2-Methylpentan-2,4-diol

Hexylene Glycol

HCID 7870CAS 107-41-5

Grundinformationen

Standard-SMILES
CC(O)CC(C)(C)O
InChIKey
SVTBMSDMJJWYQN-UHFFFAOYSA-N
Summenformel
C6H14O2
Durchschnittliche Molmasse
118,17 g/mol
Monoisotopische Masse
118,09937969

Namen und Bezeichner

Bevorzugter Name
Hexylene Glycol
IUPAC
2-methylpentane-2,4-diol
Lokaler Name
2-Methylpentan-2,4-diol
Englischer Name
2-Methyl-2,4-pentanediol
Summenformel
C6H14O2
Molmasse
118.17

Namen und Synonyme

Hexylene glycol2-METHYL-2,4-PENTANEDIOL107-41-52-Methylpentane-2,4-diolPinakonDiolane2,4-Dihydroxy-2-methylpentaneIsol2,4-Pentanediol, 2-methyl-1,1,3-Trimethyltrimethylenediol4-Methyl-2,4-pentanediol2-Methyl pentane-2,4-diol
Weitere Namen anzeigen
MPD4-MPD3-METHYL-2,4-PENTANEDIOL2-Methyl-2,4-pentadiolHexalene glycol
2-Methyl-2,4-pentandiolDTXSID5021885NSC-8098KEH0A3F75Jalpha,alpha,alpha'-Trimethyltrimethylene glycol1,3-dimethyl-3-hydroxybutanol1,3,3-trimethyl-1,3-propanediolDTXCID101885

Datenbank-Bezeichner

CAS
107-41-5
PubChem CID
7870
DTXSID
DTXSID5021885
ChEMBL
CHEMBL2104293
ChEBI
CHEBI:62995
UNII
KEH0A3F75J
EC Number
203-489-0
Nikkaji
J3.614E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,3
Polarare Oberfläche (TPSA)
40,5 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
2
Schwere Atome
8

Experimentelle und physikochemische Eigenschaften

LogP0.58
Odor · 3 Einträge

Mild sweetish

ATMOSPHERES ESSENTIALLY SATURATED AT ROOM TEMP ARE DETECTABLE BY ODOR...

Mild, sweetish odor

Density · 6 Einträge

0.923 at 68 °F (USCG, 1999) - Less dense than water; will float

0.923 g/cu cm at 15 °C

Bulk density 7.69 lb/gal

Density = 0.92109 at 20 °C; 0.9181 at 25 °C

Relative density (water = 1): 0.92

0.923

Viscosity34 cP at 20 °C
Color/Form · 2 Einträge

Liquid

Colorless liquid

Solubility · 6 Einträge

Miscible (NIOSH, 2024)

Miscible with water

Soluble in alcohol, ether, lower aliphatic hydrocarbons

Soluble in ethanol, ethyl ether; slightly soluble in carbon tetrachloride

Miscible with fatty acids

Solubility in water: miscible

Physikochemische Eigenschaften

Schmelzpunkt
-40 °C · -40 °C (lit.)
Siedepunkt
197 °C · 197 °C (lit.)
Dichte
0.925 g/mL · 0.925 g/mL at 25 °C (lit.)
Dampfdichte
4.1 · 4.1 (vs air)
Dampfdruck
0.02 mm · 0.02 mm Hg ( 20 °C)
Brechungsindex
20 · n20/D 1.427(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation];H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 5235) of reports.

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: 2,4-Pentanediol, 2-methyl-

Chemical: C.I. Acid Red 299

2,4-Pentanediol, 2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,4-Pentanediol, 2-methyl- 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: 28-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14212

Hexylene glycol: Does not have an individual approval but may be used under an appropriate group standard

C.I. Acid Red 299: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Fire HazardsCombustible. Above 96 °C explosive vapour/air mixtures may be formed.
Fire Potential · 2 Einträge

Combustible.

