1,3-Butanediol
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1,3-Butanediol
structure -
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CAS No:
107-88-0
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Formula:
C4H10O2
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Chemical Name:
1,3-Butanediol
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Synonyms:
1,3-Butanediol;β-Butylene glycol;1,3-Butylene glycol;1,3-Dihydroxybutane;Methyltrimethylene glycol;1-Methyl-1,3-propanediol;Butylene glycol;3-Hydroxy-1-butanol;DL-1,3-Butanediol;(±)-Butane-1,3-diol;(RS)-1,3-Butanediol;NSC 402145;13BGK;Jeechem Bugl;Niax DP 1022;Haisugarcane BG;Celtol 1,3-BG;18826-95-4;817176-75-3
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CAS No:
Description
1,3-Butylene glycol has a sweet flavor with bitter aftertaste and is odorless when pure. colourless liquid Butylene glycol occurs as a clear, colorless, viscous liquid with a sweet flavor and bitter aftertaste.ChEBI: A butanediol compound having two hydroxy groups in the 1- and 3-positions.1,3-Butanediol is an organic chemical which belongs to the family of secondary alcohols. At present, 1,3-butanediol is used mainly in surfactants, inks, solvents for natural and synthetic flavoring agents an
Liquid|COLOURLESS VISCOUS HYGROSCOPIC LIQUID.
Butane-1,3-diol is a butanediol compound having two hydroxy groups in the 1- and 3-positions. It is a butanediol and a glycol.
1,3-Butanediol Basic Attributes
90.122
90.12
203-529-7
1182
402145|6966
DTXSID8026773
Viscous liquid|Pure compound is colorless
29053920
Characteristics
40.5
-0.29 (est)
Liquid
1.0059 g/cm3 @ Temp: 20 °C
<-50 °C
207.5 °C @ Press: 760 Torr
121°C
n 20/D 1.44(lit.)
Solubility in water: good
2-8ºC
Vapour pressure, Pa at 20°C: 8
Relative vapour density (air = 1): 3.2
LD50 orally in Rabbit: 18610 mg/kg LD50 dermal Rabbit > 20000 mg/kg
1.9-12.6%(V)
Practically odorless
Sweet flavor with bitter aftertaste
Henry's Law constant = 2.4X10-9 atm-cu m/mol at 25 °C (est)
pKa = 15.1 at 25 °C
1 gal weighs 8.398 lb at room temp; dielectric constant: 28.8 at 25 °C. Very hygroscopic, will absorb 38.5 wt % of water within 144 hrs at 81% relative humidity.|BP: 207.5 °C; density: 1.0053 at 20 °C; index of refraction: 1.4410 at 20 °C. Soluble in chloroform /1,3-Butanediol (+/-)-/|UV: 5-22 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /1,3-Butanediol (+/-)-/|BP: 107-110 mm Hg at 23 °C; density: 1.005 at 20 °C; specific optical rotation: -18.8 deg at 25 °C/D (alcohol, 4.4%) /1,3-Butanediol (R)-/|For more Other Experimental Properties (Complete) data for 1,3-BUTANEDIOL (8 total), please visit the HSDB record page.
741 °F (393 °C)|394 °C
Heat of vaporization = 16.2 kcal/mol at 25 °C
Critical temp = 643 K; critical pressure = 5X10+6 Pa
Safety Information
NONH for all modes of transport
1
R36/37/38
24/25
EK0440000
F
Butylene glycol is hygroscopic and should be stored in a well-closed container in a cool, dry, well-ventilated place. When heated to decomposition, butylene glycol emits acrid smoke and irritating fumes.
Stable. Flammable. Hygroscopic - protect from air and moisture. Incompatible with strong oxidizing agents.
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501
H226
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.
Incompatible with oxidizing materials.
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.
Combustible.
|Warning|H226 (95.19%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 2500 companies from 7 notifications to the ECHA C&L Inventory.
Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166 (EU).|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: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Combustible when exposed to heat or flame.
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.
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.
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.
Collect leaking and spilled liquid in sealable containers as far as possible. Wash away remainder with plenty of water.
