Octanoic Acid

HCID 379CAS 124-07-2

기본 정보

표준 SMILES
CCCCCCCC(=O)O
InChIKey
WWZKQHOCKIZLMA-UHFFFAOYSA-N
분자식
C8H16O2
평균 분자량
144.21 g/mol
단동위원소 질량
144.11502975

개요

Octanoic acid appears as a colorless to light yellow liquid with a mild odor. Burns, but may be difficult to ignite. Corrosive to metals and tissue.

이름 및 식별자

우선 이름
Octanoic Acid
IUPAC
octanoic acid

이름 및 동의어

octanoic acidcaprylic acid124-07-2n-octanoic acidn-caprylic acidOctylic acidoctoic acidn-octylic acid1-heptanecarboxylic acidn-Octoic acidEnantic acidOctic acid
이름 더 보기
C-8 acidCaprylsaeureAcido octanoicoAcide octanoiqueKaprylsaeureHexacid 898FEMA No. 2799Acidum octanocium

데이터베이스 식별자

CAS
124-07-2
PubChem CID
379
DTXSID
DTXSID3021645
ChEMBL
CHEMBL324846
ChEBI
CHEBI:28837
UNII
OBL58JN025
EC Number
204-677-5
Nikkaji
J2.013C

물성

구조 계산 물성

XLogP
3
극성 표면적
37.3 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
6
무거운 원자 수
10

실험 및 물리화학적 성질

Chemical ClassesOther Classes -> Organic Acids
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]
Cosmetics · 2건

Cosmetic ingredients (Caprylic Acid) -> CIR (Cosmetic Ingredient Review)

Emulsifying

SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Octanoic acid) -> IFRA transparency List

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P273, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 2.4% (71 of 2978) of reports.

Danger

H302 (10.6%): Harmful if swallowed [Warning Acute toxicity, oral]

유해성 정보

Regulatory Information · 5건

Chemical: Octanoic acid

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

2008/127, Reg. (EU) 2017/195, Reg. (EU) 2020/1160, Reg. (EU) 2023/1446, Reg. (EU) 2024/1280, Reg. (EU) 2024/2221, Reg. (EU) No 540/2011

Status: Active Update: 05-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15370

Octanoic acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Octanoic acid: Environment tier I assessment
DOT LabelCorrosive
Fire HazardsThis chemical is combustible. (NTP, 1992)
Fire PotentialCombustible
Health Hazards · 1건

Harmful if swallowed, inhaled, or absorbed through skin. Material is extremely destructive to tissues of mucous membrane, and upper respiratory tract, eyes and skin. Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness or breath, headache, nausea and vomiting. (USCG, 1999)

안전 및 보호

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
First Aid · 1건

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Fire Fighting Procedures · 1건

If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. Use water spray to knock-down vapors..

Storage Conditions · 1건

Containers less than 1 gallon: Store in original container in areas inaccessible to children and persons unfamiliar with its proper use. Containers greater than 1 gallon: Do not contaminate water, food, feed by storage or disposal. ... Store this product in a cool, dry area, away from direct sunlight and heat../65 Disinfecting Heavy Duty Acid Bathroom Cleaner/

Cleanup Methods · 4건

Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Neutralize with agricultural lime (CaO), crushed limestone (CaCO3) or sodium bicarbonate (NaHCO3). Absorb bulk liquid with fly ash, cement powder, or commercial sorbents.

Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Neutralize with agricultural lime (CaO), crushed limestone (CaCO3) or sodium bicarbonate (NaHCO3). Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.

Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. Vapor knockdown water is corrosive or toxic and should be diked for containment.

ENVIRONMENTAL HAZARDS (5 gallons or greater): Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans, or other waters unless in accordance with the requirements of a National Pollutant Discharge Elimination System (NPDES) permit and permitting authority has been notified in writing prior to discharge. Do not discharge effluent containing this product to sewer systems without previously notifying the local sewage treatment plant authority. For guidance contact your State Water Board or Regional Office of the EPA./65 Disinfecting Heavy Duty Acid Bathroom Cleaner/

Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

독성 정보

Treatment · 1건

Management of acute MCADD includes rapid correction of hypoglycemia, rehydration and treatment of the underlying infection or other stress factor. Current long-term therapy includes avoidance of fasting and a high carbohydrate low-fat diet, but it does not fully prevent the crises and the neurological alterations. (A15457)

