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{{chembox |
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| verifiedrevid = 444237659 |
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| Reference=<ref>'']'', 11th Edition, '''9638'''.</ref> |
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| verifiedrevid = 451713079 |
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| Name = Trimyristin |
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| Reference=<ref>'']'', 11th Edition, '''9638'''.</ref> |
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| ImageFile1 = Trimyristin.png |
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| Name = Trimyristin |
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| ImageSize1 = 200px |
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| ImageFile2 = Trimyristin-from-xtal-2001-3D-balls.png |
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| ImageFile = Trimyristin.png |
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| ImageSize2 = 250px |
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| ImageSize = 200px |
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| ImageName = Skeletal formula of trimyristin |
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| ImageFile3 = Trimyristin-from-xtal-2001-3D-vdW.png |
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| ImageFile1 = Trimyristin-from-xtal-2001-3D-balls.png |
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| ImageSize3 = 250px |
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| ImageSize1 = 250px |
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| IUPACName = 1,3-Di(tetradecanoyloxy)propan-2-yl tetradecanoate |
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| ImageName1 = Ball-and-stick model of trimyristin |
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| OtherNames = glyceryl trimyristate |
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| ImageFile2 = Trimyristin-from-xtal-2001-3D-vdW.png |
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| Section1 = {{Chembox Identifiers |
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| PubChem = 11148 |
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| ImageSize2 = 250px |
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| ImageName2 = Space-filling model of trimyristin |
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| CASNo = 555-45-3 |
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| SystematicName = Propane-1,2,3-triyl tri(tetradecanoate) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| OtherNames = Glyceryl trimyristate; Glycerol tritetradecanoate;<ref name=crc /> 1,2,3-Tritetradecanoylglycerol<ref name=iucr /> |
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|Section1={{Chembox Identifiers |
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| PubChem = 11148 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 555-45-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 18L31PSR28 |
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| UNII = 18L31PSR28 |
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| SMILES = CCCCCCCCCCCCCC(=O)OCC (COC(=O)CCCCCCCCCCCCC)O C(=O)CCCCCCCCCCCCC |
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| SMILES = CCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 10675 |
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| InChI = 1/C45H86O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-43(46)49-40-42(51-45(48)39-36-33-30-27-24-21-18-15-12-9-6-3)41-50-44(47)38-35-32-29-26-23-20-17-14-11-8-5-2/h42H,4-41H2,1-3H3 |
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| InChIKey = DUXYWXYOBMKGIN-UHFFFAOYAC |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C45H86O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-43(46)49-40-42(51-45(48)39-36-33-30-27-24-21-18-15-12-9-6-3)41-50-44(47)38-35-32-29-26-23-20-17-14-11-8-5-2/h42H,4-41H2,1-3H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = DUXYWXYOBMKGIN-UHFFFAOYSA-N |
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| EINECS = 209-099-7 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=45 | H=86 | O=6 |
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| Formula = C<sub>45</sub>H<sub>86</sub>O<sub>6</sub> |
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| Appearance = White-yellowish gray solid |
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| MolarMass = 723.16 g/mol |
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| Odor = Odorless |
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| Density = 0.885 g/cm<sup>3</sup> at 60 °C |
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| Density = 0.862 g/cm<sup>3</sup> (20 °C)<ref name=mie>{{cite journal|url = http://www.eng.mie-u.ac.jp/research/activities/29/29_31.pdf|title = Phase Change Materials for Low Temperature Solar Thermal Applications|last1 = Sharma|first1 = Someshower Dutt|last2 = Kitano|first2 = Hiroaki|last3 = Sagara|first3 = Kazunobu |publisher = Mie University|accessdate = 2014-06-19|date= 2004 | journal = Res. Rep. Fac. Eng. Mie Univ. | volume = 29 | pages = 31–64 }}</ref><br> 0.8848 g/cm<sup>3</sup> (60 °C)<ref name=crc>{{CRC90}}</ref> |
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| MeltingPt = 56-57 °C |
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| BoilingPt = 311 °C |
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| MeltingPtC = 56-57 |
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| MeltingPt_notes = <br> at 760 mmHg<ref name=crc /><ref name=mie /><ref name=spring>{{Cite journal | doi = 10.1007/BF02643296| title = Thermal properties of fats and oils| journal = Journal of the American Oil Chemists' Society| volume = 24| issue = 5| pages = 140| year = 1947| last1 = Charbonnet | first1 = G. H. | last2 = Singleton | first2 = W. S.| s2cid = 101805872}}</ref> |
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| Solubility = Insoluble |
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| BoilingPtC = 311 |
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| BoilingPt_notes = at 760 mmHg<ref name=crc /> |
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| SolubleOther = Slightly soluble in ], ]<br> Soluble in ], ], ],<ref name=crc /> ], ], ] |
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| RefractIndex = 1.4428 (60 °C)<ref name=crc /> |
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}} |
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|Section3={{Chembox Structure |