No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
The substance is irritating to the eyes, skin and respiratory tract.
NO open flames.
Use ventilation.
Protective gloves.
Wear safety spectacles.
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.
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).
1,3-Butanediol is an ingredient found in >100 personal care products(1). 1,3-Butanediol was not detected in 54 electronic cigarette liquid samples purchased from 13 online venders representing 5 different countries of origin (8-Germany, 1-Spain, 3-United Kingdom, 1-Romania)(2).
Toxicity
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.
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.
2(?). 2= Slightly toxic, probable oral lethal dose human is 5-15 g/kg; between 1 pint & 1 quart for 70 kg person (150 lb). Said to be slightly more toxic than propylene glycol...
LD50 Rat oral 22800 mg/kg.|LD50 Mice sc 16.5 mL/kg|LD50 Rat sc 20.1 mL/kg|LD50 Guinea pig oral 11 g/kg|For more Non-Human Toxicity Values (Complete) data for 1,3-BUTANEDIOL (6 total), please visit the HSDB record page.
1,3-Butanediol's production and use mainly as a component of special polyester resins(1), a component of polyurethane, surface-active agents and plasticizers, and as an humectant, coupling agent, solvent, food additive and flavoring(2) may result in its release to the environment through various waste streams(SRC). Its former use as an aircraft de-icing agent(3) resulted in its direct release to the environment(SRC).
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).
The rate constant for the vapor-phase reaction of 1,3-butanediol with photochemically-produced hydroxyl radicals has been reported as 3.32X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 12 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). 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). 1,3-Butanediol does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3 was calculated in fish for 1,3-butanediol(SRC), using an estimated log Kow of -0.29(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).
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.
The Henry's Law constant for 1,3-butanediol is estimated as 2.4X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 0.02 mm Hg(1), and assigned value for water solubility, 1X10+6 mg/L (miscible)(2). This Henry's Law constant indicates that 1,3-butanediol is expected to be essentially nonvolatile from water and moist soil surfaces(3). 1,3-Butanediol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
DRINKING WATER: 1,3-Butanediol was not detected in drinking water samples collected from advanced waste treatment facilities(1).
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).
According to the 2012 TSCA Inventory Update Reporting data, one reporting facility estimates the number of persons reasonably likely to be exposed in the manufacturing, processing, or use of 1,3-butanediol in the United States may be 500-999 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 19,336 workers (5266 of these are female) were potentially exposed to 1,3-butanediol in the US(1). Occupational exposure to 1,3-butanediol may occur through inhalation and dermal contact with this compound at workplaces where 1,3-butanediol is produced or used. Monitoring and use data indicate that the general population may be exposed to 1,3-butanediol via ingestion of food, and dermal contact with consumer products containing 1,3-butanediol(SRC).
Drug Information
/EXP THER/ This study examined the effect of 1,3-butanediol on the selective loss of CA1 pyramidal neurons following a short period of near-complete forebrain ischemia. Injection of 55 mmol 1,3-butanediol/kg body weight at 24 h of recirculation and again at 36 hr following 10 min of forebrain ischemia markedly reduced damage to CA1 neurons examined at 72 hr of recirculation compared with that in saline-treated rats. Comparable treatment with ethanol did not cause significant protection. Neuronal loss was also not reduced by 1,3-butanediol treatment when the ischemic period was extended to 15 min or by single treatments at 24 hr or 36 hr following 10 min of ischemia. However, a single treatment 5 min after reversal of 10 min of ischemia was effective in ameliorating cell loss. The difference in effectiveness of 1,3-butanediol following 10 min and 15 min of ischemia is consistent with a number of previous studies, indicating that the processes leading to loss of CA1 neurons are modified when the ischemic period is extended. Previous findings that 1,3-butanediol reduced damage in other ischemia-susceptible neuronal subpopulations but not in CA1 neurons most likely reflected the longer period of ischemia which was used. The results of the present investigation demonstrate that administration of 1,3-butanediol offers a novel approach for interfering with post-ischemic loss of CA1 neurons following a brief ischemic period which is effective even when initiated after prolonged recirculation periods.