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Alpha Arbutin, Hidrokinon D-glukozid, 84380-01-8

Alpha Arbutin, Hidrokinon D-glukozid, 84380-01-8

ALPHA ARBUTIN

SECTION 1: PRODUCT IDENTITY AND CHEMICAL IDENTIFICATION

Parameter Information
Product Name Alpha Arbutin
Chemical Name (IUPAC) 4-Hydroxyphenyl-α-D-glucopyranoside
Synonyms (Turkish) Alfa Arbutin, α-Arbutin, Hidrokinon-α-D-glukozid
Synonyms (English) Alpha Arbutin, α-Arbutin, Hydroquinone-α-D-glucoside
CAS Number 84380-01-8
EC Number (EINECS) 617-761-4
Molecular Formula C₁₂H₁₆O₇
Molecular Weight 272.25 g/mol
Chemical Class Glycoside; Hydroquinone derivative; Phenolic glycoside
Source Synthetic (enzymatic) or natural extraction (bearberry, blueberry)
Physical State (20°C) Solid (crystalline powder)
Color White to off-white
Odor Characteristic faint odor
Taste Slightly bitter

SECTION 2: CHEMICAL STRUCTURE

         CH₂OH
          O
         / \
        /   \
       /     \
      /       \
     /         \
    /           \
   /    O        \
  /     |         \
 /      |          \
O       |           \
|       |            \
|   CH₂OH            \
|                     \
|     O               |
|    / \              |
|   /   \             |
|  /     \            |
| /       \           |
|/         \          |
HO          \         |
             \        |
              \       |
               \      |
                \     |
                 \   /
                  \ /
                   O

    Alpha Arbutin
    4-Hydroxyphenyl-α-D-glucopyranoside
    C₁₂H₁₆O₇

Simplified Structure:

    HO — (C₆H₄) — O — (C₆H₁₁O₅)

    Alpha Arbutin
    Glucose + Hydroquinone (α-linkage)
Parameter Description
Molecular Formula C₁₂H₁₆O₇
Molecular Weight 272.25 g/mol
Chemical Class Phenolic glycoside; Hydroquinone derivative
Structure Hydroquinone (4-hydroxyphenyl) + Glucose (α-D-glucopyranose)
Glycosidic Bond α-bond (alpha anomer)
Functional Groups Phenolic hydroxyl (-OH), glycosidic bond, glucose ring
SMILES C1=CC(=CC=C1O)O[C@@H]2C@HO
InChI InChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1
InChI Key IDGUHHHQCWSQLU-RMPHRYRLSA-N
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 7
Rotatable Bond Count 3
Polar Surface Area (PSA) 119.6 Ų
Optical Activity Optically active
Anomer α (alpha)

SECTION 3: PHYSICAL AND CHEMICAL PROPERTIES

Property Value Test Method / Note
Appearance White to off-white crystalline powder Visual
Odor Characteristic faint odor Olfactometric
Molecular Weight 272.25 g/mol Calculated
Melting Point ~195-198°C (decomposes) DSC / Capillary
Density (20°C) ~1.5 g/cm³ (estimated) -
Water Solubility (20°C) Soluble (~50-100 g/L) General Method
Hot Water Solubility Better soluble General Method
Ethanol Solubility Slightly soluble General Method
Methanol Solubility Soluble General Method
DMSO Solubility Soluble General Method
Propylene Glycol Solubility Soluble General Method
Log P (Octanol/Water) ~-0.5 to -1.0 (hydrophilic) Calculated / Experimental
pH (1% Solution) ~5.0 – 6.5 pH Meter
Vapor Pressure (25°C) Very low -
Flash Point >150°C -
Thermal Stability Stable up to 100°C; decomposes at higher temperatures -
Hygroscopicity Slightly hygroscopic -
Optical Rotation [α]D²⁰ +160° to +170° (c=1, H₂O) Polarimetry
UV Maximum (λmax) ~292 nm (water) UV-VIS Spectrophotometer
Photostability Light sensitive (photodegradation) -
Heat of Solution Exothermic (when dissolved in water) -

