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Home > Encyclopedia > Hexylresorcinol

Hexylresorcinol

pharmaceutical raw materials
Hexylresorcinol structure

Hexylresorcinol 

structure
  • CAS No:

    136-77-6

  • Formula:

    C12H18O2

  • Chemical Name:

    Hexylresorcinol

  • Synonyms:

    1,3-Benzenediol,4-hexyl-;Resorcinol,4-hexyl-;4-Hexyl-1,3-benzenediol;S.T. 37;Caprokol;Crystoids;Cystoids Anthelmintic;4-Hexyl-1,3-dihydroxybenzene;4-Hexylresorcine;Hexylresorcinol;p-Hexylresorcinol;4-Hexylresorcinol;Sucrets;4-n-Hexylresorcinol;1,3-Dihydroxy-4-hexylbenzene;Adrover;Hidesol;Antascarin;Ascaricid;Oxana;Ascarinol;Prensol;4-(1-Hexyl)resorcinol;1-(2′,4′-Dihydroxyphenyl)hexane;Mycoderm;EverFresh;KOM 14;Worm-Agen;Gelovermin;Ascaryl;NSC 1570;Synovea HR

  • Categories:

    Cosmetic Ingredient  >  Antimicrobials

Description

slightly red powderPale-yellow viscous liquid (that becomes solid on standing at room temperature) or a peach colored powder. Pungent faintly fatty odor. Sharp astringent taste.


P-hexylresorcinol appears as pale-yellow viscous liquid (that becomes solid on standing at room temperature) or a peach colored powder. Pungent faintly fatty odor. Sharp astringent taste. (NTP, 1992)|White powder|Solid


P-hexylresorcinol appears as pale-yellow viscous liquid (that becomes solid on standing at room temperature) or a peach colored powder. Pungent faintly fatty odor. Sharp astringent taste. (NTP, 1992)|4-hexylbenzene-1,3-diol is a member of resorcinols.|Hexylresorcinol is a substituted dihydroxybenzene. It exhibits antiseptic, anthelmintic, and local anesthetic properties. It can be found in topical applications for minor skin infections and in oral solutions or throat lozenges for pain relief and first aid antiseptic. The compound may also be used commonly in various commercial cosmetic anti-aging creams while ongoing studies research the possibility of using hexylresorcinol as an anti-cancer therapy - indications all of which require further study and testing at the current moment.|Hexylresorcinol is a substituted phenol with bactericidal, antihelminthic and potential antineoplastic activities. Hexylresorcinol is used as an antiseptic in mouthwashes and skin wound cleansers. Hexylresorcinol may also inhibit oxidative DNA damage by enhancing the activity of antioxidant enzymes, including glutathione peroxidase and glutathione reductase, which facilitate scavenging reactive oxygen molecules by glutathione (GSH).|A substituted dihydroxybenzene used topically as an antiseptic for the treatment of minor skin infections.

Hexylresorcinol Basic Attributes

194.27

194.27

2048312

205-257-4

R9QTB5E82N

757056|1570

DTXSID1020699

C29092

Pale yellow, heavy liq becoming solid on standing at room temp; needles from benzene or petroleum ether|WHITE, OR YELLOWISH WHITE, NEEDLE-SHAPED CRYSTALS; ACQUIRES BROWNISH PINK TINT ON EXPOSURE TO LIGHT & AIR

R - Respiratory system

29072900

Characteristics

40.5

3.5

White to pale orange or pale pink Powder and/or Chunks

1.0010 (rough estimate)

67.5-69 °C

178-180 °C @ Press: 6.7 Torr

>100°C

1.5050 (estimate)

H2O: 0.05 g/100 mL (18 ºC);chloroform: 50 mg/mL, clear

Store below +30°C.

8.4X10-6 mm Hg at 25 deg C (est)

LD50 orally in Rabbit: 550 mg/kg

Pungent odor

Sharp astringent taste

Henry's Law constant = 2.6X10-10 atm-cu m/mol at 25 °C (est)

129 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Hydroxyl radical reaction rate constant = 2.1X10-10 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Phenols and Cresols

P-HEXYLRESORCINOL may be sensitive to prolonged exposure to light. Incompatible with acid chlorides, acid anhydrides and oxidizing agents (NTP, 1992).

Safety Information

UN 3077 9 / PGIII

3

22-36/37/38-20/21/22

26-36-24/25

VH1575000

Xn

Stable. Incompatible with acid chlorides, acid anhydrides, oxidizing agents.

P261-P305 + P351 + P338

H302-H315-H319-H335

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: hexylresorcinol is included in external analgesic drug products.

