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1-Octanol, also known as octan-1-ol, is the organic compound with the molecular formula CH3(CH2)7OH. It is a fatty alcohol. Many other isomers are also known generically as octanols. 1-Octanol is manufactured for the synthesis of esters for use in perfumes and flavorings. It has a pungent odor. Esters of octanol, such as octyl acetate, occur as components of essential oils.It is used to evaluate the lipophilicity of pharmaceutical products.Octanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products. This route is known as the Ziegler alcohol synthesis.Octanol and water are immiscible. The distribution of a compound between water and octanol is used to calculate the partition coefficient, P, of that molecule (often expressed as its logarithm to the base 10, log P). Water/octanol partitioning is a relatively good approximation of the partitioning between the cytosol and lipid membranes of living systems.With a flash point of 81 °C, 1-octanol is not seriously flammable, though its autoignition point is as low as 245 °C. 1-Octanol is mainly consumed as a precursor to perfumes.It has been examined for controlling essential tremor and other types of involuntary neurological tremors because evidence indicates it can relieve tremor symptoms at lower doses than are required to obtain a similar level of symptomatic relief from consumption of ethanol, thereby reducing the risk alcohol intoxication at therapeutic dosages.
CAS Number:111-87-5
EC Number:203-917-6
Synonyms:
1-octanol; Octan-1-ol; octanol; N-octanol; 111-87-5; Octyl alcohol; Capryl alcohol; caprylic alcohol; n-Octyl alcohol; Heptyl carbinol; 1-Hydroxyoctane; Primary octyl alcohol; Alcohol C-8; n-Octan-1-ol; Octilin; Alfol 8; Sipol L8; Lorol 20; Dytol M-83; n-Caprylic alcohol; Alcohols, C6-12; 1-Octyl alcohol; n-Heptyl carbinol; EPAL 8; octyl-alcohol; N-octyl-alcohol; Octyl alcohol, normal-primary; Lorol C 8-98; n-Capryl alcohol; NSC 9823; 1-Oktanol; Alcohol C8; Prim-n-octyl alcohol; UNII-NV1779205D; Emery 3322; Emery 3324; MFCD00002988; 68603-15-6; CHEBI:16188; NV1779205D; DSSTox_CID_1940; 1-Octanol, 99%, pure; C8 alcohol; DSSTox_RID_76416; DSSTox_GSID_21940; Fatty alcohol(C8); C6-12 Alcohols; Octyl alcohol, primary; Caswell No. 611A; Octyl alcohol (natural); FEMA Number 2800; Off-shoot-T; CAS-111-87-5; OC9; 1-Octanol, 99%, anhydrous, AcroSeal(R); FEMA No. 2800; CCRIS 9099; HSDB 700; Octanol (all isomers); Caswell No. 456E; Fair 85; C6-C12 Alkyl alcohol; EINECS 203-917-6; EPA Pesticide Chemical Code 079037; (C6-C12) Alkyl alcohol; octylalcohol; AI3-02169; 1-octanol group; 2-Capryl alcohol; Off-Shoot T; Alcohol, C8; EINECS 271-642-9; Lorol C8; octan-1-ol;; Alcohols, C8-18 and C18-unsatd.; Octanol-(1); EPA Pesticide Chemical Code 079029; CCCCCCCC[O]; 2-Octanol ~99%; SDA 13-060-00; bmse000970; bmse000980; EC 203-917-6; Octan-2-ol 98+ %; SCHEMBL8822; Octyl alcohol normal-primary; WLN: Q8; MLS001055318; CHEMBL26215; 1-Octanol, analytical standard; ACMC-2099b5; GTPL4278; DTXSID7021940; BDBM22606; 1-Octanol, anhydrous, >=99%; Mixed fatty alcohols (C6-C12); NSC9823; HMS3039O07; 1-Octanol, for HPLC, >=99%
1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents. 1-Octanol is a highly attractive biofuel with diesel-like properties.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.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.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.Colorless liquid.Fresh orange rose odor.OILY, SWEET, SLIGHTLY HERBACEOUS TASTE.EXPL THER 1-Octanol (an 8-C alcohol currently used as a food-flavoring agent) is known to inhibit tremor in essential tremor (ET) animal models at a much lower dose than ethyl alcohol. The /study/ conducted a randomized, placebo-controlled pilot trial of a single oral dose of 1 mg/kg of 1-octanol in 12 patients with ET. No significant side effects or signs of intoxication were observed. 1-Octanol significantly decreased tremor amplitude for up to 90 minutes. The results suggest 1-octanol as a well-tolerated and safe potential treatment for ET.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 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. 1-Octanol is a colorless liquid. It has a fresh, orange-rose odor. 1-Octanol has an oily, sweet, slightly herbaceous taste. It is moderately soluble in water. USE: 1-Octanol is used in cosmetics and perfumery. It is used as a food flavoring. 1-Octanol is used in organic synthesis, solvent manufacturing and as an antifoaming agent. EXPOSURE: Workers that use or produce 1-octanol may breathe in mists or have direct skin contact. The general population may be exposed by eating food or drinking beverages that contain 1-octanol. Skin exposure will result from using some household cleaning products. If 1-octanol is released to air, it will be degraded by reaction with other chemicals in the air. It is not expected to be broken down by light. If released to water or soil, it is not expected to bind to soil particles or suspended particles. It will move into air from water and moist soil surfaces. It is expected to move through soil at a high rate. It will be rapidly broken down by microorganisms. 1-Octanol will not build up in aquatic organisms. RISK: 1-Octanol did not cause irritation in human skin exposure studies. No abortions or offspring with birth defects were found in female laboratory animals exposed during pregnancy to high concentrations of 1-octanol vapor in air or to high doses by mouth. Unsteady gait, drooling, nose discharge, and pneumonia, with slightly decreased body weight gain were observed in the orally exposed pregnant animals. The potentials for 1-octanol to cause decreased fertility or cancer have not been studied in laboratory animals. The potential for 1-octanol to cause cancer in humans has not been assessed by the U.S. EPA IRIS program, the International Agency for Research on Cancer, or the U.S. National Toxicology Program 13th Report on Carcinogens.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.