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4-Hexylresorcin
HEXYLRESORCINOL · Hexylcaine · 4-HEXYLRESORCINOL · Adrover · Oxana · ST-37 · s.t.37 · Ascaryl
Identifikatoren & physikalische Daten
| CAS No. | 136-77-6 |
|---|---|
| Summenformel | C12H18O2 |
| Durchschnittliche Molmasse | 194,27 g/mol |
| Monoisotopische Masse | 194,13067981 g/mol |
| SMILES | CCCCCCc1ccc(O)cc1O |
| InChIKey | WFJIVOKAWHGMBH-UHFFFAOYSA-N |
| PubChem CID | 3610 |
| ChEMBL | CHEMBL443605 |
| ChEBI | CHEBI:93749 |
| EC No. | 205-257-4 |
| DTXSID | DTXSID1020699 |
| Lokaler Name | 4-Hexylresorcin |
Chemische & physikalische Eigenschaften
| XLogP | 3,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 40,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 147 |
| LogP (Verteilungskoeffizient) | log Kow = 3.45 |
| Geruch | Pungent odor |
| Geschmack | Sharp astringent taste |
| Color/Form | Pale yellow, heavy liq becoming solid on standing at room tempneedles from benzene or petroleum etherWHITE, OR YELLOWISH WHITE, NEEDLE-SHAPED CRYSTALSACQUIRES BROWNISH PINK TINT ON EXPOSURE TO LIGHT & AIR |
| Löslichkeit | less than 1 mg/mL at 73 °F (NTP, 1992)Freely soluble in ether and acetonevery slightly soluble in waterSol in ether, chloroform, acetone, alcoholslightly sol in petroleum ethersol in about 2000 parts watersol in vegetable oilsFreely soluble in glycerolSoluble in benzene.In water, 500 mg/L at 18 °Cchloroform: 50 mg/mL, clear0.05 g/100 mL (18 ºC) |
| Siedepunkt | 631 °F at 760 mmHg (NTP, 1992)178-180 °C at 6.7 mm Hg198-100 °C at 13-14 mm HG333-335 °C at 760 mm Hg334.00 °C. @ 760.00 mm Hg333-335 °C (lit.) |
| Schmelzpunkt | 154 to 156 °F (NTP, 1992)62 to 67 °C67.5-69 °C68 - 70 °C65-67 °C (lit.) |
| Dampfdruck | 0.00000845 [mmHg]0.001Pa at 25℃ |
| Brechungsindex | Index of refraction = -53 at 20 °C/D (aq HCl)1.5050 (estimate) |
| Physical Description | 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 powderPale yellow liquid (solidifies on standing at room temperature) or solidmp = 67.5-69 deg C[Merck Index] Pale yellow liquid or peach colored solidPungent faintly fatty odor[CAMEO] Light orange, off-white, or white powder[Alfa Aesar MSDS] |
| Kovats Retention Index | 1777 |
| Collision Cross Section | 150.2 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID1020699]129 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]136.84 Ų [M+H-H2O]+ [CCS Type: TW139.61 Ų [M+Na]+ [CCS Type: TW148 Ų [M+K]+ [CCS Type: TW |
| Dichte | 1.0010 (rough estimate) |
| Flammpunkt | >100°C |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Powder and/or Chunks |
| pKa (Säurekonstante) | pKa 9.1 (Uncertain) |
| Farbe | White to pale orange or pale pink |
| pH | 7.7 (0.5g/l, H2O, 20℃) |
| Merck | 14,4712 |
| BRN | 2048312 |
| Henry-Konstante | 3.8×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with acid chlorides, acid anhydrides, oxidizing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | 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 (Verteilungskoeffizient) | 3.34 at 20℃ |
| Oberflächenspannung | 36.59mN/m at 1g/L and 20℃ |
| CAS Datenbank | 136-77-6(CAS DataBase Reference) |
| NIST chemische Informationen | Hexylresorcinol(136-77-6) |
| EPA chemische Informationen | 4-Hexylresorcinol (136-77-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.7% (1 of 60) of reports.WarningH302 (98.3%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (91.7%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (95%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (88.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 60 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 60 reports by companies.There are 12 notifications provided by 59 of 60 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: 1,3-Benzenediol, 4-hexyl-Regulation (EC) No 178/2002 (amended)Status: Active Update: 21-02-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/190334-Hexylresorcinol: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 1,3-Benzenediol, 4-hexyl-: Human health tier II assessment |
| Brandgefahren | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | 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) |
| Gefahrenübersicht | Concentrated solutions cause skin and mucous membrane irritation[Merck Index] A skin and respiratory tract irritantSolutions in alcohol have vesicant propertiesSlightly less toxic than resorcinol or phenol[HSDB] Has not been associated with an increased frequency of birth defects[REPROTOX] A skin, eye, respiratory tract, and mucous membrane irritantconcentrated solutions can burn skin and mucous membranes[NTP] A skin and strong eye irritantHarmful by ingestion[Alfa Aesar MSDS] See Resorcinol. |
