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Alpha Lipoic Acid, DL-Thioctic Acid, Dithiooctanoic Acid, ALA, 1077-28-7

Alpha Lipoic Acid, DL-Thioctic Acid, Dithiooctanoic Acid, ALA, 1077-28-7

ALPHA LIPOIC ACID (ALA)

SECTION 1: PRODUCT IDENTITY AND CHEMICAL IDENTIFICATION

Parameter Information
Product Name Alpha Lipoic Acid (α-Lipoic Acid)
Chemical Name (IUPAC) (±)-1,2-Dithiolane-3-pentanoic acid
Synonyms (Turkish) Alfa Lipoik Asit, α-Lipoik Asit, DL-Tiyoktik Asit
Synonyms (English) Alpha Lipoic Acid, DL-Thioctic Acid, 6,8-Dithiooctanoic acid, ALA
CAS Number 1077-28-7
EC Number (EINECS) 214-071-2
Molecular Formula C₈H₁₄O₂S₂
Molecular Weight 206.33 g/mol
Chemical Class Organic sulfur compound; Dithiolane derivative
Pharmacological Class Antioxidant; Coenzyme; Mitochondrial metabolite
Physical State (20°C) Solid (powder)
Color Light yellow
Odor Almost odorless

SECTION 2: CHEMICAL STRUCTURE

         O
         ‖
    HO—C—CH₂—CH₂—CH₂—CH—CH₂
                       |     \
                       S     S
                       |     |
                       CH₂—CH₂

    Alpha Lipoic Acid
    (±)-1,2-Dithiolane-3-pentanoic acid
    C₈H₁₄O₂S₂

Simplified Structure:

    HOOC—(CH₂)₄—C—CH₂—CH₂
                   \     /
                    S   S
                     \ /
                      C

    Alpha Lipoic Acid
    (Dihydrolipoic acid form: HOOC—(CH₂)₄—CH—SH
                                     |
                                    CH₂
                                     |
                                    CH₂
                                     |
                                    SH )
Parameter Description
Molecular Formula C₈H₁₄O₂S₂
Molecular Weight 206.33 g/mol
Chemical Class Organic sulfur compound; Dithiolane derivative
Functional Groups Carboxylic acid (-COOH), disulfide (-S-S-), dithiolane ring
Chirality Optically active (R and S enantiomers)
Racemic Form DL-α-lipoic acid (equal amounts of R and S)
R-Form Naturally occurring form (biologically active)
S-Form Synthetic form (less active)
SMILES C1CSSCC1CCCCC(=O)O
InChI InChI=1S/C8H14O2S2/c9-8(10)3-1-2-4-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
InChI Key AGBQKNBQESQNFD-UHFFFAOYSA-N
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
Rotatable Bond Count 5
Polar Surface Area (PSA) 40.5 Ų

SECTION 3: PHYSICAL AND CHEMICAL PROPERTIES

Property Value Test Method / Note
Appearance Light yellow powder Visual
Odor Almost odorless Olfactometric
Molecular Weight 206.33 g/mol Calculated
Melting Point 60 – 62°C DSC / Capillary
Boiling Point Decomposes >286°C -
Boiling Point (Alternative) 160-165°C (ignites) -
Density (23°C) ~1.4 g/cm³ -
Density (Estimated) 1.2888 g/cm³ Calculated
Refractive Index 1.5200 (estimated) -
pKa 4.75 ± 0.10 (estimated) -
Water Solubility (20°C) ~0.87-0.9 g/L General Method
Hot Water Solubility Increases General Method
Ethanol Solubility (20°C) 50 mg/mL General Method
Benzene, Chloroform, Ether Readily soluble General Method
10% NaOH Solution Soluble General Method
Log P (Octanol/Water, 25°C) 2.53 Calculated / Experimental
pH (Saturated Aqueous Solution) ~4.5-5.0 pH Meter
Vapor Pressure Very low -
Flash Point >100°C -
Thermal Stability Stable up to 60°C; decomposes at higher temperatures -
Hygroscopicity Low (not hygroscopic) -
Optical Activity Optically active (R/S enantiomers) Polarimetry
UV Maximum (λmax) ~330 nm UV-VIS Spectrophotometer
Surface Activity Low -

