Glycidol
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Glycidol
structure -
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CAS No:
556-52-5
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Formula:
C3H6O2
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Chemical Name:
Glycidol
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Synonyms:
2-Oxiranemethanol;Glycidol;1-Propanol,2,3-epoxy-;Oxiranemethanol;Epihydrin alcohol;Glycidyl alcohol;3-Hydroxy-1,2-epoxypropane;Glycide;2,3-Epoxy-1-propanol;Allyl alcohol oxide;3-Hydroxypropylene oxide;1,2-Epoxy-3-hydroxypropane;1-Hydroxy-2,3-epoxypropane;2-(Hydroxymethyl)oxirane;Oxiranylmethanol;Epiol OH;(RS)-Glycidol;dl-Glycidol;(±)-Glycidol;(±)-2,3-Epoxy-1-propanol;Racemic glycidol;NSC 46096;Oxiran-2-ylmethanol;61915-27-3;98913-54-3;1852481-80-1
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CAS No:
Description
colourless liquid Glycidol is a colorless liquid.
Glycidol is an odorless clear colorless liquid. (NTP, 1992)|COLOURLESS SLIGHTLY VISCOUS LIQUID.|Colorless, odorless liquid.|Colorless liquid.
Glycidol is an odorless clear colorless liquid. (NTP, 1992)|Glycidol is an epoxide and a primary alcohol. It derives from a 1,2-epoxypropane.
Glycidol Basic Attributes
74.08
74.08
209-128-3
0159
46096
2810
DTXSID4020666
Colorless, slightly viscous liquid|Colorless liquid
2910900090
Characteristics
32.8
-0.95
White to light yellow-beige Powder, Crystals or Chunks
1.115 g/cm3 @ Temp: 20 °C
-45 °C
160 °C @ Press: 760 Torr
178 °F
1.455
H2O: soluble
2-8°C
0.9 mm Hg ( 25 °C)
2.15 (vs air)
Oral-Rat LD50: 420 mg/kg; Oral-Mouse LD50: 431 mg/kg
Flammable, spicy and irritating smoke emitted from the fire
Explodes when heated or in the presence of strong acids, bases, metals (e.g., copper, zinc), and metal salts (e.g., aluminum chloride, iron(III) chloride, tin(IV) chloride).
Henry's Law constant = 5.84X10-9 atm-cu m/mol at 25 °C (est)
Specific gravity: 1.115 at 20 °C/4 °C|1 ppm = 3.03 mg/cu m at 25 °C, 760 mm Hg; 1 mg/L = 330 ppm at 25 °C, 760 mm Hg|MW: 74.079. MP: 045 °C; BP: decomposes at 167 °C; 66 °C at 2.5 mm Hg. Density: 1.1143 g/cu cm at 25 °C. Index of refraction: 1.4287 at 20 °C/D. Very soluble in water, acetone, ethyl ether, ethanol; soluble in benzene, chloroform /DL-Glycidol/|BP: 167 °C (decomposes). Density: 1.117 g/cu cm at 20 °C. Index of refraction: 1.4293 at 16 °C/D. Specific optical rotation: + 15 deg (undiluted) at 25 °C/D. Very soluble in water, acetone, ethyl ether, ethanol. /D-Glycidol/|Specific optical rotation: 15 (undiluted) at 25 °C/D. BP: 167 °C (decomposes). Index of refraction: 1.4293 at 16 °C/D. Density: 1.1050 at 18 °C. Soluble in water, ethanol, ethyl ether, acetone, benzene, chloroform /L-Glycidol/|Raman: 205 (Sadtler Research Laboratories spectral collection) /Glycidol (L)/|Hydroxyl radical reaction rate constant = 4.66X10-12 cu cm/molec-sec at 25 °C (est)
Sensitive to moisture.
