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Musk ambrette

Musk ambrette structure

Musk ambrette 

structure
  • CAS No:

    83-66-9

  • Formula:

    C12H16N2O5

  • Chemical Name:

    Musk ambrette

  • Synonyms:

    Benzene,1-(1,1-dimethylethyl)-2-methoxy-4-methyl-3,5-dinitro-;Anisole,6-tert-butyl-3-methyl-2,4-dinitro-;1-(1,1-Dimethylethyl)-2-methoxy-4-methyl-3,5-dinitrobenzene;Musk ambrette;2,6-Dinitro-3-methoxy-4-tert-butyltoluene;Amber musk;Synthetic musk ambrette;6-tert-Butyl-3-methyl-2,4-dinitroanisole;Musk ambrette (artificial);Artificial musk ambrette;4-tert-Butyl-3-methoxy-2,6-dinitrotoluene;Ambrette musk;NSC 46122;NSC 59845;2,6-Dinitro-3-methoxy-4-tetra-butyl toluene;1-tert-Butyl-2-methoxy-4-methyl-3,5-dinitrobenzene;1-(tert-Butyl)-2-methoxy-4-methyl-3,5-dinitrobenzene

  • Categories:

    Flavors and Fragrances  >  Synthetic Fragrances

Description

PHYSICAL DESCRIPTION: Pale yellow liquid. Insoluble in water. (NTP, 1992)


Musk ambrette is a pale yellow liquid. Insoluble in water. (NTP, 1992)


Musk ambrette is a pale yellow liquid. Insoluble in water. (NTP, 1992)|Musk ambrette is a C-nitro compound.

Musk ambrette Basic Attributes

268.27

268.27

201-493-7

55V150W8R6

59845|46122

2811

DTXSID7025689

Pale yellow leaves from alcohol

2909309090

Characteristics

101

4.0

Musk ambrette is a pale yellow liquid. Insoluble in water. (NTP, 1992)

1.2±0.1 g/cm3

85 °C

185 °C / 16mmHg

149.6±29.9 °C

1.542

In water, 2.41 mg/L at 25 deg C (est)

Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.

1.31X10-5 mm Hg at 25 deg C (est)

Oral-rat LD50: 339 mg/kg

Thermal decomposition to emit toxic nitrogen oxide fumes

... Sweet, heavy floral-musky odor

Henry's Law constant = 7.05X10-7 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 1.50X10-12 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Strong Oxidizing Agent

Safety Information

2811

20/21/22-36/37/38

26-36/37/39

BZ8575000

Treasury is ventilated, low temperature and dry; stored separately from food materials

P264, P270, P280, P301+P312, P302+P352, P321, P330, P332+P313, P362, P501

H302

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

The flash point of this chemical has not been determined, but it is probably combustible. (NTP, 1992)

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P302+P352, P321, P330, P332+P313, P362, and P501|Aggregated GHS information provided by 134 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P281, P301+P312, P308+P313, P314, P330, P405, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide, foam or Halon extinguisher. A water spray can also be used. (NTP, 1992)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.

Toxicity

highly toxic

LD50 Rabbits Dermal 2,000 mg/kg|LD50 Rat oral 339 mg/kg

Musk ambrette has not been reported to occur in nature(1).

Musk ambrette's production and use as a fragrance(1) 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 5,300(SRC), determined from a log Kow of 4.0(2) and a regression-derived equation(3), indicates that musk ambrette is expected to be immobile in soil(SRC). Volatilization of musk ambrette from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.05X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Musk ambrette is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.31X10-5 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2009).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5,300(SRC), determined from a log Kow of 4.0 (2)and a regression-derived equation(3), indicates that musk ambrette 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 7.05X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 85 days and 1.8 years, respectively(SRC). The volatilization half-life from a model pond is about 37 years when adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 200(SRC), from a log Kow of 4.0(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). Biodegradation data were not available(SRC, 2009).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), musk ambrette, which has an estimated vapor pressure of 1.31X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase musk ambrette 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 about 11 days(SRC), calculated from its rate constant of 1.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase musk ambrette may be removed from the air by wet or dry deposition(SRC). Musk ambrette contains chromophores that absorb at wavelengths >290 nm(4) and may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of musk ambrette with photochemically-produced hydroxyl radicals has been estimated as 1.5X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Musk ambrette is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Musk ambrette contains chromophores that absorb at wavelengths >290 nm(2) and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 200 was calculated in fish for musk ambrette(SRC), using a log Kow of 4.0(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high (SRC), provided the compound is not metabolized by the organism(SRC).

The Koc of musk ambrette is estimated as 5,300( SRC), using a log Kow of 4.0 (1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that musk ambrette is expected to be immobile in soil.

The Henry's Law constant for musk ambrette is estimated as 7.05X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that musk ambrette is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river(2) is estimated as 85 days(SRC). The volatilization half-life from a model lake(2) is estimated as 1.8 years(SRC). The volatilization half-life from a model pond is about 37 years when adsorption is considered(3). Musk ambrette's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Musk ambrette is not expected to volatilize from dry soil surfaces(SRC) based upon a an estimated vapor pressure of 1.3X10-5 mm Hg(SRC), determined from a fragment constant method(4).

