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1-NONANOL
1-Nonanol/ˈnoʊnənɒl/ is a straight chain fatty alcohol with nine carbon atoms and the molecular formula CH3(CH2)8OH. It is a colorless oily liquid with a citrus odor similar to citronella oil.
CAS Number 143-08-8
EC Number 205-583-7
Formula: C9H20O
Molecular weight: 144.2545
Synonyms:
1-Nonanol; Nonan-1-ol; Nonanol; 143-08-8; NONYL ALCOHOL; n-Nonyl alcohol; Pelargonic alcohol; Octyl carbinol; 1-Hydroxynonane; Nonalol; n-Nonanol; n-Nonan-1-ol; Alcohol C-9; Nonylalkohol; Pelargonalkohol; Alcohol C9; UNII-NGK73Q6XMC; NSC 5521; MFCD00002990; NGK73Q6XMC; 28473-21-4; CHEBI:35986; 1-Nonanol, 97%; C9 alcohol; Fatty alcohol(C9); FEMA No. 2789; HSDB 5145; EINECS 205-583-7; BRN 0969213; nonanols; nonyl-alcohol; AI3-03962; N-nonyl-alcohol; 1-nonanol group; EINECS 249-048-6; Nonanol-(1); Nonyl alcohol, 8CI; CCCCCCCCC[O]; ACMC-209cpi; 1-Nonanol, 98%; DSSTox_CID_2008; EC 205-583-7; DSSTox_RID_76457; DSSTox_GSID_22008; SCHEMBL19807; WLN: Q9; 4-01-00-01798 (Beilstein Handbook Reference); BIDD:ER0370; CHEMBL24563; Pelargonic alcohol (1-nonanol); DTXSID6022008; Nonyl alcohol, >=98%, FCC; BDBM22607; FEMA 2789; Nonyl alcohol, Pelargonic alcohol; NSC5521; NSC-5521; ZINC1686993; Tox21_300869; 8145AF; ANW-20740; LMFA05000092; SBB059907; STL283956; AKOS009031412; DB03143; MCULE-4020281400; 1-Nonanol, purum, >=98.0% (GC); NCGC00248194-01; NCGC00254773-01; CAS-143-08-8; FT-0608164; N0292; ST51046174; C14696; 81307-EP2272817A1; 81307-EP2305687A1; 81307-EP2380568A1; 89678-EP2305033A1; 89678-EP2377844A2; 218917-EP2377844A2; A808013; Q161662; J-007741; F0001-0508; 2E051A08-F94E-40C2-88CA-7030E15C76BF
1-Nonanol/ˈnoʊnənɒl/ is a straight chain fatty alcohol with nine carbon atoms and the molecular formula CH3(CH2)8OH. It is a colorless oily liquid with a citrus odor similar to citronella oil.Nonanol occurs naturally in orange oil. The primary use of nonanol is in the manufacture of artificial lemon oil. Various esters of nonanol, such as nonyl acetate, are used in perfumery and flavors.1-Nonanol shares similar toxicological properties to those of other primary alcohols. It is poorly absorbed through the skin and is severely irritating to the eyes. Vapors can be damaging to the lungs, causing pulmonary edema in severe cases. Oral exposure results in symptoms similar to those of ethanol intoxication, and like ethanol consumption, can cause liver damage.Nonanol appears as colorless liquid with a rose or fruity odor. Floats on water. Freezing point 23°F. Nonan-1-ol is a fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of nine carbon atoms. It has been isolated as a component of volatile oils from plants like Hordeum vulgare. It has a role as a plant metabolite and a volatile oil component. It derives from a hydride of a nonane.Colorless to yellowish liquid.Floral odor.Miscible with alcohol, ether.Soluble in ethanol, ether; very soluble in carbon tetrachloride.In water, 140 mg/L at 25 °C.When heated to decomposition it emits acid smoke and irritating fumes.Skin absorption is low; the dermal flux of 1-nonanol in human skin (epidermis) in vitro is 0.003 mg/sq cm/hr.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.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.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.Oxo synthesis from dimeric 1-butene and 2-butene (mixture known as raffinate II) or from dimeric isobutene.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/.Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state.Based on the eye irritation scores that were reported, 1-nonanol would be considered an eye irritant using the EU criteria.Flush eyes and skin with water for at least 15 min.Fire Extinguishing Agents Not to Be Used: Water may be ineffective Fire Extinguishing Agents: Alcohol foam, dry chemical, or carbon dioxide.Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.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). 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.Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas.NONANOL 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.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.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).Basic Treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal.Advanced Treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques, with a bag-valve-mask device, may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose strip or glucometer readings below 50 mg) and administer 50% dextrose if necessary ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Higher alcohols (>3 carbons) and related compounds/In flow through acute toxicity testing using Pimephales promelas (Fathead minnow) exposed to concentrations of 0, 0.56, 1.0, 2.3, 4.7, and 8.2 mg/L 1-nonanol for 96 hr,/ affected fish first became sluggish in movement and stopped schooling. Some fish swam at water surface and equilibrium was lost prior to death.1-Nonanol's production and use in perfumery and as a flavoring ingredient may result in its release to the environment through various waste streams. 1-nonanol is also a plant volatile and has been identified in several foods. If released to air, a vapor pressure of 2.27X10-2 mm Hg at 25 °C indicates 1-nonanol will exist solely as a vapor in the atmosphere. Vapor-phase 1-nonanol will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 28 hours. If released to soil, 1-nonanol is expected to have moderate mobility based upon an estimated Koc of 290. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 3.08X10-5 atm-cu m/mole. 1-Nonanol is not expected to volatilize from dry soil surfaces based upon its vapor pressure. 1-Nonanol has been shown to biodegrade in mixed culture and sludge screening tests. If released into water, 1-nonanol is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Biodegradation of 1-nonanol has been shown to occur in freshwater grab samples. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 1.6 days and 15 days, respectively. An estimated BCF of 160 suggests the potential for bioconcentration in aquatic organisms is high. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to 1-nonanol may occur through dermal contact with this compound at workplaces where 1-nonanol is produced or used. Monitoring data indicate that the general population may be exposed to 1-nonanol via ingestion of food and drinking water, and dermal contact with this compound and other consumer products in which 1-nonanol is used as a fragrance. 1-Nonanol is a plant volatile(1) occurring, for example in oil of orange(2), kiwi fruit flowers(3), nectarines(4) and earth almonds.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.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).1-Nonanol 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, 1-nonanol's half-life was 1.2 days(SRC), calculated from a biodegradation rate of 2.36X10-2/hr(2). 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(3).The rate constant for the vapor-phase reaction of 1-nonanol with photochemically-produced hydroxyl radicals has been estimated as 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 28 hr at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1-Nonanol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2).An estimated BCF of 160 was calculated for 1-nonanol(SRC), using a log Kow of 3.77(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).The Henry's Law constant for 1-nonanol estimated as 3.08X10-5 atm-cu m/mol(SRC) derived from its vapor pressure, 2.27X10-2 mm Hg at 25 °C(1), and water solubility, 140 mg/L(2). This Henry's Law constant indicates that 1-nonanol is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 1.6 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 15 days(SRC). 1-Nonanol's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 1-Nonanol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).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).1-Nonanol has been identified in kiwi fruit flowers(1), nectarines(2) and earth almonds.
