| Revision as of 13:53, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{chembox}} taken from revid 468365241 of page Triacetin for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 01:14, 8 October 2024 edit Dicklyon (talk | contribs)Autopatrolled, Extended confirmed users, Rollbackers477,553 edits case fix |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 429388207 |
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| verifiedrevid = 470612869 |
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| Reference=<ref>'']'', 11th Edition, '''9405'''.</ref> |
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| Reference = <ref>{{cite book | title = ] | edition = 11th | page = 9405 }}</ref> |
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| Name = Triacetin |
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| Name = Triacetin |
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| ImageFile = Triacetin.svg |
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| ImageFile = Triacetin.svg |
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| ImageSize = 200px |
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| ImageSize = 220px |
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| ImageAlt = Skeletal formula of triacetin |
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| ImageName = Triacetin |
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| ImageFile1 = Triacetin 3D ball.png |
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| IUPACName = 1,3-diacetyloxypropan-2-yl acetate |
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| ImageSize1 = 220px |
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| Section1 = {{Chembox Identifiers |
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| ImageAlt1 = Ball-and-stick model of the triacetin molecule |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SystematicName = Propane-1,2,3-triyl triacetate |
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| OtherNames = {{Unbulleted list|Glycerol triacetate<ref name=crc />|glycerin triacetate|1,2,3-triacetylglycerol|1,2,3-triacetoxypropane}} |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 102-76-1 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 9661 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1489254 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13835706 |
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| ChemSpiderID = 13835706 |
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| EINECS = 203-051-9 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00384 |
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| PubChem = 5541 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = XHX3C3X673 |
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| UNII = XHX3C3X673 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00384 |
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| InChI = 1/C9H14O6/c1-6(10)13-4-9(15-8(3)12)5-14-7(2)11/h9H,4-5H2,1-3H3 |
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| InChI = 1/C9H14O6/c1-6(10)13-4-9(15-8(3)12)5-14-7(2)11/h9H,4-5H2,1-3H3 |
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| InChIKey = URAYPUMNDPQOKB-UHFFFAOYAH |
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| InChIKey = URAYPUMNDPQOKB-UHFFFAOYAH |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = URAYPUMNDPQOKB-UHFFFAOYSA-N |
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| StdInChIKey = URAYPUMNDPQOKB-UHFFFAOYSA-N |
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| SMILES = CC(=O)OC(COC(=O)C)COC(C)=O |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 102-76-1 |
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| RTECS = AK3675000 |
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}} |
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| SMILES = CC(=O)OC(COC(=O)C)COC(C)=O |
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|Section2={{Chembox Properties |
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}} |
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| C=9 | H=14 | O=6 |
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| Section2 = {{Chembox Properties |
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| Appearance = Oily liquid |
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| Formula = C<sub>9</sub>H<sub>14</sub>O<sub>6</sub> |
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| Density = 1.155 g/cm<sup>3</sup><ref name=fca /> |
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| MolarMass = 218.21 g/mol |
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| MeltingPtC = -78 |
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| Density = 1.1562 g/cm<sup>3</sup> |
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| MeltingPt_notes = <br> at 760 mmHg<ref name=crc>{{CRC90}}</ref> |
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| MeltingPt = +3 °C <ref>http://www.inchem.org/documents/sids/sids/102761.pdf</ref> |
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| BoilingPtC = 259 |
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| BoilingPt = 258–260 °C |
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| BoilingPt_notes = <br> at 760 mmHg<ref name=crc /> |
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| Water solubility = 70g/L (25 °C) |
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| Solubility = 6.1 g/100 mL<ref name=crc /> |
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| RefractIndex = 1.4301 (20 °C)<ref name=crc /><br> 1.4294 (24.5 °C)<ref name=acs /> |
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| SolubleOther = Miscible in ]<br> Soluble in ], ], ]<ref name=crc /> |
