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Pentan-1,5-diol
Pentylene glycol · Pentane-1,5-diol · 1,5-Pentandiol · 1，5-Pentadiol · PENTAMETHYLENE GLYCOL · 1,5-Dihydroxypentan · 1,5-PENTYLENE GLYCOL · 1,5-Pentamethylene glycol
Identifikatoren & physikalische Daten
| CAS No. | 111-29-5 |
|---|---|
| Summenformel | C5H12O2 |
| Durchschnittliche Molmasse | 104,15 g/mol |
| Monoisotopische Masse | 104,08372962 g/mol |
| SMILES | OCCCCCO |
| InChIKey | ALQSHHUCVQOPAS-UHFFFAOYSA-N |
| PubChem CID | 8105 |
| ChEMBL | CHEMBL448289 |
| ChEBI | CHEBI:185431 |
| EC No. | 203-854-4 |
| DTXSID | DTXSID2041256 |
| Lokaler Name | Pentan-1,5-diol |
Chemische & physikalische Eigenschaften
| XLogP | -0,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 40,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 25,3 |
| Polymers | Other Classes -> Alcohols and Polyols, Other |
| Kosmetika | Cosmetic ingredients (1,5-Pentanediol) -> CIR (Cosmetic Ingredient Review) |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | -0.43 |
| Geschmack | Bitter taste |
| Dichte | 0.9941 g/cm cu at 20 °C0.9858 g/cm cu at 25 °C0.994 @ 20°C0.994 g/mL at 25 °C (lit.) |
| Viscosity | 128 mPa.s at 20 °C |
| Color/Form | Viscous, oily liquidColorless |
| Löslichkeit | Miscible with waterSoluble in waterMiscible with methanol, ethanol, acetone, ethyl acetate. Soluble in ether (25 °C) 11% w/w. Limited solubility in benzene, trichloroethylene, methylene chloride, petroleum ether, heptane.Soluble in alcohols, acetone, and relatively insoluble in aliphatic and aromatic hydrocarbonsMethanol (Slightly) |
| Flammpunkt | 129 °C (265 °F) (open cup)136 °C (277 °F) - closed cup135 °C |
| Siedepunkt | 240 °C239 °C @760 [mm Hg]242 °C (lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | -18 °C |
| Dampfdichte | 3.59 |
| Dampfdruck | <0.01 mm Hg ( 20 °C) |
| Brechungsindex | n20/D 1.450(lit.) |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 14.83±0.10(Predicted) |
| Aggregatzustand | Oily Liquid |
| Farbe | Clear colorless |
| Geruch | odorless |
| pH | 7.5 (H2O) |
| Explosionsgrenze | 1.3-13.1%(V) |
| Merck | 14,7117 |
| BRN | 1560130 |
| Henry-Konstante | 7.0×104 mol/(m3Pa) at 25℃, Compernolle and Müller (2014) |
| Dielektrizitätskonstante | 25.300000000000001 |
| Kosmetik-Inhaltsstoffe Funktionen | SOLVENT |
| InChI | 1S/C5H12O2/c6-4-2-1-3-5-7/h6-7H,1-5H2 |
| InChIKey | ALQSHHUCVQOPAS-UHFFFAOYSA-N |
| SMILES | OCCCCCO |
| LogP (Verteilungskoeffizient) | -0.49 at 25℃ |
| Oberflächenspannung | 43.3mN/m at 20°C |
| CAS Datenbank | 111-29-5(CAS DataBase Reference) |
| NIST chemische Informationen | 1,5-Pentanediol(111-29-5) |
| EPA chemische Informationen | 1,5-Pentanediol (111-29-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 84.9% (275 of 324) of all reports.WarningH302 (15.1%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 324 reports by companies from 5 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: 1,5-Pentanediol1,5-Pentanediol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,5-Pentanediol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 02-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/148181,5-Pentanediol: Does not have an individual approval but may be used under an appropriate group standard |
| Brandpotenzial | Combustible when exposed to heat or flame. |
| Gefahrenübersicht | Oral LD50's (rat) range from 2,000 to 10,000 mg/kgNot irritating to skin or eyes of rabbits[IUCLID] Causes somnolence, excitement, and muscle weakness in oral lethal-dose studies of guinea pigs, mice, and rabbits[RTECS] A skin and strong eye irritantToxic by ingestion[Alfa Aesar MSDS] |
| NFPA Hazard Classification | 1 - Materials that, under emergency conditions, can cause significant irritation.1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.0 - Materials that in themselves are normally stable, even under fire conditions. |
| Toxic Combustion Products | Special hazards arising from the substance or mixture: Carbon oxides. |
| Hazard Classes and Categories | Acute Tox. 4 (15.1%) |
| Skin, Eye, and Respiratory Irritations | It is essentially nonirritating to the skin and only very mildly irritating to the eyes. |