Combustile when exposed to heat or flame.

Health HazardsIrritation of eyes, nose and throat; headache, dizziness, and nausea. (USCG, 1999)
Hazards Summary · 1 Eintrag

At 1000 ppm for 5 minutes, human subjects complain of eye, throat, and respiratory irritation. Oral dosing causes central nervous system depression in experimental animals. Limited animal and human data suggesting a potential for skin sensitization were insufficient to support a DSEN notation. [ACGIH] Allergic contact dermatitis may occur; [Reference #1] A skin, eye, and respiratory tract irritant; [ICSC]

Reactive GroupAlcohols and Polyols

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.;Fire Extinguishing Agents: Alcohol foam, dry chemical, or carbon dioxide (USCG, 1999)

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 Einträge

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

First Aid · 2 Einträge

Excerpt from NIOSH Pocket Guide for Hexylene glycol:;Eye: IRRIGATE IMMEDIATELY - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: WATER WASH IMMEDIATELY - If this chemical contacts the skin, immediately wash the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and wash the skin with water. If symptoms occur after washing, get medical attention immediately.;Breathing: RESPIRATORY SUPPORT - If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform artificial respiration. Keep the affected person warm and at rest. Get medical attention as soon as possible.;Swallow: MEDICAL ATTENTION IMMEDIATELY - If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2024)

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Water wash immediately - If this chemical contacts the skin, immediately wash the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and wash the skin with water. If symptoms occur after washing, get medical attention immediately.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Safe StorageSeparated from strong oxidants and strong acids.
Exposure Control and Personal Protection10.0 [ppm]
Fire Fighting Procedures · 3 Einträge

In case of fire: keep drums, etc., cool by spraying with water.

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

Use water spray, alcohol - resistant foam, dry chemical or carbon dioxide.

Toxikologische Informationen

Target OrgansEyes, skin, respiratory system, central nervous system
Ecotoxicity Values · 5 Einträge

LC50; Species: Alburnus alburnus (bleak); Conditions: /saltwater, static, 10 °C, pH 7.8/; Concentration: 8000 mg/L for 96 hr

LC50; Species: /Oncorhynchus mykiss/ (Rainbow trout); Conditions: flow through, 11.4 °C, pH 7.99, dissolved oxygen 8.76 mg/L; Concentration: 9450 mg/L for 96 hr (95% confidence limit: 8820-10100 mg/L)

LC50; Species: Pimephales promelas (fathead minnow) weight 0.22 g; Conditions: flow through, 18.7 °C, pH mean 7.95, dissolved oxygen 6.27 mg/L; Concentration: 8690 mg/L for 96 hr

LC50; Species: Lepomis macrochirus (bluegill sunfish) mean weight 0.53 g; Conditions: flow through, 17.4 °C, pH 8.02, dissolved oxygen 6.47 mg/L; Concentration: 12,800 mg/L for 96 hr (95% confidence limits: 11,200-14,600 mg/L)

For more Ecotoxicity Values (Complete) data for 2-METHYL-2,4-PENTANEDIOL (21 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2-methyl-2,4-pentanediol is expected to have very high mobility in soil(SRC). Volatilization of 2-methyl-2,4-pentanediol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.1X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(3). 2-Methyl-2,4-pentanediol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.0X10-2 mm Hg at 25 °C(4). Utilizing the Japanese MITI test, 55.7% of the Theoretical BOD was reached in 2 weeks(5) indicating 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 2-methyl-2,4-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 4.1X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 0.58(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 55.7% of the Theoretical BOD was reached in 2 weeks(6) indicating 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), 2-methyl-2,4-pentanediol, which has a vapor pressure of 7.0X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-methyl-2,4-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 14 hrs(SRC), calculated from its rate constant of 2.77X10-11 cu cm/molecule-sec at 25 °C(3). 2-Methyl-2,4-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).

