Trimyristin

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

Trimyristin[1]

Names
IUPAC name 1,3-Di(tetradecanoyloxy)propan-2-yl tetradecanoate
Other names Glyceryl trimyristate; Glycerol tritetradecanoate;[2] 1,2,3-Tritetradecanoylglycerol[3]
Identifiers
CAS Number	555-45-3
3D model (JSmol)	Interactive image
ChemSpider	10675
ECHA InfoCard	100.008.273
EC Number	209-099-7
PubChem CID	11148
UNII	18L31PSR28
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 Key: DUXYWXYOBMKGIN-UHFFFAOYSA-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/cm^3 (20 °C)[4] 0.8848 g/cm^3 (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
Refractive index (nD)	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^o298)	1246 J/mol·K (liquid)[6]
Std enthalpy of formation (ΔfH^⦵298)	−2355 kJ/mol[6]
Std enthalpy of combustion (ΔcH^⦵298)	27643.7 kJ/mol[6]
Hazards
NFPA 704 (fire diamond)	[7] 0 1 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).
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Infobox references

Occurrence

Trimyristin is found naturally in many vegetable fats and oils.

Isolation from nutmeg

Seed of nutmeg contains trimyristin

The isolation of trimyristin from powdered nutmeg is a common introductory-level college organic chemistry experiment.[8][9][10] 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.

See also

• Linolein

References

1. Merck Index, 11th Edition, 9638.
2. Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
3. 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. doi:10.1107/S0108768100019121.
4. Sharma, Someshower Dutt; Kitano, Hiroaki; Sagara, Kazunobu (2004). "Phase Change Materials for Low Temperature Solar Thermal Applications" (PDF). Res. Rep. Fac. Eng. Mie Univ. Mie University. 29: 31–64. Retrieved 2014-06-19.
5. 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.
6. 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), http://webbook.nist.gov (retrieved 2014-06-19)
7. "MSDS of Trimyristin". fishersci.ca. Fisher Scientific. Retrieved 2014-06-19.
8. Frank, Forrest; Roberts, Theodore; Snell, Jane; Yates, Christy; Collins, Joseph (1971). "Trimyristin from nutmeg". Journal of Chemical Education. 48 (4): 255. doi:10.1021/ed048p255.
9. Vestling, Martha M (1990). "Isolation of trimyristin and cholesterol: Two microscale extractions for one laboratory period". Journal of Chemical Education. 67 (3): 274. doi:10.1021/ed067p274.
10. De Mattos, Marcio C. S; Nicodem, David E (2002). "Soap from Nutmeg: An Integrated Introductory Organic Chemistry Laboratory Experiment". Journal of Chemical Education. 79: 94. doi:10.1021/ed079p94.