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TRASEOLIDE

TRASEOLIDE structure

TRASEOLIDE 

structure
  • CAS No:

    68140-48-7

  • Formula:

    C18H26O

  • Chemical Name:

    TRASEOLIDE

  • Synonyms:

    ATII;5-ACETYL-3-ISOPROPYL-1,1,2,6-TETRAMETHYLINDANE;TRASEOLIDE;1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1h-inden-5-yl]-ethanon;1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-inden-5-yl]-Ethanone;Ethanone,1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-inden-5-yl]-;Ketone,3-isopropyl-1,1,2,6-tetramethyl-5-indanylmethyl;1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-inden-5-yl]ethan-1-one

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

Traseolide is an indane derivative in which the indane skeleton is substituted by geminal methyl groups at C-1, by single methyl groups at C-2 and C-6, by an isopropyl group at C-3 and by an acetyl group at C-6. It is a constituent of musk odorant. It has a role as an odorant receptor agonist and a fragrance. It is a member of indanes, a methyl ketone and an aromatic ketone.


Colourless Oil


TRASEOLIDE is a musk fragrance that is prepared from toluene and isobutanoyl chloride by a Friedel–Crafts reaction that yields p-tolyl isopropyl ketone; the ketone is reduced to the corresponding alcohol. Chlorination and treatment with 2-methyl-2-butene yield 1 (cipher)- isopropyl-2,3,3,5-tetramethylindane, which gives the title compound through a Friedel–Crafts reaction with acetyl chloride:It is used in perfume compositions for soaps and detergents.

TRASEOLIDE Basic Attributes

258.4

258.40

268-799-0

TSCA listed

DTXSID9052393

Colourless

Characteristics

log Kow = 8.1

0.933±0.06 g/cm3(Predicted)

-50 °C at 101.325 kPa

350.0±31.0 °C(Predicted)

Index of refraction = 1.5301 at 20 °C/D

In water, 0.085 mg/L|In water, 539 ug/L at 20 °C, pH 7

VP: 7.5X10-5 mm Hg at 20 °C (0.01 Pa)|9.0X10-3 mm Hg (1.2 Pa)

Not classified

at 100.00 %. dry sweet amber musk herbal creamy

2.3×10-1mol/(m3Pa) at 25℃, Zhang et al. (2010)

log Kow = 5.7-6 at 35 °C, pH 7|Hydroxyl radical reaction rate constant = 1.95X10-12 cu cm/molec-sec at 25 °C (est)

Safety Information

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 1608 companies from 2 notifications to the ECHA C&L Inventory.

The typical effluent concentration into Lake Michigan for traseolide was 310 ng/L in the dissolved phase(1). Traseolide concentrations were <1 ng/L in sewage treatment plant effluents from Canada (Nova Scotia, New Brunswick) and Sweden (Uppsala, Vastra, Gavleborg), sampled in Jan 2002 and Jun-Dec 2002, respectively(2). Traseolide was present in influent at concentration of <10 ng/L five of six UK sewage treatment works surveyed in late autumn and early winter 2001; one plant reported influent concentrations of 1700 and 2900 ng/L on 12/11/01 and 12/10/01, respectively(3). Traseolide was not detected in influent samples to a waste water treatment plant in Lubbock, TX. Samples collected from winter 2009 to winter 2010; detection limit = 4 ng/L(4).

SEDIMENT: Traseolide was present in two of 14 samples from sites along the Haihe River in North China, collected from Dec 29-30, 2008; detection limit = 0.25-0.33 ng/g(1). A dry-weight surface concentration of 0.27 ng/g, corresponding to a loading of 0.81 kg/yr, was reported in sediment cores from Lake Ontario (Toronto, Ontario, Canada; Rochester, NY) and Lake Erie (Cleveland, OH; Buffalo, NY), sampled during Aug 7-13, 2003(2). Traseolide was reported at concentrations ranging from <0.08 to 0.4 ug/kg dry weight in sediments from the Prachatice, Brohl and Pacov streams, Czech Republic. Samples were collected upstream and downstream from sewage treatment plants in 2009(3).