| FDA-Anforderungen | 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. |
| Reaktive Gruppe | Phenols and Cresols |
| Special Reports | DHHS/NTPToxicology & Carcinogenesis Studies of 4-Hexylresorcinol in F344/N Rats and B6C3F1 Mice Technical Report Series No. 330 (1988) NIH Publication No. 88-2586 |
| Reactivity Profile | P-HEXYLRESORCINOL may be sensitive to prolonged exposure to light. Incompatible with acid chlorides, acid anhydrides and oxidizing agents (NTP, 1992). |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (98.3%)Skin Irrit. 2 (91.7%)Eye Irrit. 2A (95%)STOT SE 3 (88.3%)Acute toxicity - category 4Reproductive toxicity - category 1B |
| Skin, Eye, and Respiratory Irritations | Concentrated solutions can cause irritation of skin, mucous membranes. |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| Erste Hilfe | 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 areatake 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 usedif 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) |
| Freisetung ohne Brand | 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) |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Personal Protective Equipment (PPE) | 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) |
| Umweltverhalten | 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). |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=136-77-6] |
| Soil Adsorption/Mobility | 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. |
| Human Toxicity Excerpts | /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 testsa 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 hours20 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. |
| Artificial Pollution Sources | 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). |
| Carcinogen Classification | 4-HexylresorcinolTR-330: Toxicology and Carcinogenesis Studies of 4-Hexylresorcinol (CASRN 136-77-6) in F344/N Rats and B6C3F1 Mice (Gavage Studies) (1988 )03/04/87No EvidenceEquivocal Evidence |
| Environmental Bioconcentration | 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). |
| Volatilization from Water/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). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ Tests on rabbit eyes have shown that surface of cornea can be irrigated for 5 min with 1:10,000 solution without injury, but that irrigation with 1:1,000 solution for 1-5 min caused diffuse edema of epithelium, followed in 2 or 3 hr by bluish stromal edema and hyperemia of iris./LABORATORY ANIMALS: Acute Exposure/ When 4-hexylresorcinol was administered to cats orally in alcohol or olive oil, no pathological effects were observed at doses up to 60 mg/kg bw, but a dose of 260 mg/kg bw was lethal to all animals./LABORATORY ANIMALS: Acute Exposure/ 4-hexylresorcinol did not induce delayed contact sensitivity in male Hartley strain guinea-pigs sensitized by the cutaneous route./LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of five F344/N rats of each sex, 8 weeks of age, were given 4-hexylresorcinol by gavage in corn oil at doses of 0 (vehicle control), 31, 63, 125, 250 or 500 mg/kg bw daily for 12 days (not including week-ends), i.e. 16 days overall. No deaths occurred as a result of treatment but final mean body weights of males in the top two dose groups were 8% and 16% lower than that of the controlsbody weights of females were comparable. Rats receiving 500 mg/kg bw/day were described as being hyperexcitable.For more Non-Human Toxicity Excerpts (Complete) data for HEXYLRESORCINOL (17 total), please visit the HSDB record page. |
| Environmental Abiotic Degradation | 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). |
| Probable Routes of Human Exposure | 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) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3077 9 / PGIII |
| Zollcode | 29072900 |
| RTECS-Nr. | VH1575000 |
| R-Sätze (R) | 22-36/37/38-20/21/22 |
| Toxizität | LD50 orally in Rabbit: 550 mg/kg |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36-24/25 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 136-77-6(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2 |
Herstellung & Synthese
synthetische
The preparation of 4-Hexylresorcinol involves two methods:The reaction of caproic acid and resorcinol in the presence of a catalyst.Reduction of hexanoylresorcinol with zinc amalgam and dilute hydrochloric acid.