Quick Search
E586 4-hexylresorcinol is a synthetic phenolic compound, widely used as an antioxidant, antibrowning agent, and antimicrobial agent in food and pharmaceutical applications.
E586 4-hexylresorcinol belongs to the class of alkylresorcinols (substituted dihydroxybenzenes).
E586 4-hexylresorcinol is commonly used to prevent discoloration in seafood.
CAS Number: 136-77-6
Molecular Formula: C12H18O2
Molecular Weight: 194.27
EINECS Number: 205-257-4
Synonyms: Hexylresorcinol, 4-Hexylresorcinol, 136-77-6, 4-hexylbenzene-1,3-diol, 4-Hexyl-1,3-benzenediol, 4-n-Hexylresorcinol, p-Hexylresorcinol, 1,3-Benzenediol, 4-hexyl-, 4-Hexylresorcine, 4-Hexyl-1,3-dihydroxybenzene, 4-(1-Hexyl)resorcinol, 1,3-Dihydroxy-4-hexylbenzene, 1,3-Dihydroxy-4-n-hexylbenzene, 1-(2',4'-Dihydroxyphenyl)hexane, 1-(2,4-Dihydroxyphenyl)hexane, benzene, 4-hexyl-1,3-dihydroxy-, Hexylresorcin, Hexylresorcinolum, Hexylresorzin, hexyl resorcinol, 4 hexylresorcinol, 4-hexyl resorcinol, Antascarin, Ascaricid, Ascarinol, Caprokol, Oxana, Crystoids, Adrover, Hidesol, Prensol, Gelovermin, Ascaryl, Worm-agen, Mycoderm, EverFresh, S.T. 37, ST 37, ST-37, Myxcin-C, Kopnol, NSC 1570, NSC-1570, INS-586, INS NO.586, E-586, DTXSID1020699, DTXCID10699, RefChem:55300, R9QTB5E82N, NCI-C55787, CHEMBL443605, CHEBI:93749, 205-257-4, EINECS 205-257-4, UNII-R9QTB5E82N, CAS-136-77-6, 1-(2',4'-Dihydroxyphenyl)hexane;1-(2,4-Dihydroxyphenyl)hexane;1,3-Benzenediol, 4-hexyl-;1,3-Benzenediol,4-Hexyl-1,3-benzenediol;1,3-Dihydroxy-4-Hexylbenzene;1,3-Dihydroxy-4-n-hexylbenzene;4-hexylresourcinol;Antascarin
E586 4-hexylresorcinol, consisting of a resorcinol ring substituted with a hexyl (C6) alkyl chain.
This structure gives both hydrophobic and phenolic properties.
E586 4-hexylresorcinol contributes to its antioxidant and antimicrobial activity.
E586 4-hexylresorcinol appears as a white to off-white crystalline solid.
E586 4-hexylresorcinol is slightly soluble in water but more soluble in organic solvents and fats.
It has a mild phenolic odor.
E586 4-hexylresorcinol exhibits antioxidant activity, helping to inhibit oxidation reactions in foods.
E586 4-hexylresorcinol prevents quality deterioration.
This improves shelf life.
E586 4-hexylresorcinol also functions as an anti-browning agent, particularly in seafood such as shrimp.
It inhibits enzymatic browning reactions.
This preserves color.
E586 4-hexylresorcinol shows antimicrobial properties, especially against certain bacteria and parasites.
E586 4-hexylresorcinol disrupts microbial cell processes.
This enhances food safety.
E586 4-hexylresorcinol is chemically stable under normal conditions, but may degrade under strong light or extreme conditions.
Proper storage is recommended.
It should be kept in a cool, dry place.
E586 4-hexylresorcinol is best described as a phenolic antioxidant and antimicrobial agent used to prevent browning and spoilage, especially in seafood and food preservation systems.
E586 4-hexylresorcinol exhibits strong affinity for biological membranes due to its amphiphilic structure (hydrophilic phenolic head and hydrophobic alkyl chain).
It can insert into lipid bilayers.
This enhances its antimicrobial effect.
E586 4-hexylresorcinol shows rapid inhibition of melanosis (black spot formation) in crustaceans such as shrimp.
This process is enzyme-driven browning after harvest.
E586 4-hexylresorcinol helps maintain visual quality.
E586 4-hexylresorcinol demonstrates broad-spectrum antimicrobial activity, particularly against Gram-positive bacteria and some fungi.
It interferes with cell membrane integrity and enzyme systems.
This contributes to preservation.
E586 4-hexylresorcinol has low volatility and good stability in solid form, making it suitable for storage and handling.
However, solutions may degrade faster under light.
This requires protective packaging.
E586 4-hexylresorcinol displays dose-dependent activity, where effectiveness increases with concentration within regulated limits.
This ensures safety and compliance.
E586 4-hexylresorcinol can act as a protein interaction modifier, binding to enzymes and altering their activity.
E586 4-hexylresorcinol exhibits strong inhibitory effects on tyrosinase-like enzymes, which are involved in pigment formation.
By blocking these enzymes, it reduces formation of melanin-like compounds.
This is critical in preventing discoloration.
