Геліотропін (піперональ)

СинтетичнийКВІТИквітковий · пудровий · солодкий
Ноти серцяПіраміда
3/5Сила
212годСтійкість
—Походження
Зразок
Геліотропін (піперональ) як парфумерна сировина
Ноти серця
Визначення

Heliotropin, or piperonal, is an organic compound which is commonly found in fragrances and flavors. Its odor is sweet and flowery, reminiscent of heliotrope.

КВІТКОВИЙ СОЛОДКИЙ ПУДРОВИЙ ВЕРШКОВИЙ
Piperonal, heliotropine, piperonyl aldehyde, protocatechuic aldehyde methylene ether, piperonaldehyde, geliotropin, heliobase
Type
Складник
Olfactive family
Квіткові
Source
Prepared from isosafrole or catechol; occurs naturally in various plants
Chemical class
Aromatic aldehyde
Інструменти
Піраміда
ВВерхні ноти
СНоти серця
ББазові ноти
3/5Сила
Середня
інтенсивність запаху
Стійкість на блотері
212годин · 9 днів
1 год6 год24 год3 дн.7 дн.400 год
за 100 %

Запах

Piperonal has a floral odor which is commonly described as being similar to that of vanillin or cherry. The odor is also described as heliotrope flower, sweet, powdery, coconut and vanilla. Other descriptions give cherry, vanilla, sweet cherry pit notes and creamy with cinnamic nuances. The odor is also sweet-floral, slightly spicy and heliotrope-like.

Докладно

Piperonal is an aromatic aldehyde that is structurally related to benzaldehyde and vanillin. The methylenedioxyphenyl group is found in other fragrances.

Piperonal naturally occurs in various plants. Examples include dill, violet flowers, and black pepper. The compound was named heliotropin after the 'cherry pie' notes in the fragrance of the heliotrope flower, although the chemical is not present in the flower's true aroma.

Piperonal, like all aldehydes, can be reduced to its alcohol (piperonyl alcohol) or oxidized to give its acid (piperonylic acid). It can be used in the synthesis of some pharmaceutical drugs including tadalafil, L-DOPA, and atrasentan. Piperonal is sensitive to light and turns red brown on exposure to it.

Helional is commonly derived from heliotropin and is used as a perfume in soap and laundry detergent. The most common route to helional is a crossed-aldol condensation between piperonal and propanal followed by selective hydrogenation of the intermediate alkene.

Explore all seven extraits in the Discovery Set.

—

Related: Acerola Blossom · Albizia · Anisaldehyde · Apple Blossom · Babys Breath · Campion Flower · Cannonball Flower · Cotton Flower

Цікавий факт

Due to their role in the manufacture of MDMA, safrole, isosafrole and piperonal are Category I precursors under regulation no. 273/2004 of the European Community.

Отримання й хімія

Спосіб отримання

Piperonal can be prepared by the oxidative cleavage of isosafrole or by using a multistep sequence from catechol or 1,2-methylenedioxybenzene. Synthesis from 1,2-methylenedioxybenzene is accomplished through a condensation reaction with glyoxylic acid followed by cleaving the resulting α-hydroxy acid with an oxidizing agent. Synthesis from catechol requires an additional step, Williamson ether synthesis using dichloromethane.

Формула
C₈H₆O₃
CAS
120-57-0
Зовнішній вигляд
Colorless or white crystals
Сила запаху
Середня
Стійкість
212 hours at 100%
Синоніми
Piperonal, heliotropine, piperonyl aldehyde, protocatechuic aldehyde methylene ether, piperonaldehyde, geliotropin, heliobase
Статус IFRA
Див. примітку

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

Фізичні властивості
Температура кипіння
263.00 to 265.00 °C. @ 760.00 mm Hg
Температура плавлення
37.00 to 39.00 °C. @ 760.00 mm Hg
Температура спалаху
> 230.00 °F. TCC ( > 110.00 °C. )

У парфумерії

Piperonal is commonly used to add vanilla or almond nuances, generally imparting balsamic, powdery, and floral aspects to a scent's character. Piperonal is used in powdery accords and also in florals such as muguet, carnation and lilac. Piperonal gives softness and creaminess. In flavors it adds hay-like, floral and powdery notes to a wide range of food preparations. Piperonal is used heavily in French vanilla flavors, in part as a replacement for coumarin which is no longer GRAS.

Роль у формулі
01модифікатор
02сполучний компонент
03формувач об’єму
Форми випуску
синтетична речовина натуральна речовина

Див. також

8 ноти