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| VaporPressure = 0.051 Pa (11.09 °C)<br> 0.267 Pa (25.12 °C)<br> 2.08 Pa (45.05 °C)<ref name=acs>{{Cite journal | doi = 10.1021/je60017a033| title = Vapor Pressure of Tiracetin, Triethylene Glycol Dinitrate, and Metriol Trinitrate| journal = Journal of Chemical & Engineering Data| volume = 8| issue = 2| pages = 241–242| year = 1963| vauthors = Woodman AL, Adicoff A }}</ref> <br> ln(P/Pa)=22.819-4493/T(K)-807000/T(K)² |
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| Viscosity = 23 cP (20 °C)<ref name=fca /> |
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}} |
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|Section4={{Chembox Thermochemistry |
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| DeltaHc = 4211.6 kJ/mol<ref name=nist>{{nist|name=Triacetin|id=C102761|access-date=2014-06-20|mask=FFFF|units=SI}}</ref> |
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| HeatCapacity = 389 J/mol·K<ref name=nist /> |
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| DeltaHf = −1330.8 kJ/mol<ref name=nist /> |
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| Entropy = 458.3 J/mol·K<ref name=nist /> |
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}} |
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|Section7={{Chembox Hazards |
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| NFPA-H = 1 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| NFPA_ref = <ref name=fca /> |
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| FlashPtC = 138 |
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| FlashPt_ref = <ref name=fca>{{cite web|url = https://www.fishersci.ca/viewmsds.do?catNo=AC139220025|title = MSDS of Triacetin|website=fishersci.ca|access-date = 2014-06-20|publisher = Fisher Scientific}}</ref> |
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| AutoignitionPtC = 430 |
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| AutoignitionPt_ref = <ref name=fca /> |
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| ExploLimits = 7.73%<ref name=fca /> |
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| LD50 = 1100 mg/kg (mice, oral)<ref name=fca /> |
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}} |
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'''Triacetin''' is the ] with the formula {{chem2|C3H5(OCOCH3)3}}. It is classified as a ], i.e., the ] of ] with ].<ref>{{cite journal | vauthors = Kong P, Aroua MK, Daud WM, Lee HV, Cognet P, Pérès Y | year = 2016 | title = Catalytic role of solid acid catalysts in glycerol acetylation for the production of bio-additives: a review | url = https://www.researchgate.net/publication/304528567 | journal = RSC Advances | volume = 6 | issue = 73| pages = 68885–68905 | doi = 10.1039/C6RA10686B | bibcode = 2016RSCAd...668885K | s2cid = 102384754 }}</ref> It is a colorless, viscous, and odorless liquid with a high boiling point and a low melting point. It has a mild, sweet taste in concentrations lower than 500 ppm, but may appear bitter at higher concentrations.<ref>{{Cite book|title=Perfume and Flavor Chemicals (II K - Z)|last=Arctander|first=Steffen |publisher=Published by the Author|year=1969|isbn=978-0-931710-37-7|location=Elizabeth, N.J.|pages=2971}}</ref> It is one of the ] compounds. |
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==Uses== |
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Triacetin is a common ], for instance as a ] in ]s, and for its ] function, with ] '''E1518''' and Australian approval code A1518. It is used as an ] in pharmaceutical products, where it is used as a humectant, a ], and as a solvent.<ref>{{cite web|url = http://drugtopics.modernmedicine.com/drugtopics/Drugtopics.com+Exclusives/Overview-of-pharmaceutical-excipients-used-in-tabl/ArticleStandard/Article/detail/561047|title = Triacetin|website = drugtopics.modernmedicine.com|access-date = 2014-06-20|publisher = Advanstar Communications, Inc.|url-status = dead|archive-url = https://web.archive.org/web/20120219203453/http://drugtopics.modernmedicine.com/drugtopics/Drugtopics.com+Exclusives/Overview-of-pharmaceutical-excipients-used-in-tabl/ArticleStandard/Article/detail/561047|archive-date = 2012-02-19}}</ref> |
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===Potential uses=== |
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The plasticizing capabilities of triacetin have been utilized in the synthesis of a biodegradable phospholipid gel system for the dissemination of the cancer drug ] (PTX).<ref>{{cite journal | vauthors = Chen T, Gong T, Zhao T, Liu X, Fu Y, Zhang Z, Gong T | title = Paclitaxel loaded phospholipid-based gel as a drug delivery system for local treatment of glioma | journal = International Journal of Pharmaceutics | volume = 528 | issue = 1–2 | pages = 127–132 | date = August 2017 | pmid = 28596136 | doi = 10.1016/j.ijpharm.2017.06.013 }}</ref> In the study, triacetin was combined with PTX, ethanol, a phospholipid and a medium chain triglyceride to form a gel-drug complex. This complex was then injected directly into the cancer cells of ]-bearing mice. The gel slowly degraded and facilitated sustained release of PTX into the targeted glioma cells. |
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Triacetin can also be used as a ] as an ] which can reduce ] in ], and to improve cold and ] properties of ].<ref>{{cite journal | last1 = Gupta | first1 = Mayank | last2 = Kumar | first2 = Naveen | title = Scope and opportunities of using glycerol as an energy source | journal = Renewable & Sustainable Energy Reviews | date = 2012 | volume = 16 | issue = 7 | pages = 4551–4556 | doi = 10.1016/j.rser.2012.04.001 | bibcode = 2012RSERv..16.4551G }}</ref> |
