Name :
5-Butylbenzene-1,3-diolCAS No. :
46113-76-2MF :
C₁₀H₁₄O₂MW :
166.22Purity :
98%Appearance :
Off-white to light beige solidStorage Condition :
Store in a cool, dry place away from oxidizersChemical Identity and Structural Features
CAS Number: 46113-76-2
Systematic IUPAC Name: 5-Butylbenzene-1,3-diol
Common Synonyms: 5-Butylresorcinol; 1,3-Dihydroxy-5-butylbenzene
Molecular Formula: C₁₀H₁₄O₂
Molecular Weight: 166.22 g/mol
Appearance: Off-white to light beige solid
Melting Point: 81.5–82.5°C
Boiling Point: 151–152°C
Density: 1.092 ± 0.06 g/cm³ (predicted)
Solubility: Slightly soluble in chloroform and methanol; insoluble in water
pKa: 9.56 ± 0.10 (predicted)
SMILES Notation: C1(O)=CC(CCCC)=CC(O)=C1
InChI: InChI=1S/C10H14O2/c1-2-3-4-8-5-9(11)7-10(12)6-8/h5-7,11-12H,2-4H2,1H3
Structure: The molecule consists of:
A resorcinol core (benzene ring with two hydroxyl groups in the meta-position).
A linear n-butyl chain (-C₄H₉) attached at the 5-position of the ring.
Key Properties: This structure combines the polar, hydrophilic character of the dihydroxy aromatic ring with the lipophilic nature of the butyl chain, giving the molecule amphiphilic properties. The phenolic hydroxyl groups are weakly acidic and can participate in hydrogen bonding.
Synthesis and Production
Synthesis Pathway:
Alkylation: Introduce butyl chain via Friedel-Crafts alkylation.
Hydroxylation: Install hydroxyl groups at positions 1 and 3 using oxidative agents (e.g., BBr₃)
Purification: Column chromatography to isolate the target compound.
Functional Properties and Mechanism of Action
The biological activity of 5-Butylresorcinol is derived from its alkylresorcinol nature:
Potent Tyrosinase Inhibition: Its primary commercial interest lies in its effective inhibition of the enzyme tyrosinase, which is crucial in the melanin production pathway in skin. This makes it a highly effective skin brightening and depigmenting agent.
Antioxidant Activity: The phenolic hydroxyl groups act as strong free radical scavengers, protecting cells and products from oxidative damage.
Antimicrobial Activity: It exhibits broad-spectrum antibacterial and antifungal properties, primarily by disrupting microbial cell membranes.
Applications
Safety, Handling and Regulatory Status
Safety Profile: While generally considered safe for topical use in cosmetics, it can be a skin irritant or sensitiser in concentrated forms, as is common with many phenolic compounds.
Handling Precautions: Should be handled in a well-ventilated area with appropriate personal protective equipment (PPE) including gloves, safety glasses, and a lab coat. Avoid inhalation of dust and direct skin contact.
Regulatory: Its use in cosmetics is subject to regional regulations (e.g., in the EU, it must comply with EC No. 1223/2009). For food applications, regulatory approval (e.g., FDA, EFSA) would be required.
Disclaimer: Always consult the specific Safety Data Sheet (SDS) provided by the supplier for detailed handling, storage, and disposal instructions before use.
Comparison and Advantages Over Similar Products
1.Similar compounds include 4-butylresorcinol (CAS 18979-61-8), olivetol (5-pentylbenzene-1,3-diol, CAS 500-66-3), and hexylresorcinol (CAS 136-77-6). 4-Butylresorcinol, with the butyl group at position 4, is more commonly used in cosmetics for hyperpigmentation and is clinically proven to be 10-20 times more effective at tyrosinase inhibition than hydroquinone, but it can cause mild irritation in sensitive skin. In comparison, 5-butylbenzene-1,3-diol’s position-5 attachment may offer better stability in formulations, reducing degradation under UV exposure, and potentially lower irritation due to its symmetric structure.
2.Olivetol, with a longer pentyl chain, is primarily a cannabinoid precursor but less effective for skin lightening; the shorter butyl chain in 5-butylbenzene-1,3-diol provides advantages in solubility and faster absorption in topical applications, making it preferable for quick-acting serums. Hexylresorcinol, with a hexyl chain, has stronger antimicrobial properties but is more lipophilic, leading to poorer water-based formulation compatibility. Overall, 5-butylbenzene-1,3-diol’s advantages lie in its balanced chain length for optimal bioavailability, cost-effective synthesis (often cheaper than longer-chain analogs), and versatility across pharma and cosmetics without the regulatory scrutiny of full cannabinoids.
