2-Undecanone

HCID 8163CAS 112-12-9

基本情報

標準SMILES
CCCCCCCCCC(C)=O
InChIKey
KYWIYKKSMDLRDC-UHFFFAOYSA-N
分子式
C11H22O
平均分子量
170.29 g/mol
単同位体質量
170.16706532

概要

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.

名称と識別子

優先名称
2-Undecanone
IUPAC
undecan-2-one
現地名
2-ウンデカノン
英語名
2-Undecanone
分子式
C11H22O
分子量
170.29

名称と別名

2-UndecanoneUndecan-2-oneMethyl nonyl ketone112-12-92-HendecanoneRue ketoneMETHYL N-NONYL KETONEKetone, methyl nonylNonyl methyl ketoneMGK Dog and Cat RepellentFEMA No. 3093DTXSID2021943
名称をさらに表示
2-ウンデカノンウンデカン-2-オンメチルn-ノニルケトンメチルノニルケトン2-ヘンデカノン2‐ウンデカノン2-ウンデカノン, 98%メチルノニルケトン, 100 µg/mL in AcCNメチルノニルケトン, 100 µg/mL in MeOHn-ノニルメチルケトンFEMA 3093undecan-2-2-UndecanonUndecan-2-onUndecanone-(2)
YV5DSO8CY9NSC-4028DTXCID301943CHEBI:17700RefChem:89515203-937-5UNDECANONE2-Oxoundecane

データベース識別子

CAS
112-12-9
PubChem CID
8163
DTXSID
DTXSID2021943
ChEMBL
CHEMBL1236582
ChEBI
CHEBI:17700
UNII
YV5DSO8CY9
EC Number
203-937-5
Nikkaji
J5.119E

物性

構造計算による物性

XLogP
4.1
極性表面積
17.1 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
8
重原子数
12

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]
SolventsSolvents -> Ketones (<C12)
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (2-Undecanone) -> IFRA transparency List
Pesticides · 2 件

Repellants

Active substance -> EU Pesticides database: Not approved

物理化学的性質

融点
11 · 11-13 °C(lit.)
沸点
231 · 231-232 °C(lit.)
比重(密度)
0.825 g/mL · 0.825 g/mL at 25 °C(lit.)
蒸気密度
5.9 · 5.9 (vs air)
蒸気圧
1 mm · <1 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.43(lit.)
化学的性質 · 1 件

化学的特性2-undecanone, also known as methyl nonyl ketone, is a colorless to slightly yellow liquid and has a characteristic rue odor with a sweet flavor reminiscent of peach (on dilution). It naturally exists in Houttuynia cordata, bananas, strawberries, cloves, ginger and Rutaceae plants. The FEMA number is 3093, the FDA number is 172.515, and the CoE number is 150. methyl nonyl ketone is the active ingredient of Houttuynia cordata, mainly used in the production of medicines and fragrances, and is safer and more effective than DEET for mosquito repellents.

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 15.2% (271 of 1781) of reports.

Warning

H400 (84.3%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1781 reports by companies from 16 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 6 件

Chemical: 2-Undecanone

Regulation (EC) No 1831/2003 (amended)

2-Undecanone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Undecanone are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

2008/127, Reg. (EU) 2017/781, Reg. (EU) No 540/2011, Reg. (EU) No 608/2012, Reg. (EU) No 629/2014

Status: Active Update: 14-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/22906

2-Undecanone: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummarySlightly toxic in animal studies; NOEL = 300 mg/kg/day; [Reference #1] Causes coma in inhalation studies of guinea pigs with a TCLo = 6900 mg/m3/12H; [RTECS] May cause irritation; [MSDSonline]
FDA Requirements · 1 件

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.

Special Reports · 2 件

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]

FIFRA Requirements · 2 件

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether products containing the active ingredients are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e. active ingredient specific) data required to support reregistration of products containing methyl nonyl ketone active ingredients. The Agency has completed its review of these generic data, and has determined that the data are sufficient to support reregistration of all products containing methyl nonyl ketone.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Methyl nonyl ketone is found on List C. Case No: 3094; Pesticide type: insecticide, rodenticide; Case Status:RED Approved 06/95; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document... ; Active ingredient (AI): methyl nonyl ketone; Data Call-in (DCI) Date(s): 09/15/92; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

NFPA Hazard Classification · 3 件

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.

安全と保護具

Fire Fighting ProceduresTo fight fire, use carbon dioxide or dry chemical.
Disposal Methods · 1 件

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.

Protective Action Criteria (PAC) · 3 件

15 [mg/m3]

170 [mg/m3]

990 [mg/m3]

毒性情報

Ecotoxicity Values · 5 件

LC50 Anas platyrhynchos (Mallard duck, 10 days old) dietary >5620 ppm/8 days

LD50 Anas platyrhynchos (Mallard duck, 19 weeks old) oral >2250 mg/kg

LD50 Colinus virginianus (Bobwhite, 20 weeks old) oral >2250 mg/kg

LC50 Colinus virginianus (Bobwhite, 10 days old) dietary >5620 ppm/8 days

For more Ecotoxicity Values (Complete) data for 2-UNDECANONE (10 total), please visit the HSDB record page.

