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1-Octanol

HCID 957
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Basic information

CAS
111-87-5
Standard SMILES
CCCCCCCCO
InChIKey
KBPLFHHGFOOTCA-UHFFFAOYSA-N
Molecular formula
C8H18O
Average molar mass
130.23 g/mol
Monoisotopic mass
130.13576519

Overview

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.

Names & identifiers

Preferred name
1-Octanol
IUPAC
octan-1-ol
English name
1-Octanol
Molecular formula
C8H18O
Molecular weight
130.23

Names & synonyms

1-octanolOctan-1-olN-octanol111-87-5Octyl alcoholcaprylic alcoholn-Octyl alcoholHeptyl carbinol1-HydroxyoctaneAlcohol C-8OctilinPrimary octyl alcohol
Show more names
OCTANOLcaprylicFEMA 2800CAPRYL ALCOHOL1-0ctanol
n-Octan-1-olDytol M-83Alfol 8Sipol L8Lorol 20n-Caprylic alcoholEPAL 8C8 alcohol

Database identifiers

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

Properties

Computed structural propertiesFilling in

XLogP
3
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
6
Heavy atoms
9
Formal charge
0
Complexity
43.8

Experimental & physicochemical properties

Chemical ClassesVolatile Organic Compound (VOC)
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty alcohols [FA05]
SolventsSolvents -> Alcohols (<C12)
CosmeticsViscosity controlling
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (1-Octanol) -> IFRA transparency List
Pesticides · 3 items

Acaricides, Algicides, Attractants, Bactericides, Desiccants, Elicitors, Fungicides, Herbicides, Insecticides, Molluscicides, Nematicides, Other Treatment, Plant Activators, Plant Growth Regulators, Prunings, Repellants, Rodenticides, Safeners, Soil Treatment, Synergists, Virus Inoculation

Active substance -> EU Pesticides database: Pending

Environmental transformation -> Pesticide transformation products (metabolite, successor)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

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

Hazard information

Regulatory Information · 4 items

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)

REACH registered substance: Octan-1-ol (EC: 203-917-6)

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 item

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]

Chemistry & industry

Pharmacology

Mechanism of Action · 2 items

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.

Related reactions

368 records
New reaction record
HRID 4732 reaction equation
HRID 4732As reactantuspto-grants-1988_02
HRID 5281 reaction equation
HRID 5281As reactantuspto-grants-1993_09
HRID 18912 reaction equation
HRID 18912As reactantuspto-grants-2010_06
HRID 19428 reaction equation
HRID 19428As reactantuspto-grants-2010_06
HRID 19429 reaction equation
HRID 19429As reactantuspto-grants-2010_06
HRID 21693 reaction equation
HRID 21693As reactantuspto-grants-1995_06
HRID 25353 reaction equation
HRID 25353As reactantuspto-grants-2005_02
HRID 33320 reaction equation
HRID 33320As reactantuspto-grants-2008_09
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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LogP · 4 items

log Kow = 3.00

3.00

3.0

3.0

Odor · 2 items

Fresh orange rose odor

Penetrating aromatic odor

TasteOILY, SWEET, SLIGHTLY HERBACEOUS TASTE
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Physicochemical properties

