1,3-ブタンジオール

Cosmetic ingredients (Butylene Glycol) -> CIR (Cosmetic Ingredient Review)

Humectant; Solvent

-0.290

-0.79

Practically odorless

Odorless when pure

1.0053 g/cu cm at 20 °C

Relative density (water = 1): 1.00

1.006 @ 20°C

Viscous liquid

Pure compound is colorless

Miscible with water

Practically insoluble in aliphatic hydrocarbons, benzene, toluene, carbon tetrachloride, ethanolamines, mineral and linseed oil; soluble in acetone, methyl ethyl ketone, ethanol, dibutyl phthalate, castor oil

Slightly soluble in ether

1000 mg/mL at 25 °C

Solubility in water: good

This chemical does not meet GHS hazard criteria for 46.2% (1160 of 2513) of reports.

Warning

H226 (51.2%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2513 reports by companies from 8 notifications to the ECHA C&L Inventory.

Chemical: 1,3-Butanediol

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

1,3-Butanediol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Butanediol 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: 20-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14962

1,3-Butylene glycol: Does not have an individual approval but may be used under an appropriate group standard

1,3-Butanediol is an indirect food additive for use only as a component of adhesives.

1,3-Butylene glycol is a food additive permitted in feed and drinking water of animals.

1,3-Butylene glycol is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.

1,3-Butylene glycol (1,3-butanediol) may be safely used in food in accordance with the following prescribed conditions: (a) The substance meets the following specifications: (1) 1,3-Butylene glycol content: Not less than 99 percent. (2) Specific gravity at 20/20 °C: 1.004 to 1.006. (3) Distillation range: 200 deg-215 °C. (b) It is used in the minimum amount required to perform its intended effect. (c) It is used as a solvent for natural and synthetic flavoring substances except where standards of identity issued under section 401 of the act preclude such use.

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 safety 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. Butylene glycol is found on List D. Case No: 4016; 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): Butylene glycol; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 1,3-Butylene glycol is produced, as an intermediate or a final product, by process units covered under this subpart.

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.

A tiny drop /of 1,3-butanediol/ applied to the human eye causes immediate severe stinging ... .

... /1,3-Butanediol/ is not irritating to human skin or mucous membranes.

A skin and eye irritant.

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

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. Rest.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for fighting if necessary.

To fight fire, use foam, alcohol foam, CO2, dry chemical.

Soak up with inert absorbent material and dispose of as hazardous wast. Keep in suitable, closed containers for disposal.

Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist, or gas. Ensure adequate ventilation.

Do not let product enter drains.

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 quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and 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.

Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.

Keep container tightly closed in a dry and well-ventilated place.

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.

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.

1,3-Butanediol and phlorhizin were used to induce ketonemia and hypoglycemia in steers. Oral administration of butanediol increased blood beta-hydroxybutyrate (BHB) and plasma nonesterified fatty acids (NEFA) and decreased serum glucose. Subcutaneous injections of phlorhizin, given in addition to butanediol orally, further increased NEFA and BHB concentrations and decreased glucose. Dietary niacin supplementation of steers given phlorhizin and butanediol caused serum glucose concentration to increase and blood BHB and plasma NEFA concentrations to decrease.

Evidence previously reported suggest that 1,3-butanediol (BD) enhances the hepatotoxic effect of a single small dose of carbon tetrachloride (CCl4) in a dose-related manner. The present study provides additional information concerning the quantitative relationship between the severity of the ketotic state produced by BD and the magnitude of the potentiation observed and emphasizes the use of ketone bodies (KB) to predict the potential hazard of the BD-CCl4 interaction. Liver damage was modulated in male Sprague-Dawley rats by varying the concentration of the BD solutions ingested prior to a CCl4 challenge (0.1 ml/kg, i.p.). These data were compared to ketone bodies in plasma, hepatic tissue and urine. BD produced a dose-dependent metabolic ketosis observable at dosages between 1.1 and 9.9 g/kg per day given for 7 days. Plasma and liver data correlated well together. Concomitantly, potentiation of the CCl4-induced liver injury was also dose-related for the same dosage range; the minimum effective dosage of BD for potentiation was estimated as 1.1 g/kg per day. The linear correlations between hepatic or plasma KB values and the indices of hepatic dysfunction (ALT, OCT) were highly significant. Using a semiquantitative method, a correlation was also found for the urinary KB data. These results suggest that plasma KB concentrations might be useful for predicting possible potentiation of the hepatonecrotic effect of CCl4 by BD.