SECTION 4: ALPHA ARBUTIN vs BETA ARBUTIN vs HYDROQUINONE

Property Alpha Arbutin Beta Arbutin Hydroquinone
Chemical Name 4-Hydroxyphenyl-α-D-glucopyranoside 4-Hydroxyphenyl-β-D-glucopyranoside 1,4-Dihydroxybenzene
CAS Number 84380-01-8 497-76-7 123-31-9
Glycosidic Bond α (alpha) β (beta) None
Skin Lightening Potency Highest (1.5-2x stronger than β) Moderate Highest
Stability High Moderate Low
Water Solubility Good Good Low
Toxicity Low (safe) Low High (cytotoxic)
Skin Irritation Low Low High
Usage Status Widespread (cosmetics) Restricted Banned (EU, Turkey)
Melanin Inhibition Effective Less effective Very effective (toxic)
Price High Low Low

SECTION 5: MECHANISM OF ACTION

Property Description
Melanin Inhibition Competitively inhibits tyrosinase enzyme (competes with tyrosine); Blocks the first step of melanin synthesis; Reduces melanin production in melanocytes.
Tyrosinase Inhibition (IC50) ~0.5-1.0 mM (alpha arbutin); 1.5-2 times stronger than beta arbutin
Hydroquinone Release Slowly hydrolyzed to hydroquinone by skin glycosidase enzymes; Hydroquinone inhibits tyrosinase; Controlled release reduces toxicity.
DNA Protection Reduces UV-induced DNA damage; Reduces oxidative stress; Exhibits antioxidant effect.
Anti-inflammatory Effect Reduces inflammatory mediators; Prevents post-inflammatory hyperpigmentation.
Antioxidant Activity Scavenges free radicals; Protects skin from oxidative damage.
Melanocyte Toxicity Less toxic to melanocytes compared to hydroquinone; Safe for long-term use.

SECTION 6: COMMERCIAL GRADES AND VARIANTS

Grade / Type Purity Appearance Primary Application
Cosmetic Grade ≥99.0% White crystalline powder Skin lightening creams, serums, lotions
Dermocosmetic Grade ≥99.5% White crystalline powder Prescription skincare, melasma treatment
Research Grade (R&D) ≥99.5% White crystalline powder Analytical standards, formulation development
Analytical Standard ≥99.8% White crystalline powder HPLC reference standards
Naturally Derived ≥99.0% White crystalline powder Natural cosmetic products (bearberry extract)
Synthetic (Enzymatic) ≥99.0% White crystalline powder High purity, standard products

SECTION 7: MAIN APPLICATION AREAS

Industry / Application Use Typical Concentration
Cosmetics (Skin Lightening) Even skin tone and brighter appearance 0.5-2%
Cosmetics (Spot Removal) Sun spots, age spots, melasma treatment 1-2%
Cosmetics (Serums) High concentration active ingredient 1-3%
Cosmetics (Creams, Lotions) Active ingredient in daily care products 0.5-2%
Dermocosmetics Hyperpigmentation disorder treatment 2%
Anti-aging Products Evening skin tone, brightening 0.5-1%
Post-Sun Care Prevention of UV-induced hyperpigmentation 0.5-1%
Post-Acne Spot Treatment Post-inflammatory hyperpigmentation treatment 1-2%

SECTION 8: FORMULATION GUIDELINES

Parameter Recommendation
Concentration Typical concentration: 0.5-3%; Effective concentration: 1-2%; Maximum: 3% (CIR approved)
Addition Method Dissolve in water phase; Add at final stage of formulation (40-50°C); Avoid high temperatures (>60°C) causing degradation
pH Range Optimum pH 4.0-6.0; More stable in acidic medium; Degradation accelerates at pH >7
Temperature Processing Dissolve at 40-50°C; Avoid high temperatures (>60°C)
Light Protection Light sensitive; Use amber glass or opaque containers; Protect with UV filters
Antioxidants Addition of Vitamin E, BHT, BHA improves photostability
Compatibility Compatible with most cosmetic ingredients; Avoid oxidizing agents; Color change with iron salts
Chelating Agents EDTA addition binds metal ions and improves stability
Humectants Can be combined with glycerin, propylene glycol, hyaluronic acid
Other Actives Synergistic effect with vitamin C, niacinamide, kojic acid, retinoids
Color Stability Slight yellowing may occur over time; Prevent by adding antioxidants

SECTION 9: SAMPLE FORMULATIONS

Skin Brightening Serum:

Component Quantity
Alpha Arbutin 1-2%
Water 80-90%
Humectants (Glycerin, Hyaluronic Acid) 2-5%
Antioxidants (Vitamin E) 0.1-0.5%
Preservatives As required
pH Adjustment (pH 5.0-6.0) As required

Instructions: Dissolve alpha arbutin in water phase at 40-50°C; Add other ingredients; Adjust pH to 5.0-6.0; Package in amber glass bottle.