ENVIRONMENTAL: Musk ambrette was detected in 94% of milk samples from nursing mothers living in Southern Bavaria in 1992 (48 samples) and 1993 (343 samples) between <0.01-0.29 mg/kg fat with a mean concentration of 0.04 mg/kg fat(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 22,736 workers (16,492 of these were female) were potentially exposed to musk ambrette in the US(1). Occupational exposure to musk ambrette may occur through inhalation and dermal contact with this compound at workplaces where musk ambrette is produced or used(SRC). Monitoring data indicate that the general population may be exposed to musk ambrette via ingestion of contaminated food or from inhalation(SRC). Dermal absorption may play a role after application of musk containing perfumes and cosmetics to the skin or from textiles containing musk fragrance residues from laundry detergents(2).

Musk ambrette was detected in 3 of 4 human adipose tissues samples, obtained from cadavers in Switzerland at autopsy, in 1983-84 and 1 of 11 samples collected in 1994 at concentrations ranging from 5 ng/g to 67 ng/g and 18 ng/g in samples from 1983-84 and 1994, respectively(1). Musk ambrette was detected in 94% of milk samples from nursing mothers living in Southern Bavaria in 1992 (48 samples) and 1993 (343 samples) between <0.01-0.29 mg/kg fat with a mean concentration of 0.04 mg/kg fat(2).

Drug Information

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin and eyes. ACUTE/CHRONIC HAZARDS: This compound is a local irritant. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

/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 the 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 /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's 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 or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ The Scandinavian photopatch test procedure has been applied to 745 patients with suspected photodermatoses during the years 1980-1981. Our experience has been encouraging with the recording of several relevant reactions. A total of 132 positive photocontact reactions and 120 ordinary contact reactions were seen. Photocontact reactions to musk ambrette (19 cases) and PABA (19 cases) were surprisingly frequent. The next most common photocontact reactions were to promethazine (24), chlorpromazine (22 cases) and fentichlor (12). Ordinary contact reactions were observed to balsam of Peru (30), PABA (23), lichen mix (21), wood mix (14) and to perfume mix (10).|/HUMAN EXPOSURE STUDIES/ 495 patients were standard photopatch tested with Musk Ambrette 5% in petrolatum and in dimethyl phthalate. 4 cases gave positive photopatches; 3 were men and 1 a woman. 2 cases, both men, had current or past relevant reactions to Musk Ambrette presented with typical perfume dermatitis. The other 2 cases had positive reactions to Musk Ambrette of uncertain relevance. Photoallergic reaction to Musk Ambrette is a rare event. Only a few relevant reactions will be missed by excluding it from standard phototesting.|/HUMAN EXPOSURE STUDIES/ Photosensitivity to musk ambrette was confirmed in 15 men previously photopatch tested and in a further 4 men currently attending the clinic. 6 of the recalled patients continued to react adversely to sunlight due either to unrecognised exposure to musk ambrette or to their having become persistent light reactors. Positive photopatch tests, possibly cross reactions, were seen in 3 of the 19 patients with the structurally-related nitromusks, moskene and musk xylene but not with musks ketone and tibetine. Musk ambrette elicited a positive patch test without light in 3 of the 19 patients.|/CASE REPORTS/ A patient with persistent photosensitivity and positive photopatch tests to musk ambrette and an after-shave lotion is reported. Phototests showed extreme sensitivity to UV radiation, especially UVB. Patch tests with the European Standard Series and some plant allergens were negative. Histology showed a granulomatous reaction with epithelioid and giant cells in the dermis.|For more Human Toxicity Excerpts (Complete) data for MUSK AMBRETTE (14 total), please visit the HSDB record page.

2-methoxy-3,5-dinitro-4-methyl-t-butylbenzene

Musk ambrette Use and Manufacturing

Methods of Manufacturing

Using m-cresol as a raw material, methylated with dimethyl sulfate to produce m-cresol methyl ether, then, m-cresol methyl ether reacts with isobutylene or tert-butanol to produce tert-butyl methoxy toluene, which is finally obtained by nitration.

Uses

Used as spice and deodorant

Production

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7346]

Use in fragrances in the USA amounts to approximately 100,000 lb/yr.|Usual concentration in final product (%): soap 0-03 (0-2 max); detergent 0-003 (0-02 max); creams, lotions 0-01 (0-07 max); perfume 0-2 (2-0 max)

Benzene, 1-(1,1-dimethylethyl)-2-methoxy-4-methyl-3,5-dinitro-: ACTIVE|In public use before the 1920s|The Council of Europe (1974) included musk ambrette at a level of 1 ppm in the list of artificial flavoring substances that may be added to foodstuffs without hazard to public health, and FEMA (1965) has given musk ambrette GRAS status.

Computed Properties

Molecular Weight:268.27
XLogP3:3.6
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:268.10592162
Monoisotopic Mass:268.10592162
Topological Polar Surface Area:101
Heavy Atom Count:19
Complexity:355
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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