|/EXP THER/ The biochemical effect of S-1,3-butanediol on streptozotocin induced diabetic rats was studied. Rats were made diabetic by the intraperitoneal injection of 40 mg/kg body weight streptozotocin in sodium citrate buffer. A dosage of 25 mmol/kg body weight of S-1,3-butanediol was injected intraperitoneally for treatment. The streptozotocin induced diabetic rats showed a marked increase in blood glucose level, and significant increase in the level of cholesterol, triglycerides and free fatty acids. The glycogen levels in liver and kidney were greatly decreased in diabetic rats. Treatment with butanediol normalized the glucose and glycogen level but had no significant effect on protein and lipid levels.|/EXP THER/ We previously showed that intrastriatal administration of aminooxyacetic acid (AOAA) produces striatal lesions by a secondary excitotoxic mechanism associated with impairment of oxidative phosphorylation. In the present study, we show that and the specific complex I inhibitor rotenone produces a similar neurochemical profile in the striatum, consistent with an effect of AOAA on energy metabolism. Lesions produced by AOAA were dose-dependently blocked by MK-801, with complete protection against GABA and substance P depletions at a dose of 3 mg/kg. AOAA lesions were significantly attenuated by pretreatment with either 1,3-butanediol or coenzyme Q10, two compounds which are thought to improve energy metabolism. These results provide further evidence that AOAA produces striatal excitotoxic lesions as a consequence of energy depletion and they suggest therapeutic strategies which may be useful in neurodegenerative diseases.|/EXP THER/ In order to assess the therapeutic value of 1,3 butanediol in ethylene glycol toxicosis, mixed-bred dogs were given an oral dose of commercial antifreeze at 6 mL/kg of body weight (0 hour) and treated (IV) 7 times at 6-hour intervals with 5.5 mL/kg of body weight 1,3 butanediol solution (20% in physiological saline solution) beginning at 8, 12, and 21 hours. Serum glycolic acid concentration was quantitated by high-pressure liquid chromatography. Three dogs that were given ethylene glycol, but no 1,3 butanediol treatment, died with elevated serum glycolic acid concentrations. Five dogs were given ethylene glycol and 1,3 butanediol treatment. Of 2 dogs treated at 8 hours, 1 survived and 1 died at 39 hours; 1 treated at 12 hours and 1 treated at 21 hours survived; 1 dog died soon (27 hours) after treatment was initiated at 21 hours. Four of the 5 dogs had dramatically decreased serum glycolic acid concentrations after 1,3 butanediol treatment, indicating its effectiveness in inhibiting alcohol dehydrogenase-dependent glycolic acid formation in vivo.|/EXP THER/ Pre-partum feeding of 1,3-butanediol to sows has been shown to improve the metabolic status and survival rate of neonatal pigs. To evaluate the efficacy of short-term, pre-partum feeding of 1,3-butanediol on pig and sow productivity on a large scale and low concentration was the focus of the research. The secondary objective was to determine if pre-partum feeding of 1,3-butanediol had any effect on survival rate and weight gain of lesser body weight pigs, sow body weight and subsequent sow reproductive performance. In a large commercial unit, 2537 sows were fed one of two pre-partum diets (0% or 4.55% 1,3-butanediol) on Day 108+/-3 of pregnancy. 1,3-butanediol provided 8% of the total metabolizable energy. Pigs born live in those litters were equalized by cross-fostering among sows receiving the same pre-partum diet. Pigs were weaned from the sows at 16+/-3 days post-partum and return of sows to estrus and conception rates were determined. Pre-partum feeding of 1,3-butanediol reduced (P=0.01) pre-weaning pig mortalities from 1.44 to 1.24 pigs per litter. The reduction in pig mortality was independent of length of 1,3-butanediol feeding (4 to 11 days). In a subset of 750 litters, four lesser birth-weight pigs from each litter were tagged and monitored to determine the effect of 1,3-butanediol on survival rates and pre-weaning weight gain of pigs with the greatest mortality risk. 1,3-butanediol reduced (P=0.01) pre-weaning mortality of these low birth weight pigs by 5.27%. Based on these data, short-term pre-partum feeding of 1,3-butanediol effectively improves pre-weaning pig productivity at a lower concentration than previously reported.
