Альдегіди: натуральний чи синтетичний матеріал?

Синтетичний матеріал.

Альдегіди

СинтетичнийПОПУЛЯРНІ Й НЕЗВИЧНІсвіжий · цитрусовий · фруктовий

Верхні нотиПіраміда

4/5Сила

368годСтійкість

—Походження

Зразок

Альдегіди як парфумерна сировина — Верхні ноти

Визначення

Aldehydes are organic compounds containing a functional group with the structure R-CH=O. Dodecanal smells soapy, waxy and citrus, while 2-methylundecanal smells metallic, waxy and coumarinic.

КВІТКОВИЙ ЦИТРУСОВИЙ СОЛОДКИЙ ФРУКТОВИЙ СВІЖИЙ ВОСКОВИЙ

Aldehyde C-8, aldehyde C-9, aldehyde C-12 lauric, aldehyde C-12 MNA

Type: Складник
Olfactive family: Цитрусові
Source: synthetic molecule, some also naturally occurring in citrus oils
Chemical class: aldehyde

Інструменти

Піраміда

ВВерхні ноти

СНоти серця

ББазові ноти

4/5Сила

Висока

інтенсивність запаху

Стійкість на блотері

368годин · 15 днів

1 год6 год24 год3 дн.7 дн.400 год

за 100 %

Запах

Short-chain aldehydes have rather sharp and unpleasant odours, which become milder as the carbon chain lengthens. Octanal has a strong fruity odour that becomes fatty, citrus and honey on dilution. Nonanal has an orange-rose odour and is also described as floral, waxy and green. Dodecanal is soapy, waxy, aldehydic, citrus, green and floral, with orange-rind nuances. Another description of dodecanal reads fatty, sweaty, soapy, fresh and clean, with a clean-soap-laundry, floral, sweet, green and balsamic side. 2-Methylundecanal is gassy, diffusive, metallic and waxy, with coumarin and citrus nuances. It is also described as fresh, amber, aldehydic, mossy, citrus, tuberose, metallic, waxy and coumarinic, and as a dry, amber-like, herbaceous odour.

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DISCOVERY SET7 × 2 мл →ЕКСТРАКТСім екстрактів →

Докладно

In an aldehyde molecule, the central carbon atom is joined by a double bond to oxygen, by a single bond to hydrogen and by a single bond to a third substituent, which is carbon or, in formaldehyde, hydrogen.

Explore all seven extraits in the Discovery Set.

Aldehydes in nature

Traces of many aldehydes occur in essential oils, where they often contribute to the pleasant odours; examples are cinnamaldehyde and vanillin. Possibly because of the high reactivity of the formyl group, aldehydes are rarely found in building-block molecules such as amino acids, nucleic acids and lipids. Octanal, undecanal and dodecanal occur naturally in citrus oils. Decanal occurs naturally in citrus, in buckwheat and in coriander essential oil. Dodecanal also occurs in peel oil from Citrus species and kumquat, and is present in ginger, coriander, chervil and scallop. Nonanal is found in at least 20 essential oils, including rose and citrus oils and several species of pine oil. Nonanal has also been identified as a compound that attracts Culex mosquitoes.

Chemistry and supply

2-Methylundecanal is a saturated fatty aldehyde and a 2-methyl-branched fatty aldehyde. It dissolves in alcohol, dipropylene glycol, fixed oils and paraffin oil. Undecanal is an eleven-carbon aldehyde with the formula C₁₁H₂₂O. Undecanal is used in the synthesis of Disparlure. Dodecanal is stored under nitrogen. A specification for dodecanal calls for at least 92%, with 3-6% tetradecanal, 2-5% decanal and 1-2% hexadecanal as secondary components.

Історія

The age of entirely natural perfumes ended in the 1880s, with synthetic coumarin used in 1882 and synthetic vanillin in 1887. In 1912, a perfumer first used 2-methylundecanal in a successful perfume. Ernest Beaux imitated this breakthrough in a new perfume of 1914. Analysis of original sealed bottles of that perfume established the use of undecanal, dodecanal and undec-10-enal, with neroli and ylang-ylang, in the top note.

Ernest Beaux was a Russian-French perfumer who created a perfume that was launched on 5 May 1921. That perfume was one of the first to make major use of aldehydes. Its present formula differs from his 1914 perfume by the important addition of 2-methylalkanals, especially 2-methylundecanal. One story holds that Beaux's assistant added too much aldehyde, and that the resulting perfume was a piece of luck.

The hydroformylation process was discovered by the German chemist Otto Roelen in 1938, during investigations of the Fischer-Tropsch process. In 1968, highly active rhodium-based catalysts were reported.

Цікавий факт

Dodecanal is called aldehyde C-12 lauric and 2-methylundecanal aldehyde C-12 MNA, yet both have the formula C₁₂H₂₄O. 2-Methylundecanal is a 2-methyl-branched fatty aldehyde, whereas dodecanal has the formula CH₃(CH₂)₁₀CHO. Most sugars are derivatives of aldehydes; these aldoses exist as hemiacetals, and in water only a tiny share of the glucose is in the aldehyde form. Hydroformylation, the industrial route to aldehydes, reached a production capacity of 6.6 × 10⁶ tons in 1995.

Отримання й хімія

Спосіб отримання

Hydroformylation, also called the oxo process, is an industrial process that produces aldehydes from alkenes. The reaction adds a formyl group and a hydrogen atom to a carbon-carbon double bond. The alkene is treated, typically, with carbon monoxide and hydrogen at pressures between 10 and 100 atmospheres and temperatures between 40 and 200 °C, and a transition metal catalyst is required. Since the 1970s, most hydroformylation relies on rhodium-based catalysts. Undecanal is produced commercially by hydroformylation of decene, and the linear nonanal by hydroformylation of 1-octene. Octanal is usually produced by hydroformylation of heptene and by dehydrogenation of 1-octanol. Commercial dodecanal is usually produced from dodecanol by dehydrogenation, and decanal can be prepared by oxidation of decanol.

Формула: General formula: R-CHO — the aldehydes named here range from C₈H₁₆O (octanal) to C₁₂H₂₄O (dodecanal and 2-methylundecanal)
Зовнішній вигляд: Colorless to light yellow liquid
Сила запаху: Висока
Стійкість: Dodecanal 368 hours, 2-methylundecanal 388 hours (at 100%)
Синоніми: Aldehyde C-8, aldehyde C-9, aldehyde C-12 lauric, aldehyde C-12 MNA

Статус IFRA

Див. примітку

No IFRA Standard for the material itself (51st Amendment)

У парфумерії

Octanal is a component of perfumes and is used in flavour production for the food industry. Undecanal is a component of perfumes. Nonanal is used as a fragrance. Dodecanal is a component of many fragrances. Dodecanal is used in odour types such as cologne, violet, pine and chypre. 2-Methylundecanal is used as an amber note in topnote complexes. It is used in all types of perfumery and blends particularly well with floral, woody, amber and tobacco accords. Both dodecanal and 2-methylundecanal have good fabric substantivity. 2-Methylundecanal also serves as a topnote in fruit flavours such as peach and apricot, and it is used as a food additive.

Роль у формулі

01кістяк

02фірмова нота

03компонент піднесення

04свіжість

Форми випуску

синтетична речовина

Див. також

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