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옥타노익에시드

Octanoic Acid

HCID 379
새 노트새 반응견적 요청하기
인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
124-07-2
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
현지명
옥타노익에시드
영어명
Octanoic acid
분자식
C8H16O2
분자량
144.21

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
카프릴산옥타노익에시드카프릴릭산옥탄오익산옥토산옥틸산헥실아세트산1-헵탄카르복실산N-옥탄오익산카프릴릭애씨드옥탄산OCTANEC8octanoicFEMA 2799
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
형식 전하
0
복잡도
89.3

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
Pesticides · 3건

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Approved

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

LogP · 3건

log Kow = 3.05

3.05

3.05

Odor · 3건

FAINT, FRUITY-ACID ODOR

UNPLEASANT AND IRRITATING ODOR

Slight odor

Taste · 2건

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

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)

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)

관련 반응

114건
반응 기록 만들기
HRID 26633 반응식
HRID 26633반응물로uspto-grants-1979_04
HRID 43302 반응식
HRID 43302반응물로uspto-grants-2013_09
HRID 61933 반응식
HRID 61933반응물로uspto-grants-2016_09
HRID 64713 반응식
HRID 64713반응물로uspto-grants-1986_09
HRID 65827 반응식
HRID 65827반응물로uspto-grants-1978_12
HRID 67681 반응식
HRID 67681반응물로uspto-grants-1982_08
HRID 94544 반응식
HRID 94544반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 100169 반응식
HRID 100169반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
1 / 15 페이지

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
더보기
새 노트새 반응견적 요청하기

Slightly sour taste

Slightly unpleasant rancid taste

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 4건

0.91 (USCG, 1999) - Less dense than water; will float

0.910 at 20 °C/4 °C

0.91

0.91 @ 20°C

물리화학적 성질

녹는점
16 °C · 16 °C
끓는 점
237 °C · 237 °C(lit.)
밀도
0.91 g/mL · 0.91 g/mL at 25 °C(lit.)
증기 밀도
5 · 5 (vs air)
증기압
1 mm · 1 mm Hg ( 78 °C)
굴절률
20 · n20/D 1.428(lit.)
FEMA
2799 · 2799 | OCTANOIC ACID
인화점
230 °F · >230 °F
저장 조건
20 · 20-25°C
용해도
0.68 g/L · 0.68g/L
산도 계수 (pKa)
4.89 · 4.89(at 25℃)
물리적 상태
액체
Specific Gravity
0.91 · 0.910 (20/4℃)
색상
무색~황색으로 투명함
수소이온지수(pH)
3.97 · 3.97(1 mM solution);3.45(10 mM solution);2.95(100 mM solution);
냄새
불쾌한 냄새
냄새 유형
지방이 많은
생물학적 소스
synthetic
폭발한계
1 % · 1%(V)
수용성
0.68 g/L · 0.68g/L(20℃)
비열
2.07 J/ · Cp(liquid): 2.07 J/(g·K), at 25℃
JECFA Number
99 · 99
Merck
14 · 14,1765
BRN
1747180 · 1747180
Henry's Law Constant
1.1 · 1.1×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Dielectric constant
3.2 · 3.2(18℃)
안정성
안정적인. 염기, 환원제, 산화제와 호환되지 않습니다. 가연성.
주요 응용
청소용품화장품향료 및 향음식 및 음료개인 위생 관리
화장품 원료 기능
계면활성제 - 유화제향기세척제향수계면활성제 - 세정
InChI
1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
InChIKey
WWZKQHOCKIZLMA-UHFFFAOYSA-N
SMILES
CCCCCCCC(O)=O
LogP
3.05 at · 3.05 at 20℃
NIST
Octanoic acid(124-07-2)
EPA
Octanoic acid (124-07-2)
화학적 성질 · 1건

Octanoic acid has a mildly unpleasant odor and a burning, rancid taste. It is also reported as having a faint, fruity–acid odor and slightly sour taste. As an eight-carbon compound, it is among the fatty acids considered to be of short or medium chain length.