Cleaning_washing Related to all forms of cleaning/washing, including cleaning products used in the home, laundry detergents, soaps, de-greasers, spot removers, etc; mod
Cleaning_washing, flooring Flooring materials (carpets, wood, vinyl flooring), or related to flooring such as wax or polish for floors
Consumer_use Term applied when the only information the source indicates is 'consumer' or 'consumer product' ; also applied to terms that the source indicates are f
Food_additive Includes spices, extracts, colorings, flavors, etc added to food for human consumption
Food_additive, flavor General flavoring agents used in foods, including condiments and seasonings
Food_contact Includes food packaging, paper plates, cutlery, small appliances such as roasters, etc.; does not include facilities that manufacture food
Fragrance Fragrances or odor agents, can be used in home products (cleaners, laundry products, air fresheners) or similar industrial products; usage indicated when known; more specific modifiers included when known
Fragrance, consumer_use Term applied when the only information the source indicates is 'consumer' or 'consumer product' ; also applied to terms that the source indicates are f
Industrial, cleaning_washing Related to all forms of cleaning/washing, including cleaning products used in the home, laundry detergents, soaps, de-greasers, spot removers, etc; mod
Industrial_manufacturing
Inert
Pesticide, inert_ingredient Inert ingredients in a pesticide
Solvent Paint removers, graffiti removers, or general solvents
Toys Toys (e.g. dress-up clothes, dolls, playground equipment, bath toys, etc); pet toys; includes additional modifiers when appropriate
Toys, detected Chemicals detected in substances or products (note that these chemicals may be absent from an 'ingredient list' for the product and thus unexpected, but have been detected in product testing studies)
Industry Uses:
Plasticizers
Surface active agents
Consumer Uses:
Building/construction materials not covered elsewhere
Laundry and dishwashing products
Plastic and rubber products not covered elsewhere
1-Nonanol
Synonym: Alcohol C9, Nonyl alcohol
CAS Number 143-08-8 Linear Formula CH3(CH2)8OH Molecular Weight 144.25 Beilstein/REAXYS Number 969213 EC Number 205-583-7 MDL number MFCD00002990
1-Nonanol inhibited the bacterial luciferase (BL) reaction in a dose-dependent manner.1-Nonanol can be used:
• As a reference material in the determination of airborne fungal spore levels using GC-MS method.
• To prepare polysulfone capsules as ideal adsorbents used in the removal of phenol from an aqueous solution.
• As a solvent in the study of swelling properties of hummers graphene oxide membranes.
vapor density 5 (vs air)
vapor pressure 13 mmHg ( 104 °C)
assay 98%
refractive index n20/D 1.433 (lit.)
bp 215 °C (lit.)
mp −8-−6 °C (lit.)
density 0.827 g/mL at 25 °C (lit.)
storage temp. room temp
SMILES string CCCCCCCCCO
InChI 1S/C9H20O/c1-2-3-4-5-6-7-8-9-10/h10H,2-9H2,1H3
InChI key ZWRUINPWMLAQRD-UHFFFAOYSA-N
1-Nonanol
Formula: C9H20O
Molecular weight: 144.2545
IUPAC Standard InChI:
InChI=1S/C9H20O/c1-2-3-4-5-6-7-8-9-10/h10H,2-9H2,1H3
Download the identifier in a file.
INChI Trust 2011 Certified Logo
IUPAC Standard InChIKey: ZWRUINPWMLAQRD-UHFFFAOYSA-N
CAS Registry Number: 143-08-8
Chemical structure: C9H20O
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Species with the same structure:
Nonanol
Other names: Nonyl alcohol; n-Nonyl alcohol; Octyl carbinol; Pelargonic alcohol; Alcohol C-9; Nonan-1-ol; Nonanol-(1); n-Nonan-1-ol; n-Nonanol; 1-Hydroxynonane; Nonanol; NSC 5521
Information on this page:
Notes
Other data available:
Gas phase thermochemistry data
Condensed phase thermochemistry data
Phase change data
Reaction thermochemistry data
Henry's Law data
Gas phase ion energetics data
IR Spectrum
Mass spectrum (electron ionization)
Gas Chromatography
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1-Nonanol is found in citrus. 1-Nonanol is widespread in nature. 1-Nonanol occurs in oils of orange, citronella and lemon. Also found in cheese, prickly pears and bread. 1-Nonanol is a flavouring agent.1-Nonanol is a straight chain fatty alcohol with nine carbon atoms and the molecular formula CH3(CH2)8OH. It is a colorless to slightly yellow liquid with a citrus odor similar to citronella oil.1-Nonanol, also known as N-nonyl alcohol or 1-hydroxynonane, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Thus, 1-nonanol is considered to be a fatty alcohol lipid molecule. 1-Nonanol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Molecular Weight 144.25 g/mol
XLogP3 4.3
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 1
Rotatable Bond Count 7
Exact Mass 144.151415 g/mol
Monoisotopic Mass 144.151415 g/mol
Topological Polar Surface Area 20.2 Ų
Heavy Atom Count 10
Formal Charge 0
Complexity 52.7
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes
