기본 정보
- 표준 SMILES
CCCCCCCCCCCO- InChIKey
KJIOQYGWTQBHNH-UHFFFAOYSA-N- 분자식
- C11H24O
- 평균 분자량
- 172.31 g/mol
- 단동위원소 질량
- 172.18271539
개요
1-undecanol appears as a water-white liquid with a mild odor. Flash point 250 °F. Slightly soluble in water. Considered a marine pollutant by DOT. Immediate steps should be taken to limit its spread to the environment. As a liquid it can easily penetrate the soil and contaminate groundwater or streams. Mildly irritating to both the eyes and skin.
이름 및 식별자
- 우선 이름
- 1-Undecanol
- IUPAC
- undecan-1-ol
- 영어명
- n-Undecanol
- 분자식
- C11H24O
- 분자량
- 172.31
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
112-42-5、143819-62-9、30207-98-8- PubChem CID
- 8184
- DTXSID
DTXSID0026915- ChEMBL
CHEMBL444525- ChEBI
CHEBI:87499- UNII
- 06MJ0P28T3
- EC Number
- 203-970-5、250-092-3
- Nikkaji
- J5.126H
물성
구조 계산 물성
- XLogP
- 4.6
- 극성 표면적
- 20.2 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 1
- 회전 가능 결합 수
- 9
- 무거운 원자 수
- 12
- 형식 전하
- 0
- 복잡도
- 71.4
실험 및 물리화학적 성질
Solvents
Solvents -> Alcohols (<C12)
Solvents -> Alcohols (<C12)
Fragrances
Fragrance Ingredient (Undecanol) -> IFRA transparency List
Fragrance Ingredient (Undecyl alcohol) -> IFRA transparency List
LogP
log Kow = 4.72
4.72
Taste
FATTY FLAVOR
CITRUS
Density
0.835 at 68 °F (USCG, 1999) - Less dense than water; will float
0.8298 at 20 °C/4 °C
Relative density (water = 1): 0.83
0.820-0.840
물리화학적 성질
- 녹는점
- 19 °C · 19 °C
- 끓는 점
- 243 °C · 243 °C
- 밀도
- 0.8298 g/cm3 · 0.8298 g/cm3
- 산도 계수 (pKa)
- 15.2 · 15.20±0.10(Predicted)
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 0.2% (3 of 1933) of reports.
Warning
H315 (18.6%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1933 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
This chemical does not meet GHS hazard criteria for 100% (89 of 89) of all reports.
유해성 정보
Regulatory Information
Chemical: 1-Undecanol
Chemical: Undecanol
1-Undecanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Undecanol 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)
PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.
Status: Active Update: 26-11-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/2096
1-Undecanol: Does not have an individual approval but may be used under an appropriate group standard
Fire Hazards
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Combustible.
Hazards Summary
Higher alcohols are not highly toxic in the industrial setting; Can cause liver injury, somnolence, and respiratory depression in experimental animals; A skin, eye, and respiratory tract irritant; [HSDB] Safe when used as a flavoring agent in food; [JECFA] An irritant; [MSDSonline]
A skin, respiratory tract, and severe eye irritant; Defats skin; [ICSC] A mild skin and eye irritant; [CAMEO] See 1-Undecanol.
FDA Requirements
Undecyl alcohol 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
OPDYKE DL J; MONOGRAPHS ON FRAGRANCE RAW MATERIALS. ALCOHOL C-11, UNDECYLIC; FOOD COSMET TOXICOL 16 (SUPPL 1): 641 (1978). A REVIEW WITH 21 REFERENCES ON ALCOHOL C-11 INCLUDING TOXICITY EFFECTS ON TISSUE COMPONENTS, IRRITATION, AND SENSITIZATION.
FIFRA Requirements
Residues of nonyl, decyl, and undecyl glycoside mixture with a mixture of nonyl, decyl, and undecyl oligosaccharides and related reaction products (primarily decanol and undecanol) produced as an aqueous-based liquid (50 to 65% solids) from the reaction of primary alcohols (containing 15 to 20% secondary alcohol isomers) in a ratio of 20% C9, 40% C10, and 40% C11 with carbohydrates (average glucose to alkyl chain ratio 1.3 to 1.8) are exempted from the requirement of a tolerance when used as a surfactant in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest.