Environmental Fate · 3 件

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).

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).

Food Survey Values · 1 件

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).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Ecotoxicity Excerpts · 1 件

/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.

Effluent Concentrations · 1 件

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).

法規制情報

FDA Requirements · 1 件

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.

FIFRA Requirements · 2 件

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether products containing the active ingredients are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e. active ingredient specific) data required to support reregistration of products containing methyl nonyl ketone active ingredients. The Agency has completed its review of these generic data, and has determined that the data are sufficient to support reregistration of all products containing methyl nonyl ketone.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Methyl nonyl ketone is found on List C. Case No: 3094; Pesticide type: insecticide, rodenticide; Case Status:RED Approved 06/95; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document... ; Active ingredient (AI): methyl nonyl ketone; Data Call-in (DCI) Date(s): 09/15/92; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

安全データ

wgk
2
tsca
TSCA listed
rtecs
YQ2820000
ridadr
UN3082
毒性
LD50 dermally in rabbits: >5 g/kg; LD50 orally in rats, mice: >5, 3.88 g/kg (Opdyke)
hs_code
29141990

化学と産業

薬理情報

MeSH Pharmacological ClassificationSubstances causing insects to turn away from them or reject them as food.
Cellular LocationsMembrane

用途と製造

Uses · 6 件

Used as a solvent in the production of vinyl resins, nitrocellulose, and synthetic rubber; as a flavoring agent; as a dog and cat repellent; [HSDB] Used to make some synthetic essential oils and as a fragrance in soaps, detergents, creams, lotions, and perfumes; [Merck Index] Used as a dog/cat repellent and iris borer deterrent; [Reference #1]

For methyl nonyl ketone (USEPA/OPP Pesticide Code: 044102) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Used as a solvent in the production of vinyl resins, nitrocellulose, and synthetic rubber.

... Flavoring

Dog and cat repellent/training aid and iris borer deterrent.

Perfumery, flavoring, animal repellent.

U.S. Production · 5 件

2023: <50,000 lb

(1986) 10 thousand-500 thousand pounds

(1994) 10 thousand-500 thousand pounds

(1998) 10 thousand-500 thousand pounds

(2002) 10 thousand-500 thousand pounds

Methods of ManufacturingOil of rue, also made synthetically.
Formulations/Preparations · 2 件

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

Household ProductsInformation on 14 consumer products that contain Methyl nonyl ketone in the following categories is provided:
Use Classification · 4 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

応用分野 · 3 件

天然物の起源Originally reported found in the essential oils of Ruta graveolens; subsequently was identified in the essential oils of Citrus limetta Risso., Fagara xanthoxyloides Lamm. and Litsea odorifera Val. (leaves); a method for the determination of methyl nonyl ketone in various rue species (Ruta montana, Ruta bracteosa) was devised; it is also present in the essential oils of Jaborandi (leaves), Hottuynia cordata, Phellodendron anaurense, Schizandar nigra Maxim., and in coconut and palm oils; also identified as the main constituent of the essential oil of Boronia ledifolia Gai; a 92% content level was reported in the essential oil of Ruta chalepensis. Also reported found in rabbiteye, blueberry, feijoa fruit, feijoa peel, peach, raspberry, fresh black berry, heated blackberry, strawberry jam, guava, allium, cloves, raw asparagus, shallot, roasted onion, ginger, Curcuma aeruginosa Roxb., Curcuma heyneana Val., banana, grapefruit, currants, peach, asparagus, shallot, onion, leek, chive, peas, potato, clove, ginger, pepper, many cheeses, wheaten bread, butter, milk, cream, yogurt, milk powder, goat and sheep milk, caviar, raw and smoked fatty fish, roast chicken, cooked beef, beef, chicken and pork fat, hop oil, beer, cognac, rum, sparkling wine, coffee, tea, roasted filberts and peanuts, coconut meat, milk and oil, passion fruit, mushroom, wild marjoram, starfruit, Brazil nut, cardamom, rice, buckwheat, corn oil, wort, elder flower, shrimp, crayfish, clam, maté and mastic gum leaf and fruit oil.

使用2-Undecanone may be used as an analytical reference standard for the quantification of the analyte in milk samples and Houttuynia cordata Thunb using gas chromatography (GC) technique.

一般的な説明2-Undecanone is a naturally available nontoxic insect repellant, introduced as an alternative to insect repellants containing N,N-diethyl-meta-toluamide. It is isolated from the trichomes of wild tomatoes 2-Undecanone is also a volatile constituent, identified in milk and Houttuynia cordata Thunb(HCT), a traditional Chinese medicine.

調製方法

製造方法Can be isolated from natural oils by fractional distillation; also by dry distillation of calcium acetate and calcium caprylate, or by boiling octylacetoacetic acid ethyl ester with and alcoholic KOH solution.

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補足説明

定義ChEBI: 2-Undecanone 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.

関連反応

30 件

関連ノート

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