DHHS/NTP; Toxicology & Carcinogenesis Studies of 4-Hexylresorcinol in F344/N Rats and B6C3F1 Mice Technical Report Series No. 330 (1988) NIH Publication No. 88-2586

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 57 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this material from exposure to light. Keep it away from oxidizing materials and store it under refrigerated temperatures. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. Splash proof safety goggles should be worn while handling this chemical. Alternatively, a full face respirator, equipped as above, may be used to provide simultaneous eye and respiratory protection. (NTP, 1992)

Concentrated solutions can cause irritation of skin, mucous membranes.

Toxicity

In the over-the-counter antiseptic and oral analgesic sprays and lozenges that hexylresorcinol is typically employed as the active ingredient, it is noted that overdosage of the agent may cause minor gastrointestinal irritation. The probable oral LD50 of hexylresorcinol in humans has been estimated to be between 500 and 5000 mg/kg body weight, between 1 oz and 1 pint (or 1 lbs) for a 70 kg person.

LD50 Rat oral 550 mg/kg|LD50 Mouse sc 750-1000 mg/kg bw (5% in olive oil)|LD50 Mouse ip 200 mg/kg bw (5% in olive oil)|LD50 Mouse ip 300 mg/kg bw (1% aqueous emulsion)|For more Non-Human Toxicity Values (Complete) data for HEXYLRESORCINOL (7 total), please visit the HSDB record page.

2 yr toxicology and carcinogenesis studies of 4-hexylresorcinol were conducted by admin 0, 62.5 or 125 mg/kg to groups of 50 F344/N rats and 50 B6C3F1 mice of each sex, 5 days/wk. Conclusions: Under the conditions of these 2 yr gavage studies, there was no evidence of carcinogenic activity of 4-hexylresorcinol for male or female F344/N rats given doses of 62.5 or 125 mg/kg. There was equivocal evidence of carcinogenic activity of 4-hexylresorcinol for male B6C3F1 mice, as shown by marginally incr incidences of pheochromocytomas (and hyperplasia) of the adrenal medulla and of harderian gland neoplasms. There was no evidence of carcinogenic activity for female B6C3F1 mice given doses of 62.5 or 125 mg/kg 4-hexylresorcinol. ...

Readily accessible data regarding the protein binding of hexylresorcinol is not available. Nevertheless, when hexylresorcinol is employed in its primary indication as a topical antiseptic or an oral anesthetic, it is generally accepted that pharmacokinetic considerations do not arise since the pharmacological action is local to the topically applied or oro-pharyngeal cavity area.

Hexylresorcinol's production and use as a topical antiseptic and anthelmintic(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,800(SRC), determined from a log Kow of 3.45(2) and a regression-derived equation(3), indicates that hexylresorcinol is expected to have low mobility in soil(SRC). Volatilization of hexylresorcinol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.6X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Hexylresorcinol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.4X10-6 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2005).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,800(SRC), determined from a log Kow of 3.45(2) and a regression-derived equation(3), indicates that hexylresorcinol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.6X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 90(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data were not available(SRC, 2005).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexylresorcinol, which has an estimated vapor pressure of 8.4X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase hexylresorcinol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 hours(SRC), calculated from its rate constant of 2.1X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase hexylresorcinol may be removed from the air by wet and dry deposition(SRC). Hexylresorcinol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of hexylresorcinol with photochemically-produced hydroxyl radicals has been estimated as 2.1X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hexylresorcinol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due the lack of chromophores that absorb at wavelengths >290 nm(SRC).

An estimated BCF of 90 was calculated for hexylresorcinol(SRC), using a log Kow of 3.45(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC).

The Koc of hexylresorcinol is estimated as 1,800(SRC), using a log Kow of 3.45(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that hexylresorcinol is expected to have low mobility in soil.

The Henry's Law constant for hexylresorcinol is estimated as 2.6X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that hexylresorcinol is expected to be essentially nonvolatile from water surfaces(2). Hexylresorcinol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.4X10-6 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to hexylresorcinol is limited but may occur through inhalation and dermal contact with this compound at workplaces where hexylresorcinol is produced. Use data indicate that the general population may be exposed to hexylresorcinol via inhalation and dermal contact with consumer products containing hexylresorcinol. Exposure to the drug among the general population may be via ingestion to those administered the drug (an anthelmintic) and via ingestion of some over-the-counter throat lozenge formulation. (SRC)

Drug Information

Hexylresorcinol is predominantly employed as the active ingredient in lotions, sprays, or lozenges indicated as a (a) topical antiseptic to help prevent skin infection in minor cuts, scrapes, or burns, or (b) as an antiseptic and local anesthetic for the relief of a sore throat and its associated pain. In addition, hexylresorcinol is used as an active ingredient in various commercial cosmetic skincare products as an anti-aging cream while other studies have looked into whether or not the compound could be used effectively as an anti-inflammatory agent or even as an anti-cancer therapy.

