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Send EmailAlpha Lipoic Acid, Thioctic Acid, Lipoic Acid, ALA, 1077-27-6
ALPHA LIPOIC ACID – ALFA LİPOİK ASİT
CAS Number: 1077-27-6
EC Number (EINECS): 214-071-8
Molecular Formula: C₈H₁₄O₂S₂
Molecular Weight: 206.33 g/mol
Chemical Class: Organosulfur compound (dithiolane derivative)
SECTION 1: CHEMICAL IDENTITY AND DEFINITION
| Parameter | Information |
|---|---|
| Chemical Name (IUPAC) | 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid |
| Other Names | Alpha Lipoic Acid, ALA, Thioctic Acid, Lipoic Acid, 1,2-Dithiolane-3-pentanoic Acid, 6,8-Dithiooctanoic Acid |
| Chemical Formula | C₈H₁₄O₂S₂ |
| Molecular Weight | 206.33 g/mol |
| CAS Number | 1077-27-6 |
| EC Number (EINECS) | 214-071-8 |
| Chemical Class | Organosulfur compound (dithiolane derivative) |
| Appearance | Yellow to yellowish-white, crystalline powder |
| Odor | Slight characteristic |
| Physical State (20°C) | Solid (crystalline powder) |
| Optical Activity | R-(+)-Lipoic Acid (natural) and racemic mixture available |
SECTION 2: PHYSICAL PROPERTIES
| Property | Value |
|---|---|
| Appearance | Yellow to yellowish-white, crystalline powder |
| Odor | Slight characteristic |
| Molecular Weight | 206.33 g/mol |
| Melting Point | 60 – 62 °C |
| Density | ~1.2 g/cm³ |
| Solubility in Water | Slightly soluble (~0.5 g/L) |
| Solubility in Ethanol | Soluble |
| Solubility in Methanol | Soluble |
| Solubility in Chloroform | Soluble |
| Solubility in Fats/Oils | Soluble (lipophilic) |
| Log P (octanol/water) | 2.03 |
| pKa | 4.7 |
| Stability | Sensitive to light, heat, and oxygen |
| Hygroscopicity | Low |
SECTION 3: CHEMICAL PROPERTIES
| Property | Information |
|---|---|
| Chemical Formula | C₈H₁₄O₂S₂ |
| Molecular Weight | 206.33 g/mol |
| Chemical Class | Organosulfur compound (dithiolane derivative) |
| Functional Groups | Carboxyl (-COOH), dithiolane ring (disulfide) |
| Structure | Dithiolane ring with a carboxylic acid side chain |
| SMILES | C1C(SSC1)CCCCC(=O)O |
| InChI Key | AGBQKNBQESQNJD-UHFFFAOYSA-N |
| Redox Activity | Reversibly reduced to dihydrolipoic acid (DHLA) |
| Optical Activity | R-(+)-Lipoic Acid (natural), S-(-)-Lipoic Acid, and racemic (R/S) mixture |
| Stability | Sensitive to light, heat, and oxygen |
| Incompatible Materials | Strong oxidizing agents, strong bases, light |
Chemical Structure:
S-S
/ \
/ \
C C
| |
| |
CH₂ CH₂
| |
C-----C
| |
H₂ CH₃
\ /
C=O
|
OH
(Alpha Lipoic Acid / Thioctic Acid)
SECTION 4: FORMS OF ALPHA LIPOIC ACID
| Form | Description | Bioavailability |
|---|---|---|
| R-(+)-Lipoic Acid | Natural, biologically active form | High |
| S-(-)-Lipoic Acid | Synthetic, less active form | Lower |
| R/S Lipoic Acid | Racemic mixture (1:1) | Moderate |
| Dihydrolipoic Acid (DHLA) | Reduced form (active antioxidant) | High |
| Sodium R-Lipoate | Sodium salt of R-lipoic acid | Highest |
| R-Lipoic Acid | Pure natural form | High |
SECTION 5: MECHANISM OF ACTION
| Parameter | Description |
|---|---|
| Primary Function | Antioxidant, mitochondrial cofactor |
| Antioxidant Activity | Scavenges free radicals; regenerates other antioxidants (vitamin C, E, glutathione) |
| Redox Cycling | Converts between oxidized (lipoic acid) and reduced (dihydrolipoic acid) forms |
| Mitochondrial Role | Cofactor for pyruvate dehydrogenase and alpha-ketoglutarate dehydrogenase |
| Energy Metabolism | Involved in ATP production in mitochondria |
| Metal Chelation | Binds metal ions (iron, copper, mercury) |
| NF-κB Inhibition | Reduces inflammation through NF-κB pathway inhibition |
| Insulin Sensitivity | May improve insulin sensitivity and glucose metabolism |
SECTION 6: HEALTH BENEFITS
| Benefit | Description |
|---|---|
| Antioxidant Protection | Neutralizes free radicals; regenerates other antioxidants |
| Mitochondrial Support | Supports energy production in mitochondria |
| Blood Sugar Control | May improve insulin sensitivity; helps regulate glucose levels |
| Neuropathy Relief | Effective for diabetic neuropathy and other nerve conditions |
| Anti-Aging | Protects cells from oxidative damage; supports skin health |
| Anti-Inflammatory | Reduces inflammation through NF-κB inhibition |
| Cognitive Function | Supports brain health and cognitive function |
