Undecanal

Chemical properties

Undecanal is a colorless liquid with a sweetish, fatty odor with an orange and rose undertone. It has a characteristic flavor. This chemical tends to polymerize unless tightly sealed. It is soluble in oils and alcohol, but insoluble in glycerol and water. Additionally, it is combustible.

Occurrence

Reported found in essential oils of citrus peels, lemon, caviar, cooked beef, chicken, lamb, pork, coriander leaf, cucumber, fish, grapefruit juice, apple, orange juice, bilberry, cranberry, raspberry, blackberry, carrot, celery, baked potato, Gruyere cheese, Russian cheese, butter, milk, fatty fish, hop oil, beer, cognac, tea, peanut oil, pecan, starfruit, coriander seed, rice, calamus, buckwheat, red sage, loganberry and maté.

The Uses of Undecanal

Undecanal is used as a pharmaceutical intermediate.

The Uses of Undecanal

Perfumery, flavors.

The Uses of Undecanal

Undecanal is a flavoring agent that is a liquid, colorless or pale yellow, with a sweet odor. it is soluble in most fixed oils, mineral oil, and propylene glycol; insoluble in glycerin. it is obtained by chemical synthesis. it is also termed aldehyde c-11 undecyclic and n-undecyl aldehyde.

What are the applications of Application

Undecanal is A greater wax moth sex pheromone

Definition

ChEBI: Undecanal is a saturated fatty aldehyde formally arising from reduction of the carboxylic acid group of undecanoic acid. It is a component of essential oils from citrus plants like Citrus reticulata. It has a role as an antimycobacterial drug, a volatile oil component and a plant metabolite. It is a saturated fatty aldehyde, a n-alkanal and a medium-chain fatty aldehyde. It is a tautomer of an undec-1-en-1-ol.

Preparation

Usually prepared by oxidation of the corresponding alcohol or reduction of the corresponding acid.

Aroma threshold values

Detection: 0.4 to 100 ppb

Taste threshold values

Taste characteristics at 10 ppm: waxy, buttery, aldehydic, soapy with a citrus note and slight laundry detergent nuance.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 1114, 1955 DOI: 10.1021/ja01610a010
The Journal of Organic Chemistry, 42, p. 393, 1977 DOI: 10.1021/jo00422a065

General Description

Undecanal is a volatile flavor compound identified in grapefruit oil and orange essential oil. It is used as a pharmaceutical intermediate.

Hazard

Toxic by ingestion and inhalation, irritant to tissue.

Flammability and Explosibility

Not classified

Safety Profile

Low toxicity by ingestion and skin contact. A skin irritant. Combustible liquid when exposed to heat or flame. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.

References

C.M Paleos Angelos Malliaris. Chemical evidence concerning the solubilization site of undecanal in micelles. Journal of Colloid and Interface Science. 1981, 82 (1), 244-247. DOI:10.1016/0021-9797(81)90145-4
George W. Mushrush, Robert N. Hazlett, Harold G. Eaton. Liquid-phase oxidation of undecanal by tert-butyl hydroperoxide in dodecane. Ind. Eng. Chem. Prod. Res. Dev. 1985, 24 (2), 290-293. DOI:10.1021/I300018A023
Kinetic Modeling of Rhodium‐Catalyzed Reductive Amination of Undecanal in Different Solvent Systems DOI:10.1002/cite.201900135
Chen Wen-kan. Synthesis of Undecanal by Selective Oxidation of Undecanol. Chemistry 2015