Tetradecanal Property

Melting point:

23°C(lit.)

Boiling point:

166°C/24mmHg(lit.)

Density 

0.8278

refractive index 

1.4410

FEMA 

2763 | MYRISTALDEHYDE

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Dark Orange

Odor

at 100.00 %. fatty waxy amber incense dry citrus peel musk

Odor Type

waxy

JECFA Number

112

InChI

InChI=1S/C14H28O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h14H,2-13H2,1H3

InChIKey

UHUFTBALEZWWIH-UHFFFAOYSA-N

SMILES

C(=O)CCCCCCCCCCCCC

LogP

6.01

EPA Substance Registry System

Tetradecanal (124-25-4)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

RTECS 

XB7900000

HS Code 

2912190090

Toxicity

The acute oral LD₅₀ value was reported as > 5Og/kg in the rat . The acute dermal LD₅₀ for sample no. 71-17 was reported to be > 10 g/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

Tetradecanal Chemical Properties,Usage,Production

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

Myristaldehyde (Tetradecanal) has a strong, fatty, orris-like odor and a sweet, fatty, “citrus-peel” flavor (diluted)

Chemical Properties

White Semi-Solid

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.

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.

Preparation

Industrially prepared from the corresponding myristic acid

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*