Glycidol: Difference between revisions

| Watchedfields = changed

| verifiedrevid = 443839891

| ImageFile = Glycidol structure.svg

| PIN = Oxiranylmethanol

| OtherNames = Glycidol<br>2,3-Epoxy-1-propanol<br>3-Hydroxypropylene oxide<br>Epoxypropyl alcohol<br>Hydroxymethyl ethylene oxide<br>2-Hydroxymethyl oxiran

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = S54CF1DV9A

|Section2={{Chembox Properties

| C=3 | H=6 | O=2

| Appearance = Viscous liquid

| Density = 1.1143 g/cm³<ref name=Merck>''Merck Index'', 11th Edition, '''4385'''</ref>

| MeltingPtC = −54

| MeltingPt_ref = <ref name=GESTIS>{{GESTIS|ZVG=37230}}</ref>

| BoilingPtC = 167

| BoilingPt_notes = (decomposes)<ref name=Merck/>

| Solubility = miscible<ref name=PGCH/>

| VaporPressure = 0.9 mmHg (25°C)<ref name=PGCH/>

}}

|Section7={{Chembox Hazards

| ExternalSDS = [https://fscimage.fishersci.com/msds/93805.htm External MSDS]

| FlashPtC =66

| FlashPt_ref = <ref name=GESTIS/>

| LD50 = 420 mg/kg (oral, rat)<ref name=GESTIS/><ref>[[Food and Cosmetics Toxicology]]. Vol. 19, Pg. 347, 1981</ref><br>1980 mg/kg (dermal, rabbit)<ref name=GESTIS/><ref>AMA Archives of Industrial Health. Vol. 14, Pg. 250, 1956</ref>

| PEL = TWA 50 ppm (150 mg/m³)<ref name=PGCH>{{PGCH|0303}}</ref>

| IDLH = 150 ppm<ref name=PGCH/>

| REL = TWA 25 ppm (75 mg/m³)<ref name=PGCH/>

| LC50 = 450 ppm (mouse, 4 hr)<br/>580 ppm (rat, 8 hr)<ref>{{IDLH|556525|Glycidol}}</ref>

}}

'''Glycidol''' is an [[organic compound]] that contains both [[epoxide]] and [[Alcohol (chemistry)|alcohol]] [[functional group]]s. Being bifunctional, it has a variety of industrial uses. The compound is a slightly viscous liquid that is slightly unstable and is not often encountered in pure form.

Glycidol is prepared by the epoxidation of [[allyl alcohol]].<ref name=Ullmann>Guenter Sienel, Robert Rieth, Kenneth T. Rowbottom "Epoxides" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. {{doi|10.1002/14356007.a09_531}}</ref>

#Alkylation of 2-methylquinazolin-4(3H)-one with glycidol affords [[diproqualone]].

#[[Dyphylline]] was made by the alkylation of [[theophylline]] with glycidol.

#[[Diproxadol]]

Glycidol is an irritant of the skin, eyes, mucous membranes, and upper respiratory tract. Exposure to glycidol may also cause [[central nervous system]] depression, followed by central nervous system stimulation.<ref>{{Cite web |url=http://www.osha.gov/SLTC/healthguidelines/glycidol/recognition.html |title=OSHA guidelines for glycidol |access-date=2006-10-20 |archive-date=2012-09-25 |archive-url=https://web.archive.org/web/20120925153135/http://www.osha.gov/SLTC/healthguidelines/glycidol/recognition.html |url-status=dead }}</ref> It is listed as an [[List of IARC Group 2A Agents - Probably carcinogenic to humans|IARC Group 2A Agent]], meaning that it is "''probably carcinogenic to humans''".<ref>{{cite web |url=https://monographs.iarc.fr/list-of-classifications |title=List of Classifications, Agents classified by the IARC Monographs, Volumes 1–124 |author=<!--Staff writer(s); no by-line.--> |date=July 7, 2019 |website=IARC Monographs on the Evaluation of Risk to Humans |publisher=IARC |access-date=July 14, 2019}}</ref> In regards to occupational exposures, the [[Occupational Safety and Health Administration]] has set a [[permissible exposure limit]] at 50 ppm over an eight-hour work shift, while the [[National Institute for Occupational Safety and Health]] [[recommended exposure limit|recommends a limit]] at 25 ppm over an eight-hour work shift.<ref>[https://www.cdc.gov/niosh/npg/npgd0303.html CDC - NIOSH Pocket Guide to Chemical Hazards]</ref>

[[Cooking oil#Extraction and refinement|Refined edible oils]] have been shown to contain glycidyl fatty acid esters that are thought to be formed primarily during deodorization; [[hydrolysis]] of these compounds in the [[Gastrointestinal tract|digestive tract]] releases free glycidol that proved to be carcinogenic in rats.<ref>{{Cite journal|last1=Cheng|first1=Wei-wei|last2=Liu|first2=Guo-qin|last3=Wang|first3=Li-qing|last4=Liu|first4=Zeng-she|date=2017|title=Glycidyl Fatty Acid Esters in Refined Edible Oils: A Review on Formation, Occurrence, Analysis, and Elimination Methods|journal=Comprehensive Reviews in Food Science and Food Safety|language=en|volume=16|issue=2|pages=263–281|doi=10.1111/1541-4337.12251|pmid=33371535|issn=1541-4337|doi-access=free}}</ref>

* [[Epichlorohydrin]]

* [[Ethylene oxide]]

* [[Glycidamide]]

* [[Glycidic acid]]

{{Reflist}}

{{Authority control}}

[[Category:Primary alcohols]]