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1-Undecanol

HCID 8184
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
112-42-5
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

1-UNDECANOLUndecan-1-olUndecyl alcoholUndecanol1-HendecanolHendecyl alcoholTip-NipDecyl carbinol1-Undecyl alcoholn-Undecan-1-olAlcohol C-11C11 alcohol
이름 더 보기
Neodol 1Alcohol, undecylUndecanol-(1)Alcohol C11NSC 403667DTXSID0026915HSDB 1089EINECS 203-970-5

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

LipidsFatty Acyls [FA] -> Fatty alcohols [FA05]
Solvents · 2건

Solvents -> Alcohols (<C12)

Solvents -> Alcohols (<C12)

CosmeticsSkin conditioning; Antiseborrhoeic
SpringerMaterials PropertiesBoiling point
Fragrances · 2건

Fragrance Ingredient (Undecanol) -> IFRA transparency List

Fragrance Ingredient (Undecyl alcohol) -> IFRA transparency List

LogP · 2건

log Kow = 4.72

4.72

OdorCitrus
Taste · 2건

FATTY FLAVOR

CITRUS

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 4건

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

Flavoring AgentsEU Flavoring substances
Viscosity17.2 mPa.s at 20 °C

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

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

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 · 6건

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.

REACH registered substance: Undecan-1-ol (EC: 203-970-5)

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

DOT LabelClass 9
Fire Hazards · 2건

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Combustible.

Health HazardsLiquid can irritate eyes. (USCG, 1999)
Hazards Summary · 2건

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 · 1건

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.

Reactive GroupAlcohols and Polyols
Special Reports · 1건

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.

EPA Safer ChemicalChemical: 1-Undecanol
FIFRA Requirements · 2건

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 · 1건

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.

Air and Water ReactionsSlightly soluble in water.

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4건

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 .

First AidWash eyes with water for at least 15 min. (USCG, 1999)
Safe StorageWell closed.
Cleanup Methods · 1건

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).

Nonfire Spill ResponseExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Disposal Methods · 1건

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.

Spillage DisposalPersonal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in covered containers as far as possible.
Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Eye PreventionWear safety goggles or eye protection in combination with breathing protection.
Fire PreventionNO open flames.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

독성 정보

Interactions · 2건

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 · 4건

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 · 3건

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).

Food Survey Values1-Undecanol was identified as a volatile component of beef(1).
Adverse Effects · 2건

Neurotoxin - Acute solvent syndrome

Neurotoxin - Acute solvent syndrome

Signs and Symptoms · 4건

Cough.

Dry skin. Redness. Roughness. Pain.

Redness. Pain. Blurred vision.

Nausea. Vomiting. Diarrhoea.

Effluent Concentrations1-Undecanol was reported at 17 ng/ul of extract in 1 occurrence from the organic chemical industry(1).
ICSC Environmental DataEnvironmental effects from the substance have not been investigated adequately.
Soil Adsorption/Mobility · 1건

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.

Natural Pollution SourcesREPORTED FOUND IN NATURE (CITRUS FRUITS).
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ The substance is severely irritating to the eyes, and is irritating to the skin and the respiratory tract.
Fish/Seafood Concentrations1-Undecanol was qualitatively identified in Lake Michigan lake trout at Charlevoix, MI on 9/25/77(1).

규제 정보

FDA Requirements · 1건

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 · 2건

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 · 1건

... 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.

Cellular LocationsExtracellular

용도 및 제조

Uses · 6건

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 · 2건

(1977) 1.08X10+9 GRAMS

(1979) No Data

U.S. Imports · 2건

(1977) No Data

(1979) No Data

U.S. Production · 6건

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

Consumer UsesIntermediate
Industry UsesIntermediate
Methods of Manufacturing · 2건

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

Formulations/PreparationsPurity: a minimum of 97-98.5% undecyl alcohol.
Use Classification · 6건

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 · 6건

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.

관련 반응

13건
반응 기록 만들기
HRID 34892 반응식
HRID 34892생성물로uspto-grants-1988_08
HRID 202103 반응식
HRID 202103반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 231001 반응식
HRID 231001반응물로uspto-grants-1989_07
HRID 358099 반응식
HRID 358099반응물로uspto-grants-1984_08
HRID 388234 반응식
HRID 388234반응물로uspto-grants-2013_02
HRID 444333 반응식
HRID 444333반응물로uspto-grants-1981_04
HRID 824779 반응식
HRID 824779반응물로Test data from https://doi.org/10.1039/C8SC04228D
HRID 1203432 반응식
HRID 1203432생성물로Training data from https://doi.org/10.1039/C8SC04228D (5/10)
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