For 28 days, four steers received l,3-butanediol, which causes ketonemia, and phlorizin, which causes glucosuria. Steers also were fasted for 9 days. Effects of treatments on concentrations of metabolites in blood and liver and on kinetics of glucose metabolism were determined. Treatments were: control, control with dietary butanediol plus injected phlorizin, and fasting. Fasting caused hypoinsulinemia and decreased liver glycogen by 60%. Butanediol plus phlorizin and fasting caused 18% and 19% decreases of plasma glucose and 2.5- and 6-fold increses of free fatty acid concentrations in blood plasma. Glucose irreversible loss averaged 371, 541, and 182 g/day during control, butanediol plus phlorizin treatment, and fasting. Butanediol plus phlorizin increased-liver ketone body concentrations, caused glucosuria, ketonuria, and ketonemia, but did not affect insulin, glucagon, or growth hormone concentrations in plasma or triglyceride and glycogen contents in liver. Steers given butane plus phlorizin did not show all the usual signs of lactation ketosis, but the treatment still offers promise for studying causes and effects of ketosis.

Rats maintained on 1,3-butanediol exhibit potentiated cholestatic responses to taurolithocholate or manganese-bilirubin injections; with alpha-naphthylisothiocyanate, the hyperbilirubinemia is enhanced but not the depression in bile flow.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 1,3-butanediol is expected to have very high mobility in soil(SRC). Volatilization of 1,3-butanediol from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 2.4X10-9 atm-cu m/mole(SRC), based upon its vapor pressure, 0.02 mm Hg(3), and assigned value for water solubility, 1X10+6 mg/L (miscible)(4). 1,3-Butanediol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). 1,3-Butanediol is expected to be readily biodegraded based on modified Sturm test results of 80.5% in 28 days(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 1,3-butanediol 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 2.4X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 0.02 mm Hg(4), and assigned value for water solubility, 1X10+6 mg/L (miscible)(5). 1,3-Butanediol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of -0.29(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 1,3-Butanediol is expected to be readily biodegraded based on modified Sturm test results of 80.5% in 28 days(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3-butanediol, which has a vapor pressure of 0.02 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3-butanediol 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 12 hours(SRC), calculated from its rate constant of 3.32X10-11 cu cm/molecule-sec at 25 °C(3). 1,3-Butanediol 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).

1,3-Butanediol was detected at <0.1 mg/kg in paprika oleoresin extracted from the Capsicum frutescens pepper obtained from Murcia, Spain(1). 1,3-Butanediol was detected in honey from Indiana and Ohio, the amount increased in some products adulterated with high fructose corn syrup(2).

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.org

IDENTIFICATION AND USE: 1,3-Butanediol is an odorless, colorless, viscous liquid with a sweet flavor and bitter aftertaste. It is used as an intermediate in manufacture of polyester plasticizers; humectant for cellophane, tobacco; and in the cosmetic and pharmaceutical industry as a glycerin substitute.1,3-Butanediol also has some mold inhibiting action. It is not registered for current pesticide 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. HUMAN EXPOSURE AND TOXICITY: 1,3-Butanediol is not irritating to human skin or mucous membranes. When applied to the human eye it causes immediate severe stinging, but irrigation with water brings rapid complete relief. ANIMAL STUDIES: Eye irritation occurred in one individual, although its irritant potency in rabbits appeared low. It was of low acute oral toxicity to rodents. No treatment-related effects on mortality, body weight gain, organ weights, hematology, histopathology or neoplastic changes were observed in rats fed 1,3-butanediol in the diet at 1, 3 or 10% (~ 643, 1960 or 6230 mg/kg-bw/day for males or ~ 844, 2330 or 7300 mg/kg-bw/day for females) for two years. Feeding studies in which 1,3-butylene glycol replaced carbohydrate as an energy source found central nervous system effects in rats, dogs and calves. 1,3-Butanediol decreased glucose and increased beta-hydroxybutyrate in lactating goats fed 1,3-butanediol in their diets.1,3-Butylene glycol was fetotoxic when fed to rats during pregnancy, and a multigeneration feeding study in rats gave some indication of reduced male fertility. No genotoxic activity (dominant lethality or chromosomal damage) was seen in rats treated orally.

Cough.

Redness.

Stinging sensation. Redness.

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of 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; Click on the "Chemical Explorer" button on the tool bar to see the data./[USEPA; ICSS Dashboard Application; Available from, as of April 22, 2015: http://actor.epa.gov/dashboard/]

1,3-Butanediol was qualitatively detected in water samples collected from an advanced waste treatment facility in Pomona, CA on Sep 25, 1974(1). 1,3-Butanediol was detected in wastewater from one of two olive oil processing sludge ponds in the months of Dec 1987, and Oct, Nov and Dec 1988; processing plants were located in Spain(2).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,3-butanediol can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,3-butanediol is expected to have very high mobility in soil.

/HUMAN EXPOSURE STUDIES/ The dermal safety of a 50% aqueous solution of 1,3-butylene glycol was evaluated using patch tests in 200 volunteers aged 6 to 67 years. Visible skin changes signifying reaction to injury were observed in 1 of the subjects. Challenge applications produced no reactions in any of the subjects.

/HUMAN EXPOSURE STUDIES/ ...Human volunteers tolerated a diet containing up to 10% of 1,3-butanediol for 5 to 7 days with no adverse effects as judged by blood tests; however, there was a slight decrease in blood glucose levels.

