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amber naphthofuran
Amber naphthofuran is a tricyclic compound with an amber, woody, and musky odor widely used in flavor and fragrance applications.
General Material Description
Amber naphthofuran, known by the trivial name Cetalox, is a synthetic fragrance compound classified chemically as 1,5,5,9-tetramethyl-13-oxatricyclo(8.3.0.0.(4.9))tridecane with molecular formula C16H28O. It appears as a colorless to pale material featuring a prominent amber odor with woody, dry, and musky nuances. The compound has many synonyms including Ambrox DL and Ambermor DL (IFF), and is recognized in chemical databases such as PubChem (PubChem). Amber naphthofuran is typically obtained via chemical synthesis, serving as an important ingredient in perfumery and flavoring applications where warm and animalic amber notes are desired.
Occurrence, Applicability & Potential Uses
Amber naphthofuran occurs naturally in essential oils such as salvia sclarea (clary sage oil) from Greece, albeit in low concentrations (~0.10%). It functions prominently in the flavor and fragrance industry, imparting a high-strength amber, ambergris, woody, and musky character to creations. According to IFRA (Global) and FEMA (US) standards, it is approved for use in fine fragrances and flavorings, respectively, within specified limits to ensure safety and regulatory compliance. Its applications include replacements for ambrette oil, animalic ambergris notes, and enhancement of woody, tobacco, and powdery accords. Amber naphthofuran's versatility extends to perfuming agents, flavor enhancers in tea and guaiacwood flavors, and fantasy blends, making it valuable across various product categories.
Physico-Chemical Properties Summary
Amber naphthofuran possesses physical properties that support its use in complex formulations. It has a melting range between 75 and 85 °C at atmospheric pressure and boils between 102 and 106 °C under reduced pressure (25 mm Hg). The compound is slightly soluble in water (approximately 2.436 mg/L at 25 °C) and readily dissolves in alcohol solvents. Its high estimated logP value (~5.26) indicates significant lipophilicity, which contributes to excellent substantivity and fixing properties in fragrance compositions, with substantivity exceeding 400 hours at 10% solution in dipropylene glycol. The flash point is around 100 °C (212 °F), implying moderate volatility and handling safety. Stability assessments show it is compatible in various personal care and fine fragrance matrices at typical use concentrations, supporting its practical utility.
FAQ
What is amber naphthofuran and what are its main characteristics?
Amber naphthofuran is a synthetic fragrance compound known for its strong amber odor with woody, ambergris, and musky nuances. Chemically, it is identified as 1,5,5,9-tetramethyl-13-oxatricyclo(8.3.0.0.(4.9))tridecane and has the molecular formula C16H28O. It is widely used in the flavor and fragrance industries for imparting long-lasting amber-type notes with a dry, animalic touch. The compound appears as a colorless to pale material and has several trade names such as Cetalox, Ambrox DL, and Ambermor DL.
Where does amber naphthofuran occur naturally and how is it typically used?
Amber naphthofuran naturally occurs in small amounts within clary sage oil (Salvia sclarea), particularly from Greece at about 0.10%. Commercially, it is produced synthetically and used as an ambergris substitute and fragrance fixative. It enhances a variety of scent profiles including woody, tobacco, powdery, and musky accords. Its usage spans perfuming agents, flavoring in tea and guaiacwood notes, and incorporation into fantasy blends for complexity and depth. Compliance with IFRA (Global) and FEMA (US) standards guide its safe concentration limits in formulations.
What safety regulations and precautions are relevant to amber naphthofuran?