SECTION 4: R AND S ENANTIOMERS COMPARISON

Property R-α-Lipoic Acid S-α-Lipoic Acid DL-α-Lipoic Acid (Racemic)
Optical Rotation [α]D +104° (R) -104° (S) 0° (racemic)
Natural Source Yes (mitochondria) No No (synthetic)
Biological Activity High (cofactor) Low (inactive) Moderate (R active, S inactive)
Enzymatic Activity Yes (coenzyme) No Partial (only R)
Mitochondrial Binding Strong Weak Moderate
Antioxidant Capacity High Low Moderate
Clinical Use Preferred (pure R) Not used Common (cheaper)
Price High - Low-Moderate

SECTION 5: BIOLOGICAL FUNCTION AND MECHANISM OF ACTION

Property Description
Antioxidant Mechanism Directly scavenges free radicals (ROS, RNS); Regenerates oxidized antioxidants (vitamin C, vitamin E, glutathione); Chelates metal ions (Cu²⁺, Fe³⁺).
Coenzyme Role Acts as a cofactor for α-keto acid dehydrogenase complexes (pyruvate dehydrogenase, α-ketoglutarate dehydrogenase) in mitochondria; Plays a critical role in energy metabolism.
Redox Cycling Undergoes redox cycling between disulfide (-S-S-) and thiol (-SH) groups; Conversion between lipoic acid and dihydrolipoic acid (DHLA); Regulates intracellular redox balance.
Mitochondrial Protection Protects mitochondrial membrane from oxidative damage; Supports mitochondrial biogenesis; Reduces age-related mitochondrial dysfunction.
Glucose Metabolism Increases insulin sensitivity; Stimulates glucose uptake (via AMPK pathway); Used in neuropathy treatment.
Neuroprotection Protects neurons from oxidative damage; Neuroprotective effect in Alzheimer's and Parkinson's disease models; Supports nerve regeneration.
Metal Chelation Binds Cu²⁺ and Fe³⁺ ions, inhibiting Fenton reaction; Reduces metal-induced oxidative damage.

SECTION 6: COMMERCIAL GRADES AND VARIANTS

Grade / Type Purity Appearance Enantiomer Primary Application
Cosmetic Grade ≥99.0% Light yellow powder DL (racemic) / R Anti-aging creams, serums, lotions
Food Supplement Grade ≥99.0% Light yellow powder DL (racemic) / R Capsules, tablets, powder blends
Pharmaceutical Grade ≥99.5% Light yellow powder R (pure) / DL Pharmaceutical formulations, neuropathy treatment
Research Grade (R&D) ≥99.5% Light yellow powder R / S / DL Analytical standards, formulation development
Pure R-Form ≥99.5% Light yellow powder R High biological activity products
DL-Form (Racemic) ≥99.0% Light yellow powder DL (50/50) Common use, economical

SECTION 7: PHARMACOKINETIC PROPERTIES

Parameter Value / Description
Oral Bioavailability ~30-40% (with first-pass metabolism)
Peak Plasma Concentration (Cmax) ~2-4 µg/mL (after 600 mg oral dose)
Peak Time (Tmax) ~1-2 hours (oral)
Plasma Half-Life (t½) ~1.5-2.5 hours
Volume of Distribution (Vd) ~0.5-1.0 L/kg
Protein Binding ~80-90% (albumin)
Metabolism Hepatic (β-oxidation, methylation, reduction)
Elimination • Urine: ~60-70% (as metabolites)
• Feces: ~20-30%
Intracellular Distribution Mitochondria, cytosol, nucleus
Redox Cycling Intracellular redox systems convert lipoic acid ↔ dihydrolipoic acid
Biological Half-Life (Intracellular) ~30-60 minutes
Placental Transfer Yes (crosses placenta)
Breast Milk Transfer Unknown

SECTION 8: CLINICAL USE AND INDICATIONS

Indication Dose Route Duration Evidence Level
Diabetic Neuropathy 600-1800 mg/day Oral / IV 3-12 months Strong Clinical Evidence
Antioxidant Support 300-600 mg/day Oral Continuous Clinical Studies
Cardiovascular Protection 300-600 mg/day Oral Continuous Preclinical / Limited
Neurodegenerative Diseases 600-1200 mg/day Oral Variable Preclinical / Pilot
Migraine Prophylaxis 600 mg/day Oral 3-6 months Clinical Studies
Inflammatory Diseases 600-1200 mg/day Oral Variable Preclinical / Limited
Anti-aging 300-600 mg/day Oral Continuous Observational
Cosmetic (Topical) 0.5-5% Cream / Serum Continuous Clinical Studies