Anti-Infective Agents, Local; Antinematodal Agents; Antiplatyhelmintic Agents|It is commonly employed in 1:1000 soln or glycerite in mouthwashes or pharyngeal antiseptic preparation.|MEDICATION (VET): Rare now, as anthelmintic especially since introduction of dichlorvos and other drugs. Topically it is effective bacteriostatic, bactericidal, virucidal, fungistatic, and fungicidal agent at dilutions greater than 1:1000 (0.1%), although latter is safe topically. In ringworm therapy with Aminoacridinium = Aacrisorcin ...|MEDICATION (VET): Effective against many viruses when aerosoled at 5 mg/cu m. ... Administer orally in oil to reduce local irritation.|For more Therapeutic Uses (Complete) data for HEXYLRESORCINOL (7 total), please visit the HSDB record page.

Hexylresorcinol should not be dispensed in ordinary, hard-gelatin capsules as these quickly become brittle, and may break in mouth causing caustic burns.|Hexylresorcinol, given orally, is ineffective but when given by enema, tedious and unpleasant experience for patients, there is immediate symptomatic relief, although cures are rarely attained.|Care should be taken that pills containing drug are swallowed whole or painful ulceration of oral mucous membrane may result.

probable oral lethal dose (human) 0.5-5 g/kg, between 1 oz and 1 pint (or 1 lbs) for 70 kg person (150 lb). Somewhat less toxic than resorcinol or phenol.

Hexylresorcinol is a phenol derivative, and in typical therapeutic usage is primarily a local anesthetic for topical use on the mucous membranes of the mouth and throat. The local anesthetic like properties of hexylresorcinol is likely due to its sodium channel blocking effects. The agent also demonstrates mild antiseptic activity as well as an apparent anti-inflammatory, demulcent action.

Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal. (See all compounds classified as Anthelmintics.)

Owing to the poor absorption of hexylresorcinol, systemic exposure and symptoms are unusual.|When two men received doses of 1 g of hexylresorcinol, an average of 18% of the dose was recovered in the urine within the first 12 hours - thereafter, the compound was not detected in urine samples.|Readily accessible data regarding the volume of distribution of hexylresorcinol is not available. Nevertheless, when hexylresorcinol is employed in its primary indication as a topical antiseptic or an oral anesthetic, it is generally accepted that pharmacokinetic considerations do not arise since the pharmacological action is local to the topically applied or oro-pharyngeal cavity area.|Readily accessible data regarding the clearance of hexylresorcinol is not available. Nevertheless, when hexylresorcinol is employed in its primary indication as a topical antiseptic or an oral anesthetic, it is generally accepted that pharmacokinetic considerations do not arise since the pharmacological action is local to the topically applied or oro-pharyngeal cavity area.|Dogs were given single doses of 1 or 3 g 4-hexylresorcinol (equivalent to 100 or 300 mg/kg bw) as crystals in gelatin capsules or as a solution in olive oil, and excretion monitored in urine and feces. After administration of 1 g crystalline compound, 29% of the dose was detected in urine and 67% in feces; when the dose was increased to 3 g, 17% was excreted in urine and 73% in feces. Urinary excretion was rapid, mainly in the first 6 hr, and levels were virtually undetectable 12 hr after the lower dose and 24-36 hr following the higher dose. When 4-hexylresorcinol was administered in olive oil, a dose of 1 g resulted in 17% being excreted in urine and 76% in feces, while 10% was excreted in urine and 80% in feces following a dose of 3 g.|When two men received doses of 1 g 4-hexylresorcinol, an average of 18% of the dose was recovered in urine within the first 12 hr; thereafter the compound was not detected in urine samples. Fecal excretion accounted for 64% of the dose.

Regarding the metabolism of hexylresorcinol, it has been reported that excretion of the compound in the urine is largely in the form of an ethereal sulfate conjugate.|Human metabolite of 4-hexylresorcinol is ethereal sulfate. /From table/|It has been reported that 4-hexylresorcinol is excreted via the urine mainly in the form of an ethereal sulfate conjugate ...