| Cardiovascular Health | Reduces oxidative stress; supports heart health |
| Chelation | Binds heavy metals; supports detoxification |
SECTION 7: NATURAL SOURCES
| Source | Content |
|---|---|
| Red Meat (beef) | Moderate |
| Organ Meats (liver, kidney) | Rich |
| Spinach | Low |
| Broccoli | Low |
| Tomatoes | Low |
| Brussels Sprouts | Low |
| Potatoes | Low |
| Yeast | Moderate |
SECTION 8: DIETARY SUPPLEMENT APPLICATIONS
| Application | Function |
|---|---|
| Antioxidant Supplements | Antioxidant protection; free radical neutralization |
| Diabetes Support | Blood sugar regulation; neuropathy relief |
| Energy Supplements | Mitochondrial support; ATP production |
| Anti-Aging Formulations | Oxidative stress reduction; cellular health |
| Neurological Support | Cognitive function; nerve health |
| Skin Care Supplements | Skin health; anti-aging |
| Weight Management | Metabolic support; energy production |
SECTION 9: COSMETIC AND SKIN CARE APPLICATIONS
| Application | Function |
|---|---|
| Anti-Aging Creams | Protects skin from oxidative damage; reduces wrinkles |
| Serums | Antioxidant protection; skin rejuvenation |
| Sun Protection | Reduces UV damage; supports skin repair |
| Moisturizers | Skin health support |
SECTION 10: TYPICAL DOSAGE
| Application | Recommended Daily Dose |
|---|---|
| General Antioxidant Support | 100-300 mg/day |
| Diabetes / Neuropathy | 300-600 mg/day (under supervision) |
| Anti-Aging | 100-300 mg/day |
| Energy Support | 100-300 mg/day |
| Neurological Support | 300-600 mg/day (under supervision) |
SECTION 11: QUALITY SPECIFICATIONS (PHARMACEUTICAL GRADE)
| Parameter | Specification (USP / Ph. Eur.) |
|---|---|
| Appearance | Yellow to yellowish-white, crystalline powder |
| Identification | Positive (IR, HPLC) |
| Assay (HPLC) | 99.0 – 101.0% |
| Melting Point | 60 – 62 °C |
| Loss on Drying | ≤ 0.5% |
| Residue on Ignition | ≤ 0.1% |
| Heavy Metals (as Pb) | ≤ 10 ppm |
| Lead (Pb) | ≤ 2 ppm |
| Arsenic (As) | ≤ 3 ppm |
| Mercury (Hg) | ≤ 1 ppm |
| Cadmium (Cd) | ≤ 1 ppm |
| Related Substances | ≤ 1.0% |
| Optical Purity (R-form) | ≥ 99.0% (for R-ALA) |
| Sulfur Content | ~31.0% |
SECTION 12: MICROBIOLOGICAL SPECIFICATIONS
| Parameter | Specification |
|---|---|
| Total Aerobic Mesophilic Bacteria | ≤ 1,000 CFU/g |
| Yeast and Mold | ≤ 100 CFU/g |
| Salmonella spp. | Negative in 25g |
| Escherichia coli | Negative in 10g |
| Staphylococcus aureus | Negative in 1g |
SECTION 13: STORAGE AND SHELF LIFE
| Parameter | Information |
|---|---|
| Storage Conditions | Cool (15-25°C), dry, well-ventilated area |
| Container Requirements | Tightly closed, light-resistant (amber glass or opaque containers) |
| Protect From | Light, heat, oxygen, moisture, strong oxidizing agents |
| Shelf Life | 24-36 months (unopened original packaging) |
| Stability Note | Light and oxygen sensitive; color change indicates degradation |
SECTION 14: PACKAGING OPTIONS
| Packaging Type | Quantity | Material |
|---|---|---|
| Aluminum foil bag | 1-5 kg | Laminated aluminum |
| Plastic pail | 20-25 kg | HDPE |
| Fiber drum | 25-50 kg | HDPE + PE |
| Glass bottle | 100-500 g | Amber glass |
| Big-Bag | 500-1000 kg | Polypropylene (with PE liner) |
SECTION 15: SAFETY AND HEALTH INFORMATION
GHS Classification (Bulk Powder)
| Hazard Class | Category |
|---|---|
| Not classified as hazardous | - |
Hazard Statements
| Code | Statement |
|---|---|
| None | Not classified as hazardous |
Precautionary Statements
| Code | Statement |
|---|---|
| P261 | Avoid breathing dust |
| P280 | Wear protective gloves/eye protection |
| P305+P351+P338 | IF IN EYES: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing |
SECTION 16: TOXICOLOGICAL INFORMATION
| Parameter | Value |
|---|---|
| Oral LD50 (Rat) | > 5,000 mg/kg |
| Skin Irritation | Non-irritant |
| Eye Irritation | Mild irritant |
| Skin Sensitization | Non-sensitizer |
| Carcinogenicity | Not classified |
| Mutagenicity | Negative in standard tests |
| GRAS Status | Generally recognized as safe |
| Side Effects | Generally well-tolerated; mild nausea at high doses |
SECTION 17: FIRST AID MEASURES
| Exposure Route | Action |
|---|---|
| Inhalation | Move to fresh air. If respiratory irritation persists, seek medical attention. |
