1-Nonanol

HCID 178850192CAS 33975-46-1

Grundinformationen

Standard-SMILES
CCCCCCCCCO
InChIKey
ZWRUINPWMLAQRD-UHFFFAOYSA-N
Summenformel
C9H20O
Durchschnittliche Molmasse
144,25 g/mol

Überblick

Nonanol appears as colorless liquid with a rose or fruity odor. Floats on water. Freezing point 23 °F. (USCG, 1999)

Namen und Bezeichner

Bevorzugter Name
1-Nonanol
IUPAC
nonan-1-ol
Englischer Name
n-Nonyl-6,6,7,7-d4 alcohol
Summenformel
C9H20O
Molmasse
144.26

Namen und Synonyme

1-NonanolNonan-1-ol143-08-8NONYL ALCOHOLPelargonic alcoholn-Nonyl alcoholn-NonanolNonalol1-HydroxynonaneOctyl carbinoln-Nonan-1-olC9 alcohol
Weitere Namen anzeigen
n-Nonyl--d4 Alcoholn-Nonyl-6,6,7,7-d4 alcohol
NonylalkoholPelargonalkoholFEMA No. 2789DTXSID6022008NGK73Q6XMCNSC-5521DTXCID402008CHEBI:35986

Datenbank-Bezeichner

CAS
33975-46-1
ChEMBL
CHEMBL24563
ChEBI
CHEBI:35986
UNII
NGK73Q6XMC
EC Number
205-583-7、249-048-6
Nikkaji
J2.549F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,3
Polarare Oberfläche (TPSA)
20,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
7
Schwere Atome
10

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty alcohols [FA05]
Solvents · 2 Einträge

Solvents -> Alcohols (<C12)

Solvents -> Alcohols (<C12)

SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Nonyl alcohol) -> IFRA transparency List
LogP · 3 Einträge

log Kow = 3.77

3.77

3.67

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 0.4% (8 of 2003) of reports.

Warning

H315 (13.4%): 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 2003 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: 1-Nonanol

Chemical: Nonanol

1-Nonanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Nonanol 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)

Nonanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Nonanol 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)

Status: Active Update: 24-04-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/2065

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

DOT LabelClass 9
Fire HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Health HazardsLiquid irritates eyes. (USCG, 1999)
Hazards Summary · 2 Einträge

In high-dose animal experiments, causes fatal intoxication, liver injury and kidney injury; [HSDB] An eye irritant; [CAMEO] An irritant; [MSDSonline] See Nonanol.

The commercial product consists of approximately 80% 3,5,5-trimethylhexanol; Members of the alkyl alcohols C6-C13 category demonstrate skin and eye irritation in rabbits; Low acute oral and dermal toxicity; Moderate to low acute inhalation toxicity; [EPA ChAMP: Hazard Characterization] See 1-Nonanol.

FDA Requirements · 1 Eintrag

Nonyl 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.

Sicherheit und Schutzausrüstung

Fire FightingFire Extinguishing Agents Not to Be Used: Water may be ineffective
First AidFlush eyes and skin with water for at least 15 min. (USCG, 1999)
Cleanup Methods · 1 Eintrag

AEROBIC: Nonyl alcohol degraded fast in aerobic biodegradation screening tests(1-3). In one 5-day BOD test using acclimated mixed cultures, 47.9% of theoretical BOD was consumed(1). In the other test which used an activated sludge inoculum, nonyl alcohol's half-life was 1.2 days(SRC), calculated from a biodegradation rate of 2.36X10-2/hr(3). In a third test, 62% of its theoretical BOD in a grab sample of freshwater incubated at 18-19 °C was expended in 4 days(2).

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

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.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Toxikologische Informationen

Interactions · 1 Eintrag

... Maximum permeation of MT was observed when fatty alcohol carbon chain length was 10. As the level of unsaturation increased from one to two double bonds, there was an increase in the permeation of MT both in porcine and human skin. However, a decrease in the permeation was observed with three double bonds. Regression analysis using the steady state flux data showed a significant positive correlation between porcine and human skin for saturated fatty alcohols (r(2)=0.8868, P=0.0005).

