化工社化工社 化学情報印刷レポート · 研究参考用
ラウリン酸
ラウリン酸 · ドデカン酸 · ラウロステアリン酸 · ドデシル酸 · ラウリン酸 ドデカン酸 · N-ドデカン酸 · ドデカン酸(ラウリン酸) · ラウリン酸標準品
識別子と物理属性
| CAS No. | 143-07-7 |
|---|---|
| 分子式 | C12H24O2 |
| 平均分子量 | 200.32 g/mol |
| 単同位体質量 | 200.17763001 g/mol |
| SMILES | CCCCCCCCCCCC(=O)O |
| InChIKey | POULHZVOKOAJMA-UHFFFAOYSA-N |
| PubChem CID | 3893 |
| ChEBI | CHEBI:30805 |
| EC No. | 205-582-1 |
| DTXSID | DTXSID5021590 |
| 現地名 | ラウリン酸 |
化学・物理的性質
| XLogP | 4.2 |
|---|---|
| 極性表面積 | 37.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 10 |
| 重原子数 | 14 |
| 形式電荷 | 0 |
| 複雑度 | 132 |
| 物質分類 | Other Classes -> Organic Acids |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| 脂質 | Lipids -> Unambiguous LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101] |
| Polymers | Plastics -> Other functions -> EmulsifierPlastics -> Polyolefin-IPolyolefin-II |
| 化粧品 | Cosmetic ingredients (Lauric Acid) -> CIR (Cosmetic Ingredient Review)SurfactantEmulsifyingCleansing |
| SpringerMaterials Properties | Boiling point |
| 香料 | Fragrance Ingredient (Lauric acid) -> IFRA transparency List |
| 農薬 | Agrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: Not approved |
| LogP（分配係数） | log Kow = 4.604.92 |
| 臭い | Characteristic, like oil of bay100.00%で。マイルドな脂肪質のココナッツベイオイル |
| 食品添加物 | FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT, LUBRICANT OR RELEASE AGENT, SURFACE-ACTIVE AGENT -> FDA Substance added to food |
| 密度 | 0.883 (USCG, 1999) - Less dense than waterwill float0.8679 g/cu cm at 50 °C0.883 g/mL at 25 °C (lit.) |
| 融点 | 44-46 °C (lit.) |
| 沸点 | 225 °C/100 mmHg (lit.) |
| 蒸気圧 | 1 mm Hg ( 121 °C) |
| 屈折率 | 1.4304 |
| FEMA | 2614 | LAURIC ACID |
| 引火点 | >230 °F |
| 貯蔵条件 | 2-8°C |
| 溶解度 | 4.81mg/l不溶性 |
| 外観・状態 | フレークの結晶性粉末 |
| pKa（酸解離定数） | pKa 4.92(H2O,t =25.0) (Uncertain) |
| 比重 | 0.883 |
| 色 | 白い |
| においのタイプ | 脂肪の多い |
| 由来生物 | plant |
| 爆発限界 | 0.6%(V) |
| 比熱容量 | Cp(crystal): 2.02 J/(g·K), at 25℃ |
| JECFA Number | 111 |
| Merck | 14,5384 |
| BRN | 1099477 |
| ヘンリー定数 | 4.5×100 mol/(m3Pa) at 25℃, Hilal et al. (2008) |
| 安定性 | 安定。可燃性。塩基、酸化剤、還元剤と相容れない。 |
| 主な用途 | 洗浄剤化粧品フレーバーそして香料食品および飲料パーソナルケア |
| 化粧品成分の機能 | 界面活性剤 - 洗浄クレンジング界面活性剤 - 乳化剤 |
| InChI | 1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14) |
| InChIKey | POULHZVOKOAJMA-UHFFFAOYSA-N |
| SMILES | CCCCCCCCCCCC(O)=O |
| LogP（分配係数） | 5 |
| CAS データベース | 143-07-7(CAS DataBase Reference) |
| NISTの化学物質情報 | Dodecanoic acid(143-07-7) |
| EPAの化学物質情報 | Lauric acid (143-07-7) |
化学的特性
Like many other fatty acids, lauric acid is inexpensive, has a long shelf-life, and is non-toxic and safe to handle. It is mainly used for the production of soaps and cosmetics. For these purposes, lauric acid is neutralized with sodium hydroxide to give sodium laurate, which is a soap. Most commonly, sodium laurate is obtained by saponification of various oils, such as coconut oil. These precursors give mixtures of sodium laurate and other soaps.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 1.5% (38 of 2566) of reports.DangerH315 (13.3%): Causes skin irritation [Warning Skin corrosion/irritation]P264, P264+P265, P280, P302+P352, P305+P351+P338, P305+P354+P338, P317, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)Aggregated GHS information provided per 2566 reports by companies from 24 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Dodecanoic acidDodecanoic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Dodecanoic 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 540/2011Status: Active Update: 19-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15262Dodecanoic acid: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - Dodecanoic acid: Human health tier I assessment |
| 火災危険 | Behavior in Fire: May cause dust explosion. (USCG, 1999) |
| 火災の可能性 | Combustible when exposed to heat or flame. |
| 健康有害性 | May be harmful by inhalation, ingestion or skin absorption. Vapor or mist is irritating to eyes, mucous membrane and upper respiratory tract. Causes eye and skin irritation. (USCG, 1999) |
| 有害性の概要 | A skin, eye, and respiratory tract irritant[CAMEO] MAK-3A (Could be carcinogenic for man but not conclusive because of insufficient data)[MAK] A mild irritant[MSDSonline] |
| FDA 要件 | Lauric 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. |
| 反応性グループ | Acids, Carboxylic |