FAQ
Q1: What is the main application of this compound?
A: Its primary application is as a highly effective skin brightening agent in cosmetics. It is a potent tyrosinase inhibitor that reduces hyperpigmentation. It also functions as a natural antioxidant and preservative in both cosmetic and food formulations.
Q2: What is the mechanism of action for skin brightening?
A: It competitively inhibits the enzyme tyrosinase, which is a key catalyst in the melanin production pathway. By blocking this enzyme, it effectively reduces the formation of dark pigments in the skin, leading to a more even tone.
Q3: Is this a natural or synthetic ingredient?
A: This is a nature-identical compound. It can be synthesized to match the exact structure of the molecule found in nature, ensuring high purity and consistent performance, which is crucial for commercial formulations.
Q4: What purity grades are available and how are they certified?
A: We supply ≥98% and ≥99% purity grades. Quality is certified by HPLC for purity and NMR for structural identity. A comprehensive Certificate of Analysis (CoA) is provided with each batch.
Q5: Is this compound safe for topical use in cosmetics?
A: When formulated within recommended concentrations, it is considered safe for topical use. However, as with many active ingredients, patch testing is recommended. Always refer to the supplied Safety Data Sheet (SDS) for detailed handling and safety information.
Q6: Do you offer this ingredient in cosmetic-grade quality?
A: Yes. We supply Cosmetic Grade material that is suitable for incorporation into final product formulations such as serums, creams, and lotions.
Q7: Can it be used in food applications?
A: It has potential as a natural preservative due to its antioxidant and antimicrobial properties. However, its regulatory status for food use (GRAS, Novel Food approval) varies by region. It is the customer's responsibility to ensure regulatory compliance for their target market.
Q8: What packaging options do you offer?
A: We offer sizes from R&D samples (1g, 5g) to commercial quantities (kg scale). Packaging is in sealed, light-proof containers to ensure stability.
Q9: What is the typical lead time for large orders?
A: Sample quantities are typically shipped within 1 week. For large-scale or custom synthesis orders, the lead time is typically 3-5 weeks after order confirmation.
Q10: What is the typical purity level available for purchase, and how does it affect applications?
A: Commercial grades are ≥98% pure. Higher purity (e.g., 99.5%) is recommended for pharmaceutical synthesis to minimize impurities in end products like CBDB, while 98% suffices for cosmetic uses where slight variations do not impact efficacy.
Q11: How should 5-butylbenzene-1,3-diol be stored to maintain stability?
A: Store in a cool, dry place at 4°C under nitrogen or inert gas to prevent oxidation. Avoid exposure to light and moisture, which can lead to discoloration or degradation over 6-12 months.
Q12: Is this compound naturally derived or synthetic, and does it contain any THC-related impurities?
A: It is synthetically produced and not naturally abundant in plants. As a resorcinol derivative, it does not contain THC, making it suitable for non-cannabinoid applications without psychoactive risks.
Q13: What are the recommended concentrations for use in skincare products?
A: For hyperpigmentation treatments, use 0.5-1% in creams or serums. Always conduct patch tests, as concentrations above 2% may increase irritation risk in sensitive users.
Q14: Can it be used in combination with other active ingredients like vitamin C or niacinamide?
A: Yes, it synergizes well with antioxidants like vitamin C for enhanced brightening effects in anti-aging formulations. Avoid combining with strong acids to prevent instability.
Q15: What safety precautions are needed when handling this compound in bulk?
A: Wear gloves and eye protection, as it can cause skin irritation. In case of ingestion, seek medical attention immediately due to its acute oral toxicity rating.
Q16: How does it compare in cost to similar alkylresorcinols for large-scale production?
A: It is generally more affordable than olivetol due to simpler synthesis, with bulk prices ranging from $300-900 per kg depending on quantity, offering cost advantages for cosmetic manufacturers scaling up production.
Disclaimer: This information is for educational and research purposes. The regulatory status and approved uses of 5-butylresorcinol vary globally. It is essential to consult local regulations, conduct thorough safety assessments, and perform compatibility/stability tests before incorporating this ingredient into any commercial formulation.
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