SECTION 9: QUALITY SPECIFICATIONS

Parameter Specification Test Method
Appearance Light yellow powder Visual
Assay (Alpha Lipoic Acid) ≥99.0% HPLC / Titration
Melting Point 60 – 62°C DSC / Capillary
Water Content ≤0.5% Karl Fischer
Residue on Ignition ≤0.1% Gravimetric
Heavy Metals (Pb) ≤10 ppm ICP-MS
Arsenic (As) ≤2 ppm ICP-MS
Lead (Pb) ≤3 ppm ICP-MS
Cadmium (Cd) ≤1 ppm ICP-MS
Mercury (Hg) ≤1 ppm ICP-MS
Related Substances (Single) ≤0.5% HPLC
Related Substances (Total) ≤1.0% HPLC
Optical Rotation (R-Form) +100° to +110° (c=1, CHCl₃) Polarimetry
Optical Rotation (DL-Form) -5° to +5° (c=1, CHCl₃) Polarimetry
Particle Size As per customer specification Laser Diffraction
Microbiological Purity TAMC ≤10² CFU/g; TYMC ≤10¹ CFU/g USP <61>
E. coli Negative in 1g USP <62>
Salmonella spp. Negative in 25g USP <62>

SECTION 10: SAFETY PROFILE AND TOXICOLOGICAL ASSESSMENT

Parameter Value / Description
GHS Classification Warning
Signal Word Warning
Hazard Pictograms GHS07 (Exclamation mark), GHS09 (Environment)
Hazard Statements (H-Codes) H302 (Harmful if swallowed); H315 (Causes skin irritation); H317 (May cause allergic skin reaction); H319 (Causes serious eye irritation); H411 (Toxic to aquatic life with long-lasting effects)
Precautionary Statements (P-Codes) P261, P273, P280, P301+P312, P302+P352, P305+P351+P338
Acute Oral Toxicity (LD50, Rat) ~1,190 mg/kg
Acute Dermal Toxicity (LD50, Rabbit) >2000 mg/kg
Skin Irritation Irritant (Category 2)
Eye Irritation Causes serious eye irritation (Category 2)
Skin Sensitization May cause allergic skin reactions (Category 1)
Carcinogenicity Not classified as carcinogenic
Mutagenicity (Ames test) Negative
Chromosomal Aberration Test Negative
Gene Mutation Test Negative
Micronucleus Test Negative
Reproductive Toxicity No reproductive toxicity
NOAEL (Rat, 90 days) ~300 mg/kg/day
RTECS JP1192000 - irritant effects, respiratory insufficiency, convulsions, fatigue
Drug Interactions • Chemotherapeutics (cisplatin, carboplatin)
• Thyroid hormones (levothyroxine)
• Antidiabetic drugs

SECTION 11: GHS CLASSIFICATION AND LABELING

GHS Classification (in accordance with 1272/2008/EC):

Hazard Class Category H-Statement
Acute Toxicity (Oral) Category 4 H302
Skin Irritation Category 2 H315
Eye Irritation Category 2 H319
Skin Sensitization Category 1 H317
Aquatic Chronic Toxicity Category 2 H411

Signal Word: Warning

Hazard Pictograms: GHS07 (Exclamation mark), GHS09 (Environment)

NFPA 704 Hazard Classification:

Health Flammability Reactivity Special
1 1 0 -
(Minimal health hazard) (Combustible) (Stable) (None)

SECTION 12: PRECAUTIONARY STATEMENTS (P-CODES)

Code Statement
P261 Avoid breathing dust/fume/gas
P264 Wash hands thoroughly after handling
P270 Do not eat, drink or smoke when using this product
P271 Use only outdoors or in a well-ventilated area
P273 Avoid release to the environment
P280 Wear protective gloves/protective clothing/eye protection/face protection
P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell
P302+P352 IF ON SKIN: Wash with plenty of soap and water
P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and continue rinsing
P332+P313 If skin irritation occurs: Get medical advice/attention
P337+P313 If eye irritation persists: Get medical advice/attention
P362+P364 Take off contaminated clothing and wash it before reuse
P403+P233 Store in a well-ventilated place. Keep container tightly closed
P405 Store locked up
P501 Dispose of contents/container in accordance with local/regional/national/international regulations

SECTION 13: FIRST AID MEASURES

Route of Exposure Action
Inhalation If inhaled as powder, move to fresh air. Seek medical attention if respiratory symptoms persist.
Skin Contact Remove contaminated clothing. Wash with plenty of soap and water. Seek medical attention if irritation develops.
Eye Contact Rinse thoroughly with plenty of water for at least 15 minutes. Keep eyelids open. Remove contact lenses if present. Seek medical attention if irritation persists.
Ingestion Rinse mouth with water. Do NOT induce vomiting. Drink 1-2 glasses of water. Seek medical attention.
Note Symptomatic treatment is administered. No specific antidote available.

