| Drug / Substance | Interaction Type | Severity | Management |
|---|---|---|---|
| Warfarin / Anticoagulants | Increased bleeding risk; INR increase | Moderate | INR monitoring; dose adjustment may be required |
| Aspirin / NSAIDs | Slightly increased bleeding risk | Low | Monitoring; generally safe |
| Antidiabetics (Metformin, Sulfonylureas, Insulin) | Increased hypoglycemia risk | Moderate | Blood glucose monitoring; dose adjustment |
| Diuretics (Thiazides, Loop) | Fluid retention due to sodium content of glucosamine sulfate | Low | Blood pressure monitoring (sulfate form) |
| Paracetamol (Acetaminophen) | No interaction expected | None | Monitoring not required |
| Corticosteroids | No interaction expected | None | Monitoring not required |
SECTION 15: RECOMMENDED DOSAGE AND ADMINISTRATION
| Form | Dose | Administration | Notes |
|---|---|---|---|
| Glucosamine Sulfate | 1500 mg/day | 500 mg 3 times/day or 750 mg 2 times/day | Take with meals (GI tolerance) |
| Glucosamine Hydrochloride | 1500 mg/day | 500 mg 3 times/day or 750 mg 2 times/day | Take with meals (GI tolerance) |
| N-Acetylglucosamine (Joint) | 500-1500 mg/day | 1-2 times/day | With or without food |
| N-Acetylglucosamine (Cosmetic) | 1-10% | Topical (cream, serum, lotion) | 1-2 times/day |
| Maximum Safe Dose | 3000 mg/day | - | Under physician supervision |
SECTION 16: FORMULATION GUIDELINES
| Parameter | Recommendation |
|---|---|
| Glucosamine Sulfate Formulation | • Stabilized with NaCl (20%) • pH 4.0-6.0 range • Soluble in water phase • Suitable binders used for tablet compression |
| Glucosamine HCl Formulation | • Stable; no additional stabilizers required • pH 4.0-6.0 range • Soluble in water phase • High glucosamine content (83%) |
| N-Acetylglucosamine Formulation | • Most stable form • Soluble in water phase in cosmetic formulations • pH 5.0-7.0 range • Used at 1-10% in topical formulations |
| Common Properties | • Hygroscopic — store protected from moisture • Degradation at high temperatures (>150°C) • Light-proof containers preferred |
SECTION 17: STORAGE AND SHELF LIFE
| Parameter | Information |
|---|---|
| Storage Conditions | Store in a cool (<25°C), dry, well-ventilated area; protect from moisture and light. |
| Temperature Limits | 15-25°C (ideal); do not exceed 30°C |
| Humidity | Low humidity environment (hygroscopic) |
| Incompatible Materials | Strong oxidizing agents, strong acids, strong bases |
| Container Requirements | Light-proof, moisture-proof containers: HDPE, aluminum foil, amber glass |
| Shelf Life (Sulfate) | 24-36 months (proper storage) |
| Shelf Life (HCl) | 36-48 months (proper storage) |
| Shelf Life (NAG) | 36-48 months (proper storage) |
| Signs of Degradation | Color change (yellowing), caking, odor change, decreased solubility |
SECTION 18: OTHER NAMES AND SYNONYMS
| Type | Name |
|---|---|
| Chemical Name | 2-Amino-2-deoxy-D-glucose |
| Common Names | Glukozamin, Glucosamine, Glucosamine Base |
| Glucosamine Sulfate | Glucosamine Sulfate, Glucosamine Sulphate, D-Glucosamine Sulfate |
| Glucosamine HCl | Glucosamine Hydrochloride, Glucosamine Chloride |
| N-Acetylglucosamine | N-Acetylglucosamine, NAG, GlcNAc, Acetylglucosamine |
| Trade Marks | Osteo Bi-Flex®, Move Free®, Dona®, Artren®, Cosequin®, Nutramax® |
| Sources | Chitin (shellfish), microbial fermentation, fungal cell walls |
| CAS Numbers | • Free Base: 3416-24-8 • HCl: 66-84-2 • Sulfate: 29031-19-4 (sodium salt) • NAG: 7512-17-6 |
SECTION 19: QUICK REFERENCE TABLE
| Property | Glucosamine Sulfate | Glucosamine HCl | N-Acetylglucosamine |
|---|---|---|---|
| CAS Number | 29031-19-4 | 66-84-2 | 7512-17-6 |
| Molecular Weight | 277.25 g/mol | 215.63 g/mol | 221.21 g/mol |
| Glucosamine Content | ~65-70% | ~83% | ~81% |
| Sulfur Content | Yes | No | No |
| Stability | Moderate | High | Highest |
| Clinical Evidence | Strongest | Moderate | Limited |
| Cosmetic Use | Limited | Limited | Widespread |
| Typical Dose | 1500 mg/day | 1500 mg/day | 500-1500 mg/day |
| Shelf Life | 24-36 months | 36-48 months | 36-48 months |
| Primary Use | Osteoarthritis | Osteoarthritis | Cosmetics, Supplements |
SECTION 20: CRITICAL WARNINGS AND BEST PRACTICES
CRITICAL WARNINGS:
Allergy: Shellfish-derived glucosamine may cause reactions in allergic individuals. Vegan/vegetarian sources (microbial fermentation) are available.
Drug Interactions: May interact with anticoagulants (warfarin, aspirin) and hypoglycemic medications.
Side Effects: Gastrointestinal discomfort (nausea, diarrhea, constipation) is common at high doses. Taking with meals is recommended.
Pregnancy/Lactation: Safety data are limited; use under medical supervision (FDA Category C).
Diabetes: May lower blood sugar; diabetic patients should monitor blood sugar regularly.
Kidney Disease: Renal function should be monitored at high doses (especially sulfate form).
Hypertension: Glucosamine sulfate (may contain sodium) should be used with caution in sodium-restricted diets.
Onset of Action: Clinical improvement begins within 4-8 weeks; optimal effect is seen in 3-6 months.
BEST PRACTICE RECOMMENDATIONS:
Form Selection: Use Glucosamine Sulfate for osteoarthritis treatment (strongest clinical evidence), Glucosamine HCl for general joint health (higher purity), and N-Acetylglucosamine for cosmetic applications (most stable).
Dosage: 1500 mg/day (sulfate or HCl) is the standard dose. Take with meals to improve GI tolerance.
Source Selection: Those with allergy risk should choose vegan/vegetarian glucosamine (microbial fermentation).
Combination: Glucosamine shows synergistic effects with chondroitin sulfate. Combination with MSM (methylsulfonylmethane) is also common.
Patience: Clinical improvement takes time (4-8 weeks). Patients should be informed to continue treatment.
Stability: Glucosamine sulfate (stabilized with NaCl), glucosamine HCl (stable), and NAG (most stable) have different shelf lives. Proper storage conditions should be observed.
Quality Control: HPLC assay of glucosamine; loss on drying; microbiological purity; heavy metals; chloride/sulfate content.
Sustainability: Microbial fermentation or fungal-derived glucosamine may be preferred for environmental sustainability.
LEGAL DISCLAIMER:
The information provided in this document is based on our current knowledge and experience and is presented in good faith; however, it does not constitute a binding specification or guarantee as all conditions of use are beyond our control. This Technical Data Sheet is for informational purposes only. Users are responsible for testing suitability for their own applications. For complete safety, storage, use, handling, waste, and regulatory compliance information, please refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. Glucosamine is a dietary supplement; its use should be under the supervision of a healthcare professional for any health condition.