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versalide
Versalide is a synthetic musk chemical (CAS 88-29-9) noted for its medium intensity musk odor, formerly used in fragrances, now restricted due to safety concerns.
General Material Description
Versalide, chemically identified as 7-acetyl-6-ethyl-1,1,4,4-tetramethyltetralin and catalogued under CAS number 88-29-9, is a synthetic organic compound classified within the musk fragrance family. It presents as a solid with a molecular formula of C18H26O and has a characteristic medium-strength musk odor reminiscent of ambrette and macrocyclic musks. Documented synonyms include musk 36A, AETT, and various systematic names reflecting its tetrahydronaphthalene core structure. Derivation of versalide involves synthetic organic processes targeting the functionalized tetralin framework. This compound is chemically stable with low vapor pressure at room temperature. It is referenced in chemical databases such as PubChem under CID 6930 for detailed structural and physicochemical data.
Occurrence, Applicability & Potential Uses
Versalide is a synthetic compound not found in nature but designed as an ambrette oil replacer and musk fragrance ingredient. Its application was primarily in the fragrance industry due to its musky odor profile, providing a sweet and intense musk character at dilute concentrations. However, current industry practice excludes its use in fragrances under IFRA (International Fragrance Association) standards (Global), which list versalide as prohibited for fragrance applications due to neurotoxicity concerns. While not employed in flavoring contexts, versalide's historical role in perfumery highlights its relevance for research on synthetic musks and musk alternatives. The compound's physicochemical and safety properties influence these usage limitations.
Physico-Chemical Properties Summary
Versalide exhibits a melting point range around 46 to 47°C at atmospheric pressure and has a notably low vapor pressure of approximately 2.0×10–5 mmHg at 25°C, indicating low volatility. Its estimated partition coefficient (log P) of about 5.0 suggests high lipophilicity, impacting solubility and bioaccumulation potential. The compound dissolves in organic solvents such as alcohols, benzyl alcohol, benzyl benzoate, diethyl phthalate, and isopropyl myristate, but is practically insoluble in water. Versalide is chemically very stable under proper storage conditions, which include cool, dry environments protected from light and heat. These properties contribute to long shelf life, over 36 months, and substantivity of musk odor, persisting up to 400 hours in dipropylene glycol at 20% concentration. The flash point is relatively high at 200°F (approximately 93°C), suggesting reduced flammability risk during handling.
FAQ
What is versalide and what are its main characteristics?
Versalide is a synthetic musk compound known chemically as 7-acetyl-6-ethyl-1,1,4,4-tetramethyltetralin with CAS number 88-29-9. It features a medium-intensity musk odor with sweet and ambrette-like nuances. The compound is a solid with low volatility and high lipophilicity. Versalide serves historically as a musk fragrance ingredient and ambrette oil substitute due to its odor profile and substantivity.
Where does versalide occur and how is it used in industry?
Versalide does not occur naturally and is synthesized for use in perfumery as a musk fragrance. Its application aimed to replace natural ambrette musk and provide a stable, persistent musk scent in fragrance formulations. However, regulatory constraints limit its current use, and it is now prohibited for fragrance and flavoring applications according to IFRA (Global) standards. The compound finds no use in flavoring and is retained mainly for informational and research purposes.
What regulatory and safety considerations apply to versalide?
Versalide is classified as harmful if swallowed and presents neurotoxicity risks. According to European safety data, it carries hazard statements advising against ingestion and contact with skin or eyes, requiring precautions such as gloves and eye protection. The International Fragrance Association (IFRA) prohibits its use in fragrances due to neurotoxicity concerns, and it is not approved for flavor use. Handling guidelines recommend storage in cool, dry, well-sealed containers, avoiding heat and light exposure. Toxicological studies have established oral and dermal LD50 values in animal models indicating moderate acute toxicity.
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
| 1-(3-ethyl-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)ethanone | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 88-29-9 |
| Pubchem (cid): | 6930 |
| Pubchem (sid): | 134972180 |
| Publications by US Patents | |
| 4,162,256 - Process for the production of compounds useful in perfumery | |
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 |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | versalide |
| Trivial Name | 7-Acetyl-6-ethyl-1,1,4,4-tetramethyltetralin |
| Short Description | ethanone, 1- (3-ethyl-5,6,7,8-tetrahydro-5,5,8, 8-tetramethyl-2-naphthalenyl)- |
| Formula | C18 H26 O |
| CAS Number | 88-29-9 |
| ECHA Number | 201-817-7 |
| FDA UNII | BM2DT9GHFQ |
| Nikkaji Number | J4.291I |
| Beilstein Number | 2126062 |
| xLogP3-AA | 5.50 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 258.40441894531 |
| Melting Point | 46 to 47°C @ 760 mm Hg |
| Vapor Pressure | 2.0E-5 mmHg @ 25 °C |
| Flash Point TCC Value | 93.33 °C TCC |
| logP (o/w) | 5.037 est |
| Shelf life | 36 months (or longer if stored properly.) |
| Storage notes | Store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Solubility | |
| alcohol | Yes |
| benzyl alcohol | Yes |
| benzyl benzoate | Yes |
| diethyl phthalate | Yes |
| isopropyl myristate | Yes |
| water, 0.07008 mg/L @ 25 °C (est) | Yes |
| water | No |
| Stability | |
| very stable | Unspecified |
Organoleptic Properties
| Odor Type: Musk | |
| sweet, musk, ambrette | |
| Odor strength | medium , recommend smelling in a 10.00 % solution or less |
| Substantivity | 400 hour(s) at 20.00 % in dipropylene glycol |
| General comment | At 10.00 % in dipropylene glycol. sweet intense musk ambrette macrocyclic |
Potential Uses
| Applications | |
| Odor purposes | Ambrette oil replacer , Musk |
| Cosmetic purposes | Not used anymore |
Safety Information
Safety information
| European information : | |
| Most important hazard(s): | |
| Xn - Harmful. | |
| R 22 - Harmful if swallowed. S 02 - Keep out of the reach of children. S 20/21 - When using do not eat, drink or smoke. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 37/39 - Wear suitable gloves and eye/face protection. | |
| 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: | |
| oral-rat LD50 260 mg/kg SKIN AND APPENDAGES (SKIN): HAIR: OTHER BEHAVIORAL: EXCITEMENT BEHAVIORAL: ATAXIA Food and Cosmetics Toxicology. Vol. 19, Pg. 753, 1981. intraperitoneal-rat LD50 126 mg/kg BEHAVIORAL: EXCITEMENT BEHAVIORAL: TREMOR BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Food and Cosmetics Toxicology. Vol. 17, Pg. 357, 1979. oral-mouse LDLo 470 mg/kg Archives of Environmental Contamination and Toxicology. Vol. 14, Pg. 111, 1985. | |
| Dermal Toxicity: | |
| skin-rat LD50 584 mg/kg BEHAVIORAL: EXCITEMENT BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR Food and Cosmetics Toxicology. Vol. 17, Pg. 357, 1979. | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| information only not used for fragrances or flavors | |||
| IFRA Critical Effect: | |||
| Neurotoxicity | |||
| View the IFRA Standard | |||
| Recommendation for versalide usage levels up to: | |||
| PROHIBITED: Should not be used as a fragrance ingredient. | |||
| Recommendation for versalide flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):88-29-9 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :6930 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 1-(3-ethyl-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)ethanone |
| Chemidplus:0000088299 |