1-Octanol

HCID 957CAS 111-87-5

Grundinformationen

Standard-SMILES
CCCCCCCCO
InChIKey
KBPLFHHGFOOTCA-UHFFFAOYSA-N
Summenformel
C8H18O
Durchschnittliche Molmasse
130,23 g/mol
Monoisotopische Masse
130,1357652

Überblick

Octanol appears as a clear colorless liquid with a penetrating aromatic odor. Insoluble in water and floats on water. Vapors heavier than air. Vapors may irritate the eyes, nose, and respiratory system.

Namen und Bezeichner

Bevorzugter Name
1-Octanol
IUPAC
octan-1-ol
Lokaler Name
Octan-1-ol
Englischer Name
1-Octanol
Summenformel
C8H18O
Molmasse
130.23

Namen und Synonyme

1-octanolOctan-1-ol111-87-5N-octanolOctyl alcoholcaprylic alcoholn-Octyl alcoholHeptyl carbinol1-HydroxyoctaneAlcohol C-8OctilinPrimary octyl alcohol
Weitere Namen anzeigen
OCTANOLcaprylicFEMA 2800CAPRYL ALCOHOL1-0ctanol
n-Octan-1-olDytol M-83Alfol 8Sipol L8Lorol 20n-Caprylic alcoholEPAL 8C8 alcohol

Datenbank-Bezeichner

CAS
111-87-5、220713-26-8、29063-28-3
PubChem CID
957
DTXSID
DTXSID7021940
ChEMBL
CHEMBL26215
ChEBI
CHEBI:16188
UNII
NV1779205D
EC Number
203-917-6、249-405-6、606-925-1
Nikkaji
J2.459G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3
Polarare Oberfläche (TPSA)
20,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
6
Schwere Atome
9

Experimentelle und physikochemische Eigenschaften

Chemical ClassesVolatile Organic Compound (VOC)
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty alcohols [FA05]
SolventsSolvents -> Alcohols (<C12)
CosmeticsViscosity controlling
SpringerMaterials PropertiesBoiling point

Physikochemische Eigenschaften

Schmelzpunkt
15 °C · −15 °C(lit.)
Siedepunkt
196 °C · 196 °C(lit.)
Dichte
0.827 g/mL · 0.827 g/mL at 25 °C(lit.)
Dampfdichte
4.5 · 4.5 (vs air)
Dampfdruck
0.14 mm · 0.14 mm Hg ( 25 °C)
Brechungsindex
20 · n20/D 1.429(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 0.2% (7 of 3216) of reports.

Warning

H302+H312 (14.7%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]

P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3216 reports by companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: 1-Octanol

1-Octanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Octanol 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: 22-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15210

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

Other Safety InformationIMAP assessments - Primary aliphatic alcohols (C7, C8): Human health tier II assessment
Fire HazardsCombustible. Above 81 °C explosive vapour/air mixtures may be formed.
Fire PotentialCombustible liquid when exposed to heat or flame...
Health HazardsIrritates skin and eyes. (USCG, 1999)
Hazards Summary · 1 Eintrag

A skin and eye irritant; [CAMEO] Inhalation of high concentrations can cause CNS depression; [CHEMINFO] An eye and respiratory tract irritant; A mild skin irritant; [ICSC] An irritant; May cause CNS depression; Targets kidneys, nerves, and liver; [MSDSonline]

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fire Extinguishing Agents: Foam, carbon dioxide, or dry chemical (USCG, 1999)

Use alcohol-resistant foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 Einträge

Fresh air, rest.

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.

First AidFlush with copious amounts of water. (USCG, 1999)
Safe StorageSeparated from strong oxidants.
Exposure Control and Personal Protection10.0 [ppm]
Fire Fighting Procedures · 3 Einträge

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

To fight fire use water foam, fog, alcohol foam, dry chemical, carbon dioxide.

