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2-Undecanone

2-Undecanone structure

2-Undecanone 

structure
  • CAS No:

    112-12-9

  • Formula:

    C11H22O

  • Chemical Name:

    2-Undecanone

  • Synonyms:

    2-Undecanone;Methyl nonyl ketone;Methyl n-nonyl ketone;Nonyl methyl ketone;2-Hendecanone;NSC 4028;BioUD 30;BioUD;BioUD 8;Mostique EGX 101

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

2-Undecanone is a volatile organic compound, which inhibits the DnaKJE-ClpB bichaperone dependent refolding of heat-inactivated bacterial luciferases. 2-Undecanone inhibits lung tumorigenesis[1][2].


Liquid|colourless to pale yellow liquid with a citrus, fatty, rue-like odour


Undecan-2-one is a dialkyl ketone with methyl and nonyl as the two alkyl groups. It has a role as a rodenticide and a plant metabolite. It is a dialkyl ketone and a methyl ketone.

2-Undecanone Basic Attributes

170.29

170.29

1749573

203-937-5

YV5DSO8CY9

4028

DTXSID2021943

Oily liquid|Colorless liquid

29141990

Characteristics

17.1

4.1

Clear colorless to light yellow Liquid

0.830 g/cm3 @ Temp: 15 °C

15 °C

231.5 °C

192 °F

1.425

H2O: INsoluble

Store below +30°C.

<1 mm Hg ( 20 °C)

5.9 (vs air)

Oral-Rat LD50: 5000 mg/kg; Oral-Mouse LD50: 3880 mg/kg

Strong odor

6.36e-05 atm-m3/mole|Henry's Law constant = 6.36X10-5 atm-cu m/mol at 25 °C

Hydroxyl radical reaction rate constant = 1.38X10-11 cu cm/molec-sec at 25 °C (est)

Safety Information

9

UN3082

2

51/53-50/53

23-24/25-61-60

YQ2820000

N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.

P273-P501

H410

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.

... Can react with oxidizing materials.

Methyl nonyl ketone is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

The U.S. high production volume (HPV) chemicals are those which are manufactured in or imported into the United States in amounts equal to or greater than one million pounds per year. Robust Summaries include health effects, ecotoxicity data, and environment fate information for selected chemicals. EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Available from: http://www.epa.gov/chemrtk/viewsrch.htm on methyl nonyl ketone as of January 19, 2006.|USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Methyl nonyl ketone. EPA 738-R-95-038 July 1995. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of February 23, 2006: http://www.epa.gov/pesticides/reregistration/status.htm]

|Warning|H400 (99.38%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 1772 companies from 12 notifications to the ECHA C&L Inventory.

To fight fire, use carbon dioxide or dry chemical.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.

2-Undecanone was identified in effluents from US-based soap and detergent manufacture at a concentration range of 336-453 ng/ul(1). 2-Undecanone emissions were measured at 1.7 mg/kg when frying beef and 4.7 mg/kg when charbroiling extralean beef and 6.5 mg/kg when charbroiling regular beef(2). Charbroiling meat emissions of 2-undecanone were measured at 107 mg/kg(3).

Toxicity

moderately toxic

LD50 Rat oral >5 g/kg|LD50 Mouse oral 3.88 g/kg|LD50 Rabbit (male and female) dermal >2 g/kg /from table/

/AQUATIC SPECIES/ /In the Fathead minnow (Pimephales promelas) 96 hr LC50 test,/ ...affected fish lost schooling behavior, swam near tank bottom, and were hypoactive. Fish were darkly colored, had increased respiration, and lost equilibrium prior to death. Mortalities at 96 hrs: 3.87 mg/L 18/20; 5.95 mg/L, 20/20. No mortalities at lower concentrations.

2-Undecanone is a volatile component of foods(1).

2-Undecanone's production and use as a solvent in the production of vinyl resins, nitrocellulose and synthetic rubber(1), a dog and cat repellent(2) and as a fragrance additive to soaps, detergents, creams, lotions and perfume(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 280(SRC), determined from a structure estimation method(2), indicates that 2-undecanone is expected to have moderate mobility in soil(SRC). Volatilization of 2-undecanone from moist soil surfaces may be expected to be an important fate process(SRC) given a Henry's Law constant of 6.36X10-5 atm-cu m/mole(3). 2-Undecanone is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.1X10-2 mm Hg(4). 2-Undecanone had a theoretical biological oxygen demand (BOD) of 1%, 6.5% and 21.8% after 6, 12 and 24 hr, respectively, when incubated with an activated sludge seed at an initial concentration of 500 ppm(5) suggesting that biodegradation in the soil may be fast(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-undecanone, which has a vapor pressure of 4.1X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-undecanone 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 1.2 days(SRC), calculated from its rate constant of 1.38X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of 2-undecanone with photochemically-produced hydroxyl radicals has been estimated as 1.38X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).