Alcohols and Polyols
Polymerizable
GLYCIDOL is sensitive to moisture. It is also sensitive to light. It may polymerize if heated above room temperature. It may darken on storage. Stability studies of this chemical stored for two week protected from light indicated definite decomposition at 140° F, and strongly indicated instability at 77° F. A solution of this compound in water was found to be unstable when stored at room temperature, even after one day in the dark. This chemical is incompatible with strong oxidizers. It will undergo explosive decomposition in the presence of strong acids or bases, salts (such as aluminum chloride, iron(III)chloride or tin(IV) chloride) or metals (such as copper and zinc). It is also incompatible with nitrates. It will attack some forms of plastics, rubber and coatings. (NTP, 1992)
415 °C
Class IIIA Combustible Liquid: Fl.P. at or above 140°F and below 200°F.
Safety Information
III
6.1(b)
UN 2810 6.1/PG 3
3
45-60-21/22-23-36/37/38-68
53-45-36/37-26
UB4375000
T
Storeroom low temperature, ventilated, dry; fireproof; stored separately from oxidants, food ingredients
Toxic
High temperature mixed with air can be explosive
Stability Stable, but may explode on contact with strong acids, strong bases, heavy metals, heavy metal salts. May decompose on exposure to water or moist air.
P201-P261-P280-P304 + P340 + P312-P308 + P313-P403 + P233
H242-H302 + H312-H315-H319-H331-H335-H341-H350-H360F
This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material.|SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for Glycidol (7 total), please visit the HSDB record page.
Violent reaction with strong oxidizers, nitrates. Decomposes on contact (especially in the presence of heat) with strong acids, strong bases, water, metal salts (e.g., aluminum chloride, ferric chloride, tin chloride) or metals (copper, zinc), causing fire and explosion hazard ... Attacks some plactics, rubber, and coatings.|Strong oxidizers, nitrates.
DHHS/NTP; Toxicology & Carcinogenesis Studies of Glycidol in F344/N Rats and B6C3F1 Mice(Gavage Studies) Technical Report Series No. 374 (1990) NIH Publication No. 90-2829|IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Geneva: World Health Organization, International Agency for Research on Cancer, vol 77, p. 477 (2000).. IARC Monographs provide critical reviews of data on carcinogenicity for agents to which humans are known to be exposed and on specific exposure situations.[Available at: http://monographs.iarc.fr/index.php]|National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Glycidol (556-52-5) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s092glyc.pdf]
This chemical is combustible. (NTP, 1992)|Combustible. Above 72 °C explosive vapour/air mixtures may be formed.|Carcinogens, Mutagens, Flammable - 2nd degree
|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P311, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|H242: Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]|P201, P202, P210, P220, P234, P260, P261, P264, P270, P271, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P321, P322, P330, P363, P370+P378, P403+P233, P403+P235, P405, P411, P420, and P501|H302 (99.65%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P311, P312, P314, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 286 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H242 (100%): Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.|P201, P202, P260, P261, P264, P270, P271, P280, P281, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|H227: Combustible liquid [Warning Flammable liquids]|P201, P202, P210, P260, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P311, P312, P314, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. (NIOSH, 2016)|Employees should be provided with and required to use impervious clothing, gloves, face shields (eight-inch minimum), and other appropriate protective clothing, necessary to prevent repeated or prolonged skin contact with liquid glycidol.|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Respirator Recommendations: Up to 150 ppm [Table#3664]|For more Personal Protective Equipment (PPE) (Complete) data for Glycidol (11 total), please visit the HSDB record page.|(See protection codes)
Forms explosive mixture with air.|Explodes when heated or in the presence of strong acids, bases, metals (e.g., copper, zinc), and metal salts (e.g., aluminum chloride, iron(III) chloride, tin(IV) chloride).
Suitable extinguishing media. For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary. Further information: Use water spray to cool unopened containers.|Use dry chemical, carbon dioxide, alcohol foam, or polymer foam extinguishers. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream users or potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or shows any signs of deforming), withdraw immediately to a secure position ... The only respirators recommended for fire fighting are self-contained breathing apparatuses that have full facepieces and are operated in a pressure-demand or other positive-pressure mode.