Interactions · 4건

The duration of the absorption-enhancing effect of sodium octanoate (C8), sodium hexanoate (C6) and glyceryl-l-monooctanoate (MO) on the rectal absorption of gentamicin using the hollow-type suppository was investigated in rabbits. To evaluate the duration of the absorption-enhancing effect by pretreatment (treatment of absorption enhancer before gentamicin administration), suppository I containing each absorption enhancer in the cavity was administered into the rectum. Then suppository II containing gentamicin in the cavity was administered at predetermined times 10.33, 2, 6 and 24 hr after the administration of suppository I. Plasma gentamicin levels obtained by the pretreatment with absorption enhancer were compared with those obtained by the simultaneous administration of gentamicin with absorption enhancer. The AUC and Cmax of gentamicin significantly decreased with the pretreatment of C8-16 and 24 hr, C6-12 and 6 hr or glyceryl-l-monooctanoate 16 and 24 hr before rectal gentamicin administration, as compared with the simultaneous administration of gentamicin with C8, C6 or glyceryl-l-monooctanoate. A marked decrease in the absorption-enhancing effect of C8, C6 and glyceryl-l-monooctanoate on rectal gentamicin absorption was observed by the prolongation of the period between the pretreatment of each absorption enhancer and gentamicin administration. The duration of the absorption-enhancing effect of C6 was shorter than that of C8, whereas this duration of glyceryl-l-monooctanoate was similar to that of C8. The effect of these absorption enhancers disappeared 24 hr after the pretreatment. These results suggested that the lowering of the membrane transport barrier function recovered about one day after the administration of C8 or MO.

Cytochrome oxidase activity was investigated histochemically in the choroid plexus epithelium. Intense staining for the enzyme was exclusively limited to the mitochondria. Rats treated with octanoic acid displayed extensive ultrastructural disruptions in the epithelial cells of the choroid plexus. Mitochondria were fewer in number and more disrupted compared to the control. The enzyme activity was greatly reduced. However, pretreatment with an equimolar dose of L-carnitine followed by octanoic acid injection produced little alteration of either ultrastructure or enzyme staining. This study suggests that L-carnitine supplementation may restore mitochondrial function of the choroid plexus subjected to toxic organic anions in metabolic disorders, and may be useful in the prevention of metabolic encephalopathy.

The effects of sodium caprate and sodium caprylate on transcellular permeation routes were examined in rats. The release of membrane phospholipids was significantly increased only by caprate, while protein release did not change from the control in the presence of caprate or caprylate, indicating that the extent of membrane disruption was insufficient to account for the extent of the enhanced permeation. Using brush border membrane vesicles prepared from colon, with their protein and lipid component labeled by fluorescent probes, the perturbing actions of caprate and caprylate toward the membrane were examined by fluorescence polarization. Caprate interacted with membrane protein and lipids, and caprylate mainly with protein, causing perturbation to the membrane. The release of 5(6)-carboxyfluorescein previously included in brush border membrane vesicles was increased by caprate but not by caprylate ... /Sodium caprylate/

/In the/ Escherichia coli reverse mutation assay ... octanoic acid inhibited the mutagenic activity of N-nitrosodimethylamine in E. coli bacteria and the extent to which this mutagen methylated DNA in cultured calf thymus cells.

Health Effects · 1건

Octanoic (OA) and decanoic (DA) acids are the predominant metabolites accumulating in medium-chain acyl-CoA dehydrogenase (MCAD; E.C. 1.3.99.3) deficiency (MCADD), the most common inherited defect of fatty acid oxidation. Glycine and l-carnitine bind to these fatty acids giving rise to derivatives that also accumulate in this disorder. The clinical presentation typically occurs in early childhood but can occasionally be delayed until adulthood. The major features of the disease include hypoglycemia, vomiting, lethargy and encephalopathy after fasting, infection or other metabolic stressors. (A15457)

Ecotoxicity Values · 5건

LC50 Leuciscus idus 173 mg/L/48 hr /Conditions of bioassay not specified/

LC100 Leuciscus idus 300 mg/L/48 hr /Conditions of bioassay not specified/

LC50 Brachydanio rerio 110 mg/L/96 hr /Sodium salt; conditions of bioassay not specified/