Toxikologische Informationen

Body BurdenAccording the National Human Adipose Tissue Survey (NHATS) of 1982, 1-octanol was found in 12 of 46 composite samples; 4 samples each from subjects in the age groups of 0-14, 15-44 and 44+, respectively(1).
Interactions · 1 Eintrag

... Whether 1-octanol (OCT) could inhibit Ethanol (ETOH) toxicity in cultured whole mouse embryos /was studied/. Embryos (3 to 5 somites) were cultured for 6 hours in the absence and presence of alcohols and transferred to control medium for an additional 20 hours. Somite pairs were counted after a total of 26 hours in culture ... Treatment with 3 uM OCT did not produce a delay in embryonic development, whereas 10 uM and 50 uM OCT caused increasing toxicity. Embryos cultured for 6 hours with 100 mM ETOH showed markedly delayed in vitro development (13.8 + or - 0.7 somite pairs after 26 hours, n = 15) as compared with control embryos (19.6 + or - 0.6 somite pairs, n = 5). The toxicity of 100 mM ETOH was significantly reduced by co-incubation with 3 uM OCT (16.9 + or - 0.6 somite pairs; n = 23, p less than 0.002). All of the control embryos and 60.9% of the ethanol/octanol-treated embryos had greater than or equal to 17 somite pairs; in contrast, only 13.4% of the embryos treated with ethanol alone had greater than or equal to 17 somite pairs. Conversely, while 33.3% of the embryos treated with ethanol alone had less than or equal to 12 somite pairs, none of the control embryos and only 4.3% of the embryos treated with ethanol plus octanol were this small.

Ecotoxicity Values · 5 Einträge

LC50; Species: Pimephales promelas (Fathead minnow); Conditions: flow-through bioassay with measured concentrations, 25.0 °C, dissolved oxygen 5.9 mg/L, hardness 47.6 mg/L calcium carbonate, alkalinity 45.8 mg/L calcium carbonate, and pH 7.64; Concentration: 13.5 mg/L for 96 hr (confidence limit 13.2-13.8 mg/L)

EC50; Species: Pimephales promelas (Fathead minnow); Conditions: flow-through bioassay with measured concentrations, 25.0 °C, dissolved oxygen 5.9 mg/L, hardness 47.6 mg/L calcium carbonate, alkalinity 45.8 mg/L calcium carbonate, and pH 7.64; Concentration: 13.5 mg/L for 96 hr (confidence limit 13.2-13.8 mg/L); Effect: loss of equilibrium

LC50; Species: Nitocra spinipes (Harpacticoid copepod); Conditions: static; Concentration: 60 mg/L for 96 hr /formulated product/

LC50; Species: Alburnus alburnus (Bleak); Conditions: static; Concentration: 16 mg/L for 96 hr /formulated product/

For more Ecotoxicity Values (Complete) data for 1-OCTANOL (11 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), a reported Koc value of 38(2), indicates that 1-octanol is expected to have very high mobility in soil(SRC). Volatilization of 1-octanol from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.5X10-5 atm-cu m/mole(3). 1-Octanol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.0794 mm Hg at 25 °C(4). A 89% of theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), a reported Koc value of 38(2), indicates that 1-octanol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 2.5X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 43 hours and 17 days, respectively(SRC). 1-Octanol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(5), an estimated BCF of 44(SRC), from its log Kow of 3.00(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Based on aqueous biodegradation screening test results, 1-octanol should biodegrade rapidly in aquatic environments(8-10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-octanol, which has a vapor pressure of 0.0794 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-octanol 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 27 hours(SRC), calculated from its rate constant of 1.44X10-11 cu cm/molecule-sec at 25 °C(3). Physical removal from air via precipitation has been shown to occur(4). 1-Octanol does not contain chromophores that absorb at wavelengths >290 nm(5) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 3 Einträge

1-Octanol was identified as a volatile component of fried bacon(1), roasted filberts(2), raw and roasted earth almonds (Cyperus esculentus L.)(3), mutton(4), chicken(4), pork(4), raw beef(4,5), frankfurters(6), nectarines(7), apple juice(8), common guava(9), Beaufort (Gruyere) cheese(10) and in food products processed from the Cassava root(11). 1-Octanol has been detected in beer, wine and spirits(12).

