Description
Myristaldehyde (Tetradecanal) has a strong, fatty, orris-like odor with a sweet, fatty, “citrus-peel” flavor (diluted). Industrially prepared from the corresponding myristic acid.
Chemical Properties
White Semi-Solid
Chemical Properties
Myristaldehyde (Tetradecanal) has a strong, fatty, orris-like odor and a sweet, fatty, “citrus-peel” flavor (diluted)
Occurrence
Tetradecanal is reported found in the essential oils of Ocotea usambarensis Engl., Pinus sabiniana Dougl.; also reported
found in kumquat peel, ginger, chicken fat, hop oil, apricot, citrus peel oils and juices, bilberry, blackberry, cucumber, cassia leaf, butter, parmesan cheese, milk powder, cooked chicken, beef, cured pork, beer, peanuts, trassi, coriander leaf, dried bonito, cherimoya,
mountain papaya, scallop and angelica root oil.
Uses
A major component of the essential oil found in the leaves of Azadirachta indica.
Preparation
Industrially prepared from the corresponding myristic acid
Definition
ChEBI: A long-chain fatty aldehyde that is tetradecane in which two hydrogens attached to a terminal carbon are replaced by an oxo group. It is found in coriander.
Taste threshold values
Taste characteristics at 10 ppm: fatty, lactonic, coconut, woody and fishy with a fruity nuance
Synthesis Reference(s)
Canadian Journal of Chemistry, 46, p. 75, 1968
DOI: 10.1139/v68-013
Synthesis
A solution of oxalylchloride (8.0 mL, 88.0 mmol, 2.2 eq.) in abs. dichloromethane (200 mL) was treated with DMSO (13.6 mL, 192 mmol, 4.8 eq.) at -60 °C. After 3 min, the reaction mixture was warmed to approx. 15 °C. Then a solution of tetradecan-1-ol (8.56 g, 40.0 mmol) in dry dichloromethane (40 mL) and after a further 3 min triethylamine (28 mL, 200 mmol, 5.0 eq.) was added. Then, the reaction mixture was slowly warmed to 5 °C and quenched with the addition of water (200 mL). The phases were separated, and the aqueous phase was extracted with dichloromethane (3 χ 100 mL). The combined organic phases were washed with brine (1 χ 200 mL) and dried over MgS04. The solvent was removed under reduced pressure, and the product was isolated as a white solid Tetradecanal, which was used in the next reaction without purification—yield: 10.4 g (100%), purity: 98% (GC).
Metabolism
See monograph on aldehyde C-8*