SECTION 14: FIREFIGHTING MEASURES

Parameter Information
Fire Hazard Combustible organic matter. Dust explosion risk.
Flash Point >100°C
Fire-Related Hazards Thermal decomposition produces carbon oxides (CO, CO₂) and sulfur oxides (SOₓ).
Suitable Extinguishing Media Water mist, CO₂, dry chemical powder, foam.
Unsuitable Extinguishing Media Water jet (may spread burning material)
Special Protective Equipment Self-contained breathing apparatus (SCBA), full protective clothing.
Special Precautions Prevent dust from entering sewers and water bodies. Avoid dust cloud formation.

SECTION 15: STORAGE AND SHELF LIFE

Parameter Information
Storage Conditions Store in a cool (<25°C), dry, well-ventilated area; protect from direct sunlight and moisture. Keep in tightly closed containers.
Temperature Limits 15-25°C (ideal); do not exceed 30°C
Humidity Low humidity environment
Light Light sensitive; Light-proof containers (amber glass, aluminum, opaque HDPE)
Oxygen Protect against oxidation; keep containers tightly closed
Incompatible Materials Strong oxidizing agents, strong acids, strong bases
Container Requirements Light-proof, moisture-proof containers: Amber glass bottles, aluminum foil bags, HDPE
Shelf Life 24-36 months (unopened original packaging, under proper storage conditions)
Shelf Life (After Opening) 12-18 months (under proper storage conditions)
Signs of Degradation Color change (darkening), caking, odor change, HPLC impurity increase
Stability Warning May degrade under light, heat, and oxygen; Oxidized product turns from yellow to dark yellow

SECTION 16: PACKAGING OPTIONS

Packaging Type Quantity / Capacity Material Application Area
Aluminum Foil Bag 1 kg, 5 kg, 10 kg, 25 kg Aluminum / PE (light and moisture proof) Cosmetic, food supplement, pharmaceutical
HDPE Drum 25 kg, 50 kg HDPE (opaque, moisture barrier) Industrial supply
Amber Glass Bottle 100 g, 500 g, 1 kg Amber glass (UV protected) Laboratory, high purity
PE-Lined Kraft Bag 10 kg, 25 kg Kraft paper / PE liner Economical packaging
IBC Container 500 kg, 1000 kg UV-protected HDPE Large-scale industrial supply

SECTION 17: TRANSPORTATION INFORMATION

Parameter Information
UN Number UN 3077 (Environmentally Hazardous Substance, Solid, N.O.S.)
Hazard Class Class 9 - Miscellaneous Dangerous Goods
Packing Group III
ADR/RID Class 9; UN 3077; Packing Group III
IMDG Code Class 9; UN 3077; Marine pollutant: Yes
IATA (Air) Class 9; UN 3077; Packing Group III
Transport Label Class 9 / Environment
Marine Pollutant Yes
Transport Temperature Ambient temperature; protect from heat, moisture, and light
Transport Precautions Light-proof packaging; keep away from strong oxidizing agents

SECTION 18: REGULATORY STATUS

Region / Authority Status
USA (FDA) Approved as dietary supplement; GRAS
European Union (EC) Approved as food supplement; EFSA approved; Approved as cosmetic ingredient
Turkey Approved as food supplement, pharmaceutical and cosmetic ingredient; Subject to KKDIK regulation
ECHA (REACH) Registered substance (pre-registered)
TSCA (USA) Listed
DSD (Dangerous Substances Directive) Xi (Irritant), N (Dangerous for the environment)
California (Prop 65) Not listed
Halal Yes (synthetic, not animal-derived)
Kosher Yes (with certification)
Vegan Yes (synthetic)