Fermented soybean (Glycine max) curds were found to contain 164.8 to 337.1 ug/kg of 1-octanol(1). 1-Octanol was isolated as a volatile component of duck meat (8.88 ppb), duck fat (12.69 ppb), Cantonese style roasted duck (32.01 ppb) and Cantonese style roasted duck gravy (32.85 ppb)(2). 1-Octanol was also identified as a volatile component of edible Korean chamchwi (Aster scaber Thunb)(3), kiwi fruit flowers(4) and in heated peanut oil(5). The concentration of 1-octanol increased in roasted almonds (Prunus dulcis) during 16-20 weeks of storage at 25 or 35 °C(6). 1-Octanol made up 0.49-10.86% of the fruit volatiles from blackberry (Rubus ulmifolius) that were collected from Italy and Spain(7).

1-Octanol has been reported in over 200 foods and beverages including apple, apricot, banana, citrus peel oils and juices, many berries, guava, grapes, melon, papaya, peach, pear, asparagus, kohlrabi, leek, peas, tomato, potato, clove, ginger, mustard, spearmint oil, wheat bread, many cheeses, cooked egg, butter, milk, fish, meats, beer, rum, whiskies, cognac, cider, sherry, grape wines, cocoa, tea, nuts, honey, soybean, coconut, passion fruit, olive, avocado, plum, rose apple, beans, mushroom, starfruit, Bantu beer, sesame seed, cauliflower, broccoli, tamarind, fruit brandies, fig, cardamom, coriander seed and leaf, rice, quince, litchi, dill, lovage, sweet corn, corn oil, malt, kiwi fruit, loquat, Bourbon vanilla, scary sage, oysters, crayfish, clam and Chinese quince(1).

Adverse EffectsNeurotoxin - Acute solvent syndrome

Regulatorische Informationen

FDA Requirements · 2 Einträge

1-Octanol 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 b) 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.

Octyl alcohol is an indirect food additive for use only as a component of adhesives.

FIFRA Requirements · 3 Einträge

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether or not products containing the active ingredient 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 aliphatic alcohols as an active ingredient. 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 aliphatic alcohols (C6 - C16). The Agency has completed its assessment of the human health and ecological risks associated with the use of pesticide products containing aliphatic alcohols (C6 - C16). The Agency has determined that aliphatic alcohol-containing products are eligible for reregistration provided that label amendments are made as outlined in Chapter V. ... The Agency has identified eye-irritation concerns that warrant specific label language concerning personal protective equipment (PPE) and the length of restricted-entry intervals after application for tobacco uses of the aliphatic alcohols (C6 - C16). If all changes outlined in this document are incorporated into the product labels, the eye-irritation concerns will have been mitigated. Should a registrant fail to implement any of the reregistration requirements identified in this document, the Agency may take regulatory action to address these concerns.

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 continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in 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 than those on List C, and with List C containing pesticides of greater concern than those on List D. Octanol is found on List D. Case No: 4004; Pesticide type: insecticide, herbicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): octanol; AI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled."

Residues of n-octyl alcohol are exempted from the requirement of a tolerance when used 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. Use: solvent or cosolvent.

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
3082
hs_code
29051680
RTECS-Nr.
RH6550000
risk_code
36/38

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 2 Einträge

The effect of various alkanols on the central nervous system was studied by using rat brain synaptosomal membranes as an in vitro model. The activity of (Ca2+/Mg2+)ATPase and the membrane fluidity were determined. The n-alkanols exhibited an increased molar inhibition of the ATPase activity with an increase in the carbon chain length up to 1-octanol. 1-octanol and 1-decanol caused a biphasic effect on the ATPase activity depending on the alkanol concentration, whereas 1-dodecanol caused a stimulation of the ATPase activity. All alkanols studied caused an increased fluidity of the membrane ... /These/ results indicate that the effect of alkanols on the ATPase activity depends on changes in the border layer between the membrane and the surrounding medium and on a binding of the alkanols to the enzyme molecule ... The two-way effect of 1-octanol and 1-decanol and the stimulatory effect of 1-dodecanol indicate that more mechanisms are involved ... Changes in the membrane fluidity do not seem to be a prerequisite of the ATPase inhibition.