ACCIDENTAL RELEASE MEASURES. Personal precautions: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.|Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Ventilate area of spill or leak. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Keep this chemical out of a confined space, such as a sewer, because of the possibility of an explosion, unless the sewer is designed to prevent the build-up of explosive concentrations. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations.|1. Remove all ignition sources. 2. Ventilate area of spill or leak. 3. For small quantities, absorb on paper towels. Evaporate in safe place (such as fume hood) ... Burn paper in suitable location away from combustible materials. Large quantities can be collected and atomized in suitable combustion chamber, or absorbed in vermiculite, dry sand, earth, or similar material and disposed in a sanitary landfill.|PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/
Obtain special instructions before use.|Avoid contact with skin and eyes. Avoid inhalation of vapour or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.|If inhaled ... , move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact, wash off with soap and plenty of water. Take victim immediately to hospital. Consult a physician. In case of eye contact, rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.|Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.|For more Preventive Measures (Complete) data for Glycidol (20 total), please visit the HSDB record page.
PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/
A skin irritant|Hazard warning: exposure to vapors has been found to have adequate warning properties (eye & resp irritation)....|Glycidol vapor is an irritant to the eyes and upper respiratory tract, & a skin irritant. ...
Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 50 ppm (150 mg/cu m).|Vacated 1989 OSHA PEL TWA 25 ppm (75 mg/cu m) is still enforced in some states.
Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 25 ppm (75 mg/cu m).
Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable glass or mild steel containers as far as possible. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations.
Store only if stabilized. Cool. Dry. Well closed. Ventilation along the floor. Separated from strong bases, strong acids and food and feedstuffs.
A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system. Exposure far above the OEL could cause lowering of consciousness.
This substance is probably carcinogenic to humans. Animal tests show that this substance possibly causes toxicity to human reproduction or development.
NO open flames. NO contact with incompatible substances. See Chemical Dangers. Above 72 °C use a closed system and ventilation.
AVOID ALL CONTACT! AVOID EXPOSURE OF (PREGNANT) WOMEN!
Use ventilation, local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield or eye protection in combination with breathing protection.
Toxicity
highly toxic
In rats pretreated with 278 mg of 2,3-epoxypropan-1-ol the acute LD50 of 1,2-dichloroethylene was decreased /by a factor of 5 (to less than 40 mg/kg/ & doses of 1,1-dichloroethylene as low as 12.5 mg/kg increased aspartate transaminase levels.
LD50 Rat oral 420 mg/kg|LD50 Rat ip 200 mg/kg|LC50 Rat inhalation 580 ppm/8 hr|LD50 Mouse oral 431 mg/kg|For more Non-Human Toxicity Values (Complete) data for Glycidol (7 total), please visit the HSDB record page.
/AQUATIC SPECIES/ The 14 day LC50 value of glycidol to the guppy (Poecilia reticulata) was determined, and investigated through the construction of a quantitative structure activity relationship (QSAR). Both hydrophobicity and alkylating potency of the compound were found to be necessary parameters for the satisfactory description of the LC50 data. The log LC50 experimental data for glycidol was 2.83 umol/L as compared to the calculated QSAR value of 3.00 umol/L.
... Groups of 15 male and 15 female haploinsufficient p16(Ink4a)/p19(Arf) mice were administered 0, 25, 50, 100, or 200 mg glycidol/kg body weight in deionized water by gavage, 5 days per week for 40 weeks. Survival of 200 mg/kg male and female mice was less than that of the vehicle control groups, but the differences were not significant. Mean body weights of 200 mg/kg male mice and 50, 100, and 200 mg/kg female mice were less than those of the vehicle controls. The left testis, left epididymis, and left cauda epididymis weights were significantly decreased in 200 mg/kg males; the number of sperm heads per cauda epididymis were also significantly decreased in this group. Enlarged spleen and foci of discolored liver were observed in 200 mg/kg male mice at necropsy. These findings corresponded to infiltration by histocytic sarcoma or extramedullary hematopoiesis. The incidences of histiocytic sarcoma were increased in dosed groups of males and in females administered 50 mg/kg or greater, and the incidences in 50 and 200 