LC100 Brachydanio rerio 130 mg/L/96 hr /Sodium salt; conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for OCTANOIC ACID (20 total), please visit the HSDB record page.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,100 for the free acid(SRC), determined from a log Kow of 3.05(2) and a regression-derived equation(3), indicates that undissociated octanoic acid is expected to have low mobility in soil(SRC). The pKa of octanoic acid is 4.89(4), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of octanoic acid from moist soil is not expected to be an important fate process because the acid is in the anion form and anions do not volatilize(SRC). Octanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.71X10-3 mm Hg(6). In Warburg respirometer tests using an activated sludge seed, octanoic acid reached 9.8, 20.4, and 32.8% of its theoretical oxygen demand after 6, 12, and 24 hours incubation, respectively(7), suggesting that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,100 for the free acid(SRC), determined from a log Kow of 3.05(2) and a regression-derived equation(3), indicates that undissociated octanoic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.89(4) indicates octanoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). In Warburg respirometer tests using an activated sludge seed, octanoic acid reached 9.8, 20.4, and 32.8% of its theoretical oxygen demand after 6, 12, and 24 hours incubation, respectively(8), suggesting that biodegradation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), octanoic acid, which has a vapor pressure of 3.71X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase octanoic acid 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 1.9 days(SRC), calculated from its rate constant of 8.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Octanoic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

Food Survey Values · 1건

Octanoic acid was identified as a volatile component of raw beef(1). Octanoic acid has been identified as a volatile flavor component of mutton and beef(2). Octanoic acid was a volatile constituent detected in strawberry jam at a concn of 2.9 mg/kg(3). Octanoic acid was found in popcorn using wet extraction method at 19 ug/kg(4). Octanoic acid was found as a volatile component of raw and roasted earth-almond (Cyperus esculentus l.)(5).

규제 정보

FDA Requirements · 2건

Substance added directly to human food affirmed as generally recognized as safe (GRAS).

Caprylic acid is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.

화학 및 산업

약리 정보

Mechanism of Action · 2건

Mitochondrial uncoupling is often invoked as a mechanism underlying cellular dysfunction; however, it has not been possible to study this phenomenon directly in intact cells and tissues. In this paper ... direct evaluation of mitochondrial uncoupling in the intact myocardium using (31)P NMR magnetization transfer techniques /are reported/. Langendorff perfused rat hearts were exposed to either a known uncoupler, 2,4-dinitrophenol, or a potential uncoupler, octanoate. Both 2,4-dinitrophenol and octanoate decreased mechanical function as measured by the rate pressure product and caused an increase in the oxygen consumption rate; with 2,4-dinitrophenol this increase in oxygen consumption rate was dose-dependent. The ATP synthesis rate measured by (31)P NMR, however, was not elevated commensurately with oxygen consumption rate; instead, the P/O ratio declined. In contrast, the linear relationship between the ATP synthesis rate and rate pressure product was not altered by the uncoupling agents. These data demonstrate that 1) (31)P NMR magnetization transfer can be utilized to measure uncoupling of oxidative phosphorylation in intact organs, 2) octanoate does not induce excess ATP utilization in the intact heart, and 3) high levels of octanoate induce mitochondrial uncoupling in the intact myocardium; and this may, in part, be the cause of the toxic effects associated with fatty acid exposure. /Octanoate/

It has been shown that polyunsaturated fatty acids such as arachidonic and docosahexanoic acids but not monounsaturated and saturated long-chain fatty acids promote basal and nerve growth factor (NGF)-induced neurite extension of PC12 cells, a line derived from a rat pheochromocytoma. On the other hand, short-chain fatty acids and valproic acid (2-propylpentanoic acid) enhance the growth of neurite processes of the cells only in the presence of inducers. In this study, /investigators/ demonstrated that straight medium-chain fatty acids (MCFAs) at millimolar concentrations alone potently induced neuronal differentiation of PC12 cells. ... Nonanoic, decanoic, and dodecanoic acids also induced growth of neurite processes, but their maximal effects were less marked than that of octanoic acid. ...

Metabolism/Metabolites · 2건

Caprylic acid administered to rats is readily metabolized by the liver and many other tissues, forming carbon dioxide and two-carbon fragments, which are incorporated into long-chain fatty acids, as well as other water-soluble products.

The enzyme MCAD (medium-chain acyl-CoA dehydrogenase) is responsible for the dehydrogenation step of fatty acids with chain lengths between 6 and 12 carbons as they undergo beta-oxidation in the mitochondria. Fatty acid beta-oxidation provides energy after the body has used up its stores of glucose and glycogen. This typically occurs during periods of extended fasting or illness when caloric intake is reduced, and energy needs are increased. Beta-oxidation of long chain fatty acids produces two carbon units, acetyl-CoA and the reducing equivalents NADH and FADH2. NADH and FADH2 enter the electron transport chain and are used to make ATP. Acetyl-CoA enters the Krebs Cycle and is also used to make ATP via the electron transport chain and substrate level phosphorylation. When the supply of acetyl-CoA (coming from the beta-oxidation of fatty acids) exceeds the capacity of the Krebs Cycle to metabolize acetyl-CoA, the excess acetyl-CoA molecules are converted to ketone bodies (acetoacetate and beta-hydroxybutyrate) by HMG-CoA synthase in the liver. Ketone bodies can also be used for energy especially by the brain and heart; in fact they become the main sources of energy for those two organs after day three of starvation. (Wikipedia)