| Special Reports | Cosmetic Ingredient ReviewFinal Report of the Cosmetic Ingredient Review Expert PanelFinal Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic AcidJune 2005. |
| EPA Safer Chemical | Chemical: Dodecanoic acid |
| FIFRA 要件 | The following inert ingredient is also eligible for inclusion in FIFRA Section 25(b) pesticide products applied to food use sites (e.g., food crops, animals used for food, etc.): lauric acid. |
| Reactivity Profile | LAURIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactionslike other acids, they often catalyze (increase the rate of) chemical reactions. This compound can react with oxidizing materials. (NTP, 1992) |
| 消火 | Fire Extinguishing Agents: Carbon dioxide, dry chemical, alcohol foam, water spray. (USCG, 1999) |
| 応急処置 | 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. |
| 暴露管理・個人防護 | 2.0 [mg/m3], inhalable fraction, (can also occur as vapor and aerosol)[German Research Foundation (DFG)] |
| 非火災時の漏出対応 | Neutralizing Agents for Acids and Caustics: Sodium bicarbonate solutionflush with water. (USCG, 1999) |
| 処分方法 | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.The following wastewater treatment technology has been investigated for lauric acid: Concentration process: Biological treatment.The following wastewater treatment technology has been investigated for lauric acid: Concentration process: Activated carbon.The following wastewater treatment technology has been investigated for lauric acid: Concentration process: Resin adsorption. |
| Preventive Measures | 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. |
| Personal Protective Equipment (PPE) | Respirator, chemical safety goggles, boots and heavy rubber gloves. (USCG, 1999) |
| 相互作用 | ...the effect of lauric acid on transdermal penetration of phenazepam /was studied/ in vivo. It was found that treatment with lauric acid 3-fold increased the maximum anticonvulsive effect of phenazepam applied in a transdermal therapeutic system in comparison with the control. Study of the pharmacokinetics of phenazepam transdermal therapeutic system showed its higher bioavailability in the presence of lauric acid (f=0.9).The effect of two fatty acids, oleic acid and lauric acid (dodecanoic acid), on the transport of the cationic drug naphazoline, neutral caffeine, and anionic sodium salicylate, across excised human skin was studied using Franz diffusion cells. Both acids increased the in vitro skin permeation of all penetrants. Oil/water partitioning data and rotating diffusion cell measurements, in the presence of the fatty acids, suggested that the enhanced flux of the cationic naphazoline could be accounted for by an increase in lipophilicity through ion pairing with the carboxylate anion of the acid. Both neutral caffeine and sodium salicylate were incapable of forming ion pairsconsequently, increases in skin permeability are also due to a disruption of the stratum corneum. This conclusion was further supported by increased transepidermal water loss, and increased in vivo skin permeation of the non ion-pairing methyl nicotinate at skin sites treated with the fatty acids.The transdermal absorption of bupranolol was studied in vitro using a model membrane and human skin samplesthe effects of oleic acid and dodecanoic acid (lauric acid) on bupranololabsorption were also evaluated. Bupranolol diffused through skin samples rapidly. The transfer of bupranolol across the model membrane was enhanced in the presence of oleic acid and dodecanoic acid. They did not, however, significantly enhance the transfer across human skin samples.Cytochromes P450IVA1 and IVA3 display 72% amino acid sequence similarity and are expressed in livers of rats treated with the hypolipidemic drug clofibrate. The catalytic activities of IVA1 and IVA3 were examined by cDNA-directed expression using vaccinia virus. cDNA-expressed IVA1 and IVA3 had relative Mrs of 51,500 and 52,000, respectively, on SDS-polyacrylamide gels. Both enzymes displayed reduced, CO-bound absorption spectra with lambda max of 452.5 nm. IVA1 and IVA3 hydroxylated lauric acid at the omega and omega-1 positions with equivalent omega/omega-1 ratios of about 12.5. IVA1 had a substrate turnover of 21/min which was about fourfold higher than that of IVA3. The omega and omega-1 hydroxylation of palmitic acid was also catalyzed by these P450s with combined turnover numbers for both metabolites of 45/min or 18/min for IVA1 and