Hazards Summary · 1건

Category of C7-C9 aliphatic aldehydes and carboxylic acids: Members and supporting chemicals demonstrate low acute toxicity by oral, dermal, and inhalation exposures; toxicity in repeated-dose studies only at relatively high levels; no evidence of reproductive toxicity, developmental toxicity, or mutagenicity; [EPA ChAMP: Hazard Characterization] Corrosive to skin; [Quick CPC] A skin, eye, and mucous membrane irritant; [HSDB] An irritant; [MSDSonline]

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.

Reactive GroupAcids, Carboxylic
Special Reports · 2건

USEPA/HPVIS; SCREENING-LEVEL HAZARD CHARACTERIZATION: C7 to C9 Aliphatic Aldehydes and Carboxylic Acids Category (August 2007) Available from http://www.epa.gov/hpvis/hazchar/Category_C7-C9%20Aliphatic%20Aldehydes%20&%20Carboxylic%20Acids_HC_August%202007.pdf as of January 16, 2008.

European Chemicals Bureau; IUCLID Dataset, Decanoic acid (CAS #334-48-5) (2000 CD-ROM edition). Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of January 21, 2008.

EPA Safer ChemicalChemical: Octanoic acid
Reactivity Profile · 1건

OCTANOIC ACID reacts exothermically to neutralize bases. Can react with active metals to form gaseous hydrogen and a metal salt. May absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Reacts with cyanide salts or solutions of cyanide salts to generate gaseous hydrogen cyanide. Reacts exothermically with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides to generate flammable and/or toxic gases. Reacts with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Reacts with carbonates and bicarbonates to generate a harmless gas (carbon dioxide) but still heat. Can be oxidized exothermically by strong oxidizing agents and reduced by strong reducing agents. A wide variety of products is possible. May initiate polymerization reactions or catalyze (increase the rate of) reactions among other materials.

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)]:
Disposal Methods · 2건

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

For containers less than 1 gallon: Do not reuse container. Wrap container and discard in the trash. (1 gal. bladder in box) Remove empty bladder from outer corrugated box. Do not reuse bladder. Wrap bladder and box and put in trash. For containers greater than 1 gallon: Pesticide Disposal: Pesticide wastes are acutely hazardous. Improper disposal of excess pesticide, spray mixture, or rinsate is a violation of Federal Law. If these wastes cannot be disposed of by use according to label instructions, contact your State Pesticide or Environmental Control Agency, or the Hazardous Waste Representative at the nearest EPA Regional Office for guidance. Container Disposal: (greater than 1 gallon): Triple rinse (or equivalent). Then offer for recycling or reconditioning, or puncture and dispose of in sanitary landfill, or incineration, or if allowed by state and local authorities, by burning. If burned, stay out of smoke. (2.5 gal. bladder in box): Remove empty bladder from outer corrugated box. Triple rinse bladder (or equivalent). Offer box and bladder for recycling or dispose of in a sanitary landfill or incineraVon, or if allowed by state and local authorities, by burning. If burned, stay out of smoke./65 Disinfecting Heavy Duty Acid Bathroom Cleaner/

Preventive Measures · 5건

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. Neutralize spilled material with crushed limestone, soda ash, or lime..

Personnel protection: Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. If contact with the material anticipated, wear appropriate chemical protective equipment.

Do not get in eyes, on skin, or on clothing. Wear protective eyewear (goggles, face shield, or safety glasses), protective clothing and rubber gloves. Wash thoroughly with soap and water after handling and before eating, drinking, chewing gum, or using tobacco. Remove and wash contaminated clothing before reuse./65 Disinfecting Heavy Duty Acid Bathroom Cleaner/

For more Preventive Measures (Complete) data for OCTANOIC ACID (6 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Allowable Tolerances · 3건

Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. (a) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Food-contact surfaces in public eating places, dairy-processing equipment, and food-processing equipment and utensils. Octanoic acid is included on this list. Limit: when ready for use, the end-use concentration is not to exceed 52 ppm.

Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. ... (b) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Dairy processing equipment, and food-processing equipment and utensils. Octanoic acid is included on this list. Limit: when ready for use, the end-use concentration is not to exceed 176 ppm.

Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. ... (c) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Food-processing equipment and utensils. Octanoic acid is included on this list. Limit: when ready for use, the end-use concentration is not to exceed 234 ppm.

Protective Action Criteria (PAC) · 3건

4.2 [mg/m3]

47 [mg/m3]

280 [mg/m3]

Personal Protective Equipment (PPE) · 2건

Full face self contained breathing apparatus, rubber boots, and heavy rubber gloves. (USCG, 1999)

Personal protection: Wear appropriate chemical protective gloves, boots and goggles.