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It has been considered as a possible source of ] in artificial food regeneration systems on long ]s. It is believed to be safe to get over half of one's dietary energy from triacetin.<ref>{{cite journal|first1 = Jacob|last1 = Shapira|first2 = Adrian D.|last2 = Mandel|first3 = Phillip D.|last3 = Quattrone|first4 = Nancie L.|last4 = Bell |year = 1968|title = Current Research On Regenerative Systems|publisher = Committee On Space Research, Eleventh Annual Meeting |place = Tokyo |url = https://ntrs.nasa.gov/api/citations/19680025022/downloads/19680025022.pdf | journal=Life Sciences in Space Research|volume = 7|pages = 123–9|pmid = 12197534|access-date = 2024-07-16}}</ref> |
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== Synthesis == |
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Triacetin was first prepared in 1854 by the French chemist ].<ref>{{cite journal|last1=Berthelot|first1=Marcellin |title=Sur les combinaisons de le glycérine avec les acides et sur la synthèse des principes immédiats des graisses des animaux|journal=Annales de Chimie et de Physique|date=1854|volume=41|pages=216–319|url=https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dyk;view=1up;seq=290|series=3rd series|trans-title=On the compounds of glycerin with acids and on the synthesis of immediate principles of animal fats|language=French}} ; see "Triacétine", pp. 282–283.</ref> Triacetin was prepared in the 19th century from ] and ].<ref>{{cite journal |doi=10.1039/CA8803800307 |doi-access=free |title=Preparation of glyceryl triacetate |journal=Journal of the Chemical Society, Abstracts |year=1880 |volume=38 |page=312 }}</ref> |
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Its synthesis from ] and glycerol is simple and inexpensive. |
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: 3 {{chem2|(CH3CO)2O}} + 1 {{chem2|C3H5(OH)3}} → 1 {{chem2|C3H5(OCOCH3)3}} + 3 {{chem2|CH3CO2H}} |
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This synthesis has been conducted with ] ] and ] to give a 99% yield of triacetin.<ref>{{Cite journal|last1=Rajabi|first1=Fatemeh|last2=Saidi|first2=Mohammad R.|date=2005|title=A Cheap, Simple, and Versatile Method for Acetylation of Alcohols and Phenols and Selective Deprotection of Aromatic Acetates Under Solvent-Free Condition|journal=Synthetic Communications|language=en|volume=35|issue=3|pages=483–491|doi=10.1081/SCC-200048988|s2cid=96001761|issn=0039-7911}}</ref> It has also been conducted with a ](II) ] catalyst supported by ] and heated to 50 °C for 55 minutes to give a 99% yield of triacetin.<ref>{{Cite journal|last=Rajabi|first=Fatemeh |date=2009|title=A heterogeneous cobalt(II) Salen complex as an efficient and reusable catalyst for acetylation of alcohols and phenols|journal=Tetrahedron Letters|language=en|volume=50|issue=4|pages=395–397|doi=10.1016/j.tetlet.2008.11.024}}</ref> |
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==Safety== |
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The ] has approved it as ]<ref>{{cite web | url = https://www.ecfr.gov/current/title-21/chapter-I/subchapter-B/part-184/subpart-B/section-184.1901 | title = 21 CFR § 184.1901 Listing of Specific Substances Affirmed as GRAS: Triacetin | date = 21 Feb 1989 | website = eCFR.gov | publisher = FDA | access-date = 25 Apr 2023 }}</ref> food additive and included it in the database according to the opinion from the Select Committee On GRAS Substances (SCOGS). Triacetin is included in the SCOGS database since 1975.<ref>{{cite web|url = https://www.fda.gov/Food/IngredientsPackagingLabeling/GRAS/SCOGS/ucm260418.htm|website = www.fda.gov|title = Glycerin and Glycerides|place = U.S. Food and Drug Administration|access-date = 2014-06-20|archive-url = https://wayback.archive-it.org/7993/20171031062709/https://www.fda.gov/Food/IngredientsPackagingLabeling/GRAS/SCOGS/ucm260418.htm|archive-date = 2017-10-31|quote = Triacetin and two types of acetooleins have been found to be without toxic effects in long-term feeding tests in rats at levels that were several orders of magnitude greater than those to which consumers are exposed. Three types of acetostearins have been found to be without toxic effects in long-term feeding tests in rats at levels up to 5 g per kg per day. This contrasts with an estimated human consumption of a fraction of a milligram per kg per day. It is recognized that at an even higher feeding level (10 g per kg per day) male rats developed testicular atrophy and female rats, uterine discoloration. However, such a level which would amount to 50 g or more for an infant and 600 g for an adult per day, is vastly higher than would be possible in the consumption of foods to which acetostearins are added for functional purposes.|url-status = live}}</ref> |
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Triacetin was not toxic to animals in studies of exposure through repeated inhalation over a relatively short period.<ref>{{cite journal | vauthors = Fiume MZ | title = Final report on the safety assessment of triacetin | journal = International Journal of Toxicology | volume = 22 Suppl 2 | issue = 3 | pages = 1–10 | year = 2003 | pmid = 14555416 | doi = 10.1080/747398359 }}</ref> |
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== References == |
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{{reflist}} |
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{{Glycerides}} |
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