chemistry

Tetramethyl acetyloctahydronaphthalenes

Tetramethyl acetyloctahydronaphthalenes is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Tetramethyl acetyloctahydronaphthalenes rather than just read about it. In short: Tetramethyl acetyloctahydronaphthalenes (International Nomenclature for Cosmetic Ingredients (INCI) name) (1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8,-tetramethyl-2-naphthyl)ethan-1-one) is a synthetic ketone fragrance also known as OTNE (octahydrotetramethyl acetophenone) and by other commercial trade names such as: Iso E Super, Iso Gamma Super, Anthamber, Amber Fleur, Boisvelone, Iso Ambois, Amberlan, Iso Velvetone, Orb…

Key takeaways

Tetramethyl acetyloctahydronaphthalenes belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Tetramethyl acetyloctahydronaphthalenes to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Tetramethyl acetyloctahydronaphthalenes from memory before moving on to harder problems.

Reference excerpt

Tetramethyl acetyloctahydronaphthalenes (International Nomenclature for Cosmetic Ingredients (INCI) name) (1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8,-tetramethyl-2-naphthyl)ethan-1-one) is a synthetic ketone fragrance also known as OTNE (octahydrotetramethyl acetophenone) and by other commercial trade names such as: Iso E Super, Iso Gamma Super, Anthamber, Amber Fleur, Boisvelone, Iso Ambois, Amberlan, Iso Velvetone, Orbitone, Amberonne. It is a synthetic woody odorant and is used as a fragrance ingredient in perfumes, laundry products and cosmetics. It has been described as "the most successful synthetic fragrance ever".

Odour According International Flavors & Fragrances Inc., OTNE has a "smooth, woody, amber[ous] [scent] with unique aspects giving a 'velvet' like sensation". Its odour is long-lasting on skin and fabric. Its fragrance has been described also as "revolutionary".

Production In commercial applications, Iso E Super is produced via a Diels–Alder reaction.

Chemical summary OTNE is the abbreviation for the fragrance material with Chemical Abstract Service (CAS) numbers 68155-66-8, 54464-57-2 and 68155-67-9 and EC List number 915-730-3. The commercial product comprises more than twenty isomeric ketones. The dominant isomer, often designated as the beta isomer, makes up most of the mixture yet is nearly odourless. The characteristic scent instead comes from a minor constituent, the gamma isomer, commonly known as Arborone, which typically represents only a few percent of the mixture. It is a multi-constituent isomer mixture containing:

1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthyl)ethan-1-one (CAS 54464-57-2) 1-(1,2,3,5,6,7,8,8a-octahydro-2,3,8,8-tetramethyl-2-naphthyl)ethan-1-one (CAS 68155-66-8) 1-(1,2,3,4,6,7,8,8a-octahydro-2,3,8,8-tetramethyl-2-naphthyl)ethan-1-one (CAS 68155-67-9)

Physical-chemical properties OTNE is a clear yellow liquid at 20 °C. Its melting point is below −20 °C at atmospheric pressure, and its boiling point is determined to be at around 290 °C (modified OECD 103 method). All physicochemical data have been obtained from the OTNE REACH registration dossier.

Safety Iso E Super may cause allergic reactions detectable by patch tests in humans and chronic exposure to Iso E Super from perfumes may result in permanent hypersensitivity. In a study with female mice, Iso E Super was positive in the local lymph node assay (LLNA) and irritancy assay (IRR), but negative in the mouse ear swelling test (MEST). No data were available regarding chemical disposition, metabolism, or toxicokinetics; acute, short-term, subchronic, or chronic toxicity; synergistic or antagonistic activity; reproductive or teratological effects; carcinogenicity; genotoxicity; or immunotoxicity. The International Fragrance Association (IFRA) has published safe use levels for Iso E Super in consumer products. OTNE is not toxic and not a CMR substance. OTNE is classified as a skin irritant (R38 EU DSD, H315 EU CLP) and is positive in the Local Lymph Node Assay (LLNA – OECD 429) and therefore classified as a skin sensitiser (R43 EU DSD, H317 EU CLP), though OTNE lacks any structural alerts for sensitisation in in silico prediction models (DEREK) and is not identified as an allergen in in vivo Human Repeated Patch Tests. Several health related studies have been conducted on OTNE, and based on these studies, OTNE has been determined to be safe under the current conditions of use. Given the sensitization classification of OTNE, and its use in fragrances, the International Fragrance Association (IFRA) has published safe use levels for OTNE in consumer products, which have been in effect since August 2009.