Food Survey Values2-Methyl-2,4-pentanediol has been detected as a volatile aroma and flavor component of Bisbee Delicious apples(1).
Adverse EffectsNeurotoxin - Acute solvent syndrome;Skin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure Routes · 2 Einträge

The substance can be absorbed into the body by inhalation of its aerosol.

inhalation, ingestion, skin and/or eye contact

Regulatorische Informationen

Regulatory Information · 6 Einträge

Chemical: 2,4-Pentanediol, 2-methyl-

Chemical: C.I. Acid Red 299

2,4-Pentanediol, 2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,4-Pentanediol, 2-methyl- 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: 28-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14212

Hexylene glycol: Does not have an individual approval but may be used under an appropriate group standard

C.I. Acid Red 299: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

FIFRA Requirements · 4 Einträge

Residues of 2-methyl-2,4-pentanediol are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest. Use: Growing crops and food animals. Limit: Without limitation.

Residues of 2-methyl-2,4-pentanediol are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: Solvent for formulations used before crop emerges from soil. Limit: None.

Residues of 2-methyl-2,4-pentanediol are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals. Use: Growing crops and food animals. Limit: Without limitation.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. 2-Methyl-2,4-pentanediol is found on List C. Case No: 3075; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): 2-Methyl-2,4-pentanediol; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Sicherheitsdaten

F
3-23
OEL
Ceiling: 25 ppm (125 mg/m3)
wgk
1
tsca
TSCA listed
hs_code
29053910
RTECS-Nr.
SA0810000

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

Some effects of gravity on early morphogenesis are correlated with microtubule locations within cells. During first cleavage in Ilyanassa obsoleta embryos, a transitory polar lobe constriction forms and then relaxes, allowing the polar lobe to merge with one daughter cell. If the polar lobe is equally divided or removed, morphogenesis is severely disrupted. To examine microtuble locations during early Ilyanassa development, eggs were fixed and stained for polymerized alpha-tubulin during first cleavage. The mitotic apparatus assembles at the animal pole. The cleavage furrow forms between the asters, constricting to a stabilized intercellular bridge encircling midbody-bound microtubules, whereas the polar lobe constriction forms below and parallel to the spindle, constricting to a transitory intercellular bridge encircling no detectable microtubules. At metaphase an alpha-tubulin epitope is distributed throughout the spindle, whereas a beta-tubulin epitope is present predominantly in the asters. Incubation in hexylene glycol, a drug that increases microtubule polymerization, during mitosis causes the polar lobe constriction to tighten around polymerized alpha-tubulin and remain stably constricted. If hexylene glycol is removed, alpha-tubulin staining disappears from the polar lobe constriction, which relaxes, whereas microtubules remain in the cleavage furrow, which remains constricted. These observations suggest that asymmetric distribution of microtubules affects early Ilyanassa cleavage patterns, and that continued presence of microtubules extending through an intercellular bridge is important for stabilization of the bridge constriction prior to completion of cytokinesis. These data provide the basis for further analysis of the role of microtubules in possible microgravity disruptions of Ilyanassa development.

Biological Half-Life...after a single oral (gavage) administration of Hexylene glycol at the dose-level of 590 mg/kg to male Sprague-Dawley rats ...t1/2 21.2 hr
Metabolism/Metabolites · 4 Einträge

...Five human subjects ... /had/ both free & conjugated hexylene glycol in the urine after single or repeated oral doses. ...

(14)C-hexylene glycol fed to rabbits... urine contained 7 metabolites incl glucuronide of hexylene glycol (46% of dose), unchanged hexylene glycol (2.5%), diacetone alcohol (1.4%) & an unidentified glucuronide which could be conjugate of diacetone alcohol. ...Converted into diacetone alc by incubation with rat liver slices.

... Oral administration of hexylene glycol to rats & rabbits resulted in a substantial increase in the amt of hexuronates in the plasma & in the urine.