mg/kg males were significantly greater than that in the vehicle control group. In the lung, incidences of alveolar/bronchiolar adenoma were significantly increased in 100 mg/kg males and 200 mg/kg females; multiple adenomas were seen in some dosed males. Squamous cell papillomas of the forestomach were seen in one 200 mg/kg male, one 100 mg/kg female, and three 200 mg/kg females. Significantly increased incidences of epithelial hyperplasia occurred in the forestomach of 200 mg/kg males and females. Neuronopathy, gliosis, and hemorrhage of the brain were observed at various sites in a few 200 mg/kg males and 100 and/or 200 mg/kg females. ... Under the conditions of this 40-week gavage study, there was clear evidence of carcinogenic activity of glycidol in male haploinsufficient 16(Ink4a)/p19(Arf) mice based on the occurrence of histiocytic sarcomas. The increased incidences of alveolar/bronchiolar adenomas in male mice were also considered to be related to glycidol administration. There was some evidence of carcinogenic activity of glycidol in haploinsufficient p16(Ink4a)/p19(Arf) female mice based on the occurrence of alveolar/bronchiolar adenoma. The occurrence of forestomach papillomas in female mice may also have been related to glycidol administration. Treatment of male and female haploinsufficient p16(Ink4a)/p19(Arf) mice with glycidol was associated with forestomach hyperplasia and neuronopathy in the and brain.|The frequency of micronucleated erythrocytes was monitored in peripheral blood of male and female haploinsufficient p16(Ink4a)/p19(Arf) mice in the 40-week study. No significant increases were observed at 6.5, 13, or 19.5 weeks; small but statistically significant increases were seen in both male and female mice sampled at 26 and 40 weeks.|... Toxicology and carcinogenesis studies were conducted by administering glycidol (94% pure, containing 1.2% 3-methoxy-1,2-propanediol, 0.4% 3-chloro-1,2-propanediol, 2.8% diglycidyl ether, and 1.1% 2,6-dimethanol-1,4-dioxane) in water by gavage to groups of F344/N rats and B6C3F1 mice of each sex for ... 2 yr. ... Doses selected for the 2 yr studies of glycidol were 37.5 and 75 mg/kg for rats and 25 and 50 mg/kg for mice. Conclusions: Under the conditions of these 2 yr gavage studies, there was clear evidence of carcinogenic activity of glycidol for male F344/N rats, based on increased incidences of mesotheliomas of the tunica vaginalis; fibroadenomas of the mammary gland; gliomas of the brain; and neoplasms of the forestomach, intestine, skin, Zymbal gland, and thyroid gland. There was clear evidence of carcinogenic activity for female F344/N rats, based on increased incidences of fibroadenomas and adenocarcinomas of the mammary gland; gliomas of the brain; neoplasms of the oral mucosa, forestomach, clitoral gland, and thyroid gland; and leukemia. There was clear evidence of carcinogenic activity for male B6C3F1 mice based on increased incidences of neoplasms of the harderian gland, forestomach, skin, liver, and lung. There was clear evidence of carcinogenic activity for female B6C3F1 mice, based on increased incidences of neoplasms of the harderian gland, mammary gland, uterus, subcutaneous tissue, and skin. Other neoplasms that may have been related to the administration of glycidol were fibrosarcomas of the glandular stomach in female rats and carcinomas of the urinary bladder and sarcomas of the epididymis in male mice.|... Glycidol was ... selected for immunotoxicity studies /using female B6C3F1 mice/. ... Female B6C3F1 mice ... were administered glycidol daily for 14 days at doses of 25, 125 and 250 mg/kg. Glycidol was administered by gavage as a solution in sterile distilled water. ... Mice exposed to glycidol at doses up to and including 250 mg/kg did not have significant decreases in body weight or body weight gain when evaluated over the two-week exposure period. While the brain, thymus, spleen and lungs were unaffected by the glycidol exposure, an increasing trend was observed in liver weights. Additionally, kidney weights were increased (42%) in the glycidol exposure animals dose dependently. No statistically significant effects were observed on leukocyte numbers, leukocyte differentials, reticulocytes, mean corpuscular volume, mean corpuscular hemoglobin or mean corpuscular hemoglobin concentrations. A slight, albeit statistically significant, decrease was observed in the erythroid elements, erythrocytes (4%), hemoglobin (4%), and hematocrit (5%) which was dose related. ... Exposure to glycidol decreased the number of B cells (23%) and decreased the number of CD4+CD8- (15%) in the T cell subsets. Total T cells and the other T cell subsets were not affected. Glycidol produced a dose-dependent decrease (41%) in the antibody-forming cell response to sheep erythrocytes. The proliferative response to mitogens, both Con A and LPS, was not affected. However, a decreasing trend in the proliferative