URBAN/SUBURBAN: Traseolide was present in the gas-phase in Milwaukee, WI air samples at a concentration of 0.17 ng/cu m, sampled in June, 2001(1).|RURAL/REMOTE: Traseolide was present in the gas-phase over Lake Michigan at a concentration of 0.040 ng/cu m, sampled during June 1999 and May 2000(1).

Traseolide concentration in dust samples from barbershops, bathhouses, dormitories, and households in Tianjin, China, collected during April and July, 2012 and tested for synthetic musks; detectino limit = 0.25 ng/g(1).[Table#8491]

Toxicity

IDENTIFICATION AND USE: 1-(2,3-Dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-inden-5-yl)ethanone is a synthetic polycyclic musk fragrance used in perfuming soap and cosmetics. HUMAN STUDIES: It was examined for genotoxicity in the micronucleus test with human lymphocytes in vitro in the presence and absence of metabolic activation and revealed no genotoxicity. ANIMAL STUDIES: It was negative when tested for mutagenicity using the Salmonella/mammalian microsome assay with Salmonella typhimurium strains TA97, TA98, TA100 and TA102 with and without metabolic activation.

/AQUATIC SPECIES/ This study demonstrates the effects of synthetic polycyclic musks such as Galaxolide (HHCB), Tonalide (AHTN), Traseolide (ATII), Celestolide (ADBI), Phantolide (AHMI) and Cashmeran (DPMI), both on the early life stage and on gene expression in the livers of male medaka (Oryzias latipes). The toxicity ranking (the 96-hr median lethal concentration) of the chemicals tested on 24-hr-old medaka larvae descended in the order HHCB (0.95 mg/L)=ATII (0.95 mg/L)>AHTN (1.0 mg/L)>AHMI (1.2 mg/L)>ADBI (2.0 mg/L)>>DPMI (12 mg/L), indicating high acute toxicity of these compounds on the early life stages of medaka. ...

Traseolide's production and use as a musk fragrance for perfuming soap and cosmetics(1,2), biocides, polishes and waxes, and washing and cleaning products(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9800(SRC), determined from a structure estimation method(2), indicates that traseolide is expected to be immobile in soil(SRC). Volatilization of traseolide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.6X10-2 atm-cu m/mole(SRC) based upon its vapor pressure, 9.0X10-3 mm Hg(3), and water solubility, 8.5X10-2 mg/L(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Traseolide is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Traseolide is considered not readily biodegradable(4) indicating that biodegradation is not an important environmental fate process in soil(SRC).[(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Jun 3, 2018: http://www2.epa.gov/tsca-screening-tools (3) Peck AM, Hornbuckle KC; Environ Sci Technol 38: 367-372 (2004) (4) ECHA; Search for Chemicals. 1-|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9800(SRC), determined from a structure estimation method(2), indicates that traseolide is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.6X10-2 atm-cu m/mole(SRC) based upon its vapor pressure, 9.0X10-3 mm Hg(4), and water solubility, 8.5X10-2 mg/L(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5 hrs and 6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is about 80 days when adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 1000(SRC), from its log Kow of 8.1(4) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Traseolide is considered not readily biodegradable(7) indicating that biodegradation is not an important environmental fate process in water(SRC).[(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Jun 3, 2018: http://www2.epa.gov/tsca-screening-tools (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990) (4) Peck AM, Hornbuckle KC; Environ Sci Technol 38: 367-372 (2004) (5) UBurns LA et al; Exposure Analysis Modeling System (EXAMS): User Manual and System Documentation. EPA-600/3-82-023, U.S. EPA. (1982). ver. 2.94, Feb 1990. Available from, as of Jun 1, 2018: https://www.epa.gov/exposure-assessment-models/exams-version-index (6) Franke C et al; Chemosphere 29: 1501-14 (1994) (7) ECHA; Search for Chemicals. 1-|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), traseolide, which has a vapor pressure of 9.0X10-3 mm Hg(2), will exist solely in the vapor phases in the ambient atmosphere. Vapor-phase traseolide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 20 hours(SRC), calculated from its rate constant of 2.0X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Traseolide contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of traseolide with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 20 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Traseolide is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Traseolide contains chromophores that absorb at wavelengths >290 nm(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 1000 was calculated in fish for traseolide(SRC), using a log Kow of 8.1(1) and a regression-derived equation(2). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of traseolide can be estimated to be 9800(SRC). According to a classification scheme(2), this estimated Koc value suggests that traseolide is expected to be immobile in soil(SRC).