Ecotoxicity Values · 5 Einträge

LC50 Pimephales promelas (Fathead minnow, weight 0.12 g) 5.7 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 Pimephales promelas (Fathead minnow, age 30-31 days, mean weight 0.124 g, mean length 20.0 mm) 5.7 mg/L/96 hr (95% confidence limit: 5.4-6.0 mg/L); flow through bioassay, temp 24.8 °C, pH 7.63, dissolved oxygen 7.2 mg/L, hardness 44.3 mg/L CaCO3, alkalinity 43.0 mg/L CaCO3 /purity 97%/

LC50 Alburnus alburnus (Bleak) 18 mg/L/96 hr (95% confidence limit: 16-20 mg/L); static /formulated product/

LC50 Nitocra spinipes (Harpacticoid copepod) 25 mg/L/96 hr (95% confidence limit: 21-30 mg/L); static /formulated product/

For more Ecotoxicity Values (Complete) data for 1-NONANOL (6 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 290(SRC), determined from a water solubility of 140 mg/L(2) and a regression-derived equation(3), indicates that 1-nonanol is expected to have moderate mobility in soil(SRC). Volatilization of 1-nonanol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.08X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 2.27X10-2 mm Hg(4) and water solubility(2). 1-Nonanol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). 1-Nonanol has been demonstrated to be readily biodegradable in aerobic screening tests(5-7) and therefore may readily biodegrade in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 290(SRC), determined from a water solubility of 140 mg/L(2) and a regression-derived equation(3), indicates that 1-nonanol 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 3.08X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 2.27X10-2 mm Hg(4), and water solubility(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1.6 days and 15 days, respectively(SRC). 1-Nonanol has been demonstrated to be readily biodegradable in aerobic screening tests(5-7) and therefore may biodegrade in natural water(SRC). According to a classification scheme(8), an estimated BCF of 160(SRC), from a log Kow of 3.77(9) and a regression-derived equation(10), suggests the potential for bioconcentration in aquatic organisms is high(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-nonanol, which has a vapor pressure of 2.27X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-nonanol 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 28 hours(SRC), calculated from its rate constant of 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Food Survey Values · 1 Eintrag

1-Nonanol has been identified in a variety of foods including nectarines(1), oil of orange(7), cassava(2), duck(3), peanut oil(4), earth almonds (Cyperus esculentus L.)(5), and a French mountain cheese(6). Unspecified nonyl alcohol isomers have been identified in pork and beef(7,8).

Adverse Effects · 2 Einträge

Neurotoxin - Acute solvent syndrome

Neurotoxin - Acute solvent syndrome

Toxicity Summary · 1 Eintrag

The existing information was reviewed by the independent Expert Panel for Fragrance Safety and supports the use of nonyl alcohol as described in this fragrance ingredient safety assessment. Data from read-across analog heptyl alcohol (CAS # 111-70-6) show that nonyl alcohol is not expected to be genotoxic and provide a calculated Margin of Exposure (MOE) >100 for the repeated dose toxicity and reproductive toxicity endpoints. Data from read-across analog 1-decanol (CAS # 112-30-1) provided nonyl alcohol a No Expected Sensitization Induction Level (NESIL) of 10000 μg/cm2 for the skin sensitization endpoint. The photoirritation/photoallergenicity endpoints were evaluated based on ultraviolet/visible (UV/Vis) spectra; nonyl alcohol is not expected to be photoirritating/photoallergenic. The local respiratory toxicity endpoint was evaluated using the Threshold of Toxicological Concern (TTC) for a Cramer Class I material, and the exposure to nonyl alcohol is below the TTC (1.4 mg/day).

Regulatorische Informationen

FDA Requirements · 1 Eintrag

Nonyl 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.