Readily accessible data regarding the half-life of hexylresorcinol is not available. Nevertheless, when hexylresorcinol is employed in its primary indication as a topical antiseptic or an oral anesthetic, it is generally accepted that pharmacokinetic considerations do not arise since the pharmacological action is local to the topically applied or oro-pharyngeal cavity area.

When acting as an oral anesthetic for relieving sore throats, it is generally believed that hexylresorcinol is possibly capable of blocking voltage-gated neuronal sodium channels, which in turn would inhibit the initiation and conduction of nerve impulses for feeling or transmitting pain signals in the local area to which the hexylresorcinol is applied. As an antiseptic agent, studies have demonstrated that hexylresorcinol is capable of eliciting actions like reducing or inhibiting the generation of bacterial biofilm, interfering with bacterial cell chain formation, reducing bacterial adherence of the pharynx, inhibition of glycolytic enzyme and pH drops, and alteration of cell surface hydrophobicity. Unfortunately, there are either antibiotics that function even more effectively at formally treating bacterial growth or there are also other plant-derived phenolic compounds similar to hexylresorcinol that elicit stronger such mechanisms of action. Nevertheless, it is useful for hexylresorcinol to have both anesthetic and certain antiseptic actions for its use in treating various relatively self-limiting scrapes and sore throats that are treated by the over-the-counter products that feature the compound. Early studies in the 1930s and 1940s suggested that there were more effective medicines over hexylresorcinol that could be employed for their anthelmintic effects. As an anti-inflammatory and anti-aging agent, some studies have shown that it may be possible for hexylresorcinol to inhibit the phosphorylation of the immune response mediator NF-kappaB and also elicit a significant skin lightening effect owing to a strong inhibitory effect on tyrosinase and peroxidase and a stimulatory effect on glutathione and E-cadherin syntheses. It is proposed that hexylresorcinol can bind to tyrosinase directly and inhibits its enzyme activity. Literature data suggests that low glutathione levels relates to the deposition of melanin in the skin of humans and other animals, while high glutathione levels inhibit melanogenesis. And ultimately, it is also reported that glutathione depletion increases tyrosinase activity in human melanoma cells, which makes hexylresorcinol's effects on tyrosinase desirable. Finally, there are ongoing studies that have reported hexylresorcinol's abilities to induce the differentiation of SCC-9 squamous cell cell-line by way of the modulation of the E2F-mediated signaling pathway and suppress the growth of squamous cell carcinoma SCC-9 cells in a dose-dependent manner. Moreover, such studies have also shown that hexylresorcinol is seemingly capable of dose-dependent induction of SCC-9 cell apoptosis as well as the inhibition of transglutaminase-2 enzyme activity which can facilitate chemotherapy resistance.

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and respiratory tract. Depending on the intensity and duration of exposure, effects may vary from mild irritation to severe destruction of tissue. Prolonged contact can cause damage to the eyes, severe irritation or burns. Exposure may also cause profuse sweating, nausea, vomiting and diarrhea. Some cutaneous reactions occur due to hypersensitivity. If ingested, large doses cause irritation and erosion of gastric and intestinal mucosa. Ingestion or application of phenolic compounds to the skin or mucous membranes may result in painless blanching or erythema, corrosion, intense thirst, cyanosis from methemoglobinemia, hyperactivity, stupor, blood pressure fall, hyperpnea, abdominal pain, hemolysis, convulsions, coma, and pulmonary edema followed by pneumonia. If death from respiratory failure is not immediate, jaundice and oliguria or anuria may occur. Skin sensitivity reactions occur occasionally. ACUTE/CHRONIC HAZARDS: This compound is harmful if swallowed, inhaled or absorbed through the skin. It is an irritant to the skin, eyes, respiratory tract and mucous membranes. Concentrated solutions can cause burns of the skin and mucous membranes. When heated to decomposition it emits acrid smoke and fumes. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)

Basic treatment. Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary. Monitor for shock and treat if necessary. Anticipate seizures and treat if necessary. For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline during transport. Administer activated charcoal. Dilution may be contraindicated because it may increase absorption. Do not use emetics. Cover skin burns with dry, sterile dressings after decontamination. Maintain body temperature. Advanced treatment. Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema. Monitor cardiac rhythm and treat arrhythmias if necessary. Start IV administration of D5W TKO. Use 0.9% saline or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. DIRECT PHYSICIAN ORDER ONLY. Treat seizures with diazepam (Valium) or lorazepam (Ativan). Use proparacaine hydrochloride to assist eye irrigation. /Phenols and related compounds/