Residues of nonyl, decyl, and undecyl glycoside mixture with a mixture of nonyl, decyl, and undecyl oligosaccharides and related reaction products (primarily decanol and undecanol) produced as an aqueous-based liquid (50 to 65% solids) from the reaction of primary alcohols (containing 15 to 20% secondary alcohol isomers) in a ratio of 20% C9, 40% C10, and 40% C11 with carbohydrates (average glucose to alkyl chain ratio 1.3 to 1.8) are exempted from the requirement of a tolerance when used as a surfactant in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals.
Reactivity Profile
1-UNDECANOL is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.
안전 및 보호
Fire Fighting
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Use water spray, powder, alcohol-resistant foam, carbon dioxide.
First Aid Measures
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention .
Cleanup Methods
AEROBIC: Using acclimated mixed microbial cultures, the theoretical and 5-day BOD for 1-undecanol were determined to be 16.50% and 4.5 mmol/mmol chemical, respectively(1). After 5 days at 21 °C in sewage, the theoretical BOD for 1-undecanol was 27.6%(2). 1-Undecanol had a zero order biodegradation rate of 0.125 ppm/hour and a first order biodegradation rate constant of 6.1X10-3/hour by activated sludge(3). Using this biodegradation rate constant a half-life of 4.7 days can be calculated(SRC).
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.
독성 정보
Interactions
ALCOHOL-INDUCED NUTRITIONAL ENCEPHALOMALACIA IN STARTING CHICKS COULD BE COMPLETELY PREVENTED BY DIETARY SUPPLEMENTATION OF D,L-ALPHA-TOCOPHERYL ACETATE.
WITH USE OF SURFACTANTS EG TWEEN 80, ALCOHOL EMULSIONS WERE PHYTOTOXIC ONLY TO YOUNG MERISTEMATIC TISSUE. WITHOUT THE SURFACANT, C11 ALCOHOLS & ESTERS SHOWED NONSELECTIVE TISSUE KILL.
Ecotoxicity Values
LC50 Pimephales promelas (Fathead minnow, weight 0.12 g) 1.04 mg/L/96 hr; flow-through bioassay, water hardness 45.5 mg/L CaCO3, temp: 25 +/- 1 °C, pH 7.5, dissolved oxygen >60% of saturation
LC50 Nitocra spinipes (Harpacticoid copepod) 1.4 mg/L/96 hr (95% confidence limit: 1.1-1.8 mg/L); static /formulated product/
LC50 Alburnus alburnus (Bleak) 4.6 mg/L/96 hr (95% confidence limit: 4.2-5.1 mg/L); static /formulated product/
EC50 Tetrahymena pyriformis (Ciliate; decreased population growth) 2.3 mg/L/48 hr (95% confidence limit: 1.88-2.75 mg/L); static /formulated product/
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 8,800(SRC), determined from a log Kow of 4.72(2) and a regression-derived equation(3), indicates that 1-undecanol is expected to be immobile in soil(SRC). Volatilization of 1-undecanol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.3X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). 1-Undecanol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.97X10-3 mm Hg(5). The theoretical BOD for 1-undecanol was 27.6% after 5-day incubation in sewage(6), indicating that biodegradation may be an important environmental fate process in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8,800(SRC), determined from a log Kow of 4.72(2) and a regression-derived equation(3), indicates that 1-undecanol 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 7.3X10-5 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 20 hours and 10 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 estimated volatilization half-life from a model pond is 9 months if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 86(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). The theoretical BOD for 1-undecanol was 27.6% after 5-day incubation in sewage(8), indicating that biodegradation may be an important environmental fate process in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-undecanol, which has a vapor pressure of 2.97X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-undecanol 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 23 hours(SRC), calculated from its rate constant of 1.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).
Adverse Effects
Neurotoxin - Acute solvent syndrome
Neurotoxin - Acute solvent syndrome
Signs and Symptoms
Cough.
Dry skin. Redness. Roughness. Pain.
Redness. Pain. Blurred vision.
Nausea. Vomiting. Diarrhoea.
