기본 정보
- 표준 SMILES
CCCCCCCCCC(C)=O- InChIKey
KYWIYKKSMDLRDC-UHFFFAOYSA-N- 분자식
- C11H22O
- 평균 분자량
- 170.29 g/mol
- 단동위원소 질량
- 170.16706532
개요
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.
이름 및 식별자
- 우선 이름
- 2-Undecanone
- IUPAC
- undecan-2-one
- 현지명
- 메틸 노닐 케톤
- 영어명
- 2-Undecanone
- 분자식
- C11H22O
- 분자량
- 170.29
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
112-12-9- PubChem CID
- 8163
- DTXSID
DTXSID2021943- ChEMBL
CHEMBL1236582- ChEBI
CHEBI:17700- UNII
- YV5DSO8CY9
- EC Number
- 203-937-5
- Nikkaji
- J5.119E
물성
구조 계산 물성
- XLogP
- 4.1
- 극성 표면적
- 17.1 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 1
- 회전 가능 결합 수
- 8
- 무거운 원자 수
- 12
- 형식 전하
- 0
- 복잡도
- 108
실험 및 물리화학적 성질
Pesticides
Repellants
Active substance -> EU Pesticides database: Not approved
LogP
log Kow = 4.09
4.09
Density
0.8260 to 0.8263 at 20 °C/4 °C
0.822 -0.826
0.829 @ 30°C
Color/Form
Oily liquid
Colorless liquid
물리화학적 성질
- 녹는점
- 11 · 11-13 °C(lit.)
- 끓는 점
- 231 · 231-232 °C(lit.)
- 밀도
- 0.825 g/mL · 0.825 g/mL at 25 °C(lit.)
- 증기 밀도
- 5.9 · 5.9 (vs air)
- 증기압
- 1 mm · <1 mm Hg ( 20 °C)
- 굴절률
- 20 · n20/D 1.43(lit.)
- FEMA
- 3093 · 3093 | 2-UNDECANONE
- 인화점
- 192 °F · 192 °F
- 저장 조건
- 30 °C · Store below +30°C.
- 물리적 상태
- 액체
- 색상
- 무색투명~연황색
- 냄새
- 100 %에서 · 100.00%에서. 왁시 프루티 크리미 지방 오리스 플로랄
- 냄새 유형
- 과일 같은
- 생물학적 소스
- synthetic
- 수용성
- 불용성
- Merck
- 14 · 14,6104
- JECFA Number
- 296 · 296
- BRN
- 1749573 · 1749573
- Henry's Law Constant
- 1.9 · 1.9×10-2 mol/(m3Pa) at 25℃, Plyasunov and Shock (2001)
- Dielectric constant
- 8.4 · 8.4000000000000004
- 안정성
- 안정적인. 타기 쉬운. 강한 산화제, 강한 염기와 호환되지 않습니다.
- 주요 응용
- 청소용품화장품음식 및 음료개인 위생 관리
- 화장품 원료 기능
- 향수
- InChI
- 1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
- InChIKey
- KYWIYKKSMDLRDC-UHFFFAOYSA-N
- SMILES
- CCCCCCCCCC(C)=O
- LogP
- 3.69 at · 3.69 at 25℃
- NIST
- 2 · 2-Undecanone(112-12-9)
- EPA
- Methyl nonyl ketone (112-12-9)
화학적 성질
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.
안전 및 규제
GHS 분류
GHS Classification
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.
유해성 정보
Regulatory Information
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
FDA Requirements
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
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
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
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.
안전 및 보호
Disposal Methods
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)
15 [mg/m3]
170 [mg/m3]
990 [mg/m3]
독성 정보
Ecotoxicity Values
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
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
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).
Ecotoxicity Excerpts
/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
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).
Soil Adsorption/Mobility
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.
Fish/Seafood Concentrations
2-Undecanone was found in the legs of Charybdis feriatus crabs at 0.6 ug/kg(1). 2-Undecanone was detected not quantified in lake trout (Salvelinus namycush) from Lake Michigan at Saugatuck and from Lake Ontario at Oswego(2). 2-Undecanone was identified in short-necked clams(3).
Artificial Pollution Sources
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).
Environmental Biodegradation
AEROBIC: 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 a activated sludge seed at an initial concentration of 500 ppm(1). The available data on biodegradaton of ketones in general suggest that n-alkyl ketones are susceptible to biodegradation, with methyl branching tending to decrease the rate of biodegradation(2).
Environmental Bioconcentration
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).
규제 정보
FDA Requirements
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
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.
안전 데이터
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- YQ2820000
- ridadr
- UN3082
- 독성
- LD50 dermally in rabbits: >5 g/kg; LD50 orally in rats, mice: >5, 3.88 g/kg (Opdyke)
- HS 번호
- 29141990
- risk_code
- 51/53-50/53
- hazard_code
- N
- safety_code
- 23-24/25-61-60
- 포장분류
- III
- 위험 등급
- 9
- 기존화학 물질
- KE-35072
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1
- 스토리지 클래스
- 10 - Combustible liquids
- 유해 물질 데이터
- 112-12-9(Hazardous Substances Data)
화학 및 산업
약리 정보
용도 및 제조
Uses
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
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
Formulations/Preparations
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
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
응용 분야
출처Originally 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.
용도2-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.
일반 설명2-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.
제조 방법
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.
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
추가 설명
정의ChEBI: 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.
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