response to F(ab)2+BSF-1 was observed. The proliferative response to allogeneic cells as evaluated in the MLR was not affected and overall the CTL response was not affected. A dose-dependent decrease was observed in the natural killer cell activity (29%) when evaluated at the highest (25:1) effector:target ratio. An increase in cytotoxicity of both resident macrophages alone and resident macrophages stimulated with gamma interferon was observed in animals receiving low dose glycidol exposure. No effect was observed on macrophage cytotoxicity at the middle and high dose groups. The peritoneal cell numbers were not affected at any dose level. In the three host resistance studies conducted, host resistance to Listeria monocytogenes was not affected, while an increase in host resistance to Streptococcus pneumoniae and a decrease in host resistance to the B16F10 Melanoma tumor model was observed. In summary, while most of the immunosuppressive effects resulting from glycidol exposure were observed at the 125 mg/kg and above dose levels, a true no-effect level for glycidol in the female B6C3F1 mouse could not be established since the lowest dose administered significantly altered several parameters including erythrocyte number, hemoglobin, spleen cell number and macrophage cytotoxicity.
Glycidol's production and use as a stabilizer, chemical intermediate, and additive for oil and synthetic hydraulic fluids(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a log Kow of -0.95(2) and a regression-derived equation(3), indicates that glycidol is expected to have very high mobility in soil(SRC). Volatilization of glycidol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.8X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Glycidol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.6 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Utilizing the Japanese MITI test, 85% of the Theoretical BOD was reached in 4 weeks(6) indicating that biodegradation is an important environmental fate process in soil(SRC). Hydrolysis in moist soil may be an important environmental fate process based upon reported hydrolysis half-lives ranging from 12 hours to 4 days at pH 7 in water(7,8).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a log Kow of -0.95(2) and a regression-derived equation(3), indicates that glycidol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 5.8X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 85% of the Theoretical BOD was reached in 4 weeks(7) indicating that biodegradation is an important environmental fate process in water(SRC). The hydrolysis half-lives of glycidol range from 12 hours(8) to 4 days(9) at pH 7.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), glycidol, which has an estimated vapor pressure of 5.6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase glycidol 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 3 days(SRC), calculated from its rate constant of 4.7X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Glycidol 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 glycidol with photochemically-produced hydroxyl radicals has been estimated as 4.7X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The hydrolysis half-life of glycidol is 12 hours at 298 K and pH 7(2). Glycidol reaction rates in water were reported as 0.0071/hr, 0.050/hr, and 4.75/hr at pH values of 7, 3, and 1, respectively(3), corresponding to half-lives of 4 days, 3 hours, and 15 minutes, respectively(SRC). The percentage reacting with water was 15.6%(3). Glycidol 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).
An estimated BCF of 3 was calculated in fish for glycidol(SRC), using a log Kow of -0.95(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
The Koc of glycidol is estimated as 1(SRC), using a log Kow of -0.95(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that glycidol is expected to have very high mobility in soil.
The Henry's Law constant for glycidol is estimated as 5.8X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that glycidol is expected to be essentially nonvolatile from water surfaces(2). Glycidol is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.6 mm Hg(SRC), determined from a fragment constant method(3).
SURFACE WATER: Glycidol was tested for but not detected as part of a monitoring study of 14 hydrophilic chemicals in natural waters in the Kitakyushu area, Japan(1).
According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use for glycidol is 1 to 99; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 4,872 workers (580 of these were female) were potentially exposed to glycidol in the US(1). Occupational exposure to glycidol may occur through inhalation and dermal contact with this compound at workplaces where glycidol is produced or used. Use data indicate that the general population may be exposed to glycidol via inhalation and dermal contact with fuel oils(SRC).
