Fatty aldehydes are aliphatic, long-chain aldehydes which may be mono- or polyunsaturated. The fatty aldehydes include compounds such as octanal, nonanal, decanal or dodecanal. The nomenclature is derived from the nomenclature of the alkanes, the ending -al is added to indicate the aldehyde group.
Fatty aldehydes are a natural component of many natural ingredients such as the essential oils of various citrus fruits. Decanal, for example, is a component of orange peel. [1] The pheromone cocktails of various insect pheromones contain fatty aldehydes. [2] Fat aldehydes were also detected in the heart muscle of mammals. [3]
Fatty aldehydes can be prepared by dehydrogenation of fatty alcohols on copper-zinc catalysts. [4] By the hydroformylation of alkenes, fatty aldehydes are produced on a large industrial scale. [5]
A large proportion of the fatty aldehydes prepared by hydroformylation is directly processed further to fatty alcohols. Many fatty aldehydes find use as a fragrance in perfume production. An example is 2-methylundecanal which is the typical odor component of Chanel No. 5. [6] Decanal, whose sweet, flowery odor reminiscents of orange peels, is used, among other things, as a flavoring agent in the food industry and as a perfume in the perfume industry.
Ambergris, ambergrease, or grey amber, is a solid, waxy, flammable substance of a dull grey or blackish colour produced in the digestive system of sperm whales. Freshly produced ambergris has a marine, fecal odor. It acquires a sweet, earthy scent as it ages, commonly likened to the fragrance of rubbing alcohol without the vaporous chemical astringency.
A carboxylic acid is an organic acid that contains a carboxyl group (C(=O)OH) attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.
Chemically, an aldehyde is a compound containing a functional group with the structure −CHO, consisting of a carbonyl center with the carbon atom also bonded to hydrogen and to any generic alkyl or side chain R group. The functional group itself is known as an aldehyde or formyl group.
Skatole or 3-methylindole is an organic compound belonging to the indole family. It occurs naturally in the feces of mammals and birds and is the primary contributor to fecal odor. In low concentrations, it has a flowery smell and is found in several flowers and essential oils, including those of orange blossoms, jasmine, and Ziziphus mauritiana.
1-Hexanol (IUPAC name hexan-1-ol) is an organic alcohol with a six-carbon chain and a condensed structural formula of CH3(CH2)5OH. This colorless liquid is slightly soluble in water, but miscible with diethyl ether and ethanol. Two additional straight chain isomers of 1-hexanol, 2-hexanol and 3-hexanol, exist, both of which differing by the location of the hydroxyl group. Many isomeric alcohols have the formula C6H13OH. It is used in the perfume industry.
An aroma compound, also known as an odorant, aroma, fragrance or flavor, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently volatile for transmission via the air to the olfactory system in the upper part of the nose. As examples, various fragrant fruits have diverse aroma compounds, particularly strawberries which are commercially cultivated to have appealing aromas, and contain several hundred aroma compounds.
Hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes from alkenes. This chemical reaction entails the net addition of a formyl group (CHO) and a hydrogen atom to a carbon-carbon double bond. This process has undergone continuous growth since its invention: Production capacity reached 6.6×106 tons in 1995. It is important because aldehydes are easily converted into many secondary products. For example, the resulting aldehydes are hydrogenated to alcohols that are converted to detergents. Hydroformylation is also used in speciality chemicals, relevant to the organic synthesis of fragrances and drugs. The development of hydroformylation is one of the premier achievements of 20th-century industrial chemistry.
Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula CH
3(CH
2)
3COOH. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. It is found in the perennial flowering plant Valeriana officinalis, from which it gets its name. Its primary use is in the synthesis of its esters. Salts and esters of valeric acid are known as valerates or pentanoates. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Several, including ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.
Fatty alcohols (or long-chain alcohols) are usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4–6 carbons to as many as 22–26, derived from natural fats and oils. The precise chain length varies with the source. Some commercially important fatty alcohols are lauryl, stearyl, and oleyl alcohols. They are colourless oily liquids (for smaller carbon numbers) or waxy solids, although impure samples may appear yellow. Fatty alcohols usually have an even number of carbon atoms and a single alcohol group (–OH) attached to the terminal carbon. Some are unsaturated and some are branched. They are widely used in industry. As with fatty acids, they are often referred to generically by the number of carbon atoms in the molecule, such as "a C12 alcohol", that is an alcohol having 12 carbons, for example dodecanol.
Orange oil is an essential oil produced by cells within the rind of an orange fruit. In contrast to most essential oils, it is extracted as a by-product of orange juice production by centrifugation, producing a cold-pressed oil. It is composed of mostly d-limonene, and is often used in place of pure d-limonene. D-limonene can be extracted from the oil by distillation.
3-Methylbutanoic acid, also known as β-methylbutyric acid or more commonly isovaleric acid, is a branched-chain alkyl carboxylic acid with the chemical formula (CH3)2CHCH2CO2H. It is classified as a short-chain fatty acid. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. The compound occurs naturally and can be found in many foods, such as cheese, soy milk, and apple juice.
Salicylic aldehyde (2-hydroxybenzaldehyde) is the organic compound with the formula C6H4CHO-2-OH. Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. This colorless oily liquid has a bitter almond odor at higher concentration. Salicylaldehyde is a key precursor to a variety chelating agents, some of which are commercially important.
The Shell higher olefin process is a chemical process for the production of linear alpha olefins via ethylene oligomerization and olefin metathesis invented and exploited by Royal Dutch Shell. The olefin products are converted to fatty aldehydes and then to fatty alcohols, which are precursors plasticizers and detergents. The annual global production of olefines through this method is over one million tonnes.
Oct-1-en-3-one (CH2=CHC(=O)(CH2)4CH3), also known as 1-octen-3-one, is the odorant that is responsible for the typical "metallic" smell of metals and blood coming into contact with skin. Oct-1-en-3-one has a strong metallic mushroom-like odor with an odor detection threshold of 0.03–1.12 µg/m3 and it is the main compound responsible for the "smell of metal", followed by decanal (smell: orange skin, flowery) and nonanal (smell: tallowy, fruity). Oct-1-en-3-one is the degradative reduction product of the chemical reaction of skin lipid peroxides and Fe2+. Skin lipid peroxides are formed from skin lipid by oxidation, either enzymatically by lipoxygenases or by air oxygen. Oct-1-en-3-one is a ketone analog of the alkene 1-octene.
Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbonylation also refers to oxidation of protein side chains.
Octanal is the organic compound, an aldehyde, with the chemical formula CH3(CH2)6CHO. A colorless fragrant liquid with a fruit-like odor, it occurs naturally in citrus oils. It is used commercially as a component in perfumes and in flavor production for the food industry. It is usually produced by hydroformylation of heptene and the dehydrogenation of 1-octanol.
Decanal is an organic compound classified as an aldehyde with the chemical formula C10H20O.
Heptanal or heptanaldehyde is an alkyl aldehyde. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants.
2-Methylundecanal is an organic compound that is found naturally in kumquat peel oil. This compound smells herbaceous, orange, and ambergris-like. At high dilution it has a flavor similar to honey and nuts. It is a colorless or pale yellow liquid that is soluble in organic solvents such as ether and ethanol. It is used as a fragrance component in soaps, detergents, and perfumes.
Lavandulol is a monoterpene alcohol found in a variety of essential oils such as lavender oil. The term refers to either of two enantiomers. The (R)-enantiomer is natural and has an aroma described as "weak floral, herbal odor with slightly lemon-like, fresh citrus fruity nuance"; the (S)-enantiomer has only a weak odor.