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).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesIngestion
Milk ConcentrationsThe octanoic acid content in milk fat of cows ranges from 0.53 to 1.04% of total fatty acids, with an average octanoic acid content of 0.79% of total fatty acids(1).
Toxicity Summary · 4건

The CIR Expert Panel concluded that the following ingredients are safe in the present practices of use andconcentration described in the safety assessment when formulated to be non-irritating and non-sensitizing, which may be basedon a QRA...Caprylic Acid...

Safe for use in cosmetics, with qualifications

The existing information was reviewed by the independent Expert Panel for Fragrance Safety and supports the use of Octanoic acid as described in this fragrance ingredient safety assessment. Data show that it is not genotoxic and provide a calculated Margin of Exposure (MOE) greater than 100 for the repeated dose toxicity and reproductive toxicity endpoints. Data show that there are no safety concerns for skin sensitization under the current declared levels of use. Octanoic acid is not expected to be photoirritating/photoallergenic based on evaluation of the ultraviolet/visible (UV/Vis) spectra. The local respiratory toxicity endpoint was evaluated using the TTC for a Cramer Class I material and the exposure is below the TTC (1.4 mg/day).

It has been demonstrated that octanoic (OA) and decanoic (DA) acids compromise the glycolytic pathway and citric acid cycle functioning, increase oxygen consumption in the liver and inhibit some activities of the respiratory chain complexes and creatine kinase in rat brain (A15454, A15455). These fatty acids were also shown to induce oxidative stress in the brain (A15456). Experiments suggest that OA and DA impair brain mitochondrial energy homeostasis that could underlie at least in part the neuropathology of MCADD. (A15457)

Average Daily Intake · 2건

Fatty acids are an important part of the normal daily diet of mammals, birds and invertebrates.

Annual consumption is 12,616.67 lb. Individual consumption is 0.01069 mg/kg/day.

Ecotoxicity Excerpts · 5건

/AQUATIC SPECIES/ Cyprinus carpio (Fish, fresh water) /was/ tested /with octanoic acid at/ concentrations ranging from 32 to 560 mg/L (could only be reached using TWEEN 80) /for/ 48 hr. LC0 = 100 mg/L, LC50 = 134 mg/L, LC100 = 180 mg/L ... The results indicate that at least part of the toxicity can be explained by its pH-lowering property.

/OTHER TERRESTRIAL SPECIES/ Sinapis alba (mustard) seeds were incubated on filter paper moistened with solution of /octanoic acid/ for 7 days at 25 °C in the dark. Germination % /were/ 0 for 1000 mg/L and 500 mg/L, and 43 for 100 mg/L. /Sodium salt/

/OTHER TERRESTRIAL SPECIES/ Abnormalities of cell division were seen in palmate newt eggs (Trituris helveticus) after 1 hr immersion in 1400 mg/L (described as saturated).

/OTHER TERRESTRIAL SPECIES/ Paecilomyces sp. (fungus) /was incubated/ at 25 °C for 24 hr. No germination after exposure to octanoic acid at 500 mg/L (acetone as solvent, same concn in controls).

For more Ecotoxicity Excerpts (Complete) data for OCTANOIC ACID (8 total), please visit the HSDB record page.

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.

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
RH0175000
ridadr
UN 3265 8/PG 3
독성
LD50 orally in rats: 10,080 mg/kg (Jenner)
HS 번호
2915 90 70
risk_code
34
hazard_code
C,Xi
safety_code
26-36/39-45-36/37/39-25-27
포장분류
III
위험 등급
8
기존화학 물질
KE-26628
위험 참고 사항
Irritant
자연 발화 온도
>300 °C
Hazard Classifications
Aquatic Chronic 3Eye Dam. 1Skin Corr. 1C
스토리지 클래스
8A - Combustible corrosive hazardous materials
유해 물질 데이터
124-07-2(Hazardous Substances Data)
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.

Formulations/Preparations · 5건

Grades: Technical, 99%, FCC.