Melting point
15 °C · −15 °C(lit.)
Boiling point
196 °C · 196 °C(lit.)
Density
0.827 g/mL · 0.827 g/mL at 25 °C(lit.)
vapor density
4.5 · 4.5 (vs air)
vapor pressure
0.14 mm · 0.14 mm Hg ( 25 °C)
refractive index
20 · n20/D 1.429(lit.)
FEMA
2800 · 2800 | 1-OCTANOL
FLAVIS Number
2.006 · 02.006 | Octan-1-ol
Flash point
178 °F · 178 °F
storage temp.
30 °C · Store below +30°C.
solubility
107 g/L · water: partially soluble107g/L at 23°C
form
liquid
pka
15.27 · 15.27±0.10(Predicted)
color
10 · APHA: ≤10
Odor
Alcohol like
Relative polarity
0.537 · 0.537
Odor Threshold
0.0027 ppm · 0.0027ppm
Odor Type
waxy
biological source
synthetic
explosive limit
0.8 % · 0.8%(V)
Evaporation Rate
0.007 · 0.007
Viscosity
5.58 mm2/s · 5.58mm2/s
Water Solubility
insoluble
Thermal Conductivity
0.142 W/ · 0.142 W/(m·K) at 25 ℃
Specific Heat Capacity
2.34 J/ · Cp(liquid): 2.34 J/(g·K), at 25℃
λmax
215 nm · λ: 215 nm Amax: 1.00λ: 225 nm Amax: 0.50λ: 235 nm Amax: 0.20λ: 250 nm Amax: 0.05λ: 300-400 nm Amax: 0.01
JECFA Number
97 · 97
Merck
14 · 14,6751
BRN
1697461 · 1697461
Henry's Law Constant
3.4 · 3.4×10-1 mol/(m3Pa) at 25℃, Brockbank (2013)
Dielectric constant
10.3 · 10.3(20℃)
Stability
Stable. Flammable. Incompatible with strong oxidizing agents.
Cosmetics Ingredients Functions
PERFUMINGFRAGRANCE
InChI
1S/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3
InChIKey
KBPLFHHGFOOTCA-UHFFFAOYSA-N
SMILES
CCCCCCCCO
LogP
3.5 at · 3.5 at 23℃
Surface tension
26.02 mN/m · 26.02mN/m at 293.15K
CAS DataBase Reference
111 · 111-87-5(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
1 · 1-OCTANOL
FDA 21 CFR
175.105 · 175.105; 175.300; 177.1200;177.1390; 178.3480
EWG's Food Scores
1 · 1
FDA UNII
1779205 D · NV1779205D
NIST Chemistry Reference
1 · 1-Octanol(111-87-5)
EPA Substance Registry System
1 · 1-Octanol (111-87-5)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
319 · H319-H412
Precautionary statements
264 · P264-P273-P280-P305+P351+P338-P337+P313-P501
Hazard Codes
Xi
Risk Statements
36 · 36/38
Safety Statements
26 · 26-36/37-37/39
RIDADR
3082 · 3082
WGK Germany
1 · 1
RTECS
6550000 · RH6550000
Autoignition Temperature
523 °F · 523 °F
TSCA
TSCA listed
HazardClass
9 · 9
PackingGroup
III
HS Code
29051680 · 29051680
Storage Class
10 · 10 - Combustible liquids
Hazard Classifications
3 Eye · Aquatic Chronic 3Eye Irrit. 2
Hazardous Substances Data
111 · 111-87-5(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 2000 mg/kg
REACH Registrations
Active
FDA Requirements · 2 items

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.

Reactive GroupAlcohols and Polyols
Special Reports · 1 item

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Aliphatic Alcohols, EPA 738-R-07-004 (March 2007). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of June 2, 2015: http://www.epa.gov/pesticides/reregistration/status.htm]

FIFRA Requirements · 3 items

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.

Reactivity Profile · 1 item

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].

Chemical DangersReacts with strong oxidants.

Safety & protection

Fire Fighting · 2 items

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 items

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 items

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.

Storage Conditions · 2 items

Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Combustible liquids

Separated from strong oxidants.

Cleanup Methods · 4 items

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.

Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Do NOT let this chemical enter the environment.

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.

ANAEROBIC: 1-Octanol was completely removed and lost 75% of the starting material during 49(1) and 56(2) day anaerobic acclimated studies.

Disposal Methods · 4 items

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.

The following wastewater treatment technologies have been investigated for octanol: Concentration process; Biological treatment.

The following wastewater treatment technologies have been investigated for octanol: Concentration process: Activated carbon.

The following wastewater treatment technologies have been investigated for octanol: Concentration process: Resin adsorption.

Spillage Disposal · 1 item

Personal 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. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment.

Preventive Measures · 2 items

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.

Eye PreventionWear safety goggles.

Toxicology

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 item

... 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 items

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 items

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 items

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
Exposure RoutesThe substance can be absorbed into the body by inhalation and by ingestion.
Milk Concentrations1-Octanol was detected, not quantified, in milk purchased in stores in Australia(1).
Toxicity Summary · 2 items

IDENTIFICATION AND USE: 1-Octanol is a colorless liquid used in the determination of partition coefficients, perfumery, cosmetics, organic synthesis, solvent manufacture of high-boiling esters, antifoaming agent, and as a flavoring agent. 1-octanol is registered for pesticide 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. It has been used as experimental medication to treat tremor in patients. HUMAN EXPOSURE AND TOXICITY: In a human patch test, 1-octanol in 2% petrolatum was neither a skin irritant nor a skin sensitizer. Octanol has caused transient injury of corneal epithelium, with recovery in 48 hr. Common signs of exposure to 1-octanol are CNS: headache, muscle weakness, giddiness, ataxia, confusion, delirium, coma. Gastrointestinal: nausea, vomiting, diarrhea (odor of the alcohol in excreta). Irritation of skin, eyes, throat from vapor or liquid with cough and dyspnea. The annoying odor of 1-octanol may mask sensory irritation and prevent subjects with enhanced chemical sensitivity from concentrating on performance in a demanding task. ANIMAL STUDIES: 1-Octanol was slightly irritating to the skin of rabbits and is considered an eye irritant using the EU criteria. n-Octanol (0.55 g/kg) produced the largest decrease in body temperature. No evidence of tumors in the lung adenoma study in which mice were injected intraperitoneally with 100 and 500 mg/kg 1-octanol three times a week for 8 weeks. Studies indicate that T-type calcium channels (T-channels) in the thalamus are cellular targets for general anesthetics. The study 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. 1-Octanol inhibited native T-currents at subanesthetic concentrations with an IC(50) of approximately 4 uM. 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. In developmental studies in rats no treatment-related effects were observed in pregnant females, including frequency of resorptions, fetal weights, or skeletal/visceral malformations. 1-Octanol was negative in an Ames Salmonella assay with strains Ta 98, TA 100, TA 1535, TA 1537, and TA 1538 at concentrations ranging from 4 to 2500 ug/plate with and without metabolic activation.