The Henry's Law constant for traseolide is estimated as 3.6X10-2 atm-cu m/mole(SRC) derived from its vapor pressure, 9.0X10-3 mm Hg(1), and water solubility, 8.5X10-2 mg/L(1). This Henry's Law constant indicates that traseolide is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 5 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 6 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is about 80 days when adsorption is considered(3). Traseolide's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Traseolide is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

DRINKING WATER: Traseolide was tested for but not detected in 19 US drinking water utilities analyzed between 2006 and 2007(1).|SURFACE WATER: Traseolide was present in the dissolved phase at a concentration of 0.11 ng/L in Lake Michigan water, sampled during June 1999 and May 2000(1). Traseolide was detected in 2 of 14 water samples from the Haihe River in North China collected from Dec 29-30, 2008(2).

Traseolide was tested for but not detected in 6 breast milk samples from Schleswig-Holstein, Germany, sampled in 1995(1). Traseolide median concentration was <23.0 ng/g lipid (max 12.6 ng/g lipid) in mother's milk from 101 women living in Uppsala County, Sweden; 77 samples were <2.0 ng/g lipid. Samples were collected from 1996-2003(2). Traseolide was present at a maximum concentration of 2.58 ug/kg fat in a sampling of 10 Danish human milk samples collected in 1999(3).

Occupational exposure to traseolide may occur through inhalation and dermal contact with this compound at workplaces where traseolide is produced or used. Monitoring/use data indicate that the general population may be exposed to traseolide via inhalation of and dermal contact with personal care products containing this compound, inhalation of contaminated dust and ingestion of contaminated fish. (SRC)|Occupational exposure of traseolide to barbers in Tianjin, China from barbershop dust was studied; samples were collected during April and July, 2012. Traseolide exhibited a 98.2% detection frequency with an average concentration of 149 ng/g; detection limit = 0.25 ng/g(1).

Traseolide levels in blood samples from 50 hairdressers and 10 non-hairdresser adults in Tianjin, China, collected during April and July, 2012 were below the detection limit of 0.27 ng/L(1). Traseolide was tested for but not detected in 6 breast milk samples from , sampled in 1995. A concentration range of not detected (10 of 15 samples) to 10 ug/kg fat was reported in 15 adipose tissue samples from Schleswig-Holstein, Germany, sampled in 1993; detection limit = 1 ug/kg fat(2). Traseolide median concentration was <23.0 ng/g lipid (max 12.6 ng/g lipid) mother's milk from 101 women living in Uppsala County, Sweden; 77 samples were <2.0 ng/g lipid. Samples were collected from 1996-2003(3).