/SIGNS AND SYMPTOMS/ 4-hexylresorcinol is irritating to ... the respiratory tract and to skin ... its solution in alcohol has vesicant properties.|/SIGNS AND SYMPTOMS/ Concentrated solutions can cause irritation of skin, mucous membranes.|/SIGNS AND SYMPTOMS/ In a study of cross-reactivity in patients with resorcinol-induced dermatitis, 2 out of 8 subjects reacted positively to 4-hexylresorcinol in patch tests; a further 3 responded with one-degree irritation and 2 were negative.|/CASE REPORTS/ A patient with contact dermatitis following occupational exposure reacted strongly to 4-hexylresorcinol in a patch test at 48 and 72 hours; 20 controls were all negative. The patient did not cross-react with resorcinol.|For more Human Toxicity Excerpts (Complete) data for HEXYLRESORCINOL (6 total), please visit the HSDB record page.

4 Hexylresorcinol

Hexylresorcinol Use and Manufacturing

Methods of Manufacturing

Put 1/2 amount of hexanoic acid into the dissolution pot, add anhydrous zinc chloride, and heat and stir to dissolve the mixture at about 120°C; put the other half of hexanoic acid into the condensation pot, and add resorcinol, stir to dissolve ; Drop the above zinc chloride/hexanoic acid solution at about 120℃, depressurize to 93kPa, keep the reaction for 3h, and distill out the water generated by the reaction; after the reaction is completed, reduce the temperature to 80℃, wash with water 5 times, and transfer to distillation In the boiler, dehydration is frequently performed, dehydration under reduced pressure, and unreacted hexanoic acid is recovered to obtain the condensation product caproyl resorcinol. The zinc amalgam is added to hexanoyl resorcinol, and then industrial hydrochloric acid is added, and the temperature is raised to 75-80°C with stirring, and the temperature is naturally raised to 104-110°C, and the heat preservation reaction is 1.5-2.0h. Reduce the temperature to 80 ℃, check the end of the reaction; after the reaction is completed, reduce the temperature to below 40 ℃, separate the reduced product, wash the water under reduced pressure to distill off the water, collect 145 ~ 152 ℃ (133 ~ 266Pa) fractions, to obtain 4-hexyl m-phenylene The crude phenol product has a 90% yield; the crude product is obtained by recrystallization from petroleum ether.

Uses

anthelmintic, topical antiseptic

Production

(1972) Probably greater than 4.54x10+5 grams|(1975) Probably greater than 4.54x10+5 grams

St 37, Caprokol, Crystoids, Sucrets.|Official hexylresorcinol pills ... are coated by patented process, gelatin coating being so tough that it cannot be readily broken even though chewed.|Dosage forms-- pills NF: 100 & 200 mg.|Formulation: Sorunex

1,3-Benzenediol, 4-hexyl-: ACTIVE|While data specific to hexylresorcinol were not loacted,SRC, 2005), the literature suggests that some pharmaceutically active compounds originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2). Selected organic waste compounds may be degrading to new and more persistent compounds that may be released instead of or in addition to the parent compound(2). Studies have indicated that several polar pharmaceutically active compounds can leach through subsoils into aquifers(1).

Isolation and thin-layer chromatography identification of hexylresorcinol. Determination by ultraviolet and visible spectrophotometry.|Method: AOAC 933.10; Procedure: Titrimetric method; Analyte: hexylresorcinol; Matrix: drugs; Detection Limit: not provided.|Quantitative determination of hexylresorcinol in commercial antiseptic solution by high-pressure liquid chromatography.|Analyte: hexylresorcinol; matrix: chemical identification; procedure: visual reaction (light red color appears) with nitric acid|Analyte: hexylresorcinol; matrix: chemical identification; procedure: visual reaction (precipitate) with ammonium hydroxide

Food additives|Food Additives -> ANTIOXIDANT; COLOUR_RETENTION_AGENT; -> JECFA Functional Classes|Pharmaceuticals

Food Additives -> ANTIOXIDANT; COLOUR_RETENTION_AGENT;

Computed Properties

Molecular Weight:194.27
XLogP3:3.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:194.130679813
Monoisotopic Mass:194.130679813
Topological Polar Surface Area:40.5
Heavy Atom Count:14
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Antiseptic, anaesthetic, antibacterial, local anaesthetic, antiparasitic, tyrosinase inhibitor, induces apoptosis in squamous carcinoma cells, reversible non-competitive alpha-glucosidase inhibitor, protective effect against DNA oxidative damage

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • Ferak Berlin GmbH

    European Union European Union
    Active
  • KUMAR ORGANIC PRODUCTS LIMITED

    European Union European Union
    Active
  • IMCD UK LIMITED

    European Union European Union
    Inactive

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