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.Grades: Technical; chemically pure; pure; perfume, Food Chemical Codex.Royaltac-M (Macdermid Agricultural Solutions, Inc.): Active ingredient: lauryl alcohol 0.3%; 1-octanol 36.2%; 1-decanol 48.2%.Off-Shoot-T (Macdermid Agricultural Solutions, Inc.): Active ingredient: lauryl alcohol 0.3%; 1-octanol 36.2%; 1-decanol 48.2%.C8-C10 Fatty Alcohol Technical (Macdermid Agricultural Solutions, Inc.): Active ingredient: lauryl alcohol 0.3%; 1-octanol 42.6%; 1-decanol 56.7%.Irritates skin and eyes.Combustible. Above 81 °C explosive vapour/air mixtures may be formed.Combustible liquid when exposed to heat or flame.Octanol ... has caused transient injury of corneal epithelium, with recovery in 48 hr.Flush with copious amounts of water.Fresh air, rest.Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas.; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.; Methods and materials for containment and cleaning up Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.AEROBIC: A number of aerobic biological screening studies, which utilized settled waste water, sewage, or activated sludge for inocula, have demonstrated that 1-octanol is readily biodegradable(1-8). Five day BOD tests show BODTs of 33(1), 37(2) and 62.4%(3). A ring test involving 14 laboratories found a mean degradation of 85% in 28 day test(4). A study which measured theoretical carbon dioxide evolved revealed 71% ultimate degradation of 1-octanol after an inoculation with activated sludge, in the dark, at 20 degrees C for 7 days(5). Other screening test data yielded a half-life of 22 hours(SRC) based on a first order biodegradation rate of 0.0313/hr(6) for 1-octanol.SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Combustible liquids.A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.The substance is irritating to the eyes and respiratory tract. The substance is mildly irritating to the skin. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis.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.Attacks plastics [Handling Chemicals Safely 1980. p. 236]. Acetyl bromide reacts violently with alcohols or water [Merck 11th ed. 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: an explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73. 1967; J, Org. Chem. 28:1893. 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M. 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].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.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.Emergency and supportive measures. 1. General. Provide basic supportive care for all symptomatic patients. Maintain an open airway and assist ventilation if necessary. Administer supplemental oxygen. Monitor arterial blood gases or oximetry, chest radiographs, and ECG and admit symptomatic patients to an intensive care setting. Use epinephrine and other beta-adrenergic medications with caution in patients with significant hydrocarbon intoxication because arrhythmias may be induced. 2. Pulmonary aspiration. Patients who remain completely asymptomatic after 4-6 hours of observation may be discharged. In contrast, if the patient is coughing on arrival, aspiration probably has occurred. Administer supplemental oxygen and treat bronchospasm and hypoxia if they occur. Do not use steroids or prophylactic antibiotics. 3. Ingestion. In the vast majority of accidental childhood ingestions, less than 5-10 mL is actually swallowed and systemic toxicity is rare. Treatment is primarily supportive. Injection. For injections into the fingertip or hand, especially those involving a high-pressure paint gun, consult with a plastic or hand surgeon immediately, as prompt wide exposure, irrigation, and debridement are often required. /Hydrocarbons/1-Octanol's production and use in perfumery, cosmetics, organic synthesis, solvent manufacture of high boiling esters, anti-foam agents and in food flavoring may result in its release to the environment through various waste streams. 1-Octanol is released to the environment as a constituent of many plants. If released to air, a vapor pressure of 0.0794 mm Hg at 25 °C indicates 1-octanol will exist solely as a vapor in the atmosphere. Vapor-phase 1-octanol 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 27 hours. Physical removal from air via precipitation has been shown to occur. 1-Octanol does not contain chromophores that absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight. If released to soil, 1-octanol is expected to have very high mobility based upon a Koc of 38. Volatilization from moist soil surfaces is expected to be an important fate process based upon a Henry's Law constant of 2.5X10-5 atm-cu m/mole. 1-Octanol is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Utilizing the Japanese MITI test, 89% of the theoretical BOD was reached in 4 weeks indicating that biodegradation is an important environmental fate process. If released into water, 1-octanol is not expected to adsorb to suspended solids and sediment based upon the Koc. Based on aqueous biodegradation screening test results, 1-octanol should biodegrade rapidly in aquatic environments. Volatilization from water surfaces is expected to be an important fate process based upon this compound's Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 43 hours and 17 days, respectively. An estimated BCF of 44 suggests the potential for bioconcentration in aquatic organisms is moderate. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions (pH 5 to 9). Occupational exposure to 1-octanol may occur through inhalation and dermal contact with this compound at workplaces where 1-octanol is produced or used. Monitoring data indicate that the general population may be exposed to 1-octanol via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with consumer products containing 1-octanol. (SRC)
Industry Uses:
Fuels and fuel additives
Intermediates
Paint additives and coating additives not described by other categories
Plasticizers
Processing aids, not otherwise listed
Processing aids, specific to petroleum production
Solvents (for cleaning and degreasing)
Solvents (which become part of product formulation or mixture)
Surface active agents
Viscosity adjustors
Consumer Uses:
Agricultural products (non-pesticidal)
Air care products
Building/construction materials - wood and engineered wood products
Fabric, textile, and leather products not covered elsewhere
Lubricants and greases
Metal products not covered elsewhere
Non-TSCA use
Paints and coatings
Paper products
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