Toscanol

СинтетичнийПРЯНОЩІпряний · теплий · ароматичний
Ноти серцяПіраміда
4/5Сила
—Стійкість
1Походження
Зразок
Toscanol як парфумерна сировина
Ноти серця
N/A — synthetic molecule
Визначення

Anisic, sweet-spicy, herbal. Toscanol is a synthetic aromatic ether, 1-(cyclopropylmethyl)-4-methoxybenzene, with a tarragon and liquorice character close to estragole.

ЗЕЛЕНИЙ ПРЯНИЙ СОЛОДКИЙ ТЕПЛИЙ СВІЖИЙ
1-(CYCLOPROPYLMETHYL)-4-METHOXYBENZENE P-(CYCLOPROPYLMETHYL)ANISOLE
Type
Складник
Olfactive family
Пряні
Source
Synthetic molecule
Chemical class
synthetic aroma chemical
Інструменти
Піраміда
ВВерхні ноти
СНоти серця
ББазові ноти
4/5Сила
Висока
інтенсивність запаху
Країни-виробники
Синтезують у всьому світі

Запах

Powerful and linear: an anisic, sweet-spicy scent close to estragole (methyl chavicol), with a liquorice and sassafras-oil character. At 10% in dipropylene glycol it reads sweet, anisic, tarragon, spicy, black liquorice, root beer and herbal (The Good Scents Company). Its territory is that of tarragon, basil and anise, not clove.

Докладно

Toscanol is the trade name of 1-(cyclopropylmethyl)-4-methoxybenzene (CAS 16510-27-3, C11H14O, 162.23 g/mol), a synthetic aromatic ether. Its structure is an anisole carrying a cyclopropylmethyl group in the para position. It has no phenol group and no allyl chain, so it is not a eugenol derivative. The molecule has no stereocentre: the CAS number covers a single compound, not a mixture of isomers.

Its scent is anisic and sweet-spicy, close to estragole (methyl chavicol), liquorice and sassafras, with a herbal side. Perfumers use it in place of basil oil, tarragon oil, estragole and safrole, usually at 0.1 to 5% of the concentrate.

—

Related: Allspice · Anethole · Anise · Asafoetida · Baking Spices · Bay Leaf · Biryani · Caraway

Sources

  1. 1-(Cyclopropylmethyl)-4-methoxybenzene (CID 6422476), CAS 16510-27-3. PubChem, NCBI. https://pubchem.ncbi.nlm.nih.gov/compound/6422476
  2. 1-cyclopropylmethyl-4-methoxybenzene, EC 444-110-0, CAS 16510-27-3. ECHA CHEM, European Chemicals Agency. https://chem.echa.europa.eu/100.103.938
  3. Sassafras acetate (Toscanol), CAS 16510-27-3. The Good Scents Company. https://www.thegoodscentscompany.com/data/rw1589981.html
  4. Fragrance and flavour compositions, US 7,704,942 B2, granted 27 April 2010 (priority EP 01115991, 30 June 2001). https://patents.google.com/patent/US7704942B2/en

Цікавий факт

Toscanol is made from estragole, the main scent molecule of tarragon and basil: the patent adds a single carbon to its side chain to close a three-membered cyclopropane ring. According to the same patent, its detection threshold, measured by olfactometer, is 80 times lower than that of estragole.

Отримання й хімія

Спосіб отримання

Fully synthetic. Toscanol is not made from eugenol or clove oil: its structure has no phenol group and no allyl chain. Patent US 7,704,942 describes its preparation from estragole by cyclopropanation of the allyl side chain (dibromomethane, zinc, copper(I) chloride), followed by distillation.

Формула
C₁₁H₁₄O
CAS
16510-27-3
Ботанічна назва
N/A — synthetic molecule
Зовнішній вигляд
Colourless liquid
Сила запаху
Висока
Синоніми
1-(CYCLOPROPYLMETHYL)-4-METHOXYBENZENE P-(CYCLOPROPYLMETHYL)ANISOLE
Статус IFRA
Див. примітку

Not subject to an IFRA Standard (51st Amendment)

Фізичні властивості
Температура кипіння
240.00 to 241.00 °C @ 760.00 mm Hg (est)
Відносна густина
0.986 to 0.990 @ 25.00 °C
Показник заломлення
1.522 to 1.526 @ 20.00 °C

У парфумерії

Toscanol is a synthetic anisic material used to bring an anisic, agrestic and aromatic character to accords. It is offered as a substitute for basil oil, tarragon oil, synthetic estragole and safrole, at 0.1 to 5% of the concentrate, in fine fragrance and consumer products. In the patent's fougère example it blends with the anisic and spicy notes and, compared with estragole, gives more character and freshness. It is stable in most bases, including soap and candles.

Роль у формулі
01модифікатор
02фірмова нота
03сполучний компонент
04формувач об’єму
05свіжість
Форми випуску
стандартна форма

Див. також

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