Spot Removal Cream:

Component Quantity
Alpha Arbutin 2%
Niacinamide 2-5%
Oil Phase 20-25%
Water 65-75%
Emulsifiers As required
Antioxidants As required
Preservatives As required

Instructions: Dissolve alpha arbutin in water phase at 40-50°C; Emulsify with oil phase; Adjust pH to 5.0-6.0; Package in light-proof containers.

SECTION 10: QUALITY SPECIFICATIONS

Parameter Specification Test Method
Appearance White to off-white crystalline powder Visual
Assay (Alpha Arbutin) ≥99.0% HPLC
Melting Point 195-198°C (decomposes) DSC / Capillary
pH (1% Solution) 5.0 – 6.5 pH Meter
Water Content ≤1.0% 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 (Hydroquinone) ≤10 ppm HPLC
Related Substances (Beta Arbutin) ≤1.0% HPLC
Related Substances (Single) ≤0.5% HPLC
Related Substances (Total) ≤1.0% HPLC
Optical Rotation +160° to +170° (c=1, H₂O) Polarimetry
UV Spectrum λmax 292 ± 2 nm (water) UV-VIS
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>
S. aureus Negative in 1g USP <62>
P. aeruginosa Negative in 1g USP <62>

SECTION 11: SAFETY PROFILE AND TOXICOLOGICAL ASSESSMENT

Parameter Value / Description
GHS Classification Generally not classified as hazardous substance
Signal Word None (not hazardous) or Warning
Hazard Pictograms None (generally)
Hazard Statements (H-Codes) H315 (Causes skin irritation), H319 (Causes serious eye irritation)
Acute Oral Toxicity (LD50, Rat) >5000 mg/kg (very low toxicity)
Acute Dermal Toxicity (LD50, Rabbit) >2000 mg/kg (low toxicity)
Skin Irritation May cause mild irritation (rare)
Eye Irritation May cause mild irritation
Skin Sensitization May cause sensitization (very rare)
Carcinogenicity Not classified as carcinogenic
Mutagenicity Not mutagenic
Reproductive Toxicity No reproductive toxicity
Target Organs Skin, eyes
Hydroquinone Toxicity Alpha arbutin is much safer than hydroquinone; Controlled hydroquinone release in skin; No cytotoxic effects
Side Effects (Topical) Rarely mild irritation or sensitivity; Redness, itching, dryness
Pregnancy Category FDA Category B (no risk in animal studies); Considered safe during pregnancy

SECTION 12: GHS CLASSIFICATION AND LABELING

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

Hazard Class Category H-Statement
Generally not classified as hazardous substance
Skin Irritation Category 2 (optional) H315
Eye Irritation Category 2 (optional) H319

Signal Word: None (Not classified as hazardous) or Warning (optional)

Hazard Pictograms: None (generally) or GHS07 (Exclamation mark)

NFPA 704 Hazard Classification:

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

SECTION 13: 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
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 14: 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 15: ADVERSE EFFECTS AND MANAGEMENT

Adverse Effect Frequency Severity Management
Mild Irritation Rare (1-3%) Mild Reduce frequency; combine with moisturizer
Redness Rare (1-2%) Mild Temporarily discontinue use; cold compress
Itching Rare (1-2%) Mild Antihistamine cream; consult physician
Dryness Rare (1-2%) Mild Use with moisturizer
Allergic Reaction Very rare (<0.1%) Moderate Discontinue use; consult physician

SECTION 16: STORAGE AND SHELF LIFE

Parameter Information
Storage Conditions Store in a cool (<25°C), dry, well-ventilated area; protect from direct sunlight and moisture.
Temperature Limits 15-25°C (ideal); do not exceed 30°C
Humidity Low humidity environment (slightly hygroscopic)
Light Light sensitive - photodegradation; Light-proof containers (amber glass, aluminum, opaque HDPE)
Oxygen Protect against oxidation; keep containers tightly closed
Incompatible Materials Strong oxidizing agents, iron salts, 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 (yellowing), caking, decreased solubility, HPLC impurity increase
Stability Warning May degrade under light and moisture; Oxidized product may form colored impurities

SECTION 17: 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 manufacturing, high purity
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 18: TRANSPORTATION INFORMATION

