Trimyristin

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.

Trimyristin^[1]

Skeletal formula of trimyristin
Ball-and-stick model of trimyristin
Space-filling model of trimyristin
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 (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⦵298)	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] 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

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] 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.

See also

• Linolein