E586 4-hexylresorcinol shows good penetration into tissue surfaces, especially in seafood when applied as a dip.
E586 4-hexylresorcinol reaches sites where enzymatic browning occurs.
E586 4-hexylresorcinol demonstrates fast-acting activity, meaning it begins inhibiting browning and microbial growth shortly after application.
This is important for post-harvest treatment.
E586 4-hexylresorcinol preserves freshness early.
E586 4-hexylresorcinol has relatively low sensory impact at approved levels, meaning it does not significantly alter taste or odor when used correctly.
This maintains product acceptability.
E586 4-hexylresorcinol can function as part of a multi-hurdle preservation system, combined with refrigeration, modified atmosphere packaging, or other additives.
Melting point: 65–67 °C (lit.)
Boiling point: 333–335 °C (lit.)
Density: 1.0010 (rough estimate)
Bulk density: 340 kg/m³
Vapor pressure: 0.001 Pa at 25 °C
Refractive index: 1.5050 (estimate)
Flash point: >100 °C
Storage temperature: 2–8 °C
Solubility: chloroform: 50 mg/mL, clear
pKa: 9.1 (uncertain)
Form: Powder and/or chunks
Color: White to pale orange or pale pink
pH: 7.7 (0.5 g/L, H₂O, 20 °C)
Water solubility: 0.05 g/100 mL (18 °C)
Merck index: 14,4712
BRN: 2048312
Henry's law constant: 3.8 × 10⁴ mol/(m³·Pa) at 25 °C (HSDB, 2015)
Stability: Stable; incompatible with acid chlorides, acid anhydrides, oxidizing agents
Cosmetic ingredient function: Antimicrobial
InChI: 1S/C12H18O2/c1-2-3-4-5-6-10-7-8-11(13)9-12(10)14/h7-9,13-14H,2-6H2,1H3
InChIKey: WFJIVOKAWHGMBH-UHFFFAOYSA-N
SMILES: CCCCCCc1ccc(O)cc1O
LogP: 3.34 at 20 °C
Surface tension: 36.59 mN/m at 1 g/L and 20 °C
E586 4-hexylresorcinol is a mushroom tyrosinase inhibitor.
E586 4-hexylresorcinol, a copper-containing enzyme, is distributed in microorganisms, animals, and plants widely.
Mushroom tyrosinase has been becoming popular due to its availability and usages in various applications.
E586 4-hexylresorcinol exhibits compatibility with various food systems, especially seafood and protein-rich matrices.
However, interactions with lipids and proteins may influence performance.
This requires formulation optimization.
E586 4-hexylresorcinol is often applied via surface treatments (dips or sprays) rather than bulk addition.
This targets areas prone to browning or contamination.
E586 4-hexylresorcinol is a surface-active, enzyme-inhibiting phenolic compound with strong antibrowning and antimicrobial performance, particularly effective in seafood preservation.
E586 4-hexylresorcinol exhibits limited water solubility, which helps it remain active at surfaces rather than diffusing away quickly.
This prolongs its local effect.
It improves treatment efficiency.
E586 4-hexylresorcinol shows stability under typical food processing conditions, but extreme pH or prolonged exposure to light can reduce activity.
Proper handling maintains effectiveness.
This ensures consistent performance.
E586 4-hexylresorcinol is also used in non-food applications, such as antiseptic or anti-parasitic treatments in certain formulations.
It disrupts biological processes in target organisms.
This extends its functionality.
E586 4-hexylresorcinol is a fast-acting, surface-active phenolic compound with strong enzyme inhibition, antimicrobial effects, and stability in targeted applications, especially valuable in seafood preservation and hygiene systems.
E586 4-hexylresorcinol exhibits phenolic hydroxyl groups, which are responsible for its antioxidant activity.
These groups can donate hydrogen atoms to neutralize free radicals.
The molecule has a hydrophobic hexyl chain, which enhances its interaction with lipid phases.
E586 4-hexylresorcinol can partition into fatty environments.
This improves effectiveness in foods.
E586 4-hexylresorcinol shows inhibition of polyphenol oxidase (PPO), the key enzyme responsible for enzymatic browning.
This prevents formation of dark pigments.
This preserves product appearance.
E586 4-hexylresorcinol demonstrates surface-active properties, allowing it to interact with biological membranes.
E586 4-hexylresorcinol can disrupt microbial cell membranes.
This contributes to antimicrobial action.
E586 4-hexylresorcinol is effective at low concentrations, typically in ppm levels.
Small amounts provide functional benefits.
This improves efficiency and cost-effectiveness.
E586 4-hexylresorcinol exhibits moderate lipophilicity, balancing solubility between aqueous and lipid systems.
This enables use in diverse formulations.
This increases versatility.
E586 4-hexylresorcinol may show synergistic effects with other preservatives or antioxidants, enhancing overall protection.
Combined systems improve stability.
This supports multi-hurdle preservation.
E586 4-hexylresorcinol is sensitive to strong oxidizing conditions and prolonged light exposure.
Degradation can reduce effectiveness.
E586 4-hexylresorcinol is a lipophilic phenolic compound with enzyme-inhibiting, antioxidant, and antimicrobial properties, making it highly effective in preventing browning and spoilage in food systems.
