Ацетофенон

СинтетичнийПОПУЛЯРНІ Й НЕЗВИЧНІсолодкий · мигдаль · вишня
Верхні ноти·Ноти серцяПіраміда
4/5Сила
7годСтійкість
4Походження
Зразок
Ацетофенон як парфумерна сировина
Верхні ноти й ноти серця
N/A — synthetic (also found naturally in Castoreum)
Визначення

Marzipan left in a warm tin. Acetophenone has the almond-cherry sweetness of benzaldehyde but rounder, less volatile, with a hawthorn-floral undertone that drifts toward mimosa.

СОЛОДКИЙ ФРУКТОВИЙ
METHYL PHENYL KETONE ACETYLBENZENE
Type
Складник
Olfactive family
Гурманські
Source
synthetic molecule
Chemical class
ketone (aromatic)
Інструменти
Піраміда
ВВерхні ноти
СНоти серця
ББазові ноти
4/5Сила
Висока
інтенсивність запаху
Стійкість на блотері
7годин
1 год6 год24 год3 дн.7 дн.400 год
за 100 %
Країни-виробники
Китай Індія Німеччина Сполучені Штати

Запах

Sweet, almond-kernel, with a powdery hawthorn-floral quality absent from benzaldehyde. Less sharp, less volatile, more rounded. At low concentration, a waxy-narcotic quality surfaces — closer to the indolic sweetness of orange blossom than to cherry-pit sharpness. On blotter, the initial almond-marzipan note is prominent; after two hours, only a warm, clean, faintly powdery residue remains. Substantivity is moderate: roughly 7 hours at 100% on a strip.

Докладно

CAS 98-86-2. Molecular weight 120.15. The simplest aromatic ketone: one benzene ring, one acetyl group. Colourless crystals below 20°C; a pale yellow oily liquid above. Industrially, acetophenone is produced as a byproduct of the cumene-to-phenol process (Hock rearrangement), where a methyl group migrates instead of the expected phenyl group. It also forms during the oxidation of ethylbenzene.

The smell sits in the almond-cherry corridor occupied by benzaldehyde, but acetophenone is softer. Less cyanide-sharp, more powdery. At dilution (below 1%), a hawthorn-floral quality emerges — closer to mimosa absolute than to almond extract. There is also a faint waxy-narcotic undertone, almost orange-blossom, that makes it useful in white-floral bases where a touch of edible sweetness is wanted without going fully gourmand.

Acetophenone occurs naturally in castoreum (beaver castor sacs) and in foods such as apple, apricot, banana, cheese, beef and cauliflower. It is also a natural constituent of several plant extracts used in perfumery, Cistus (labdanum) oils and extracts in particular.

Regulatory note: in March 2025, ECHA's Risk Assessment Committee (RAC) published an opinion recommending that acetophenone be classified Repr. 1B (H360FD). The EU Cosmetics Regulation bans substances classified CMR 1B unless an exemption is granted, and the cosmetics industry chose not to defend acetophenone as an ingredient in its own right. A consortium formed with the help of the European Federation of Essential Oils (EFEO) defended instead its presence as a constituent of natural complex substances. In its final opinion of 14 October 2026, the SCCS judged it safe in that role up to 100 ppm (0.01%) in finished cosmetic products, for adults and children from the age of three. TGSC recommends a maximum of 2.0% in the fragrance concentrate.

Explore all seven extraits in the Discovery Set.

—

Related: Almond · Benzaldehyde · Black Walnut · Brazil Nut · Breadnut · Candlenut · Cashew · Chestnut

Sources

  1. PubChem — Acetophenone (CID 7410)
  2. Wikipedia — Acetophenone
  3. Wikipedia — Castoreum
  4. The Good Scents Company — acetophenone
  5. IFRA — Acetophenone (ECHA RAC opinion, 2025)
  6. European Commission — Request for an SCCS opinion on acetophenone
  7. EFEO — Call for interest to defend natural complex substances containing acetophenone (via CTPA)
  8. SCCS — Opinion on the safety of acetophenone (SCCS/1689/26, 2026)
  9. Dias & Ressler (2014), Nature Neuroscience 17: 89–96

Цікавий факт

In 2013, Brian Dias and Kerry Ressler at Emory University conditioned male mice to fear the smell of acetophenone by pairing it with mild footshocks. Their offspring — and their offspring's offspring — showed heightened sensitivity to acetophenone and enlarged olfactory glomeruli for the Olfr151 receptor, despite never encountering the molecule. The study, published in Nature Neuroscience, found CpG hypomethylation of the Olfr151 gene in the sperm of the conditioned males; in vitro fertilisation and cross-fostering experiments indicated that the effect passed through the gametes rather than through upbringing.

Отримання й хімія

Спосіб отримання

Not extracted from natural sources commercially. Industrial acetophenone is a byproduct of the Hock process (cumene oxidation to phenol and acetone), where an alternate rearrangement of isopropylbenzene hydroperoxide yields acetophenone and methanol instead of the expected phenol and acetone. It also forms, alongside 1-phenylethanol, when ethylbenzene hydroperoxide is converted during styrene production. Commercial purity: 98-100%. Inexpensive, bulk-scale production. Melting point 19-20°C means it crystallises in cool storage and must be gently warmed before use.

Формула
C8H8O
CAS
98-86-2
Ботанічна назва
N/A — synthetic (also found naturally in Castoreum)
Зовнішній вигляд
Colorless to pale yellow oily liquid; crystallizes below 20 °C
Сила запаху
висока, рекомендовано нюхати в розчині з концентрацією не більше 1,00 %
Стійкість
7 hour(s) at 100.00 %
Синоніми
METHYL PHENYL KETONE ACETYLBENZENE
Статус IFRA
Обмежено

TGSC recommends max 2.0% in fragrance concentrate. ECHA RAC opinion (March 2025): Repr. 1B (H360FD) classification recommended. SCCS final opinion (14 October 2026): safe as a constituent of natural complex substances up to 100 ppm (0.01%) in finished cosmetic products.

Фізичні властивості
Температура кипіння
202.00 to 203.00 °C. @ 760.00 mm Hg
Температура плавлення
19.00 to 20.00 °C. @ 760.00 mm Hg
Температура спалаху
179.00 °F. TCC ( 81.67 °C. )
Відносна густина
1.02500 to 1.03200 @ 25.00 °C.
Показник заломлення
1.53300 to 1.53600 @ 20.00 °C.

У парфумерії

Modifier in almond, cherry-blossom, and hawthorn accords. Acetophenone delivers a softer, more floral version of the almond character that benzaldehyde provides — less cyanide-sharp, more powdery. It functions in the top-to-heart zone (boiling point 202°C, substantivity 7 hours), bridging fruity-sweet openings into floral hearts. In cherry-blossom bases, it rounds out the benzaldehyde core. In hawthorn reconstructions, it is nearly indispensable. It also is a sweet modifier in white-floral and mimosa compositions, contributing a narcotic-edible quality at low dosages (typically below 1% in concentrate). In gourmand ambers, small additions enhance marzipan and nougat effects. The molecule is also a precursor in synthesis: starting material for methyl styryl ketone and various chalcones used in fragrance chemistry. FEMA 2009.

Роль у формулі
01модифікатор
02сполучний компонент
03піднесення верхніх нот
Форми випуску
синтетична речовина

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