... Studies indicate that T-type calcium channels (T-channels) in the thalamus are cellular targets for general anesthetics. Here, we recorded T-currents and underlying low-threshold calcium spikes from neurons of nucleus reticularis thalami (nRT) in brain slices from young rats and investigated the mechanisms of their modulation by an anesthetic alcohol, 1-octanol. We found that 1-octanol inhibited native T-currents at subanesthetic concentrations with an IC(50) of approximately 4 muM. In contrast, 1-octanol was up to 30-fold less potent in inhibiting recombinant Ca(V)3.3 T-channels heterologously expressed in human embryonic kidney cells. Inhibition of both native and recombinant T-currents was accompanied by a hyperpolarizing shift in steady-state inactivation, indicating that 1-octanol stabilized inactive states of the channel. To explore the mechanisms underlying higher 1-octanol potency in inhibiting native nRT T-currents, we tested the effect of the protein kinase C (PKC) activator phorbol 12-myristate 13-acetate (PMA) and PKC inhibitors. We found that PMA caused a modest increase of T-current, whereas the inactive PMA analog 4alpha-PMA failed to affect T-current in nRT neurons. In contrast, 12-(2-cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5-oxo-5H-indolo(2,3-a)pyrrolo(3,4-c)-carbazole (Go 6976), an inhibitor of calcium-dependent PKC, decreased baseline T-current amplitude in nRT cells and abolished the effects of subsequently applied 1-octanol. The effects of 1-octanol were also abolished by chelation of intracellular calcium ions with 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid. Taken together, these results suggest that inhibition of calcium-dependent PKC signaling is a possible molecular substrate for modulation of T-channels in nRT neurons by 1-octanol.

Metabolism/Metabolites · 2 Einträge

The primary aliphatic alcohols undergo two general reactions in vivo, namely oxidation to carboxylic acids and direct conjugation with glucuronic acid. The first reaction proceeds with the intermediate formation of an aldehyde, and the carboxylic acid from the aldehyde may be either oxidized completely to carbon dioxide or excreted as such or combined with glucuronic acid as an ester glucuronide. The extent to which an alcohol undergoes the second reaction, i.e. direct conjugation to an ether glucuronide, appears to depend upon the speed of the first reaction. Alcohols which are rapidly oxidized form very little ether glucuronide unless given in high doses.

The urinary metabolites of n-octane in Fischer 344 rats given the hydrocarbon by gavage included 2-octanol, 3-octanol, 5-oxohexanoic acid, and 6-oxoheptanoic acid. The sex of the animals influenced the relative amounts of metabolites formed. Analyses were performed by gas-liquid chromatography (GC) and gas-liquid chromatography/mass spectrometry (GC/MS). This is the first reported finding of keto acids in hydrocarbon oxidative metabolism. No kidney damage was found as a result of n-octane dosing although the 2,2,4-trimethylpentane (iso-octane) isomer does cause kidney lesions in male rats. /n-Octane/

MeSH Pharmacological ClassificationLiquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant &amp; Hackh&apos;s Chemical Dictionary, 5th ed)
Absorption, Distribution and ExcretionIn vitro dermal flux in human skin (epidermis) was reported as 0.008 mg/sq cm/hr, suggesting a low rate of penetration.
Tissue LocationsAdipose Tissue
Cellular LocationsExtracellular

Verwendung und Herstellung

Uses · 6 Einträge

Used in perfumery, cosmetics, shampoos, emulsifiers, detergents, and food flavors; Also used as a solvent (esters, coatings, lacquers, printing inks, textile additives, and pesticides), citric acid extractant, frothing agent, antifoaming agent in drilling muds, and growth inhibitor in tobacco production; [HSDB]

For 1-octanol (USEPA/OPP Pesticide Code: 079037) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

... plant growth regulator ... of tobacco.