SECTION 19: OTHER NAMES AND SYNONYMS

Type Name
Chemical Name (IUPAC) (±)-1,2-Dithiolane-3-pentanoic acid
Common Names (Turkish) Alfa Lipoik Asit, α-Lipoik Asit, DL-Tiyoktik Asit
Common Names (English) Alpha Lipoic Acid, DL-Thioctic Acid, 6,8-Dithiooctanoic acid, ALA
Abbreviations ALA, α-LA, THT
R-Form R-α-Lipoic Acid (natural form)
S-Form S-α-Lipoic Acid
Reduced Form Dihydrolipoic Acid (DHLA)
CAS Number 1077-28-7
EC Number 214-071-2
BRN 81853
PubChem CID 6112
DrugBank ID DB00142
FDA UNII 73Y7P0K73Y
HS Code 2930.90

SECTION 20: SUMMARY TABLE

Parameter Value
CAS Number 1077-28-7
Molecular Formula C₈H₁₄O₂S₂
Molecular Weight 206.33 g/mol
Appearance Light yellow powder
Melting Point 60 – 62°C
Water Solubility ~0.87-0.9 g/L
Log P 2.53
Primary Function Antioxidant; Coenzyme; Free radical scavenger
Clinical Indications Diabetic neuropathy, antioxidant support, neurodegeneration
Typical Dose 300-600 mg/day (oral); 600-1800 mg/day (neuropathy)
Bioavailability ~30-40% (oral)
Plasma Half-Life ~1.5-2.5 hours
Shelf Life 24-36 months
Storage Cool (<25°C), dry, light-protected
GHS Signal Word Warning
UN Number 3077
Hazard Class Class 9
FDA Status Approved as dietary supplement (GRAS)
Halal / Kosher / Vegan Yes

SECTION 21: CRITICAL WARNINGS AND BEST PRACTICES

CRITICAL WARNINGS:

  1. Light Sensitivity: Alpha Lipoic Acid is light sensitive. Store in light-proof containers (amber glass, aluminum, HDPE).

  2. Temperature Sensitivity: Melting point is 60-62°C. Melts and may degrade above 60°C.

  3. Oxidation Sensitivity: Sensitive to oxygen; oxidizes from yellow to dark yellow. Antioxidant addition recommended.

  4. Skin Sensitization: May cause allergic skin reactions (H317). Avoid skin contact.

  5. Environmental Toxicity: Toxic to aquatic life with long-lasting effects (H411). Avoid release to the environment.

  6. Drug Interactions: Potential interaction with chemotherapeutics (cisplatin, carboplatin), thyroid hormones (levothyroxine), and antidiabetic drugs.

  7. High Doses: High doses (≥1800 mg/day) may cause gastrointestinal discomfort, nausea, headache.

  8. Dust Explosion: Dust explosion risk; avoid dust formation and ensure adequate ventilation.

BEST PRACTICE RECOMMENDATIONS:

  1. Form Selection: Use R-α-lipoic acid (pure, natural form) for applications requiring high biological activity; DL-α-lipoic acid (racemic) for common use and economical products.

  2. Concentration (Cosmetic): Typical concentration 0.5-5%; Optimum concentration 1-2%; Up to 5% considered safe.

  3. Formulation (Cosmetic): Dissolve in water phase or oil phase; dissolve at 40-50°C; avoid high temperatures (>60°C); stabilize at pH 4.0-6.0.

  4. Antioxidant Use: Add Vitamin E (0.1-0.5%) or BHT (0.01-0.1%) to formulations; prevents oxidation and color change.

  5. Chelator Use: Add EDTA (0.05-0.1%) to bind metal ions; improves stability.

  6. Dosage (Oral): Diabetic neuropathy: 600-1800 mg/day; antioxidant support: 300-600 mg/day; take with meals (GI tolerance).

  7. Light Protection: Use amber glass, aluminum or opaque HDPE containers; protect with UV filters.

  8. Personal Protective Equipment: Nitrile or neoprene gloves (minimum 0.11 mm thickness), safety goggles, dust mask (P2 type), protective clothing.

  9. Hygiene: Wash hands thoroughly after handling; Do not eat, drink or smoke when using this product.

  10. Storage: Store in cool, dry, light-proof containers; Inert atmosphere (nitrogen) recommended to prevent oxidation; Shelf life 24-36 months.

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 guarantee. This Technical Data Sheet is for informational purposes only and does not constitute medical advice. Users are responsible for testing suitability for their own applications and for complying with all local, regional, and national regulations. 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. Alpha Lipoic Acid is a dietary supplement/cosmetic ingredient; its medical use should be under the supervision of a healthcare professional.

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