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| CrystalStruct = ] (β-form)<ref name=iucr>{{Cite journal | doi = 10.1107/S0108768100019121| title = Structure of β-trimyristin and β-tristearin from high-resolution X-ray powder diffraction data| journal = Acta Crystallographica Section B| volume = 57| issue = 3| pages = 372–377| year = 2001| last1 = Van Langevelde | first1 = A. | last2 = Peschar | first2 = R. | last3 = Schenk | first3 = H. | pmid = 11373397| doi-access = }}</ref> |
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| SpaceGroup = P{{overline|1}} (β-form)<ref name=iucr /> |
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| PointGroup = |
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| LattConst_a = 12.0626 Å |
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| LattConst_b = 41.714 Å |
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| LattConst_c = 5.4588 Å (β-form)<ref name=iucr /> |
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| LattConst_alpha = 73.888 |
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| LattConst_beta = 100.408 |
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| LattConst_gamma = 118.274 |
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|Section4={{Chembox Thermochemistry |
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| Entropy = 1246 J/mol·K (liquid)<ref name=nist>{{nist|name=Trimyristin|id=C555453|accessdate=2014-06-19|mask=FFFF|units=SI}}</ref> |
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| DeltaHc = 27643.7 kJ/mol<ref name=nist /> |
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| DeltaHf = −2355 kJ/mol<ref name=nist /> |
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| HeatCapacity = 1013.6 J/mol·K (β-form, 261.9 K)<br> 1555.2 J/mol·K (331.5 K)<ref name=spring /><ref name=nist /> |
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}} |
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|Section7={{Chembox Hazards |
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| FlashPt = > |
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| FlashPtC = 110 |
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| FlashPt_ref = <ref name=fca /> |
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| AutoignitionPtC = 421.1 |
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| AutoignitionPt_ref = <ref name=fca /> |
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| NFPA-H = 1 |
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| NFPA-F = 0 |
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| NFPA-R = 0 |
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| NFPA_ref = <ref name=fca>{{cite web|url = https://www.fishersci.ca/viewmsds.do?catNo=AC422090250|title = MSDS of Trimyristin|website = fishersci.ca|accessdate = 2014-06-19|publisher = Fisher Scientific}}</ref> |
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'''Trimyristin''' is an ] with the chemical formula C<sub>45</sub>H<sub>86</sub>O<sub>6</sub>. It is a ] which is the ] of ]. Trimyristin is found naturally in many ]. Trimyristin is a white to yellowish-gray solid that is insoluble in water, but soluble in ], ], ], ], and ]. |
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'''Trimyristin''' is a ] and the ] of ] with the ] C<sub>45</sub>H<sub>86</sub>O<sub>6</sub>. Trimyristin is a white to yellowish-gray solid that is insoluble in water, but soluble in ], ], ], ], ], ], and ]. |
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==Occurrence== |
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The isolation of trimyristin from powdered ] is a common introductory-level college organic chemistry experiment. It is an uncommonly simple natural product ] because nutmeg oil generally consists of over eighty percent trimyristin. Trimyristin makes up between 20-25% of the overall mass of dried, ground nutmeg. Separation is generally effected by ] and purification uses extraction from ether followed by distillation or ] to remove the volatile ]. The extraction of trimyristin can also be done with diethyl ether at room temperature, due to its high solubility in the ether. The experiment is frequently included in curricula, both for its relative ease and to provide instruction in these techniques. |
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Trimyristin is found naturally in many ]. |
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===Isolation from nutmeg=== |
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] |
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The isolation of trimyristin from powdered ] is a common introductory-level college organic chemistry experiment.<ref>{{Cite journal | doi = 10.1021/ed048p255| title = Trimyristin from nutmeg| journal = Journal of Chemical Education| volume = 48| issue = 4| pages = 255| year = 1971| last1 = Frank| first1 = Forrest| last2 = Roberts| first2 = Theodore| last3 = Snell| first3 = Jane| last4 = Yates| first4 = Christy| last5 = Collins| first5 = Joseph| bibcode = 1971JChEd..48..255F}}</ref><ref>{{Cite journal | doi = 10.1021/ed067p274| title = Isolation of trimyristin and cholesterol: Two microscale extractions for one laboratory period| journal = Journal of Chemical Education| volume = 67| issue = 3| pages = 274| year = 1990| last1 = Vestling| first1 = Martha M| bibcode = 1990JChEd..67..274V}}</ref> It is an uncommonly simple natural product ] because nutmeg oil generally consists of over eighty percent trimyristin. Trimyristin makes up between 20-25% of the overall mass of dried, ground nutmeg. Separation is generally carried out by ] and purification uses extraction from ether followed by distillation or ] to remove the volatile ]. The extraction of trimyristin can also be done with diethyl ether at room temperature, due to its high solubility in the ether. The experiment is frequently included in curricula, both for its relative ease and to provide instruction in these techniques. Trimyristin can then be used to prepare ]<ref>{{cite journal|first = G. D.|last = Beal|url = http://www.orgsyn.org/demo.aspx?prep=CV1P0379|doi = 10.15227/orgsyn.006.0066|title = Myristic Acid|journal = ]|volume = 6|pages = 66|year = 1926}}</ref> or one of its salts<ref>{{Cite journal | doi = 10.1021/ed079p94| title = Soap from Nutmeg: An Integrated Introductory Organic Chemistry Laboratory Experiment| journal = Journal of Chemical Education| volume = 79| pages = 94| year = 2002| last1 = De Mattos| first1 = Marcio C. S| last2 = Nicodem| first2 = David E| issue = 1| bibcode = 2002JChEd..79...94D}}</ref> as an example of ]. |
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==See also== |
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==See also== |
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{{biochem-stub}} |