An estimated BCF of 28 was calculated for 2-undecanone(SRC), using a log Kow of 4.09(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-undecanone can be estimated to be 278(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-undecanone is expected to have moderate mobility in soil.

The Henry's Law constant for 2-undecanone is 6.36X10-5 atm-cu m/mole(1). This Henry's Law constant indicates that 2-undecanone 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 13 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 11 days(SRC). 2-Undecanone's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 2-Undecanone is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.1X10-2 mm Hg(3).

SURFACE WATER: 2-Undecanone was detected not quantified in the southern basin of Lake Michigan and in the eastern basin of Lake Ontario(1).

2-Undecanone is present, at unreported concentrations, as a volatile component of aroma of cooked beef, mutton, and pork(1). 2-Undecanone was identified in the volatile components of short necked clams(2), raw beef(3), and distilled oils of welsh onions (Allium fistulosum L. variety Maichuon) and scallions (Allium fistulosum L. variety Caespitosum)(4). 2-Undecanone was identified in Beaufort cheese(5), blue cheese(6), roasted filberts(7), and fresh ginger rhizomes (Zingiber officinale Roscoe)(8), at unreported concentrations. 2-Undecanone was identified in pineapple guava at 0.41 ug/g(9). 2-Undecanone was measured at 281 ng/g, 887 ng/g and 49.1 ng/g in anchovy paste, big eyed herring paste and shrimp paste, respectively(10).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 9,071 workers (6864 of these are female) are potentially exposed to 2-undecanone in the US(1). Occupational exposure to 2-undecanone may occur through dermal contact with this compound at workplaces where 2-undecanone is produced or used(SRC). Monitoring data indicate that the general population may be exposed to 2-undecanone via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this compound and other consumer products containing 2-undecanone(SRC).

Drug Information

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . For contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline 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. Administer activated charcoal ... . /Ketones and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ketones and related compounds/

2-undecanone

2-Undecanone Use and Manufacturing

Methods of Manufacturing

Derived from condensation and elimination of decanoic acid and glacial acetic acid. The pumice catalyst with magnesium acetate adsorbed in the reaction tube was heated up, activated at 450°C for 2h, cooled to 400°C, and then at 380-400°C, a mixture of capric acid and glacial acetic acid was added from the top of the reaction tube at a flow rate of 2000ml per hour After passing through the vaporization section equipped with ceramic rings, and then into the reaction section equipped with catalyst, and finally discharged through the cooling section. The collected reaction liquid was washed with hot water, the aqueous layer was separated, the oil layer was taken for distillation under reduced pressure, and the fractions of 130-146°C (2.67 kPa) were collected to obtain methylnonanone. The yield is over 75%.

Uses

In the compounding of some synthetic essential oils.As fragrance additive in soaps, detergents, creams, lotions, and perfume.As dog and cat repellant.


Solvents (which become part of product formulation or mixture)


Lawn and garden care products

Production

(1986) 10 thousand-500 thousand pounds|(1994) 10 thousand-500 thousand pounds|(1998) 10 thousand-500 thousand pounds|(2002) 10 thousand-500 thousand pounds

Formulation Types Registered: Pressurized liquid: 1.9% methyl nonyl ketone +0.1% related compounds; 2.0% methyl nonyl ketone; Granular: 1.9% methyl nonyl ketone +0.1% related compounds; 0.08% methyl nonyl ketone +0.42% cinnamaldehyde; 6.25% thiram, 6.25% methyl nonyl ketone and 5.50% castor oil (USP); Liquid ready-to-use (pump/sprayer): 1.8-1.9% methyl nonyl ketone +0.1% related compounds; 2.0% methyl nonyl ketone; Solid (crystalline): 1.8% methyl nonyl ketone +0.1% related compounds; Liquid for reformulating use only: 63.33% methyl nonyl ketone and 3.34% related compounds.|Major component... about 90% in Algerian rue oil

Pesticide, fertilizer, and other agricultural chemical manufacturing|2-Undecanone: ACTIVE

Food additives -> Flavoring Agents|Agrochemicals -> Repellants|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]

Flavoring Agents

Computed Properties

Molecular Weight:170.29
XLogP3:4.1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:8
Exact Mass:170.167065321
Monoisotopic Mass:170.167065321
Topological Polar Surface Area:17.1
Heavy Atom Count:12
Complexity:108
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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