Absorption, Distribution and Excretion · 2건

Children who suffer from seizures which are not controllable by drugs have apparently been successfully treated with MCT (medium chain triglyceride) diet. The MCT diet is an emulsion containing primarily (81%) octanoic acid, but also contains 15% decanoic acid. In this study 15 children were receiving 50 to 60% of their energy requirement s from the MCT emulsion. Blood samples were analyzed for decanoic and octanoic acid levels. There was a wide variation in absolute levels, possibly due to poor patient compliance, but all patients showed low levels in the mornings, rising to high levels in the evenings. This suggested that both acids are rapidly metabolized. /Medium chain triglyceride/

To assess the disposition kinetics of selected structural analogs of valproic acid, the pharmacokinetics of valproic acid and 3 structural analogs, cyclohexanecarboxylic acid, l-methyl-l-cyclohexanecarboxylic acid (1-methylcyclohexanecarboxylic acid; and octanoic acid were examined in female rats. All 4 carboxylic acids evidenced dose-dependent disposition. A dose-related decrease in total body clearance was observed for each compound, suggesting saturable eiminination processes. The apparent volume of distribution for these compounds was, with the exception of cyclohexanecarboxylic acid, dose-dependent, indicating that binding to proteins in serum and/or tissues may be saturable. Both valproic acid and 1-methylcyclohexanecarboxylic acid exhibited enterohepatic recirculation, which appeared to be dose- and compound-dependent. Significant quantities of both valproic acid and 1-methylcyclohexanecarboxylic acid were excreted in the urine as conjugates. Octanoic acid and cyclohexanecarboxylic acid were not excreted in the urine and did not evidence enterohepatic recirculation. It was concluded that minor changes in chemical structure of low molecular weight carboxylic acids have an influence on their metabolism and disposition.

Tissue LocationsEpidermis
Cellular LocationsCytoplasm
Metabolite PathwaysBiosynthesis of unsaturated fatty acids

용도 및 제조

Uses · 6건

CIR ingredient: Caprylic Acid

Used to make dyes, drugs, perfumes, flavors, antiseptics, and fungicides; Also used in ore separations, hydraulic fluids, machining oils, flotation agents, and wood preservatives; [HSDB]

Metal Machining [Category: Heat or Machine]

For Octanoic acid (USEPA/OPP Pesticide Code:128919) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Detergent-disinfectant; bactericide; virucide; deodorizer /for use in/ Hospitals; Nursing Homes; Institutions; Schools; Restaurants, Food Service, Beverage and Food Processing Plants;Veterinary and Industrial Use. ... recommended for use in bathrooms, shower rooms and spas for disinfecting and cleaning walls, floors, tubs, showers, and other hard non-porous environmental surfaces such as bathroom fixtures, sinks, exterior surfaces of toilets, non-food contact surfaces of coolers, glazed tile, linoleum, plastic ... , chrome, glazed porcelain, stainless steel and glass. ... This product is not to be used as a terminal sterilant or high level disinfectant on any surface or instrument that ...(1) is introduced directly into the human body, either into or in contact with the bloodstream or normally sterile areas of the body, or (2) contacts intact mucous membranes but which does not ordinarily penetrate the blood barrier or otherwise enter normally sterile areas of the body. /65 Disinfecting Heavy Duty Acid Bathroom Cleaner/

Synthesis of various dyes, drugs, perfumes, antiseptics and fungicides, ore separations, synthetic flavors.

Impuritieshexanoic acid; heptanoic acid; nonanoic acid; decanoic acid; valproic acid; methyl octanoate; ethyl octanoate; methyl decanoate; undecan-2-one; 5-butyltetrahydrofuran-2-one (gamma-hydroxyoctanoic acid lactone)
U.S. Production · 5건

2023: 10,000,000 - <25,000,000 lb

(1972) GREATER THAN 4.54X10+5 G

(1975) GREATER THAN 4.54X10+5 G

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2232]

Octanoic acid is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Consumer UsesEmulsifier
Industry UsesIntermediate
Methods of Manufacturing · 4건

By saponification and subsequent distillation of coconut oil; method of purification: crystallization or rectification.

Preparation from 1-heptene; by oxidation of octanol.

C8-C10 fatty acids (fractionation; coproduced with capric acid)

By fermentation and fractional distillation of the volatile fatty acids present in coconut oil.

관련 반응

114건

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