5-Hexylbenzene-1,3-diol CAS 5465-20-3(5-Hexylresorcinol) is a versatile amphiphilic phenolic compound prized for its strong tyrosinase inhibition, antimicrobial, and antioxidant properties. It serves critical roles in cosmetic skin-lightening agents, food preservatives, and pharmaceutical antiseptics. Its value lies in its dual functionality, bridging efficacy with formulation flexibility.
Nome :
5-Hexylbenzene-1,3-diolNº CAS. :
5465-20-3MF :
C₁₂H₁₈O₂MW :
194.27Pureza :
99%Aparência :
Typically appears as white to light-beige crystalline flakes or powderCondição de armazenamento :
Store in a cool, dry place (2-8°C recommended) in airtight, light-resistant containers.
Chemical Properties
IUPAC Name: 5-Hexylbenzene-1,3-diol
Common Name: 5-Hexylresorcinol
CAS Registry Number: 5465-20-3
Molecular Formula: C₁₂H₁₈O₂
Molecular Weight: 194.27 g/mol
Chemical Structure: A resorcinol (1,3-dihydroxybenzene) derivative with a linear hexyl chain (-C₆H₁₃) substituted at the 5-position of the aromatic ring.
Appearance: Typically appears as white to light-beige crystalline flakes or powder.
Key Features: Combines the aromatic diol reactivity of resorcinol with the lipophilic character of a hexyl chain, making it amphiphilic.
Melting Point: ~68-72 °C.
Solubility: Moderately soluble in organic solvents (ethanol, acetone, ether, chloroform). Very low solubility in water.
Reactivity:
Acidic Phenolic Groups: Can form salts, esters, and ethers.
Electrophilic Substitution: The aromatic ring is activated for substitution (e.g., halogenation, acylation) due to the two electron-donating hydroxyl groups.
Chelation Potential: Can act as a bidentate ligand for metal ions.
Antioxidant Activity: Acts as a radical scavenger, inhibiting oxidation processes.
Stability: Stable under ambient conditions but may darken upon prolonged exposure to air and light. Should be stored in a cool, dark place in airtight containers.
Biological Activities
This compound exhibits a range of bioactive properties, primarily attributed to the resorcinol core and its alkyl chain:
Antimicrobial/Antiseptic: Effective against bacteria, fungi, and parasites. The mechanism involves disrupting microbial cell membranes and enzyme inhibition.
Anthelmintic: Used as a treatment for certain parasitic worm (e.g., tapeworm) infections in medicine.
Tyrosinase Inhibition: Acts as a competitive inhibitor of the enzyme tyrosinase, which is involved in melanin production. This forms the basis for its use in skin-lightening cosmetics.
Antioxidant: Scavenges free radicals, providing protective effects against oxidative stress.
Local Anesthetic & Analgesic: Has mild numbing properties on mucous membranes.
Biosynthesis
5-Hexylresorcinol is not a major natural product but is related to alkylresorcinols, which are naturally synthesized in plants (e.g., in cereal bran like wheat and rye) and some bacteria and fungi.
Natural Pathway (Alkylresorcinols): In plants, biosynthesis typically involves a type III polyketide synthase. A starter fatty acyl-CoA (e.g., hexanoyl-CoA) undergoes sequential malonyl-CoA additions, cyclization, and aromatization to form the alkylresorcinol structure.
Commercial Production: It is primarily manufactured via chemical synthesis for industrial use, not through biosynthesis. Common synthetic routes involve the Friedel-Crafts acylation of resorcinol followed by reduction, or other alkylation methods.
Applications
FAQs
Q1: What is the main selling point of 5-Hexylresorcinol for cosmetic formulations?
A: Its primary advantage is its powerful and well-documented tyrosinase-inhibiting activity, making it one of the most effective non-hydroquinone ingredients for skin whitening, brightening, and treating hyperpigmentation (e.g., melasma, age spots).
Q2: What purity grades do you offer, and how is quality ensured?
A: We supply High Purity Grade (≥99%, HPLC) for cosmetic/pharmaceutical R&D and Technical Grade (≥95%) for industrial applications. Every batch is accompanied by a comprehensive Certificate of Analysis (CoA) including HPLC purity, melting point, and heavy metals testing.
Q3: Is this compound safe (GRAS) for use in food or topical products?
A: It is approved for use as a food additive (color stabilizer) in certain jurisdictions (e.g., for shrimp treatment) at specified levels. For cosmetics, it is generally recognized as safe when formulated within recommended concentrations (typically 0.1%-1%). Always conduct patch tests and comply with regional regulations (e.g., FDA, EU CosIng).
Q4: How should it be stored to maintain stability?
A: Store in a cool, dry place (2-8°C recommended) in airtight, light-resistant containers under an inert atmosphere (e.g., nitrogen) for long-term storage to prevent oxidation and discoloration.
Q5: Can you provide formulation guidance for cosmetic creams?
A: Yes. Our technical support team can provide basic guidelines. It is often solubilized in the oil phase or using solvents like propylene glycol. A typical effective concentration in the final product ranges from 0.2% to 0.5%. We recommend combining it with other antioxidants (e.g., Vitamin E) for enhanced stability.
Q6: Do you offer custom synthesis or derivative production?
A: Absolutely. We provide custom synthesis services for:
Scale-up production from gram to kilogram scales.
Structural analogs (e.g., different alkyl chain lengths).
Derivatization into esters or other protected forms for specific application needs.
Q7: What is the typical lead time and minimum order quantity (MOQ)?
A:
R&D Samples (1-25g): Shipped within 3-5 business days.
Bulk Orders (≥1kg): Lead time of 2-3 weeks.
MOQ: 10g for the High Purity Grade; 100g for the Technical Grade.
Q8: Is it compatible with common cosmetic ingredients?
A: Generally, yes. It is compatible with most oils, surfactants, and emollients. Incompatibility may occur with strong oxidizing agents, strong bases, and heavy metal ions (which may cause chelation/discoloration). Pre-formulation compatibility testing is advised.
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