IVA3, respectively. The omega/omega-1 oxidation ratio of IVA1 for palmitate was 1.25 which was almost fourfold higher than that obtained for IVA3. These enzymes also catalyzed omega oxidation of the physiologically important eicosanoids prostaglandins E1 and F2 alpha with turnover numbers of about one-tenth those calculated for fatty acid oxidations. No omega-1 hydroxy metabolites were produced. These studies indicate that the P450 enzymes IVA1 and IVA3 are able to catalyze the oxidations of both fatty acids and prostaglandins.The influence of ciprofibrate, a potent oxyisobutyrate derivative, on several hepatic enzyme parameters was studied in five rat strains following a 14 day treatment period. Ciprofibrate dependent hepatomegaly was observed at two dose levels (2 and 20 mg/kg) in all rat strains examined. A 10 to 15-fold induction in the 12-hydroxylation of lauric acid with a less marked 1.5 to 5-fold induction of 11-hydroxylation was observed in treated animals. This dose-dependent increase in fatty acid hydroxylase activity was associated with a maximal 10-fold increase in the specific content of cytochrome p-450 IVA1 isoenzyme apoprotein, as assessed immunochemically using an ELISA technique. The activities of the cytochrome p-450 I (IA1 and IA2) and II (IIB1 and IIB2) families, as measured by ethoxyresorufin-O-deethylase and benzphetamine-N-demethylase activities respectively, were decreased on treatment. In the mitochondria, monoamine oxidase activity was significantly decreased at the higher dose level whereas alpha-glycerophosphate dehydrogenase activity was elevated. Total carnitine acetyltransferase activity (mitochondrial and peroxisomal) and peroxisomal beta-oxidation were markedly increased at both dose levels in all strains examined. Cytosolic glutathione peroxidase activity, measured using both t-butylhydroperoxide and hydrogen peroxide as substrates, was decreased on treatment to approximately 50% of the control value. In treated animals, a marked increase in mRNA levels coding for cytochrome p-450 IVA1 and the peroxisomal bifunctional protein of the fatty acid beta-oxidation spiral was observed. However, mRNA levels coding for glutathione peroxidase appeared unchanged following ciprofibrate administration, in contrast to the above-noted decrease of glutathione peroxidase enzyme activity. Taken collectively, our results have further substantiated a close association between the induction of microsomal cytochrome p-450 IVA1, peroxisomal beta-oxidation and total carnitine acetyltransferase activity in rat liver, and have performed a conceptual basis for the rationalization of the chronic toxicity of peroxisome proliferators in this species. |
| 生態毒性値 | EC50Species: Xenopus laevis (African clawed frog, embryo)Conditions: freshwater, renewal, pH 7.0-7.8Concentration: 21300 ug/L for 96 hr (20000-23000 ug/L)Effect: increased developmental changes, general (craniofacial defects, abnormal gut coiling) /> or =98% purity/LC50Concentration: 32100 ug/L for 96 hr (31000-33000 ug/L) /> or =98% purity/Species: Daphnia magna (Water flea, age <24 hr)Conditions: freshwater, staticConcentration: 16900 ug/L for 48 hr (13000-22000 ug/L)Effect: intoxication, immobilizationSpecies: Lepomis macrochirus (Bluegill)Concentration: 35000 ug/L for 96 hr (25000-50000 ug/L)For more Ecotoxicity Values (Complete) data for DODECANOIC ACID (8 total), please visit the HSDB record page. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7,600 for the free acid(SRC), determined from a log Kow of 4.60(2) and a regression-derived equation(3), indicates that undissociated dodecanoic acid is expected to be immobile in soil(SRC). The pKa of dodecanoic acid is 5.3(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 dodecanoic acid from moist soil surfaces is not expected to be an important fate process(SRC) based on the pKa. Dodecanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.6X10-5 mm Hg(6). Dodecanoic acid had a one-day theoretical BOD of 6.1% in a Warburg respirometer using activated sludge inocula(7), and a 100% TOC reduction in activated sludge within 100 hrs(8), suggesting biodegradation of dodecanoic acid an important environmental fate(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7,600 for the free acid(SRC), determined from a log Kow of 4.60(2) and a regression-derived equation(3), indicates