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.
Crude diol often contains acetaldehyde, butyraldehyde, crotonaldehyde, various oligomers of the aldehydes, as well as several acetals.
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.
Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Higher alcohols (>3 carbons) and related compounds/|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 shock and treat if necessary ... . Monitor for pulmonary edema 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 (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Higher alcohols (>3 carbons) and related compounds/|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 as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) 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 ... . Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose strip or glucometer readings below 50 mg) and administer 50% dextrose if necessary ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Higher alcohols (>3 carbons) and related compounds/|Emergency and supportive measures. 1. Maintain an open airway and assist ventilation if necessary. Administer supplemental oxygen. 2. Treat coma, convulsions, cardiac arrhythmias, and metabolic acidosis if they occur. Observe the patient for several hours to monitor for development of metabolic acidosis, especially if the patient is symptomatic or there is known co-ingestion of ethanol. 3. Treat hypocalcemia with IV calcium gluconate or calcium chloride. /Ethylene glycol and other glycols/
/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
The substance can be absorbed into the body by inhalation of its vapour.
Cough.
Redness.
Stinging sensation. Redness.
1,3-Butanediol Use and Manufacturing
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.
1,3-Butanediol is used in the synthesis of colchicine derivatives as anticancer agents. Also used in the synthesis of dual peroxisome proliferator-activated gamma and delta agonists acting as euglycem ic agents in the treatment of diabetes. Its most extensive use is as an intermediate in the manufacture of polyester plasticisers and other chemical products. It finds some use as a solvent and humectant, a useful chemical intermediate. It has extensive application in the manufacture of structura
Intermediates
Personal care products
10,000,000 - 50,000,000 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).
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.
Method: NIOSH 5523, Issue 1; Procedure: gas chromatography with flame ionization detection; Analyte: 1,3-butylene glycol; Matrix: air; Detection Limit: 6 ug/sample.|GC/MS.
A young man was found to have 1,3-butanediol in his blood, much more after ethanol ingestion. This substance reacted in the enzyme procedure for measuring blood alcohol, giving falsely high values. The 1,3-butanediol was detected by gas chromatography.|We developed gas chromatographic-mass spectrometric assays for the enantiomers of 1,2-propanediol, 1,3-butanediol, 1,3-pentanediol, and their corresponding hydroxyacids, lactate, beta-hydroxybutyrate, and beta-hydroxypentanoate (3-hydroxyvalerate) in biological fluids. The corresponding ketoacids, acetoacetate and beta-ketopentanoate, can be assayed simultaneously by pretreating the samples with NaB2H4. The assays involve spiking the samples with deuterated internal standards, deproteinization, ether extraction, and derivatization of the carboxyl groups with (R,S)-2-butanol/HCl and of the hydroxyl groups with chiral (S)-(+)-2-phenylbutyryl chloride. Mass spectrometric analysis is conducted under ammonia positive chemical ionization. We used these assays to follow the metabolism of diol enantiomers in dogs. For (R,S)-1,3-butanediol and (R,S)-1,3-pentanediol, the uptakes from dog plasma of the R and S enantiomer of each diol were identical. In contrast, the metabolism of (S)-1,2-propanediol was faster than that of (R)-1,2-propanediol. (R)-1,2-Propanediol is formed during acetone metabolism, while (R,S)-1,3-butanediol and (R,S)-1,3-pentanediol are potential nutrients.
EPA Safer Chemical Functional Use Classes -> Solvents|Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern|Food additives -> Flavoring Agents|Food Additives -> CARRIER_SOLVENT; -> JECFA Functional Classes|Cosmetics -> Humectant; Solvent
Flavoring Agents|Food Additives -> CARRIER_SOLVENT;
Computed Properties
Molecular Weight:90.12
XLogP3:-0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:90.068079557
Monoisotopic Mass:90.068079557
Topological Polar Surface Area:40.5
Heavy Atom Count:6
Complexity:28.7
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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