Trimyristin

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.

Name	Trimyristin
Synonyms	Glycerol trimyristate
Name in Chemical Abstracts	Tetradecanoic acid, 1,2,3-propanetriyl ester
CAS No	555-45-3
EINECS No	209-099-7
Molecular formula	C45H86O6
Molecular mass	723.18
SMILES code	CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC

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. 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.

¹H-NMR

1H-NMR: Trimyristin
300 MHz, CDCl3
delta [ppm]	mult.	atoms	assignment
0.90	m	9 H	14-H (CH3)
1.2-1.4	m	60 H	4-13-H (CH2)
1.5-1.7	m	6 H	3-H
2.33	m	6 H	2-H
4.16	dd	2 H	glycerol-C1-Ha
4.31	dd	2 H	glycerol-C1-Hb
5.28	m	1 H	glycerol-C2-H
7.26			CHCl3
2.11			acetone (impurity)

Isolation of trimyristin from nutmeg

Reaction type:	isolation of natural products
Substance classes:	carboxylic acid ester, triglyceride, natural product
Techniques:	extracting with Soxhlet extractor, evaporating with rotary evaporator, recrystallizing, filtering, heating under reflux, heating with oil bath, stirring with magnetic stir bar
Degree of difficulty:	Easy

Batch scale:

25 g

Nutmeg

Reaction……….http://kriemhild.uft.uni-bremen.de/nop/en/instructions/pdf/1021_en.pdf The reaction apparatus consists of a 250 mL round-bottom flask with a magnetic stir bar and a 100 mL soxhlet extraction unit with a reflux condenser. 25 g of finely ground nutmeg are placed into the extraction sleeve and covered with a little glass wool. 150 mL tert-butyl methyl ether are placed into the flask and whilst stirring, the solvent is heated to reflux until the solvent leaving the extraction sleeve is colourless (approximately 5 hours). Work up The solvent is evaporated with a final pressure of 20 hPa. The flask containing the residue is cooled in an ice bath or the refrigerator until the contents has crystallized to a thick slurry. Crude product yield: 12 g; The crude product is recrystallized from the minimum amount of ethanol. Prior to filtering the crystals, the flask is placed into the refrigerator for at least 30 minutes. The crystalline slurry is filtered and the product is dried in an evacuated desiccator over silica gel. Should the crystals not be colourless after the first recrystallization, a second recrystallization is carried out. Yield: 6.5 g; melting point 54-55 °C; Duration of the experiment Without recrystallization 6 hours Where can I stop the experiment? Before and after the evaporation of the solvent Recycling The evaporated tert-butyl methyl ether and the evaporated ethanol from the mother liquor are collected and redistilled.

Suggestions for waste disposal

Waste Disposal residue from mother liquor domestic waste residue from extraction domestic waste

Operating scheme

Substances required

Batch scale:

25 g

Nutmeg

Educts		Amount	Risk	Safety
Nutmeg		25 g	R	S
Solvents		Amount	Risk	Safety
Ethanol	F	~ 150 mL	R 11	S 2-7-16
tert-Butyl methyl ether	F Xi	150 mL	R 11-38	S 2-9-16-24
Others		Amount	Risk	Safety
Iodine	Xn N	0.1 g	R 20/21-50	S 2-23.2-23.4-25-61
Solvents for analysis		Amount	Risk	Safety
Cyclohexane	F Xn N	?	R 11-38-50/53-65-67	S 2-9-16-33-60-61-62
Acetic acid ethyl ester	F Xi	?	R 11-36-66-67	S 2-16-26-33

Substances produced

Batch scale:

25 g

Nutmeg

Products		Amount	Risk	Safety
Trimyristin		6.5 g	R	S

Equipment

Batch scale:

25 g

Nutmeg

	round bottom flask 250 mL			Soxhlet extractor 100 mL
	glass wool			extraction cone
	heatable magnetic stirrer with magnetic stir bar			oil bath
	reflux condenser			rotary evaporator
	ice bath			exsiccator with drying agent
	suction filter			suction flask

Simple evaluation indices

Batch scale:

25 g

Nutmeg

Atom economy		not defined
Yield		not defined
Target product mass		6.5	g
Sum of input masses		250	g
Mass efficiency		26	mg/g
Mass index		39	g input / g product
E factor		38	g waste / g product
Energy input		1500	kJ
Energy efficiency		4.3	mg/kJ

Chromatogram

TLC: crude product
TLC layer	Polygram SilG/UV precoated TLC layer; 0.2 mm; silica gel; Macherey & Nagel
mobile phase	cyclohexane / EtOAc = 95 : 5
staining reagent	Vaughn’s reagent or iodine vapor
Rf (product)	0.51

¹³C-NMR

13C-NMR: Trimyristin
300 MHz, CDCl3
delta [ppm]	assignment
14.08	C14
22.66	C13
24.85-24.89	C3, C17
29.06-31.90	C4-C12
34.04-34.2	C2
62.08	glycerol-C1
68.85	glycerol-C2
172.85	C15
173.26	C1
76.5-77.5	CDCl3

IR

IR: Trimyristin
[KBr, T%, cm-1]
[cm-1]	assignment
2950-2850	aliph. C-H valence
1730	C=O valence, ester

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 Registry Number	555-45-3
ChemSpider	10675
EC number	209-099-7
InChI[show]
Jmol-3D images	Image
PubChem	11148
SMILES[show]
UNII	18L31PSR28
Properties
Chemical formula	C45H86O6
Molar mass	723.18 g·mol−1
Appearance	White-yellowish gray solid
Odor	Nutmeg-like
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)
Boiling point	311 °C (592 °F; 584 K)
Solubility	Slighty soluble in alcohol, ligroin Soluble in (C2H5)2O, acetone, C6H6,[2] CH2Cl2, CHCl3
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
Specific 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 (So298)	1246 J/mol·K (liquid)[6]
Std enthalpy of formation (ΔfHo298)	−2355 kJ/mol[6]
Std enthalpy of combustion (ΔcHo298)	27643.7 kJ/mol[6]
Hazards
NFPA 704	[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).

7. References

8. Merck Index, 11th Edition, 9638.
9. 
   
10. Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
11. 
    
12. 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 Structural Science 57 (3): 372. doi:10.1107/S0108768100019121. edit
13. 
    
14. Sharma, Someshower Dutt; Kitano, Hiroaki; Sagara, Kazunobu (2004). “Phase Change Materials for Low Temperature Solar Thermal Applications” (PDF). http://www.eng.mie-u.ac.jp. Mie University. Retrieved 2014-06-19.
15. 
    
16. 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. edit
17. 
    
18. Trimyristin in Linstrom, P.J.; Mallard, W.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)
19. 
    

“MSDS of Trimyristin”

.

http://www.fishersci.ca

. Fisher Scientific. Retrieved 2014-06-19.

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