65 DISINFECTING HEAVY DUTY ACID BATHROOM CLEANER: Active Ingredient 3.05% Octanoic acid

KX-6176: Active Ingredients 7.52% Hydrogen peroxide, 0.940% Octaneperoxoic acid, 2.72% Octanoic acid

KX-6178: Active Ingredients 7.52% Hydrogen peroxide, 1.00% Octaneperoxoic acid, 2.85% Octanoic acid

For more Formulations/Preparations (Complete) data for OCTANOIC ACID (10 total), please visit the HSDB record page.

Household ProductsInformation on 10 consumer products that contain Caprylic acid in the following categories is provided:
Use Classification · 6건

EPA Safer Chemical Functional Use Classes -> Surfactants

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENTFood Additives -> ANTIFOAMING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENTFood Additives -> ANTIFOAMING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 4건

Pharmaceutical and Medicine Manufacturing

Octanoic acid: ACTIVE

NON-ALCOHOLIC BEVERAGES: 2.9 PPM; ICE CREAM, ICES, ETC: 2.0 PPM, CANDY: 13 PPM; BAKED GOODS: 18 PPM; CONDIMENTS: 12 PPM. /FROM TABLE/

MANY PROPRIETARY PREPN ARE AVAILABLE FOR TREATING DERMATOPHYTIC INFECTIONS, ESP TINEA PEDIS (ATHLETE'S FOOT). THESE INCL...ORGANIC ACIDS: ...CAPRYLIC...

응용 분야 · 4건

출처It is found naturally in the milk of various mammals, and it is a minor constituent of coconut oil and palm kernel oil. Octanoic acid has also been identified in trace amounts in beer, brandy distillate, the essential oil of fermented Russian black tea leaves and raw soybeans.

용도Octanoic acid (Caprylic acid) is an oily liquid with a slightly unpleasant rancid taste and used commercially in the production of esters used in perfumery and also in the manufacture of dyes. Octanoic acid is also a tremor-suppressing agent.

용도Octanoic acid is a flavoring agent considered to be a short or medium chain fatty acid. It occurs normally in various foods and is commercially prepared by oxidation of n-octanol or by fermentation and fractional distillation of the volatile fatty acids present. It is used in maximum levels, as served, of 0.13% for baked goods; 0.04% for cheeses; 0.005% for fats and oils, frozen dairy desserts, gelatins and puddings, meat products, and soft candy; 0.016% for snack foods; and 0.001% or less for all other food categories.

일반 설명Octanoic 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.

제조 방법

Octanoic acid is produced by fermentation and fractional distillation of the volatile fatty acids present in coconut oil.

상·하류 제품 정보

상류 원료

Limonin(SH)옥틸알데히드1-옥타놀과산화아세트산1-옥텐야자유말론산

하류 제품

Mono-caprylin glyceratefluoro surfactant FC-154옥틸알데히드N-Methyloctylamineglycerin caprylate polyoxethylene ether2,6-다이브로모-4-시아노페닐옥타노에이트알릴옥타노에이트FEMA 3222Emollient for chewing gums1-옥타놀6-Methoxy-2-naphthoic acid카프릴산에틸로우 B-12 휴먼 세룸 알부민글리세릴카프릴레이트노닐옥탄산FEMA 2080HEPTYL CAPRYLATEFEMA 2079사이클로헥산올카프릴릭/카프릭트라이글리세라이드카프릴로일 염화물FEMA 25752-Bromooctanoic acid3-Octanol메틸 카프릴레이트Nonafluoro-3,6-dioxaheptanoic acid
추가 설명 · 3건