Drug Information
Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)
The comparative disposition of glycidol was investigated in rats following oral (po) or intravenous (iv) administration at doses of 37.5 and 75 mg/kg. These were the doses used in the National Toxicology Program (NTP) oncogenicity study with glycidol. Approximately 87-92% of the dose was absorbed from the gastrointestinal tract of the rat. (14)C-Glycidol equivalents were eliminated in urine (40-48% of dose in 72 hr), feces (5-12%), and exhaled as CO2 (26-32%). At both doses, 9-12% and 7-8% (estimated) of the dose remained in tissues at 24 and 72 hr following dosing, respectively. In general, the concentrations of glycidol equivalents in tissues were proportional to the dose. The highest concentrations of radioactivity were observed in blood cells, thyroid, liver, kidney, and spleen, and the lowest in adipose tissue, skeletal muscle, and plasma. The pattern of distribution of radioactivity in tissues was similar for both the iv and po routes. The total recovery of radioactivity ranged from 87 to 91% of dose. Urinary radioactivity was resolved by high-performance liquid chromatography (HPLC) analysis into 15 metabolites. There were one major (14-21% of the dose) and four lesser metabolites (each representing 2-8%); the others were minor, each representing 1% or less of the dose. In general, the urinary metabolic profile was similar following either iv or po administration at the two doses studied. Previous studies by other investigators suggested that alpha-chlorohydrin, which was presumably formed from glycidol by the HCl in the stomach, was metabolized and excreted in urine as beta-chlorolactic acid. The results of the present study show that very little, if any, urinary radioactivity coeluted with authentic beta-chlorolactic acid following either iv or po administration. Therefore, it is concluded that the conversion of glycidol to alpha-chlorohydrin is quantitatively insignificant. However, it may be significant with regard to glycidol reproductive toxicity. Also, the NTP oncogenicity study with glycidol was carried out within the dose range in which its disposition characteristics were linear.|Absorbed through skin.|Approximately 87-92% of 37.5 or 75 mg/kg body weight (bw) orally administered glycidol is absorbed from the gastrointestinal tract of male Fischer 344 rats. Seven to eight per cent of the dose remained in tissues 72 hr following administration. The highest concentrations of radioactivity were observed in blood cells, thyroid, liver, kidney and spleen.
Glycidol is rapidly hydrolyzed to glycerol (97.2%) and alpha-chlorohydrin (3-chloro-1,2-propanediol, 2.8%) in 0.1 M hydrochloric acid, with a half-life of 10 min. At pH 7 or 8, glycidol readily reacts with glutathione to form S-(2,3-dihydroxypropyl)glutathione.|S-(2,3-Dihydroxypropyl)glutathione, S-(2,3-dihydroxypropyl)cysteine and beta-chlorolactic acid are the major metabolites isolated from rat urine after intraperitoneal administration of glycidol. The generation of beta-chlorolactic acid is presumably a result of initial formation of alpha-chlorohydrin, with subsequent oxidation by alcohol and aldehyde dehydrogenases. Glycidol is hydrolyzed to glycerol by rat liver microsomal preparations.|Liver epoxide hydrase converted glycidol to glycerol. Glycidol was a substrate for lung and liver cytosolic glutathione S-transferases.|... The DNA damaging effects of 3-MCPD and its metabolites, glycidol and beta-chlorolactic acid, /were also studied/ in the in vitro comet assay on CHO cells. /The/ results show the absence of genotoxic potential of 3-MCPD in vivo in the target as well as in the non-target organs. Glycidol, the epoxide metabolite, induced DNA damages in CHO cells. beta-Chlorolactic acid, the main metabolite of 3-MCPD in rats, was shown to be devoid of DNA-damaging effects in vitro in mammalian cells.
Exposure Routes: inhalation, ingestion, skin and/or eye contact Symptoms: Irritation eyes, skin, nose, throat; narcosis Target Organs: Eyes, skin, respiratory system, central nervous system (NIOSH, 2016)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)|(See procedures)
Fresh air, rest. Refer for medical attention.
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.