Uses:
E586 4-hexylresorcinol is an inhibitor of transglutaminase-2 in KB cells.
Studies indicate that 4-Hexylresorcinol reduces DNA oxidative damage in human lymphocytes.
E586 4-hexylresorcinol is a substituted dihydroxybenzene used topically as an antiseptic for the treatment of minor skin infections.
E586 4-hexylresorcinol is a substituted phenol with bactericidal, antihelminthic and potential antineoplastic activities.
The combination of E586 4-hexylresorcinol and Cisplatin has been shown to inhibit tumor growth, cell growth, and KB cell viability.
E586 4-hexylresorcinol is used as the starting material to synthesize a potent immune suppressor, celastramycin A.
It is a precursor to prepare resorcinol-sn-glycerol derivatives, that exhibit high affinity with cannabinoid type 1 receptor.
E586 4-hexylresorcinol can also be incorporated as a linker while building catenanes.
E586 4-hexylresorcinol shows antiimnflammatory activity acting on the human 5-LO (5-Lipoxygenase) proinflammatory enzyme.
E586 4-hexylresorcinol is primarily used in the food industry as an anti-browning agent, especially in seafood such as shrimp and prawns.
It inhibits enzymatic melanosis (black spot formation).
In fresh and processed seafood, it is applied as a dip or surface treatment.
E586 4-hexylresorcinol acts directly on the surface where browning occurs.
This improves effectiveness.
E586 4-hexylresorcinol is used as an antioxidant in food systems, helping to slow oxidative deterioration.
It protects product quality.
E586 4-hexylresorcinol is applied as an antimicrobial agent to control certain bacteria and spoilage organisms.
In post-harvest treatment of crustaceans, it is widely used to maintain freshness during storage and transport.
E586 4-hexylresorcinol prevents discoloration over time.
This improves marketability.
E586 4-hexylresorcinol is used in combination with other preservation methods, such as refrigeration or modified atmosphere packaging.
It supports multi-hurdle preservation systems.
This enhances overall stability.
In pharmaceutical and medical applications, it has been used as an antiseptic and anti-parasitic agent.
E586 4-hexylresorcinol helps control microorganisms.
This supports hygiene and treatment.
E586 4-hexylresorcinol is also applied in oral care products (e.g., lozenges, throat preparations) for its antimicrobial properties.
It helps reduce microbial load.
This improves product function.
In industrial and hygiene formulations, it may be used as a preservative component.
E586 4-hexylresorcinol helps inhibit microbial growth.
This supports product stability.
E586 4-hexylresorcinol is used wherever anti-browning, antioxidant, and antimicrobial surface protection are required, particularly in seafood preservation, as well as in selected pharmaceutical and hygiene applications.
E586 4-hexylresorcinol is also used in frozen seafood products to prevent melanosis during long-term storage.
It maintains color stability even under freezing conditions.
This improves product quality after thawing.
In ready-to-cook seafood preparations, it helps preserve appearance during distribution and retail display.
E586 4-hexylresorcinol slows discoloration during shelf life.
E586 4-hexylresorcinol is applied in seafood processing lines as part of washing or dipping steps.
It ensures uniform treatment of products.
This improves processing efficiency.
E586 4-hexylresorcinol is used in anti-parasitic treatments, historically for controlling certain intestinal parasites.
It interferes with parasite metabolism.
This supports therapeutic applications.
In throat lozenges and oral antiseptic products, it acts as an antimicrobial agent.
E586 4-hexylresorcinol helps reduce microbial load in the mouth and throat.
This improves hygiene.
E586 4-hexylresorcinol is used in surface sanitizing and preservation systems for food-contact applications (where permitted).
It helps inhibit microbial growth.
This supports food safety.
In combined preservation systems, it works alongside antioxidants, chelating agents, and cold storage.
These combinations improve effectiveness.
This extends shelf life further.
E586 4-hexylresorcinol may also be used in specialized cosmetic or dermatological formulations for its antimicrobial properties.
It helps control microbial contamination.
E586 4-hexylresorcinol is used wherever surface-level protection against browning, oxidation, and microbial growth is required, especially in seafood processing, food preservation, and certain pharmaceutical or hygiene applications.
Safety Profile
E586 4-hexylresorcinol presents moderate hazard potential, depending on concentration and exposure conditions.
E586 4-hexylresorcinol is approved for specific food uses at controlled levels.
However, it requires careful handling in concentrated form.
Skin contact may cause irritation, especially with prolonged or repeated exposure.
E586 4-hexylresorcinol can affect sensitive skin.
Protective gloves are recommended during handling.
Eye contact can cause moderate to severe irritation.
Symptoms may include redness, pain, and tearing.
Immediate rinsing with plenty of water is required.
Inhalation of dust or vapors may cause respiratory irritation.
E586 4-hexylresorcinol can irritate the nose, throat, and lungs.
Adequate ventilation and protective equipment are recommended.
Ingestion is safe at regulated food-use levels, but higher doses may cause adverse effects.
Possible effects include irritation of the gastrointestinal tract or systemic toxicity at excessive exposure.