| Hazardous Reactivities and Incompatibilities | Incompatible materials: Acid chlorides, acid anhydrides, oxidizing agents, chloroformates, reducing agents.Can react with oxiziding materials. |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.To fight fire, use foam, /carbon doixide/, dry chemical. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. Hygroscopic. Storage class (TRGS 510): Combustible liquids. |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid breathing vapors, mist or gas. Environmental precautions: No special environmental precautions required. Methods and materials for containment and cleaning up: Keep in suitable, closed containers for disposal. |
| Entsorgungsverfahren | SRP: 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 air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Offer surplus and non-recyclable solutions to a licensed disposal companyContaminated packaging: Dispose of as unused product. |
| Preventive Measures | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid breathing vapours, mist or gas. Environmental precautions: No special environmental precautions required.Appropriate engineering controls: General industrial hygiene practice.Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Protective Action Criteria (PAC) | 6.0 [mg/m3]66 [mg/m3]400 [mg/m3] |
| Personal Protective Equipment (PPE) | Eye/face protection: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).Skin protection: Handle with gloves.Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.Respiratory protection: Respiratory protection not required. For nuisance exposures use type OV/AG (US) or type ABEK (EU EN 14387) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). |
| Wechselwirkungen | The ability of propanediol, 1,4-butanediol, and 1,5-pentanediol to enhance the penetration of the drug estradiol in human skin was evaluated in an in vitro experiment using a Franz diffusion cell. The test substance (100 uL of 0.12% [(3)H]estradiol in 1:10 propanediol, 1,4-butanediol, or 1,5-pentanediol/ethanol solution) was applied to the dermis, which faced the receptor side of the cell. Receptor fluid samples were collected at various time points. The steady-state flux of propanediol, 1,4-butanediol, and 1,5-pentanediol was determined to be 0.11, 0.017, and 0.005 ug/sq cm/hr, respectively, indicating a decrease in steady-state flux with increasing alkyl chain length. After ~ 85-90 minutes the permeability of [(3)H]estradiol in human skin was ~ 5-6 ug/sq cm with propanediol and < 1 ug/sq cm with 1,4-butanediol or 1,5-pentanediol.Penetration enhancement tests in vitro showed 1,5-pentanediol to be a penetration enhancer for certain pharmaceutical drugs. Test cream formulations containing 0.1% tri-iodothyroacetic acid (TRIACa thyroid hormone analog) and either 1,5-pentanediol (10%) or 1,2-propanediol (10%) showed 1,5-pentanediol to be a more effective penetration enhancer than 1,2-propanediol for TRIAC in a multilayer membrane system (MMS) experiment. Results for 1,5-pentanediol indicated that 33% of the TRIAC (pharmacologically active agent) was released from the carrier vehicle, or formulation (in MMS), to enable TRIAC to contact the skin at the epidermal surface by 30 minutes post-application62% TRIAC was released from the formulation by 300 minutes. In a separate experiment, test cream formulations containing 1% hydrocortisone and either 1,5-pentanediol (25%) or 1,2-propanediol (25%) were evaluated using human breast skin. Both 1,5-pentanediol (increased drug absorption 4-fold, compared to controls) and 1,2-propanediol (increased drug absorption 13-fold, compared to controls) were shown to be penetration enhancers. However, 1,2-propanediol enhanced the transfer of the drug through the skin more effectively and 1,5-Pentanediol increased retention of the drug in the skin more effectively (receptor fluid collected up to 60 hours post-application). Another experiment evaluating test cream formulations containing 0.1% mometasone furoate and either 1,5-pentanediol (25%) or hexylene glycol (12%) revealed that both formulations were percutaneous absorption enhancers in human breast skin (receptor fluid collected up to 60 hours post-application). The absorption of 0.1% mometasone furoate into the skin was 6% using 1,5-pentanediol and 7% using hexylene glycol as penetration enhancers.1,5-Pentanediol (5% and 20%) and 1,2-propanediol (5% and 20%) were ... evaluated in an in vitro experiment investigating the penetration enhancement of 1% terbinafine, a lipophilic drug