/SIGNS AND SYMPTOMS/ A tiny drop /of 1,3-butanediol/ applied to the human eye causes immediate severe stinging, but irrigation with water brings rapid complete relief.

/SIGNS AND SYMPTOMS/ ... /1,3-Butanediol/ is not irritating to human skin or mucous membranes.

1,3-Butanediol is an indirect food additive for use only as a component of adhesives.

1,3-Butylene glycol is a food additive permitted in feed and drinking water of animals.

1,3-Butylene glycol is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.

1,3-Butylene glycol (1,3-butanediol) may be safely used in food in accordance with the following prescribed conditions: (a) The substance meets the following specifications: (1) 1,3-Butylene glycol content: Not less than 99 percent. (2) Specific gravity at 20/20 °C: 1.004 to 1.006. (3) Distillation range: 200 deg-215 °C. (b) It is used in the minimum amount required to perform its intended effect. (c) It is used as a solvent for natural and synthetic flavoring substances except where standards of identity issued under section 401 of the act preclude such use.

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 safety 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. Butylene glycol is found on List D. Case No: 4016; 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): Butylene glycol; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 1,3-Butylene glycol is produced, as an intermediate or a final product, by process units covered under this subpart.

Butanediol is metabolized by the liver... beta-hydroxybutyric acid /a main metabolite/ is further metabolized in the tricarboxylic acid cycle to carbon dioxide, which accounts for about 90% of the dose administered. In other studies... in which rats were fed 1,3-butanediol for 3 to 7 weeks, it was found that the blood level of beta-hydroxybutyrate, was also higher than normal.

R- and S-1,3-butylene glycol are taken up by the isolated liver of fed or starved rats at the same rate. R-1,3-butylene glycol is mainly transformed to the physiological ketone bodies R-3-hydroxybutyrate and acetoacetate. Only 29-38&% of the S-enantiomer are converted into physiological ketone bodies. The S-enantiomer is further metabolised to S-3-hydroxybutyrate (not a natural compound), lipids and carbon dioxide. Based on these results it can be concluded that the test item is metabolised via physiological pathways, suggesting that it has a low potential to accumulate.

CIR ingredient: Butylene Glycol

Used as an intermediate in the manufacture of polyester plasticizers; as a humectant for cellophane and tobacco; in polyurethanes and special polyester resins; in surface active agents; as a coupling agent; as a solvent; as a food additive and flavoring; in the cosmetics and pharmaceutical industries as a glycerin substitute; for deicing of aircraft; [HSDB]

For 1,3-butanediol (USEPA/OPP Pesticide Code: 042205) 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."

Intermediate in manufacture of polyester plasticizers; humectant for cellophane, tobacco. Has some mold inhibiting action.

Polyesters, polyurethanes, surface active agents; plasticizers, humectant, coupling agent, solvent, food additive, flavoring.

2023: 25,000,000 - <40,000,000 lb

1,3-Butanediol 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).

Acetaldol is prepared by acetaldehyde self-condensation in aqueous alkaline solutions. Acetaldehyde conversion cannot be carried higher than 66.6% because aldol and acetaldehyde combine to yield 2,6-dimethyl-1,3-dioxan-4-ol. The bound acetaldehyde is held so tenaciously that most commercial aldol is essentially equivalent to 2,6-dimethyl-1,3-dioxan-4-ol: Higher condensation products are often present. It is difficult to decompose 2,6-dimethyl-1,3-dioxan-4-ol into aldol without simultaneously dehydrating it to crotonaldehyde. Steam stripping is one of the most practical ways of removing the bound acetaldehyde. Aldol is led directly to a hydrogenation system where it is reduced in the presence of Raney nickel or other catalysts. Any of the acetaldehyde or 2,6-dimethyl-1,3-dioxan-4-ol left is reduced to ethanol and 2,4-dimethyl-1,3-dioxane, both of which are efficiency losses for the process. Low-boilers are striped from the hydrogenated product and pure 1,3-butylene glycol is obtained by distillation under reduced pressure.

Usually prepared by catalytic hydrogenation of aldol using Raney nickel.

From formaldehyde and propylene via pressure and a catalyst.

1,3-Butylene glycol can be recovered as a by-product of ethyl acetate manufactured through the Tischenko reaction of acetaldehyde.

EPA Safer Chemical Functional Use Classes -> Solvents

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Fragrance Ingredients

Food Additives -> CARRIER_SOLVENT -> JECFA Functional Classes

Food Additives -> CARRIER_SOLVENT -> JECFA Functional Classes

Food Additives -> CARRIER_SOLVENT -> JECFA Functional Classes

All Other Basic Organic Chemical Manufacturing

1,3-Butanediol: ACTIVE

1,3-Butylene glycol efficient antimicrobial agent, inhibiting gram-neg & gram-pos microorganisms, molds & yeasts. It is not sporicidal.

Produced as an intermediate in the manufacture of butadiene from acetadol. This process has, however, been abandoned by most companies.