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

... Intermediate-chain alcohols (pentanol to octanol) caused channel currents to fluctuate between the fully open and closed state level so that openings occurred in bursts interrupted by brief gaps ... The number of gaps within a burst was dependent on alcohol concentration whereas gap duration was independent of concentration but increased with increasing chain length of the alcohol up to octanol. Nonanol and decanol reduced the mean duration of bursts of openings but did not cause an increase in the number of short closed intervals within a burst. Beyond decanol there was a decline in the ability of the n-alcohols to affect channel function. A saturated solution of undecanol (0.07 mM) reduced the mean open time by 33 + or - 17%, whereas a saturated solution of dodecanol had no significant effect. The current integral per burst was reduced by all the n-alcohols between pentanol and undecanol. The IC50s were as follows: hexanol, 0.53 + or - 0.14 mM; heptanol, 0.097 + or - 0.02 mM; octanol, 0.04 mM and nonanol, 0.16 + or - 0.035 mM ... Blocking rate constants (k+B) for pentanol through to nonanol were calculated to be between 2.8 and 5.7 X 10(6) /M/sec ... Equilibrium dissociation constants (KD), calculated from the blocking and unblocking rate constants (KD = k-B/k+B), decreased with increasing chain length from 8 mM for pentanol to 0.15 mM for octanol. The standard free energy per methylene group for adsorption to the site of action was calculated to be about -3.3 kJ/mol.

Metabolism/Metabolites · 1 Eintrag

Nonanol, like other primary alcohols, undergoes two general reactions in vivo. The first is oxidation to the carboxylic acid derivative and next the direct conjugation with glucuronic acid. It was reported that nonanol undergoes direct glucuronic conjugation to the extent of 4.1%. This oxidation proceeds with very little inhibition as opposed to that shown by methyl amyl alcohol and 2-ethyl butyl alcohol which form ester glucuronides.

Absorption, Distribution and ExcretionSkin absorption is low; the dermal flux of 1-nonanol in human skin (epidermis) in vitro is 0.003 mg/sq cm/hr.
Cellular LocationsExtracellular

Verwendung und Herstellung

Uses · 6 Einträge

Used as a fragrance, flavoring agent, chemical intermediate, and to make artificial lemon oil; [HSDB]

Perfumery, flavoring (lemon oil)

In manufacture of artificial lemon oil

Fragrance, eg, in perfumes & soaps; flavoring agent, eg, in chewing gum & candy; chemical intermediate for plasticizers (as alcohol mixture) & surfactants (as alcohol mixture)

A major use of 1-nonanol is as a chemical intermediate in the production of esters ...

Used in the rubber and dyestuff industry, in the production of plasticizers, emulsifiers, etc.

U.S. Production · 5 Einträge

2023: <50,000 lb

2023: 10,000,000 - <50,000,000 lb

(1977) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(2002) >1 million-10 million pounds

Industry UsesIntermediate
Methods of Manufacturing · 3 Einträge

By sodium or high-pressure catalytic reduction of esters of pelargonic acid; hydroformylation of C8 linear alpha-olefins or internal olefins (occurs in a mixt); natural constituent of rose, grapefruit & orange oils.

Preparation by reduction of ethyl delta (superscript 1)-nonylenate ... by reduction of pelargonic aldehyde ... by oxo process: Russum, Hengstebeck, US patent 2,638,487 (1953 to Standard Oil of Indiana); by reductive cleavage of oleic acid ozonide ... from diborane and propylene trimer: Marshall, Smith, British patent 879,242(1961 to I.C.I.).

... Oxo synthesis from dimeric 1-butene and 2-butene (mixture known as raffinate II) or from dimeric isobutene. /C9 Alcohol mixtures/

Use Classification · 5 Einträge

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 4 Einträge

Plastics Material and Resin Manufacturing

1-Nonanol: ACTIVE

Nonanol: ACTIVE

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-nonanol/, and the mixtures are called "-yl alcohol /eg, nonyl alcohol/ or "iso...yl alcohol" /eg, isononyl alcohol/.

Anwendungen

Verwendenn-Nonyl-6,6,7,7-d4 Alcohol (CAS# 33975-46-1) is a useful isotopically labeled research compound.

Anbieter5 Anbieter

盐城通铭生物科技有限公司15195160625 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
成都思天德生物科技有限公司028-83243028 19136088901 · [email protected]
Clearsynth Labs Limited+91-22-26355700 · [email protected]
南京昊绿生物科技有限公司025-84622273 17361806303 · [email protected]

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