Drug Information

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/GENOTOXICITY/ The synthetic polycyclic musk fragrance compounds galaxolide (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-(g)-2-benzopyrane), tonalide (7-acetyl-1,1,3,4,4,6-hexamerthyltetraline), celestolide (4-acetyl-1,1-dimethyl-6-tert-butylindane), phantolide (6-acetyl-1,1,2,3,3,5-hexamethylindane), cashmeran (6,7-dihydro-1,1,2,3,3-pentamethyl-4-(5H) indanone) and traseolide (5-acetyl-1,1,2,6-tetramethyl-3-isopropylindane) were examined for their genotoxicity in the micronucleus test (MNT) with human lymphocytes in vitro in the presence and absence of an exogenous metabolizing system containing rat liver S9 and the metabolically competent human hepatoma cell line Hep G2. Compound concentrations were employed up to cytotoxic doses. Galaxolide, tonalide, celestolide, phantolide, cashmeran and traseolide revealed no genotoxicity in the micronucleus test with human lymphocytes and with the human hepatoma cell line Hep G2.

5-acetyl-1,1,2,6-tetramethyl-3-isopropylindane

TRASEOLIDE Use and Manufacturing

Uses

Perfuming soap and cosmetics.


A component of Musk fragrances.

Ethanone, 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-inden-5-yl]-: ACTIVE

Musk compounds play an important role as perfuming agents for household chemicals, detergents and cosmetics. It has been demonstrated that the oral absorption pathway of these compounds in humans is significant in the case of contaminated fish. In this study we developed a new extraction procedure, using an accelerated solvent extraction system and a gas chromatography-mass spectrometry detection method, for the determination of 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[g]-2-benzopyran, 7-acetyl-1,1,3,4,4,6-hexamethyltetralin, 4-acetyl-1,1-dimethyl-6-tert.-butylindan, 6-acetyl-1,1,2,3,3,5-hexamethylindan and 5-acetyl-1,1,2,6-tetramethyl-3-isopropylindan in freshwater fish samples, collected from several Italian rivers and one lake. 6,7-Dihydro-1,1,2,3,3-pentamethyl-4-(5H)-indanon was used as internal standard. The method provides a rapid and highly selective extraction procedure, and is sensitive in determining these musk compounds in freshwater fish samples. This is the first report on the contamination from musk compounds in freshwater fish collected in Italy.|Headspace solid-phase microextraction, followed by GC-MS analysis is presented as a suitable technique for the determination of musk compounds in sewage treatment plant sludge. Five polycyclic musks (celestolide, phantolide, traseolide, galaxolide and tonalide) and four nitro musks (musk xylene, musk moskene, musk tibetene and musk ketone) were considered in the optimization of the analytical method. The influence of extraction temperature, fiber coating, agitation, pH and salting out on the efficiency of the extraction along with the extraction kinetics were studied. An extraction temperature of 100 °C and sampling the headspace over the stirred sludge sample using polydimethylsiloxane-divinylbenzene as fiber coating lead to effective extraction. The method proposed is very simple and yields high sensitivity, good linearity and repeatability for all the analytes with limits of detection at the sub-ng/g level. The total analysis time, including extraction and GC analysis, was only 40 min, and no manipulation of the sample was required.|A solid-phase microextraction method (SPME) for determining trace levels of synthetic musk fragrances in residual waters has been developed. Six polycyclic musks (cashmeran, phantolide, celestolide, traseolide, galaxolide and tonalide), and a macrocyclic musk (ambrettolide) have been analyzed. A detailed study of the different parameters affecting the extraction process is presented. The main important factors affecting the microextraction process have been studied and optimised by means of a categorical factorial design. Two extraction modes (direct SPME and headspace SPME) were tried at different extraction temperatures using four different fiber coatings [polydimethylsiloxane (PDMS), Carboxen (CAR)-PDMS, PDMS-divinylbenzene (DVB) and Carbowax (CW)-DVB]. An extraction temperature of 100 °C sampling the headspace over the sample using CAR-PDMS or PDMS-DVB as fiber coatings were found to be the experimental conditions that lead to a more effective extraction. The method proposed is very simple and yields high sensitivity, with detection limits in the low pg/ml, good linearity and repeatability for all the target compounds. The total analysis time, including extraction and GC analysis, was only 45 min. The optimized method performed well when it was applied to waste water from an urban treatment plant.

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