Parameter Information
UN Number Not applicable (not classified as dangerous substance)
Hazard Class Not applicable
Packing Group Not applicable
ADR/RID Not classified as dangerous goods
IMDG Code Not marine pollutant; not classified as dangerous goods
IATA (Air) Not classified as dangerous goods; can be transported by air
Transport Temperature Ambient temperature; protect from heat, moisture, and light
Transport Precautions Light-proof packaging; keep away from strong oxidizing agents
Spill Cleanup Collect mechanically; clean with absorbent material; avoid dust generation
Marine Pollutant No

SECTION 19: REGULATORY STATUS

Region / Authority Status
USA (FDA) Approved as cosmetic ingredient; No OTC monograph available
European Union (EC) Approved as cosmetic ingredient; Permitted under EC 1223/2009 (max. 3%)
Turkey Approved as cosmetic ingredient; Ministry of Health approval required; Subject to KKDIK regulation
CIR (Cosmetic Ingredient Review) Considered safe (up to 3%)
ECHA (REACH) Registered substance
TSCA (USA) Listed
FDA (Food) Not approved as food additive
California (Prop 65) Not listed
Halal Yes (synthetic, not animal-derived)
Kosher Yes (with certification)
Vegan Yes (synthetic)

SECTION 20: OTHER NAMES AND SYNONYMS

Type Name
Chemical Name (IUPAC) 4-Hydroxyphenyl-α-D-glucopyranoside
Common Names (Turkish) Alfa Arbutin, α-Arbutin
Common Names (English) Alpha Arbutin, α-Arbutin, Hydroquinone-α-D-glucoside
Trade Marks Alpha Arbutin (bulk), α-Arbutin, Arbutin Alpha
CAS Number 84380-01-8
EC Number 617-761-4
PubChem CID 98098
FDA UNII 8MNL1J9R56
HS Code 2938.90

SECTION 21: SUMMARY TABLE

Property Value
CAS Number 84380-01-8
Molecular Formula C₁₂H₁₆O₇
Molecular Weight 272.25 g/mol
Appearance White to off-white crystalline powder
Melting Point 195-198°C (decomposes)
Water Solubility Soluble (~50-100 g/L)
Log P ~-0.5 to -1.0 (hydrophilic)
Primary Function Tyrosinase inhibitor; Skin lightening
Typical Concentration 0.5-3%
Maximum Usage Rate (EU) 3%
Shelf Life 24-36 months
Storage Cool (<25°C), dry, light-protected
GHS Classification Generally not hazardous
FDA Status Approved as cosmetic ingredient
Halal / Kosher / Vegan Yes
Main Applications Skin lightening, spot removal, melasma treatment

SECTION 22: CRITICAL WARNINGS AND BEST PRACTICES

CRITICAL WARNINGS:

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

  2. Temperature Sensitivity: Degrades at high temperatures (>60°C). Add to formulations at 40-50°C.

  3. pH Sensitivity: Stable in pH 4.0-6.0; degradation accelerates at pH >7.

  4. Hydroquinone Content: Hydroquinone impurity should be ≤10 ppm (toxicity risk).

  5. External Use Only: For external use only. Not for ingestion.

  6. Do Not Confuse with Hydroquinone: Alpha arbutin is a glycoside derivative of hydroquinone; do not confuse with hydroquinone (toxic).

  7. Oxidizing Agents: Do not contact with oxidizing agents (color change).

  8. Iron Salts: Color change may occur with iron salts; use chelators (EDTA).

BEST PRACTICE RECOMMENDATIONS:

  1. Concentration: Typical concentration 0.5-3%; Effective concentration 1-2%; Maximum 3% (CIR approved).

  2. pH Adjustment: Keep formulation pH at 4.0-6.0.

  3. Temperature: Dissolve at 40-50°C; avoid high temperatures (>60°C).

  4. Antioxidant Use: Add Vitamin E (0.1-0.5%) or BHT (0.01-0.1%) to formulations; improves photostability.

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

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

  7. Combination with Other Actives: Synergistic effect with vitamin C, niacinamide, kojic acid, retinoids.

  8. Storage: Store in cool, dry, light-proof containers. Keep tightly closed after opening.

  9. Quality Control: Regularly perform assay (HPLC), hydroquinone content (≤10 ppm), melting point, pH, optical rotation, microbiological purity tests.

  10. Patient Education: Inform patients about external use only, regular application, sunscreen use, and treatment duration.

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. 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 Arbutin is a cosmetic active ingredient; its use should be according to a healthcare professional's recommendation.

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