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Trimyristin - Wikipedia

From Wikipedia, the free encyclopedia

Trimyristin^[1]
Names



Systematic IUPAC name Propane-1,2,3-triyl tri(tetradecanoate)
Other names Glyceryl trimyristate; Glycerol tritetradecanoate;^[2] 1,2,3-Tritetradecanoylglycerol^[3]
Identifiers
CAS Number	555-45-3^Y
3D model (JSmol)	Interactive image
ChemSpider	10675^N
ECHA InfoCard	100.008.273
EC Number	209-099-7
PubChem CID	11148
UNII	18L31PSR28^Y
CompTox Dashboard (EPA)	DTXSID701014651
InChI InChI=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^N Key: DUXYWXYOBMKGIN-UHFFFAOYSA-N^N 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 Key: DUXYWXYOBMKGIN-UHFFFAOYAC
SMILES CCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC
Properties
Chemical formula	C₄₅H₈₆O₆
Molar mass	723.177 g·mol⁻¹
Appearance	White-yellowish gray solid
Odor	Odorless
Density	0.862 g/cm³ (20 °C)^[4] 0.8848 g/cm³ (60 °C)^[2]
Melting point	56–57 °C (133–135 °F; 329–330 K) at 760 mmHg^[2]^[4]^[5]
Boiling point	311 °C (592 °F; 584 K) at 760 mmHg^[2]
Solubility	Slightly soluble in alcohol, ligroin Soluble in diethyl ether, acetone, benzene,^[2] dichloromethane, chloroform, TBME
Refractive index (n_D)	1.4428 (60 °C)^[2]
Structure
Crystal structure	Triclinic (β-form)^[3]
Space group	P1 (β-form)^[3]
Lattice constant	a = 12.0626 Å, b = 41.714 Å, c = 5.4588 Å (β-form)^[3] α = 73.888°, β = 100.408°, γ = 118.274°
Thermochemistry
Heat capacity (C)	1013.6 J/mol·K (β-form, 261.9 K) 1555.2 J/mol·K (331.5 K)^[5]^[6]
Std molar entropy (S^⦵₂₉₈)	1246 J/mol·K (liquid)^[6]
Std enthalpy of formation (Δ_fH^⦵₂₉₈)	−2355 kJ/mol^[6]
Std enthalpy of combustion (Δ_cH^⦵₂₉₈)	27643.7 kJ/mol^[6]
Hazards
NFPA 704 (fire diamond)	^[7] 1 0 0
Flash point	> 110 °C (230 °F; 383 K)^[7]
Autoignition temperature	421.1 °C (790.0 °F; 694.2 K)^[7]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Trimyristin is a saturated fat and the triglyceride of myristic acid with the chemical formula C₄₅H₈₆O₆. Trimyristin is a white to yellowish-gray solid that is insoluble in water, but soluble in ethanol, acetone, benzene, chloroform, dichloromethane, ether, and TBME.

Occurrence

Trimyristin is found naturally in many vegetable fats and oils.

Isolation from nutmeg

The isolation of trimyristin from powdered nutmeg is a common introductory-level college organic chemistry experiment.^[8]^[9] It is an uncommonly simple natural product extraction 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 steam distillation and purification uses extraction from ether followed by distillation or rotary evaporation to remove the volatile solvent. 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 myristic acid^[10] or one of its salts^[11] as an example of saponification.

References

^ Merck Index, 11th Edition, 9638.
^ ^a ^b ^c ^d ^e ^f Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
^ ^a ^b ^c ^d Van Langevelde, A.; Peschar, R.; Schenk, H. (2001). "Structure of β-trimyristin and β-tristearin from high-resolution X-ray powder diffraction data". Acta Crystallographica Section B. 57 (3): 372–377. doi:10.1107/S0108768100019121. PMID 11373397.
^ ^a ^b Sharma, Someshower Dutt; Kitano, Hiroaki; Sagara, Kazunobu (2004). "Phase Change Materials for Low Temperature Solar Thermal Applications" (PDF). Res. Rep. Fac. Eng. Mie Univ. 29. Mie University: 31–64. Retrieved 2014-06-19.
^ ^a ^b Charbonnet, G. H.; Singleton, W. S. (1947). "Thermal properties of fats and oils". Journal of the American Oil Chemists' Society. 24 (5): 140. doi:10.1007/BF02643296. S2CID 101805872.
^ ^a ^b ^c ^d Trimyristin in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-06-19)
^ ^a ^b ^c "MSDS of Trimyristin". fishersci.ca. Fisher Scientific. Retrieved 2014-06-19.
^ Frank, Forrest; Roberts, Theodore; Snell, Jane; Yates, Christy; Collins, Joseph (1971). "Trimyristin from nutmeg". Journal of Chemical Education. 48 (4): 255. Bibcode:1971JChEd..48..255F. doi:10.1021/ed048p255.
^ Vestling, Martha M (1990). "Isolation of trimyristin and cholesterol: Two microscale extractions for one laboratory period". Journal of Chemical Education. 67 (3): 274. Bibcode:1990JChEd..67..274V. doi:10.1021/ed067p274.
^ Beal, G. D. (1926). "Myristic Acid". Organic Syntheses. 6: 66. doi:10.15227/orgsyn.006.0066.
^ De Mattos, Marcio C. S; Nicodem, David E (2002). "Soap from Nutmeg: An Integrated Introductory Organic Chemistry Laboratory Experiment". Journal of Chemical Education. 79 (1): 94. Bibcode:2002JChEd..79...94D. doi:10.1021/ed079p94.

v t e Types of lipids
General	Saturation: Saturated fat Unsaturated fat Monounsaturated fatty acid Polyunsaturated fatty acid Essential fatty acid Other: Fat Oil
Geometry	Trans fat Omega−3 fatty acid Omega−6 fatty acid Omega−9 fatty acid
Eicosanoids	Arachidonic acid Prostaglandins Prostacyclin Thromboxane Leukotrienes
Fatty acids	Caprylic acid Capric acid Lauric acid Myristic acid Palmitic acid Stearic acid Arachidic acid Behenic acid Lignoceric acid
Glycerides	Monoglyceride Diglyceride Triglyceride Triheptanoin Trimyristin Tripalmitin Tristearin Trilinolein Triolein
Phospholipids	Phosphatidylserine Phosphatidylinositol Phosphatidyl ethanolamine Cardiolipin Dipalmitoylphosphatidylcholine
Sphingolipids	Ceramide
Steroids	Cholesterol Corticosteroids Sex steroids Secosteroids

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Occurrence

Isolation from nutmeg

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References