Amber naphthofuran is classified as an irritant under European regulations, with hazard statements indicating potential irritation to eyes, respiratory system, and skin. Appropriate protective measures include keeping it out of children’s reach, rinsing eyes thoroughly if in contact, and using protective clothing. IFRA (Global) provides guidelines limiting its concentration to a maximum of 5% in fragrance concentrates to mitigate risks. FEMA (US) has reviewed it as a Generally Recognized as Safe (GRAS) flavor ingredient with specified use levels in food categories. Toxicological data are limited, but regulatory bodies including EFSA and RIFM continuously evaluate its safety profile.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| Leffingwell: | Chirality or Article |
| 3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 3738-00-9 |
| Pubchem (cid): | 107166 |
| Pubchem (sid): | 135063926 |
| Pherobase: | View |
Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2932.19.0000 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
| EFSA Update of results on the monitoring of furan levels in food: | Read Report |
| EFSA Previous report: Results on the monitoring of furan levels in food: | Read Report |
| EFSA Report of the CONTAM Panel on provisional findings on furan in food: | Read Report |
General Material Information
| Preferred name | amber naphthofuran |
| Trivial Name | Cetalox |
| Short Description | 1,5,5,9-tetramethyl-13-oxatricyclo(8.3.0.0.(4.9))tridecane |
| Formula | C16 H28 O |
| CAS Number | 3738-00-9 |
| Deleted CAS Number | 193980-58-4 |
| FEMA Number | 3471 |
| Flavis Number | 13.072 |
| ECHA Number | 223-118-6 |
| FDA UNII | Search |
| Nikkaji Number | J205.641K |
| COE Number | 10514 |
| xLogP3-AA | 4.70 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1240 1,5,5,9-tetramethyl-13-oxatricyclo(8.3.0.0.(4.9))tridecane |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 236.39836120605 |
| Melting Point | 75 to 85°C @ 760 mm Hg |
| Boiling Point | 102 to 106°C @ 25 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.009 mmHg @ 25 °C |
| Flash Point TCC Value | 100 °C TCC |
| logP (o/w) | 5.256 est |
| Solubility | |
| alcohol | Yes |
| water, slightly | Yes |
| water, 2.436 mg/L @ 25 °C (est) | Yes |
| Stability | |
| APC: traces - 1% | Unspecified |
| candle: traces - 1% | Unspecified |
| detergent: traces - 1% | Unspecified |
| fine fragrances: 0.5 - 5% | Unspecified |
| shampoo: traces - 0.5% | Unspecified |
| shower gel: traces - 0.5% | Unspecified |
| soap: traces - 0.5% | Unspecified |
| softener: traces - 1% | Unspecified |
Organoleptic Properties
| Odor Type: Amber | |
| dry, woody, amber, ambergris, musk, sweet | |
| Odor strength | high , recommend smelling in a 10.00 % solution or less |
| Substantivity | > 400 hour(s) at 10.00 % in dipropylene glycol |
| Luebke, William tgsc, (1986) | At 10.00 % in dipropylene glycol. dry woody amber ambergris musk sweet |
| Flavor Type: Amber | |
| amber, woody old wood, tobacco, powdery, dry, ambergris, animal | |
| Luebke, William tgsc, (1986) | Amber old wood tobacco powdery dry ambergris animal |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Agate , Amber , Ambergris , Ambreine , Ambrette oil replacer , Animal , Baby powder , Balsam , Bay rum , Bayberry , Blackberry , Blue grass , Blueberry , Bouquet , Cabreuva wood , Castoreum , Cedar forest , Christmas , Cigar , Clean linen , Coronilla , Deertongue absolute replacer , Earth , Fern , Fir balsam , Floral , Guaiacwood , Habuba , Hay new mown hay , Heather , Herbal , Hollyberry , Incense , Juniper berry , Labdanum , Leather , Leather russian leather , Maja , Moss , Musk , Ocean sea , Oriental , Patchouli , Pine forest , Powder , Rain , Raspberry , Sandalwood , Sea breeze , Spice , Spring rain , Sweet grass , Tobacco , Tonka bean , Vanilla , Woodruff , Woody |
| Flavoring purposes | Guaiacwood , Tea |
| Other purposes | Dry , Fantasy blends , Tweed |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36 - Wear suitable protective clothing. | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavor and fragrance agents | |||
| RIFM Fragrance Material Safety Assessment: Search | |||
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice | |||
| Recommendation for amber naphthofuran usage levels up to: | |||
| 5.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 1.20 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.10 (μg/capita/day) | ||
| Structure Class: | III | ||
| Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). | |||
| The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library | |||
| publication number: 9 | |||
| Click here to view publication 9 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 0.01000 | |
| beverages(nonalcoholic): | - | 0.01000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | 0.01000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 0.01000 | |
| fruit ices: | - | 0.01000 | |
| gelatins / puddings: | - | 0.01000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
Safety references
| European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
| European Food Safety Authority (EFSA) reference(s): |
| Flavouring Group Evaluation 59 (FGE.59): Consideration of aliphatic and aromatic ethers evaluated by JECFA (61st meeting) structurally related to aliphatic, alicyclic and aromatic ethers including anisole derivatives evaluated by EFSA in FGE.23 (2006) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Flavouring Group Evaluation 33 (FGE.33)[1] - Six Tetrahydrofuran Derivatives from Chemical Groups 13, 14, 16 and 26 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 59, Revision 1 (FGE.59Rev1): Consideration of aliphatic and aromatic ethers evaluated by JECFA (61st meeting and 63rd meeting) structurally related to aliphatic, alicyclic and aromatic ethers including anisole derivatives evaluated by EFSA in FGE.23 Rev2 (2010) View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):3738-00-9 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :107166 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| 3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran |
| Chemidplus:0003738009 |