| Skin Contact | Wash with plenty of soap and water. |
| Eye Contact | Rinse immediately with plenty of water for at least 15 minutes. Seek medical attention. |
| Ingestion | Rinse mouth. Drink plenty of water. Seek medical attention. |
SECTION 18: REGULATORY STATUS
| Region / Authority | Status |
|---|---|
| European Union | Approved as food supplement ingredient |
| USA (FDA) | Approved as dietary supplement ingredient |
| Turkey | Approved as food supplement ingredient |
| EFSA | Approved; health claims evaluated |
| JECFA | Approved |
SECTION 19: TRANSPORT INFORMATION
| Parameter | Information |
|---|---|
| UN Number | Not regulated (not dangerous goods) |
| Hazard Class | Not applicable |
| Packing Group | Not applicable |
| ADR/RID | Not regulated |
| IMDG Code | Not regulated |
| IATA (Air) | Not regulated |
| Marine Pollutant | No |
SECTION 20: FIRE-FIGHTING MEASURES
| Parameter | Information |
|---|---|
| Fire Hazard | Combustible organic solid |
| Suitable Extinguishing Media | Water spray (mist), CO₂, dry chemical powder, alcohol-resistant foam |
| Specific Hazards | When heated, emits sulfur dioxide (SO₂), CO, CO₂ |
| Decomposition Products | SO₂, CO, CO₂ |
| Protective Equipment | Self-contained breathing apparatus (SCBA), full protective clothing |
SECTION 21: ACCIDENTAL SPILLAGE AND CLEANUP
| Parameter | Information |
|---|---|
| Personal Protection | Nitrile gloves, protective goggles, dust mask (N95) |
| Cleaning Methods | Collect mechanically (sweep or spatula) |
| Environmental Precautions | Prevent entry into drains, soil, and surface waters |
| Waste Disposal | According to local regulations; incineration or landfilling at licensed facilities |
SECTION 22: OTHER NAMES AND SYNONYMS
| Type | Name |
|---|---|
| Turkish Names | Alfa Lipoik Asit, Tiyoktik Asit, Lipoik Asit |
| English Names | Alpha Lipoic Acid, ALA, Thioctic Acid, Lipoic Acid |
| Chemical Names | 1,2-Dithiolane-3-pentanoic acid, 6,8-Dithiooctanoic acid |
| Abbreviations | ALA |
| CAS Number | 1077-27-6 |
| EC Number | 214-071-8 |
| INCI | Lipoic Acid |
Trade Names (Partial List):
-
Thioctacid®
-
Alpha-Lipon®
-
Various generics
SECTION 23: COMPARISON: R-ALA VS S-ALA VS RACEMIC
| Property | R-ALA (Natural) | S-ALA (Synthetic) | Racemic (R/S-ALA) |
|---|---|---|---|
| Bioavailability | Highest | Low | Moderate |
| Activity | Active form | Less active | Moderate |
| Cost | Higher | Lower | Moderate |
| Stability | Good | Good | Good |
| Recommended | Yes | No | Sometimes |
SECTION 24: SUMMARY AND CRITICAL NOTES
Product Summary
| Parameter | Value |
|---|---|
| Product | Alpha Lipoic Acid |
| CAS Number | 1077-27-6 |
| Appearance | Yellow to yellowish-white, crystalline powder |
| Molecular Weight | 206.33 g/mol |
| Primary Function | Antioxidant, mitochondrial cofactor |
| GRAS | Yes |
Critical Notes
-
Powerful Antioxidant: ALA is a potent antioxidant that scavenges free radicals and regenerates other antioxidants (vitamin C, E, glutathione).
-
Mitochondrial Cofactor: Essential for energy production (ATP) in mitochondria.
-
Two Forms: Available as natural R-(+)-ALA, synthetic S-(-)-ALA, and racemic mixture (R/S).
-
R-ALA is Superior: Natural R-ALA has higher bioavailability and activity than synthetic S-ALA or racemic mixture.
-
Light and Oxygen Sensitive: Protect from light and oxygen; store in airtight, light-resistant containers.
-
Slightly Soluble: Slightly soluble in water; soluble in ethanol, methanol, and chloroform.
-
Diabetes Support: May improve insulin sensitivity and relieve diabetic neuropathy.
-
Cellular Protection: Supports cellular health; reduces oxidative stress.
-
Anti-Aging: Used in skin care products for its antioxidant properties.
-
Regulatory Status: Approved as food supplement ingredient in major markets.
IMPORTANT DECLARATION: This Technical Data Sheet (TDS) is for informational purposes only and has been prepared based on available technical data. The user is responsible for determining the product's suitability for their specific application and for complying with all local, national, and international regulations. For complete safety, storage, use, transport, waste, and regulatory compliance information, refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. This document does not replace medical advice.
