Amberketal

СинтетичнийМУСКУС, АМБРОВИЙ АКОРД, ТВАРИННІ ЗАПАХИамбровий · теплий · деревний

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Базові нотиПіраміда
3/5Сила
>384годСтійкість
·Походження
Зразок
Amberketal як парфумерна сировина
Базові ноти
N/A — synthetic amber molecule
Визначення

Dry amber with a pronounced trigeminal bite — closer to warm stone than to honeyed resin. A ketal derived from manool that smells like the inside of a cedarwood box left in direct sun.

ДЕРЕВНИЙ СОЛОДКИЙ ПУДРОВИЙ АМБРОВИЙ ГУРМАНСЬКИЙ ТЕПЛИЙ СМОЛИСТИЙ
Dodecahydro-3,8,8,11a-tetramethyl-5H-3,5a-epoxynaphth[2,1-c]oxepin
Type
Складник
Olfactive family
Амброві й мускусні
Source
synthetic molecule
Chemical class
synthetic aroma chemical
Інструменти
Піраміда
ВВерхні ноти
СНоти серця
ББазові ноти
3/5Сила
Середня
інтенсивність запаху
Стійкість на блотері
>384годин · 16 днів
1 год6 год24 год3 дн.7 дн.400 год
Країни-виробники
N/A: виробляють синтетично

Запах

Dry, powdery amber with a sharp trigeminal prickle that hits before the warmth registers. Less creamy than ambroxide, less mineral than racemic ambroxide. The woody quality recalls sun-heated driftwood rather than freshly cut timber. Underneath, a musky-animalic undertone surfaces — subtle but persistent, like the skin-scent left on a worn leather glove. The finish is chalky and warm, with none of the sweetness typically associated with the word “amber.”

Докладно

Amberketal is a semi-synthetic amber molecule (CAS 57345-19-4, C₁₈H₃₀O₂, MW 278.43) built from manool, a labdane diterpenoid extracted from the pink pine (Halocarpus biformis) of New Zealand. The synthesis pathway involves epoxidation of one of manool’s double bonds, oxidative degradation of the allylic alcohol into a ketone, and intramolecular acetalization to form the characteristic ketal ring. The result is a tetracyclic oxepin structure with five asymmetric carbons; only a specific mixture of isomers is used commercially.

Scent Character

The scent is dry, woody-amber with a strong trigeminal effect — a prickling sensation at the back of the nose that sets it apart from smoother amber molecules like ambroxide or its racemate. Where ambroxide reads mineral and airy, Amberketal is warmer, denser, more tactile. It has animalic-musky undertones and a powdery finish that anchors it firmly in the base of a composition. Scent strength is medium but substantivity is extreme: TGSC reports persistence above 384 hours on a smelling strip.

Technical Use

Amberketal is almost always diluted to 8.5–10% in isopropyl myristate (IPM) or dipropylene glycol before use, owing to its extreme potency. It functions as a fixative and volume builder, lending dry amber depth to amber, woody, and chypre structures. It works with other labdane derivatives (ambroxide and racemic ambroxide) but provides a distinct, rougher quality. Not currently restricted under IFRA 51st Amendment for fine fragrance use.

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Related: Amber · Amber Xtreme · Ambertonic · Anthamber · Karanal

Цікавий факт

Amberketal has five asymmetric carbon centers, theoretically yielding 32 possible stereoisomers. Only a specific mixture of these isomers carries the desired amber scent. The molecule's extreme substantivity — over 384 hours on a smelling strip according to TGSC data — means a single application on fabric can remain detectable for more than two weeks.

Отримання й хімія

Спосіб отримання

Semi-synthesis from manool, a labdane diterpenoid extracted from the heartwood and foliage of the pink pine (Halocarpus biformis), endemic to New Zealand. Manool content in H. biformis is exceptionally high: 6-8% by dry weight, the richest known plant source. The conversion involves three steps: (1) epoxidation of one of manool's olefinic double bonds, (2) oxidative cleavage of the allylic alcohol side chain to yield a ketone intermediate, and (3) intramolecular acetalization to close the ketal ring, producing the final tetracyclic oxepin structure. An alternative route from L-abietic acid has been published (Tetrahedron, 2007). The commercial product is a colorless to pale yellow liquid, diluted to 8.5-10% in isopropyl myristate for handling.

Формула
C₁₈H₃₀O₂
CAS
57345-19-4
Ботанічна назва
N/A — synthetic amber molecule
Зовнішній вигляд
Colorless to pale yellow clear liquid
Сила запаху
Середня
Стійкість
> 384 hours
Синоніми
Dodecahydro-3,8,8,11a-tetramethyl-5H-3,5a-epoxynaphth[2,1-c]oxepin
Статус IFRA
Див. примітку

Not subject to an IFRA Standard (51st Amendment)

Фізичні властивості
Температура кипіння
300-301°C @ 760 mmHg
Температура спалаху
252°F / 122°C (TCC)
Відносна густина
0.864 to 0.874 @ 25.00°C
Показник заломлення
1.436 to 1.446 @ 20.00°C

У парфумерії

Amberketal operates as a fixative and dry-amber modifier in the base of a composition. Its primary function is to extend longevity while adding a tactile, woody-amber warmth without overt sweetness. It sits at the drier end of the amber spectrum, making it valuable in masculine ambers, woody-amber accords, and modern chypres where creamier molecules like ambroxide would read too soft. It strengthens woody-ambergris accords alongside racemic ambroxide (CAS 3738-00-9), with which it shares a labdane-derived origin: Amberketal from manool, ambroxide from sclareol. In functional perfumery (soaps, detergents), its stability in non-aggressive media makes it a reliable base anchor.

Роль у формулі
01фіксатор
02модифікатор
03натуралізатор
04формувач об’єму
05свіжість
Форми випуску
синтетична речовина

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