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

Plant Concentrations · 2 items

1-Octanol was identified as a volatile component of earth almonds (Cyperus esculentus L.)(1), nectarines(2), litchi (Litchi chinensis Sonn)(3), Meeker raspberries (Rubus idaeus L.)(4) and kiwi fruit flowers(5). 1-Octanol comprised 13.62% of essential oil from Heracleum sibiricum L. (Apiaceae)(6). 1-Octanol emission rates from green leaf composite samples and dead leaves were 48 ug/g and 16 ug/g, respectively(7).

1-Octanol detections in plants(1).[Table#1991]

Animal Concentrations1-Octanol was detected in the alarm pheromone of bees (Apis dorsata) at 3.7%(1).
Signs and Symptoms · 4 items

Cough. Sore throat.

Dry skin.

Redness. Pain.

Burning sensation.

Regulatory information

FDA Requirements · 2 items

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 items

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.

Safety data

wgk
1
tsca
TSCA listed
rtecs
RH6550000
ridadr
3082
hs_code
29051680
Toxicity
LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 2000 mg/kg
risk_code
36/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36/37-37/39
hazard_class
9
Storage Class
10 - Combustible liquids
packing_group
III
Hazard statements
H319-H412
REACH Registrations
Active
Hazard Classifications
Aquatic Chronic 3Eye Irrit. 2
Autoignition Temperature
523 °F
Precautionary statements
P264-P273-P280-P305+P351+P338-P337+P313-P501
Hazardous Substances Data
111-87-5(Hazardous Substances Data)
Metabolism/Metabolites · 2 items

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

Uses & manufacturing

Uses · 6 items

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 items

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 items

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.

Formulations/Preparations · 5 items

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%.

For more Formulations/Preparations (Complete) data for 1-OCTANOL (14 total), please visit the HSDB record page.

Household ProductsInformation on 3 consumer products that contain Caprylic Alcohol in the following categories is provided:
Use Classification · 6 items

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

Cosmetics -> Viscosity controlling

General Manufacturing Information · 4 items

Agriculture, Forestry, Fishing and Hunting

1-Octanol: ACTIVE

The single product listed under PC code 079037, although listed as 1-octanol, is also in fact a mixture of 1-octanol and 1-decanol. The earliest registered label for use of aliphatic alcohols for tobacco sucker control included in the Agency's Pesticide Product Label System (PPLS) was issued to Uniroyal in 1964.

In industrial practice, the term octyl alcohol has been used for both 1-octanol and 2-ethylhexanol. The latter is also sometimes called isooctanol. The term capryl alcohol has been used for both 1-octanol and 2-octanol.

Applications · 4 items

Description1-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.

Uses1-Octanol is used as a precursor to prepare esters, which is used in perfumes and flavorings. It is used as food additive, anti-foaming agent and emulsifier in anti-rust emulsions. It is widely involved in chemical industry for the synthesis of ethoxylates, alkyl sulfates and ether sulfates. It is used as a solvent in paints, varnishes, waxes, and surface coatings and mainly involved in agricultural chemistry to inhibit excessive growth of tobacco plants.

General DescriptionA 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.

Preparation methods

Preparation1-Octanol may be prepared by reduction of some caprylic esters such as methyl caprylate with sodium ethoxide.

Upstream & downstream products

Upstream raw materials

Octanalgreen tea2-Amino-3-chlorobenzoic acidPROPYLENEVioletOctanoic acid1-HEPTENEHydrogenCoconut oil

Downstream products

Petroleum additiveUndecan-4-olide2-Ethylhexyl acrylateDiethyl phthalateTri-n-octylamineacrylate ternary copolymer bound disulfide platinum complex catalystBis(2-ethylhexyl) phosphateDioctyl adipateoctyl benzoate1-Bromooctanefinishing agent for polyester fiberOctanoic acidDioctyl maleate2-Ethylhexanoic acidSEBACIC ACID DI-N-OCTYL ESTERISOOCTYL NITRATEDioctyl phthalatePenetrating agentDibutyl phthalateOctyl cyanoacetateDioctyl sulfosuccinate sodium saltDispersing agent for coatingDIOCTYL ETHERDiisooctyl sebacateBis(2-ethylhexyl) phthalateTetradecanalAntioxidant and antiseptic agent T202Triphenyl phosphateDioctyl terephthalate

Additional notes

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.