순도시험(1) 산가 : 이 품목 0.5g을 정밀히 달아 유지류시험법 중 산가에 따라 시험할 때, 366~396이어야 한다. (2) 응고점 : 이 품목의 응고점은 8~15℃이다. (3) 납 : 이 품목 5.0g을 취하여 원자흡광광도법 또는 유도결합플라즈마발광광도법에 따라 시험할 때, 그 양은 1.0ppm 이하이어야 한다. (4) 비소 : 이 품목을 비소시험법에 따라 시험할 때, 그 양은 4.0ppm 이하이어야 한다. (5) 수은 : 이 품목을 수은시험법에 따라 시험할 때, 그 양은 1.0ppm 이하이어야 한다. (6) 요오드가 : 이 품목은 약 12.5g을 정밀히 달은 다음 미리 빙초산․시클로헥산의 혼액(1 : 1) 20mL 및 위이스시액 25mL를 넣어 둔 500mL 공전삼각플라스크에 가해주고 마개를 하고 격렬히 흔들어 준 다음 1시간 어두운 곳에 방치시킨 후 요오드칼륨시액 20mL, 끓여서 식힌 물 100mL를 가하여 과량의 요오드를 0.1N 치오황산나트륨용액으로 적정한다. 이때, 황색이 거의 없어질 때까지 계속 흔들어 주면서 일정하게 0.1N 치오황산나트륨용액을 적가한 다음 다시 전분시액을 가하여 청색이 완전히 없어질 때까지 적정을 계속한다. 종말점 가까이에서는 마개를 하여 격렬히 흔들어 준다. 따로 같은 방법으로 공시험을 행하고 다음 계산식에 따라 요오드가를 구할 때, 그 값은 2.0 이하이어야 한다.B : 공시험의 0.1N 치오황산나트륨용액의 소비량(mL)S : 본시험의 0.1N 치오황산나트륨용액의 소비량(mL) (7) 검화가 : 이 품목 2g을 정밀히 달아 250mL 플라스크에 넣고 0.5N 알콜성수산화칼륨용액 50mL를 가해주고 환류냉각기를 부착한 다음 약 30분 내지 1시간 조용히 검화시킨다. 이 액을 시험용액으로 하여 유지류시험법 중 검화가의 방법에 따라 시험하고, 다시 플라스크의 내용물이 끓을 때까지 가열하고 나타난 홍색이 없어질 때까지 적정하여 검화가를 구할 때, 그 값은 366~398이어야 한다. (8) 불검화물 : 이 품목 5g을 정밀히 달아 250mL 플라스크에 취하고 수산화칼륨 2g 및 에탄올 40mL를 가해주고 환류냉각기를 부착한 다음 조용히 1시간 가열한다. 플라스크의 내용물을 40mL, 80mL, 130mL 눈금이 표시되어 있는 분액여두(길이 30cm, 직경 3.5cm)에 옮기고 플라스크는 충분한 양의 에탄올로 씻어 분액여두에 합하여 40mL로 하고, 다시 더운물과 찬물을 사용하여 플라스크를 씻어 옮겨주고 전량을 80mL로 한다. 마지막으로 석유에테르 수 mL로 플라스크를 씻어 분액여두에 옮겨주고 식힌 다음 석유에테르 50mL를 가해주고 실온이 될 때까지 내용물을 식힌 후 마개를 하고 최소한 1분간 격렬히 진탕한 후 방치하여 두 층으로 분리시킨다. 상층액인 에테르층을 500mL 분액여두에 모은 다음 물층을 석유에테르 50mL씩으로 6번 더 추출한 다음 추출액을 처음의 추출액과 합치고 이를 10% 에탄올 25mL로 씻어 주고 물층이 페놀프탈레인시액으로 정색하지 않을 때까지 이 조작을 반복한 후 물층을 완전히 제거한다. 에테르추출액은 미리 무게를 달아둔 비이커에 옮겨주고 에테르 10mL를 사용하여 분액여두를 씻은 다음 비이커에 합해 주고 비이커의 에테르를 수욕상에서 증발건고 한 후 100℃에서 30분간 항량이 될 때까지 건조하고 데시케이타내에서 방냉한 다음 잔류물의 양을 구한다. 이어서 잔류물을 미리 페놀프탈레인시액을 지시약으로 하여 수산화나트륨시액으로 중화시킨 따뜻한 알콜 50mL에 녹이고 0.02N 수산화나트륨용액으로 엷은 홍색이 지속될 때까지 적정하고 그 소비 mL수에 5.659(mg)를 곱하여 올레인산으로서의 양을 구하고 다음 계산식에 따라 불검화물 값을 구할 때, 그 양은 0.2% 이하이어야 한다.

정의이 품목은 지방에서 얻어지는 포화지방산으로서 그 주성분은 카프릴산(C8H16O2)이다.

정의ChEBI: Octanoic acid is a straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid. It has a role as an antibacterial agent, a human metabolite and an Escherichia coli metabolite. It is a straight-chain saturated fatty acid and a medium-chain fatty acid. It is a conjugate acid of an octanoate.