used to treat foot and nail fungus, in a hydrogel formulation. Both alkane diols were found to be percutaneous absorption enhancers in human breast skin (receptor fluid collected up to 60 hours post-application). Results indicated that 21% and 11% terbinafine was absorbed into the skin with 20% 1,2-propanediol or 20% 1,5-pentanediol, respectively. The 5% 1,2-propanediol or 5% 1,5-pentanediol yielded 19% and 52% terbinafine absorption into skin, respectively. For comparison, the control (1% terbinafine in hydrogel without either alkane diol) resulted in 8% drug absorption into the skin.1,5-Pentanediol (5%) was not phototoxic and not photosensitizing in a 24-hour occlusive patch test performed following UV-A/UV-B exposure to the treated skinstudy authors stated that it does not absorb in the long-wave ultra-violet range. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 1,5-pentanediol is expected to have very high mobility in soil(SRC). Volatilization of 1,5-pentanediol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.1X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 1,5-Pentanediol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.9X10-3 mm Hg at 25 °C(4). An 83-89% of theoretical BOD using activated sludge in the OECD Manometric Respiromerty test(5) suggests that biodegradation is an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 1,5-pentanediol is not 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 3.1X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of 0.27(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). An 83-89% of theoretical BOD using activated sludge in the OECD Manometric Respiromerty test(6) suggests that biodegradation is an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,5-pentanediol, which has a vapor pressure of 3.9X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,5-pentanediol 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 31 hours(SRC), calculated from its rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) (that was derived using a structure estimation method(3). 1,5-Pentanediol does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Toxizitätsübersicht | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.orgIDENTIFICATION AND USE: 1,5-Pentanediol has antimicrobial and antifungal properties in pharmaceutical applications. Additionally, 1,5-pentanediol has reported uses in products for hair loss, cold sores, nail problems, dry and scaly feet, and eczemait can be used as a moisturizing substance and solvent. In addition, it is used as a plasticizer in cellulose products and adhesives, and in brake fluid compositions. It forms esters and polyesters which can be used as plasticizers, emulsifying agents and resin intermediates. HUMAN STUDIES: 1,5-Pentanediol (5%) was non-irritating to skin in an occlusive patch test. 1,5-Pentanediol (5% and 25% in different tests) was non-sensitizing to skin. A patient was diagnosed with allergic contact dermatitis from resveratrol-containing cream which also contained 1,5-pentanediol. The reaction was attributed to sensitization to 1,5-pentanediol and potential co-sensitization to resveratrol. ANIMAL STUDIES: No-to-mild irritation was observed for undiluted 1,5-pentanediol in rabbit eyes. 1,5-Pentanediol (undiluted) was non-irritating to rabbit skin in both a 24-hour non-occlusive skin test and a 20-hour occlusive patch test on intact and scarified skin. Rats exposed to essentially saturated vapors generated at room temperature for 8 hr survived. In an Ames test, up to 5000 ug/plate 1,5-pentanediol was negative for mutagenicity. |
| Ongoing Test Status | EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of July 27, 2017: http://actor.epa.gov/dashboard/] |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,5-pentanediol can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,5-pentanediol is expected to have very high mobility in soil(SRC). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ 1,5-Pentanediol (5%) was non-irritating /to skin/ in an occlusive patch test ... ./HUMAN EXPOSURE STUDIES/ 1,5-Pentanediol (5% and 25% in different tests) was non-sensitizing /to skin/ ... ./CASE REPORTS/ A patient was prescribed a resveratrol-containing cream (also contained 1,5-pentanediol, concentration not specified) for recurrent scaling erythematous dermatitisdermatitis intensified after 2 weeks of cream applicationafter use of cream was discontinued eczema eventually cleared. Patient underwent patch testing (Test 1: propylene glycol and the resveratrol cream unchanged were applied). Four months later an additional patch test (Test 2) was performed on the patient and controls using the ingredients in the resveratrol cream. A final patch test (Test 3) was performed on the patient and controls using resveratrol diluted in petrolatum. Test 1 on patient: the resveratrol cream produced +/++ reactions by days 2 and 3. Test 2 on patient and controls: patient had strong reaction to 1,5-pentanediol (++ with 5% and 10% doses and +/++ with 0.5% dose)patient had slight reactions to resveratrol showing erythema on days 2 and 3 with all dose levels9 of 10 controls were negative and 1 control subject developed slight erythema with all doses levels of 1,5-pentanediol and resveratrol (this control subject had not been previously exposed to resveratrol and had no prior reactions to cosmetics, but did report hyperirritable skin type). Test 3 on patient and controls: patient reacted to 5% resveratrol only (+ by days 2 and 3)controls were negative. Final conclusion: patient was diagnosed with allergic contact dermatitis from resveratrol containing cream attributed to sensitization to 1,5-pentanediol and potential co-sensitization to resveratrol./CASE REPORTS/ A 62-year-old man, with a 20-year history of seborrhoeic dermatitis, presented with a worsening of his dermatitis. He had previously been demonstrated to be allergic to various topical corticosteroids, so he had been using an emollient cream (Sebclair), containing piroctone olamine and various anti-inflammatory substances, for 6 months, with good effect. Patch testing to the cream and its ingredients revealed positive reactions to both propyl gallate and pentylene glycol. A positive reaction to propylene glycol was also detected, whereas patch testing to butylene glycol was negative. Complete remission followed avoidance of the offending substances. |
| Artificial Pollution Sources | 1,5-Pentanediol's production and use in cosmetics(1), in consumer and commercial ink, toner, and colorant products(2), as a plasticizer in cellulose products and adhesives, in brake and hydraulic fluid compositions(3,4), as a lubricating-oil additive, in antifreeze, and as a polyester resin intermediate(4) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: 1,5-Pentanediol reached 83% and 89% of its theoretical BOD using a sapromat system and an oxitop system, respectively, in 4 weeks, after a 3 day lag phase, using an activated sludge inoculum in the OECD Manometric Respirometry test(1). Other screening studies give similar results(2,3). 1,5-Pentanediol reached 90% of its theoretical BOD after 10 days in a test using a sewage inoculum(3)therefore, 1,5-pentanediol is confirmed to be biodegradable(2,3). |
| Sediment/Soil Concentrations | SEDIMENT: Water quality data compiled from the Retrieval (STORET) Data Warehouse and the USGS National Water Information System (NWIS) reports sediment monitoring data for various chemicals but does not include 1,5-pentanediol as of 2017(1). |
| Environmental Bioconcentration | An estimated BCF of 3.2 was calculated in fish for 1,5-Pentanediol(SRC), using an estimated log Kow of 0.27(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for 1,5-pentanediol is estimated as 3.1X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1,5-pentanediol is expected to be essentially nonvolatile from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 122 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as greater than a year(SRC). 1,5-Pentanediol's Henry's Law constant indicates that volatilization from moist soil surfaces is not likely to occur(SRC). 1,5-Pentanediol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.9X10-3 mm Hg(3). |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29053980 |
| RTECS-Nr. | SA0480000 |
| Toxizität | LD50 orally in Rabbit: 10000 mg/kg LD50 dermal Rabbit > 19800 mg/kg |
| Sicherheitshinweise (S) | 24/25 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 111-29-5(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 635 °F |
Anwendungen & Verwendung
Verwenden
1,5-Pentanediol is used largely as a chemical intermediate. Industrial exposure is likely to be from direct contact.