It was also shown that approximately 40% of the hexylene glycol was accounted for in the urine, but only 4% of the amount excreted was free glycol; the other 36% was conjugated with glycuronic acid.

Absorption, Distribution and Excretion · 5 Einträge

... Mice /were fed hexylene glycol/ orally 20 mg/day in 2 mL of whole milk for up to 81 days ... . approximately 40% of the hexylene glycol was accounted for in the urine, but only 4% of the amount excreted was free glycol; the other 36% was conjugated with glycuronic acid.

... Not readily absorbed through the skin ... .

Eliminated in urine, partly (20-25%) in conjugated forms.

... Oral administration of hexylene glycol to rats & rabbits resulted in a substantial increase in the amt of hexuronates in the plasma & in the urine.

For more Absorption, Distribution and Excretion (Complete) data for 2-METHYL-2,4-PENTANEDIOL (8 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 6 Einträge

CIR ingredient: Hexylene Glycol

Used as a solvent plasticizer in paints and lacquers; Also used in the chemical, petroleum refining, and cosmetic industries and as an additive to hydraulic fluids, inks, cement, leather, paper, and textiles; [ACGIH]

Petroleum Production and Refining [Category: Industry];Pulp and Paper Processing [Category: Industry];Textiles (Fiber & Fabric Manufacturing) [Category: Industry];Painting (Pigments, Binders, and Biocides) [Category: Paint];Leather Tanning and Processing [Category: Industry];Cement Producing [Category: Industry]

For 2-methyl-2,4-pentanediol (USEPA/OPP Pesticide Code: 068601) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

... Hydraulic brake fluids (as coupling agent to castor oil).

U.S. Production · 6 Einträge

2023: 25,000,000 - <40,000,000 lb;2022: 40,000,000 - <55,000,000 lb;2021: 25,000,000 - <40,000,000 lb;2020: 25,000,000 - <40,000,000 lb

(1975) Greater than 9.08x10+5 grams

2,4-Pentanediol, 2-methyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#2863]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2,4-Pentanediol, 2-methyl-. Aggregated National Production Volume: 10 to < 50 million pounds.

For more U.S. Production (Complete) data for 2-METHYL-2,4-PENTANEDIOL (6 total), please visit the HSDB record page.

Consumption PatternsSales quantity in 1992 = 9,379,000 kg
Consumer UsesSolvent;Not Known or Reasonably Ascertainable;Flame retardant;Cleaning agent;Fragrance;Etching agent
Industry Uses · 1 Eintrag

Etching agent;Chelating agent;Intermediate;Filler;Not Known or Reasonably Ascertainable;Hydraulic fluids;Cleaning agent;Plating agent;Processing aids not otherwise specified;Tanning agents not otherwise specified;Lubricating agent;Solvent;Anti-freeze agent

Methods of Manufacturing · 3 Einträge

The condensation of acetone leads to the formation of diacetone alcohol (DAA) ... DAA can be hydrogenated to 2-methyl-2,4-pentanediol.

Preparation: ... Leopold, Germany patent 486767 (1925 to I. G. Farben), ... Arundale, Mikeska, United States of America patent 2367324 (1945 to Standard Oil.

Hydrogen of diacetone alcohol

Anwendungen · 1 Eintrag

Verwenden(^+)-2-Methyl-2,4-pentanediol is used to control the flow properties of industrial products such as paints, coatings, cleansers, solvents, and hydraulic fluids. It acts as a thickening agent in cosmetic products. It serves as a coupling agent and an additive to hydraulic fluids, inks and cement. It is also employed as a blood volume expander. Further, it is used as a solvent for cleaning and colorant products. In addition to this, it is used in laboratory studies as a precipitant and cryoprotectant in protein crystallography.

Anbieter50 Anbieter

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Ergänzende Hinweise

DefinitionChEBI: A glycol in which the two hydroxy groups are at positions 2 and 4 of 2-methylpentane (isopentane).

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