Циклопентадеканолід

СинтетичнийМУСКУС, АМБРОВИЙ АКОРД, ТВАРИННІ ЗАПАХИмускусний · чистий · солодкий
Базові нотиПіраміда
—Сила
—Стійкість
—Походження
Зразок
Циклопентадеканолід як парфумерна сировина
Базові ноти
Визначення

Cyclopentadecanolide is a macrolide lactone, a colorless solid with a musklike odor. It has also been described as having an odor of amber and musk.

СОЛОДКИЙ МУСКУСНИЙ ПУДРОВИЙ
Angelica lactone, Muskalactone, Muskolactone, Exaltolide, Pentalide, Pentadecanolide
Type
Складник
Olfactive family
Амброві й мускусні
Chemical class
macrolide lactone
Інструменти
Піраміда
ВВерхні ноти
СНоти серця
ББазові ноти

Запах

Its aroma is described as musk, animal, powdery, natural, fruity, tobacco, coumarinic, heliotrope and licorice. Another description lists tobacco, coumarin, heliotropine, powdery, licorice and brown, with musk as the odor type. An older chemical reference gives an odor of amber and musk, and the musk compound of angelica root oil is said to give that oil a pleasant odor.

Докладно

Identity

Cyclopentadecanolide is classified as a macrolide lactone. Its CAS number is 106-02-5. Its preferred IUPAC name is 1-Oxacyclohexadecan-2-one. Its molecular formula is C₁₅H₂₈O₂, written structurally as (CH₂)₁₄CO₂, and its molar mass is about 240.39 g/mol.

Occurrence

Small quantities of it are found in angelica root essential oil, and it accounts for that oil's musklike odor.

Chemistry and synthesis

In one later laboratory study, 10-hydroxydecanoic acid served as the starting material for pentadecanolide, and the related lactone 11-oxahexadecanolide was easy to prepare from the same acid.

Flavour use

It is a flavouring agent with the FEMA number 2840. Its latest safety evaluation as a flavouring agent, in 1997, found no concern at current levels of intake. The same evaluation gives it the JECFA number 239 and the Council of Europe number 181.

Oxygen-containing analogues

Chain extension is far easier when a hetero-atom can be used instead of a carbon atom, so for economic reasons these heterocyclic lactones met with some success. After the war, 12-oxahexadecanolide was introduced under several trade names and was used by many perfumers in their cheaper compounds.

Explore all seven extraits in the Discovery Set.

—

Related: Aldron · Ambretone · Ambrette Musk Mallow · Ambrettolide Natural Musk · Ambrinol · Coral Reef · Exaltolide · Galaxolide

Цікавий факт

Muscone and civetone, macrocyclic ketone scents derived from the musk deer and the civet cat, were the first natural products shown to have rings with more than six atoms. Synthetic techniques at the time allowed only rings of up to eight members.

Отримання й хімія

Спосіб отримання

Cyclopentadecanolide is produced by ring expansion of cyclotetradecanone. Another synthesis route is the depolymerization of polyesters of 15-hydroxypentadecanoic acid.

Формула
C₁₅H₂₈O₂
CAS
106-02-5
Зовнішній вигляд
Colorless solid
Синоніми
Angelica lactone, Muskalactone, Muskolactone, Exaltolide, Pentalide, Pentadecanolide
Статус IFRA
Обмежено

Restricted — IFRA Standard « Cyclopentadecanolide » (Amendment 49)

Фізичні властивості
Температура кипіння
137.00 °C. @ 2.00 mm Hg
Температура плавлення
34.00 to 38.00 °C. @ 760.00 mm Hg
Температура спалаху
> 220.00 °F. TCC
Відносна густина
0.9447 (33 °C)
Показник заломлення
1.4669 (33 °C)

У парфумерії

It is used as a musklike perfume fixative in fine fragrances and as a flavoring agent. It is a substitute for the extremely expensive animal musk.

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

Див. також

7 ноти
Cashmeran мускусний · деревний · пряний Амбровий акорд теплий · смолистий · солодкий Ambroxan деревний · амбровий · мускусний Боби тонка Сіра амбра тваринний · морський · амбровий Мускус-ксилол мускусний · солодкий · мильний Sylkolide мускусний · пудровий · теплий
Сім екстрактів
INSULINE SAFRINE DOPPEL DANCERS ALBÂTRE SÉPIA GRAVITAS CAPITALE SIMILI MIRAGE ROSE MONOTONE NUIT ÉLASTIQUE DISCOVERY SET
Парфумерний глосарій PREMIEREPEAU →