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6,7,8,9-tetrahydro-7,7,8,9,9-pentamethyl-5H-cyclopenta[H]quinazoline
6,7,8,9-tetrahydro-7,7,8,9,9-pentamethyl-5H-cyclopenta[H]quinazoline is a fragrance compound known for its musky, ambery, and powdery odor characteristics.
General Material Description
6,7,8,9-tetrahydro-7,7,8,9,9-pentamethyl-5H-cyclopenta[H]quinazoline is a synthetic organic compound characterized by a bicyclic quinazoline fused ring structure with multiple methyl substitutions, resulting in the molecular formula C16H22N2. This compound exhibits a musky, ambery, and powdery odor profile when formulated at 10% concentration in dipropylene glycol. Its chemical structure includes a tetrahydrocyclopentaquinazoline core, and it is known under several synonyms reflecting stereochemistry and ring substitutions. As a fragrance agent, its sensory properties are valued in perfumery. The compound is documented in chemical databases such as PubChem, which provide detailed physicochemical and spectral data. It is generally sourced through chemical synthesis rather than extraction from natural materials due to its complex structure.
Occurrence, Applicability & Potential Uses
Although not naturally occurring, 6,7,8,9-tetrahydro-7,7,8,9,9-pentamethyl-5H-cyclopenta[H]quinazoline is utilized as a fragrance ingredient, primarily contributing musky notes in perfumery formulations. The compound's synthetic origin allows for controlled manufacturing suited to fragrance applications. It has been evaluated under the IFRA (Global) Code of Practice for fragrance material safety, where usage levels and restrictions are documented. Its role as a musky odorant enables its use in fine fragrances and other scented products where rich, ambery musk nuances are desired. Regulatory frameworks such as REACH (EU) influence its commercial application by requiring safety data and responsible use in consumer products.
Physico-Chemical Properties Summary
The compound possesses a molecular weight of 242.36 g/mol and exhibits limited aqueous solubility, estimated at approximately 1.45 mg/L at 25 °C, indicating its preference for non-polar or moderately polar solvents. An estimated log P (XLogP3-AA) of around 3.3 reflects moderate hydrophobicity, influencing its distribution in fragrance matrices. These physicochemical traits affect its volatility and interaction with other formula components, facilitating sustained musk aroma release. The chemical structure’s multiple methyl groups and bicyclic quinazoline system contribute to thermal and chemical stability, properties relevant in fragrance formulation where endurance and consistency are key factors.
FAQ
What is 6,7,8,9-tetrahydro-7,7,8,9,9-pentamethyl-5H-cyclopenta[H]quinazoline used for?
6,7,8,9-tetrahydro-7,7,8,9,9-pentamethyl-5H-cyclopenta[H]quinazoline is primarily used as a fragrance agent in perfumery. It imparts a musky, ambery, and powdery aroma at typical formulation levels. Its unique odor profile makes it suitable for enriching musky accords in various scented products. This compound is valued for its stability and moderate hydrophobicity, which allow for sustained scent release and compatibility with a range of fragrance ingredients.
How soluble is this compound and in what types of formulations is it typically found?
This compound has low water solubility, estimated at 1.45 mg/L at 25 °C, reflecting its hydrophobic nature. It is typically dissolved in solvents such as dipropylene glycol for use in fragrance formulations. Its moderate log P value suggests that it is well-suited for oil-based or solvent blends rather than aqueous preparations. These properties make it ideal for incorporation into perfumes, deodorants, and other scented consumer products requiring musky aroma notes.
Are there any regulatory guidelines or safety considerations for its use in fragrances?
6,7,8,9-tetrahydro-7,7,8,9,9-pentamethyl-5H-cyclopenta[H]quinazoline falls under safety evaluation by organizations such as IFRA (International Fragrance Association, Global), which issues usage recommendations and restrictions as part of its Code of Practice. The compound does not have classified hazards under OSHA’s Hazard Communication Standard in the United States. Current assessments indicate no specific hazard or precautionary labeling requirements, but manufacturers must comply with relevant chemical safety regulations including REACH (EU) and other regional standards. It is not approved for use as a flavoring agent.
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
| (8S)-7,7,8,9,9-pentamethyl-6,8-dihydro-5H-cyclopenta[h]quinazoline | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 68161970 |
| Pubchem (cas): | 1315251-11-6 |
| Publications by US Patents | |
| 9,068,143 - Quinazoline compounds and their use in perfume compositions | |
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 |
General Material Information
| Preferred name | 6,7,8,9-tetrahydro-7,7,8,9,9-pentamethyl-5H-cyclopenta[H]quinazoline |
| Trivial Name | 6,7,8,9-Tetrahydro-7,7,8,9,9-pentamethyl-5H-cyclopenta[h]quinazoline |
| Formula | C16 H22 N2 |
| CAS Number | 1315251-11-6 |
| FDA UNII | Search |
| xLogP3-AA | 3.30 (est) |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 242.36534118652 |
| Solubility | |
| water, 1.454 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Musk | |
| musk, amber, powdery, floral | |
| General comment | At 10.00 % in dipropylene glycol. musky, ambery, and powdery |
Safety Information
Safety information
| 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: | |||
| 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 6,7,8,9-tetrahydro-7,7,8,9,9-pentamethyl-5H-cyclopenta[H]quinazoline 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):1315251-11-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :68161970 |
| National Institute of Allergy and Infectious Diseases:Data |
| (8S)-7,7,8,9,9-pentamethyl-6,8-dihydro-5H-cyclopenta[h]quinazoline |
| Chemidplus:1315251116 |