Environmental data OTNE is classified as H410 Very toxic to aquatic life with long-lasting effects (EU-CLP) or R51/53 Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment (EU DSD). The biodegradation of OTNE in fresh water (T1/2) is at most 40 days, and at most 120 days in sediment (OECD 314 test), though the biodegradation within the 28day window was around 11% (OECD 301-C). Given the outcome of the OECD 314 test OTNE does not meet the criteria for “Persistent” (P) or “very Persistent” (vP). The measured Bio Concentration Factor (BCF) is 391 L/kg, which is well below the EU limit of 2000 and US limit of 1000 for Bioaccumulation (B) classification. The LogKow for OTNE has been measured to be 5.65. OTNE is therefore not classified as a PBT or vPvB substance for the EU or any other global criteria. OTNE has been detected in surface water at levels of 29–180 ng/L, These values are well below the Predicted No Effect Concentration (PNEC) and as a result the overall environmental risk ratio (also referred to as RCR or PEC/PNECS) is determined to be below 1.

Regulatory status OTNE is registered on all major chemical inventories (US, Japan, China, Korea, Philippines, and Australia) and has been EU REACH registered in 2010. In 2014 the US National Toxicology Program (NTP) conducted a 13-week repeat dose toxicity study and found no adverse effects. OTNE has been recommended for inclusion in an update for the EU Fragrance Allergens labelling for cosmetic products based on a small number of positive reactions in dermatological clinics of around 0.2% to 1.7% of patients tested in three studies If the proposed SCCS Opinion is taken forward into legislation then OTNE will be labelled on cosmetic products in the EU, several years after publication of a new legislation.

Commercial products The fragrance Molecule 01 (Escentric Molecules, 2005) is a specific isomer of Iso E Super, by the company IFF. Its partner fragrance Escentric 01 contains Iso E Super along with ambroxan, pink pepper, green lime with balsamic notes like benzoin mastic and incense. The fragrance Eternity by Calvin Klein (1988) contained 11.7% Iso E Super in the fragrance portion of the formula. The fragrance Scent of a Dream by Charlotte Tilbury contains Iso E Super. The fragrance No.1 Invisible by Perfume Extract contains Iso E Super. The fragrance I Don't Know What by D.S. & Durga leans heavily into Iso E Super. Most fragrances from the Danish brand Zarkoperfume contain Iso E Super.

History OTNE was patented in 1975 as an invention of International Flavors and Fragrances.

References

Illustrations

Worked examples

Example 1 — a first encounter with Tetramethyl acetyloctahydronaphthalenes

Start with the simplest possible case. Write down what Tetramethyl acetyloctahydronaphthalenes claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Tetramethyl acetyloctahydronaphthalenes before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Tetramethyl acetyloctahydronaphthalenes ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Tetramethyl acetyloctahydronaphthalenes

In research: Tetramethyl acetyloctahydronaphthalenes appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Tetramethyl acetyloctahydronaphthalenes in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Tetramethyl acetyloctahydronaphthalenes is common in secondary-school and first-year university syllabi. It links to neighbouring topics Cosmetics chemicals, Flavors, Ketones, so understanding it makes those chapters shorter.
In everyday life: Look for Tetramethyl acetyloctahydronaphthalenes outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Tetramethyl acetyloctahydronaphthalenes in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Tetramethyl acetyloctahydronaphthalenes means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
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Frequently asked questions

What is Tetramethyl acetyloctahydronaphthalenes in simple terms?

Why does Tetramethyl acetyloctahydronaphthalenes matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Tetramethyl acetyloctahydronaphthalenes?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Tetramethyl acetyloctahydronaphthalenes.