Soil Adsorption/Mobility
The Koc of 1-undecanol is estimated as 8,800(SRC), using a log Kow of 4.72(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1-undecanol is expected to be immobile in soil.
규제 정보
FDA Requirements
Undecyl alcohol 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
Residues of nonyl, decyl, and undecyl glycoside mixture with a mixture of nonyl, decyl, and undecyl oligosaccharides and related reaction products (primarily decanol and undecanol) produced as an aqueous-based liquid (50 to 65% solids) from the reaction of primary alcohols (containing 15 to 20% secondary alcohol isomers) in a ratio of 20% C9, 40% C10, and 40% C11 with carbohydrates (average glucose to alkyl chain ratio 1.3 to 1.8) are exempted from the requirement of a tolerance when used as a surfactant in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest.
Residues of nonyl, decyl, and undecyl glycoside mixture with a mixture of nonyl, decyl, and undecyl oligosaccharides and related reaction products (primarily decanol and undecanol) produced as an aqueous-based liquid (50 to 65% solids) from the reaction of primary alcohols (containing 15 to 20% secondary alcohol isomers) in a ratio of 20% C9, 40% C10, and 40% C11 with carbohydrates (average glucose to alkyl chain ratio 1.3 to 1.8) are exempted from the requirement of a tolerance when used as a surfactant in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals.
안전 데이터
- 신호 어
- Warning
- 유해·위험 문구
- 암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H319
화학 및 산업
약리 정보
Mechanism of Action
... Undecanol was the most potent fungicide followed by decanol. The time-kill curve study showed that undecanol was fungicidal against S. cerevisiae at any growth stages was not influenced by pH values. The alcohols tested inhibited glucose-induced acidification by inhibiting the plasma membrane H(+)-ATPase. The primary antifungal action of amphipathic medium-chain (C(9)-C(12)) alkanols comes mainly from their ability as nonionic surfactants to disrupt the native membrane-associated function of the integral proteins.
용도 및 제조
Uses
Used as a synthetic flavoring for food and in perfumes; [HSDB]
Used as intermediate for linear phthalate plasticizers and detergent alcohol ethoxylates; [HSDB]
Food additive-synthetic flavor
Perfumery, flavoring
CHEM INT FOR DIUNDECYL PHTHALATE
CHEM INT FOR LINEAR PHTHALATE PLASTICIZERS-AS C7-C11 MIXT
U.S. Exports
(1977) 1.08X10+9 GRAMS
(1979) No Data
U.S. Imports
(1977) No Data
(1979) No Data
U.S. Production
2023: 100,000,000 - <250,000,000 lb
This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
(1990) >1 million-10 million pounds
(1994) >10 million-50 million pounds
(1998) >10 million-50 million pounds
(2002) >10 million-50 million pounds
Methods of Manufacturing
By reduction of the corresponding aldehyde.
HYDROFORMYLATION OF C6, C8, AND C10 LINEAR ALPHA-OLEFINS TO YIELD A MIXTURE OF C7, C9, AND C11 ALCOHOLS FOLLOWED BY SEPARATION OF THE C11 FRACTION
Use Classification
EPA Safer Chemical Functional Use Classes -> Solvents
Safer Chemical Classes -> Green half-circle - The chemical is expected to be of low concern
Fragrance Ingredients
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing Information
All Other Chemical Product and Preparation Manufacturing
1-Undecanol: ACTIVE
Undecanol: ACTIVE
Decane, hydroxymethyl deriv.: INACTIVE
Commercial products from the family of 6 to 11 carbon alcohols that make up the plasticizer range are available both as ... pure single carbon chain materials and as complex isomeric mixtures. Commercial descriptions of plasticizer range alcohols are ... in general a ... pure material is called "-anol" /eg, 1-undecanol/, and the mixtures are called "-yl alcohol /eg, undecyl alcohol/ or "iso...yl alcohol" /eg, isoundecyl alcohol/.
Reported uses /include/ non-alcoholic beverages 4.09 ppm; ice cream, ices, etc 15.47 ppm; candy 17.65 ppm; baked goods 17.66 ppm; alcoholic beverages 4.50 ppm.
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