/SRP:/ 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 if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the 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. /Poisons A and B/|/SRP:/ 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 needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ 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 ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . 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 if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/SIGNS AND SYMPTOMS/ Short Term Exposure: Glycidol affects you when breathed in and by passing through your skin. Irritates the eyes, skin, and respiratory tract. Vapor exposure can damage vision. Exposure can irritate the eyes, nose, throat, and lungs. Higher exposures can cause pulmonary edema, a medical emergency that can be delayed for several hours. This can cause death. High levels can cause you to feel dizzy, lightheaded, confused, excited, to pass out , and even die. May affect the central nervous system. Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. It can irritate the lungs; bronchitis may develop. May cause personality changes, depression, anxiety, or irritability. Possibly carcinogenic to humans. Because this is a mutagen, handle it as a possible carcinogen, with extreme caution. May cause sterility in males. Based on animal tests, this substance may have toxic effects on human reproduction.|/SIGNS AND SYMPTOMS/ Potential symptoms of overexposure are irritation of eyes, nose, throat, and skin; ... /CNS depression/.|/SIGNS AND SYMPTOMS/ Slightly toxic after ingestion or percutaneous absorption. Moderately toxic upon inhalation. Moderately irritating to surface tissues. Stimulant & depressant of nervous system.|/SIGNS AND SYMPTOMS/ Short-term Exposure: Overexposure to glycidol may cause irritation of the eyes, nose, and throat. Long-term Exposure: Prolonged overexposure might produce irritation of the skin.|For more Human Toxicity Excerpts (Complete) data for Glycidol (10 total), please visit the HSDB record page.
2,3-epoxypropan-1-ol
The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.|inhalation, ingestion, skin and/or eye contact
irritation eyes, skin, nose, throat; narcosis
Cough. Sore throat. Dizziness. Drowsiness.
MAY BE ABSORBED! Redness.
Redness. Pain.
Eyes, skin, respiratory system, central nervous system
Glycidol Use and Manufacturing
1. The glycerol chlorohydrin method is derived from the reaction of chloropropanediol in the presence of alkali. The reaction is carried out at about 0°C, and the salt is separated from the reaction product and refined by vacuum distillation to obtain pure glycidol. 2. Alcohol Propylene Method Epoxidize allyl alcohol with hydrogen peroxide or peracetic acid to obtain glycidol. When peracetic acid is used as the epoxidant, the reaction speed is faster. The glycidol in the product easily reacts with acetic acid to form glycidyl acetate, which makes distillation and separation difficult, and the mixture of glycidol and acetic acid can undergo a strong exothermic reaction at room temperature Causes an explosion, so the law is very difficult to apply in industry. When hydrogen peroxide is used as the epoxidant, hexavalent tungstic acid is used as the catalyst, the reaction temperature is 40-45°C, the molar ratio of raw materials is water: allyl alcohol: hydrogen peroxide = 33.5: 1.5: 1.0, and the amount of catalyst is 1.5- 2.0g/mol hydrogen peroxide, the pH value of the reaction mixture is 4-5, and the reaction residence time is 2.5-3h.
An important fine chemical raw material, used as a stabilizer for natural oils and vinyl polymers, demulsifiers, dyeing and layering agents, as well as intermediates for the synthesis of glycerin and glycidyl ethers (amines, etc.). It can be used for surface coating, chemical synthesis, medicine, pharmaceutical chemical industry, bactericide and solid fuel gel agent.
(1976) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1978) PROBABLY GREATER THAN 2.27X10+6 GRAMS|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3668]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2-Oxiranemethanol. Aggregated National Production Volume: <500,000 lbs.
2-Oxiranemethanol: ACTIVE|TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.
Method: NIOSH 1608, Issue 2; Procedure: gas chromatography with flame ionization detector; Analyte: glycidol; Matrix: air; Detection Limit: not provided.|Colorimetric procedure for determining glycidol in the air of industrial premises is presented. The epoxide group of glycidol reacts with KSCN in the presence of bromothymol blue with a color exchange which is proportional to the concentration of glycidol in the reaction mixture. Sensitivity of the method is 3 mg/cu m glycidol in the atmosphere.
Fire Hazards -> Carcinogens, Mutagens, Flammable - 2nd degree
Computed Properties
Molecular Weight:74.08
XLogP3:-0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:74.036779430
Monoisotopic Mass:74.036779430
Topological Polar Surface Area:32.8
Heavy Atom Count:5
Complexity:35.9
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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