Perfumery, cosmetics, organic synthesis, solvent manufacture of high-boiling esters, antifoaming agent, flavoring agent.

Mixtures of 1-hexanol and 1-octanol serve as frothing agents (bubbling promoters) in flotation, e.g., of coal. Large amounts are added to aqueous drilling muds to prevent frothing during drilling for oil and gas.

For more Uses (Complete) data for 1-OCTANOL (9 total), please visit the HSDB record page.

U.S. Imports(1984) 9.42X10+9 G /OCTYL ALCOHOLS/
U.S. Production · 6 Einträge

2023: 50,000,000 - <100,000,000 lb

(1984) 1.28X10+11 G /ALCOHOLS C11 OR LOWER/

(1986) >10 million-50 million pounds

(1990) >10 million-50 million pounds

(1994) >10 million-50 million pounds

For more U.S. Production (Complete) data for 1-OCTANOL (9 total), please visit the HSDB record page.

Consumer UsesOxidizing agent
Industry UsesOxidizing agent
Methods of Manufacturing · 5 Einträge

Prepared from the esterified products of coconut oil, the methyl caprylate being reduced by sodium and alcohol.

By reduction of some caprylic esters such as methyl caprylate with sodium ethoxide.

1-Octanol is manufactured by the Alfol process and from natural products.

1-Octanol is made commercially by sodium reduction or high-pressure catalytic hydrogenation of the esters of naturally occurring caprylic acid or by oligomerization of ethylene using aluminum alkyl technology.

... Manufactured by the hydrodimerization of 1,3-butadiene, followed by catalytic hydrogenation of the resulting dienol, and distillation to produce n-octyl alcohol with a minimum purity of 99 percent.

Anwendungen · 2 Einträge

Beschreibung1-Octanol (111-87-5) is a colorless and transparent liquid with the chemical formula C8H18O. It is a fatty alcohol consisting of a linear, saturated chain of eight carbon atoms. Although 1-Octanol is not highly soluble in water, it can dissolve easily in alcohol, ether, and chloroform. This compound is commonly used as a raw material in the production of fragrances, octanal, octanoic acid, and its esters. It also functions as a solvent, defoamer, and lubricating oil additive. Notably, 1-Octanol poses a low level of toxicity, but it can be irritating to the skin and eyes. Nonetheless, it is considered safe to use under normal conditions because of its low vapor pressure.

OccurrenceReported as frequently occurring in essential oils as an ester; the free alcohol has been reported found in the essential oils of green tea, grapefruit, California orange, Andropogon intermedius, Heracleum villosum, violet leaves, Anethum graveolens and bitter orange. Also reported in over 200 foods and beverages including apple, apricot, banana, citrus peel oils and juices, many berries, guava, grapes, melon, papaya, peach, pear, asparagus, kohlrabi, leek, peas, tomato, potato, clove, ginger, mustard, spearmint oil, wheat bread, many cheeses, cooked egg, butter, milk, fish, meats, beer, rum, whiskies, cognac, cider, sherry, grape wines, cocoa, tea, nuts, honey, soybean, coconut, passion fruit, olive, avocado, plum, rose apple, beans, mushroom, starfruit, Bantu beer, sesame seed, cauliflower, broccoli, tamarind, fruit brandies, fig, cardamom, coriander seed and leaf, rice, quince, litchi, dill, lovage, sweet corn, corn oil, malt, kiwifruit, loquat, Bourbon vanilla, clary sage, oysters, crayfish, clam and Chinese quince.

Darstellung

synthetische1-Octanol may be prepared by reduction of some caprylic esters such as methyl caprylate with sodium ethoxide.

Anbieter50 Anbieter

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Ergänzende Hinweise

DefinitionChEBI: Octan-1-ol is an octanol carrying the hydroxy group at position 1. It has a role as a plant metabolite. It is an octanol and a primary alcohol.

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