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Damascone

Q: Is Damascone natural or synthetic?

. Extraction: Beta-damascone and alpha-damascone occur naturally in Rosa damascena oil at trace concentrations (low ppm range), far below what is commercially extractable. All commercial damascone is produced by total synthesis. The dominant industrial route starts from ketoisophorone (2,6,6-trimethylcyclohex-2-ene-1,4-dione), proceeding through Wittig or Horner-Wadsworth-Emmons olefination. The (E)-isomer is the primary product. Alpha-damascone commercial material typically contains 92-99% (E)-isomer and 4-8% (Z)-isomer..

SYNTHETIC / fruity · floral · rich

Damascone

Category	SYNTHETIC
Subcategory	fruity · floral · rich
Origin
Volatility	Heart Note
Botanical	N/A (synthetic molecule, inspired by Rosa damascena)
Appearance	pale yellow clear liquid
Odor Strength	High
Producing Countries	N/A — synthetic molecule, manufactured globally
Pyramid	Heart

Dark plum skin, blackcurrant jam caught in a warm draft. Beta-damascone is the molecule that makes a rose reconstruction smell like a living garden rather than a chemical sketch — fruity, wine-stained, almost overripe.

Scent
The Full Story
Fun Fact
Extraction & Chemistry
In Perfumery

Scent

Beta-damascone opens with a burst of overripe plum and blackcurrant, denser and darker than any fruit ester. Within minutes the tobacco-leaf quality emerges — dry, warm, faintly honeyed. Compared to beta-ionone (which reads more violet-raspberry), beta-damascone sits lower on the spectrum: heavier, jammier, closer to stewed fruit than fresh berry. Alpha-damascone, by contrast, is lifted and metallic, with a green-apple bite similar to of a clean rose absolute. Neither isomer smells sweet in the confectionery sense; the sweetness is the sweetness of fermentation, of wine must.

Evolution over time

Immediately

Explosive dark-fruit burst — stewed plum, blackcurrant jam, a flash of green-apple metallic brightness from the alpha isomer

After a few hours

Tobacco-leaf warmth, wine-must sweetness, dried rose petal; the fruit recedes into a honeyed, resinous warmth

After a few days

Persistent warm-fruity residue on fabric; faint dried-plum and tobacco character; beta-damascone 264-hour substantivity keeps a ghost note present

The Full Story

The commercially dominant isomers are beta-damascone (CAS 23726-91-2) and alpha-damascone (CAS 43052-87-5). Both occur naturally in rose oil at trace concentrations — parts-per-million range — yet exert outsized olfactory impact.

Beta-damascone smells of stewed plum, blackcurrant preserve, and sun-warmed tobacco leaf, with a wine-like undertone. It is classified as fruity-floral with high odor strength; TGSC recommends evaluation at 1% dilution or less. Alpha-damascone is more floral and cleaner: rose petal, green apple skin, a metallic brightness absent from the beta isomer. Its substantivity (66 hours at 100%) is markedly shorter than beta (264 hours at 100%), making alpha better suited for heart-note transparency.

These molecules derive biosynthetically from carotenoid degradation — specifically the enzymatic cleavage of neoxanthin. Commercial supply is entirely synthetic; natural occurrence in rose oil is too dilute for extraction. The synthesis typically proceeds from ketoisophorone (2,6,6-trimethylcyclohex-2-ene-1,4-dione) or related cyclohexenone precursors.

Damascones belong to the rose ketone family alongside damascenones and ionones. Beta-damascenone (CAS 23696-85-7), often confused with beta-damascone, is a distinct molecule — it has a lower molecular weight (C13H18O, MW 190.28), a different structure (additional unsaturation in the ring), and an even lower odor threshold (approximately 0.002 micrograms per liter in water). Perfumers must distinguish carefully: damascone contributes dark-fruit body; damascenone contributes honeyed, apple-skin transparency.

This note in Première Peau. Rose Monotone. Sample all seven extraits in the Discovery Set.

Did You Know?

Did you know?

The damascone family owes its name to Rosa damascena, but the discovery story is tangled. They isolated 0.8 milligrams of an unknown compound, proposed an incorrect structure, then synthesized what they thought was a close analogue — which turned out to be the actual molecule. The resulting paper, prepared in 1972, was embargoed from publication until 1987 because of its commercial value.

Extraction & Chemistry

Extraction method: Beta-damascone and alpha-damascone occur naturally in Rosa damascena oil at trace concentrations (low ppm range), far below what is commercially extractable. All commercial damascone is produced by total synthesis. The dominant industrial route starts from ketoisophorone (2,6,6-trimethylcyclohex-2-ene-1,4-dione), proceeding through Wittig or Horner-Wadsworth-Emmons olefination. The (E)-isomer is the primary product. Alpha-damascone commercial material typically contains 92-99% (E)-isomer and 4-8% (Z)-isomer.

Molecular Formula	C13 H20 O
CAS Number	23726-91-2
Botanical Name	N/A (synthetic molecule, inspired by Rosa damascena)
IFRA Status	Restricted. Rose ketones (damascones, damascenones, ionones) are collectively capped at 0.043% in fine fragrance (IFRA 51st Amendment, Category 4). Critical effect: dermal sensitization. Alpha-damascone also restricted individually with limits as low as 0.0023% in axillary products.
Synonyms	DAMASCONE A · DAMASCONE B · (E)-BETA-DAMASCONE · ALPHA-DAMASCONE · ROSE KETONE · trans-BETA-DAMASCONE
Physical Properties
Odor Strength	High
Lasting Power	264 hour(s) at 100.00 %
Appearance	pale yellow clear liquid
Boiling Point	200.00 °C. @ 760.00 mm Hg
Flash Point	212.00 °F. TCC ( 100.00 °C. )
Specific Gravity	0.92800 to 0.93600 @ 25.00 °C.
Refractive Index	1.49200 to 1.49900 @ 20.00 °C.

In Perfumery

Damascones function as high-impact fruity-floral modifiers used at very low concentrations — typically 0.01-0.2% of a fragrance concentrate. Beta-damascone provides dark-fruit body to rose reconstructions. Without it, synthetic roses tend toward a flat citronellol-geraniol sketch. With it, the accord gains the overripe depth found in the natural oil. Alpha-damascone serves a different purpose: it sharpens and lifts floral accords with a green-metallic transparency. Its shorter substantivity (66 hours vs 264 for beta) makes it a heart-note material rather than a base contributor. Both isomers appear across fragrance families: rose soliflores, fruity chypres, dark ambers, and tobacco-leather compositions. They are classified as rose ketones alongside damascenones and ionones. IFRA restricts the cumulative rose ketone load to 0.043% in fine fragrance (Category 4, 51st Amendment), making dosage precision critical. In the Premiere Peau collection, rose-facing compositions such as Rose Monotone benefit from damascone-type materials, where they provide the dark-fruit counterpoint to crystalline lychee-rose transparency.