Chemical Properties
Nonanal occurs in citrus and rose oils. It is a colorless or light yellow liquid with a fatty, rose-like odor and is used in floral compositions, particularly those with rose characteristics. It is soluble in alcohol, most fixed oils, mineral oil, and propylene glycol, but insoluble in glycerin. It is obtained by chemical synthesis. It is also termed aldehyde c-9 and pelargonic aldehyde.
Occurrence
Reported as a constituent in the oils of sweet and bitter orange, mandarin, lemon, lime, grapefruit, kumquat,
orris, Ceylon cinnamon, ginger, Xanthoxylum rhetsa, rose and clary sage; in the turpentines from Pinus jeffreyi Grev. and Balf.,
Pinus sabiniana Dangl. and others. Also reported in over 200 food and beverages including apple, apricot, citrus peel oils and juices,
many berries, grapes, melon, papaya, peach, pear, currants, pineapple, carrot, celery, cucumber, peas, cooked potato, tomato, ginger,
Mentha oils, thyme, breads, cheeses, butter, milk, cream, cooked egg, fish, meats, beer, cognac, rum, whiskies, grape wines, tea,
roasted filberts and peanuts, oats, soybean, coconut, olive, plum, plumcot, beans, mushroom, starfruit, macadamia nut, mango, cauliflower, broccoli, tamarind, fig, artichoke, cardamom, coriander leaf, gin, rice, litchi, sweet potato, avocado, calamus, dill, lovage,
caraway seed, corn oil, corn tortillas, loquat, endive, lemon balm, clary sage, shrimp, oyster, clam, scallop, Chinese quince, maté,
sweet grass oil and mastic gum fruit oil.
Uses
1-Nonanal is used very extensively, but
also very sparingly in volume, in perfume
formulations. Trace ambunts, often less than
0.1 %, are used in Rose, Lily, Peony, Orris,
Geranium, Citrus, Orangeblossom, Jasmin,
Tuberose, Opopanax and many other fragrance types, The aldehyde will supply very
natural "flower-wax" or "petal"-notes, and
give tremendous "lift" to a perfume.
It often
forms part of an "aldehydic base" which in
turn may form part of a topnote composition.
In flavor compositions, the aldehyde is used
for imitation Citrus, particularly Lemon and
Mandarin. Concentrations are very low, normally about 0.2 up to about 6 ppm in the
finished product.
Uses
Nonanal has a strong odor that is a mix of oil and sweet orange. When mixed with ethanol, it produces a solution that has a fragrance reminiscent of vanillin. This compound is often added to food as a flavoring agent and can be used in the creation of scents such as rose, orange blossom, fragrant violet, and a variety of other fragrances.
Definition
ChEBI: Nonanal is a saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism. It has a role as a human metabolite and a plant metabolite. It is a saturated fatty aldehyde, a n-alkanal and a medium-chain fatty aldehyde. It is functionally related to a nonanoic acid.
Preparation
1-Nonanal can be synthesized by catalytic oxidation of the corresponding alcohol (n- nonanol) or by reduction of the corresponding acid.
Aroma threshold values
1 to 8 ppb; aroma characteristics at 1.0%: sweet waxy, orange citrus with oily fatty and melon
skin nuances and a slightly lactonic nuance
Taste threshold values
aste characteristics at 2 ppm in 5% sugar and 0.1% CA: aldehydic citrus orange body with waxy and oily
melon-like nuances
General Description
Clear brown liquid characterized by a rose-orange odor. Insoluble in water. Found in at least 20 essential oils, including rose and citrus oils and several species of pine oil.
Air & Water Reactions
Sensitive to air. Insoluble in water.
Reactivity Profile
1-Nonanal is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation. Polymerizes readily with sulfuric acid and oxidized to nonanoic acid.
Fire Hazard
1-Nonanal is combustible.
Biochem/physiol Actions
Taste at 3-10 ppm
Safety Profile
A severe skin irritant.
Combustible liquid. Mutation data reported.
When heated to decomposition it emits
acrid smoke and irritating fumes. See also
ALDEHYDES.
Metabolism
See aldehyde C-8
