Methyl Naphtyl Ketone Beta
Synthetic Ingredient for Perfumery
Methyl Naphthyl Ketone Beta, a key component in fragrance and flavor compositions, offers a medium-strength, sweet Orange blossom aroma with a slight fruity undertone. Its powdery, floral scent profile distinguishes it from Methyl anthranilate, lacking its harshness.
Used extensively in perfumery for NeroIi, Orange blossom, and exotic florals, it enhances terminal notes even at concentrations below 1%. In flavoring, it's used for imitation Strawberry, Grape, Citrus, and Vanilla flavors.
🏭 Manufacturer — Symrise
📂 CAS N° 93-08-3
⚖️ MW — 170,21 g/mol
📝 Odor Type – Powdery + floral (orange blossom)
📈 Odor Strength – Medium
👃🏼 Odor Profile – Overall more powerful and also more pleasant than the alpha-isomer. Sweet and very tenacious Orange blossom type odor with a remotely fruity undertone.
👅 Flavor Profile – In extreme dilution, it has a Strawberry, Grape-like taste.
⚗️ Uses – Stable in soap and most other mild alkalis. Although its odor has often been compared to that of Methyl anthranilate, it represents an entirely different type of Orange blossom sweetness, without the aggressive harshness of the Anthranilate. The material is widely used in perfume compositions, mainly in NeroIi, Orange blossom, Sweet Pea, Magnolia, Honeysuckle, Wistaria, Narcisse, Jasmin, various exotic florals such as Frangipani, etc. It may have a perceptible effect in the perfume (or base) at concentrations well below one percent, and the effect is particularly noticeable in the terminal notes. In flavor compositions, the ketone finds a place in imitation Strawberry, Grape, various Citrus and berry-compositions, in Neroli and other floral flavors, in fruit complexes and in certain types of Vanilla flavor. The normal concentration used will vary from 0.5 to 5 ppm, but in chewing gum, it may be as high as 400 to 700 ppm.
WHAT IS METHYL NAPHTYL KETONE, BETA?
Discovery
In public use before the 1920s.
Beta Methyl naphthyl ketone was given GRAS status by FEMA (1965) and is approved by the FDA for food use (21 CFR 121.1164). The Council of Europe (1974) included 0-methyl naphthyl ketone at a level of 5 ppm in the list of artificial flavoring substances that may be added to foodstuffs without hazard to public health.
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Natural Occurrence
Has apparently not been reported to occur in nature.
Production
From Naphthaiene plus Acetyl chloride and Aluminum chloride (Friedel-Craft’s synthesis) in Nitrobenzene solvent — (Bedoukian, 1967).
Notes
Attempts have even been made to market “condensation products” of the two materials under various flowery trade names.
Biological Data
Acute toxicity — The acute oral L D 50 in rats was reported as 599 mg/kg (Bär & Griepentrog, 1967).
Subacute toxicity — The no-effect level for ß-methyl naphthyl ketone fed to rats for 12 wk was 34-2 mg/kg (Bär & Griepentrog, 1967).
Irritation — A patch test using β-methyl naphthyl ketone at full strength for 24 hr produced one irritation reaction in 24 human subjects (Katz, 1946).
Sensitization — A maximization test (Kligman, 1966; Kligman & Epstein, 1975) was carried out on 25 volunteers. The material was tested at a concentration of 2% in petrolatum and produced no sensitization reactions (Kligman. 1971).
Other Names:
2’-Acetonaphtone
beta-Acetonaphthylene
Orenolia
Cetone D
oranger Crystals
Nerolys (also alpha-)
NeroIon.
Orangeol
Anthralone (also alpha-)
Source:
National Center for Biotechnology Information (2020). PubChem Compound Summary for CID 7122, 2-Acetylnaphthalene. Retrieved November 24, 2020 from https://pubchem.ncbi.nlm.nih.gov/compound/2-Acetylnaphthalene.