that undissociated dodecanoic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 5.30(4) indicates dodecanoic 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), a BCF of 255 in zebrafish (Danio rerio)(7), suggests bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). Dodecanoic acid had a one-day theoretical BOD of 6.1% in a Warburg respirometer using activated sludge inocula(8), and a 100% TOC reduction in activated sludge within 100 hrs(9), suggesting biodegradation of dodecanoic acid is 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), dodecanoic acid, which has a vapor pressure of 1.6X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dodecanoic 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 27 hours(SRC), calculated from its rate constant of 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase dodecanoic acid may be removed from the air by wet or dry deposition(SRC). Dodecanoic 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). |
| 食品調査値 | Dodecanoic acid was found to be a volatile constituent of strawberries at a concn of 4.1 mg/kg and strawberry jam at a concn of 5.8 mg/kg(1). Dodecanoic acid is a constituent of mandarin oil(2) and coconut oil(3). Dodecanoic acid has been identified in mutton and beef volatiles(4). Dodecanoic acid was found in paprika oleoresin at <0.1 mg/kg(5). Dodecanoic acid was identified in raw beef using supercritical carbon dioxide extraction0.06% of the volatile fraction area was identified as dodecanoic acid(6). Dodecanoic acid was identified in roasted Chinese chestnuts (Castanea molissima)(7). |
| 毒性の概要 | 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...Lauric Acid...Safe for use in cosmetics, with qualifications |
| Average Daily Intake | Fatty acids are an important part of the normal daily diet of mammals, birds and invertebrates.Annual consumption is 23,833.33 lb. Individual consumption is 0.02019 mg/kg/day. |
| Plant Concentrations | Dodecanoic acid is a constituent of Juniperus turkestanica essential oils(1), mandarin oil(1), coconut oil, arecanut fat, and Holoptelea integrifolia seed oil(2). Dodecanoic acid was found to be a volatile constituent of strawberries at a concn of 4.1 mg/kg(3). Dodecanoic acid was found in fine particulate abrasion products from green leaves at a concn of 64.5 ug/g and from dead leaves at a concn of 91.4 ug/gsamples collected were from trees characteristic of the Los Angeles, CA area(4). |
| Effluent Concentrations | Dodecanoic acid was qualitatively identified in effluents from four Illinois Publicly Owned Treatment Works (POTWs)(1). Dodecanoic acid has been detected in wastewater effluents from the paint and ink industry at a concn of 434 ng/uL extract, the organics and plastics industry at a concn of 123,836 ng/uL extract, textile mills at a concn of 39 ng/uL extract, the soaps and detergents industry at a concn of 14,979 ng/uL extract, auto and other laundries at a concn of 61 ng/uL extract, pesticide manufacturing at a concn of 207 ng/uL extract, the pharmaceutical industry at a concn of 45 ng/uL extract, porcelain and enameling industry at a concn of 69 ng/uL extract, and the amusements and athletic goods industry at a concn of 1,096 ng/uL extract(2). Dodecanoic acid has been qualitatively identified in advanced waste treatment concentrates from Orange County, CA on February 3, 1976(3). Dodecanoic acid was found at a concn of 14 ng/L in wastewater from shale oil processing(4). Dodecanoic acid was identified in effluents and sludge being discharged into the Lake Michigan water basin(5). Wastewater effluents collected from the Los Angeles County waste treatment plant in 1980 and 1981 contained dodecanoic acid levels of 1,000 ug/L(6). Monitoring of effluents from a coal-fired power plant found dodecanoic acid at a concn of 80-800 ng/cu m in the vapor-phase and 90 ng/cu m in the particulate phase26 extracts were measured in the vapor phase and only one was measured in the particulate phase(7). Dodecanoic acid was found at a concn of 11-64 ug/L in wastewater at the Iona treatment plant in Vancouver, British Columbia(8). Dodecanoic acid was found at a maximum concn of 117 ng/L in groundwater contaminated by industrial wastes near Barcelona, Spain(9). Dodecanoic acid was identified in the emissions of a municipal waste incineration plant in Germany as having a concn of 0.94 ug/cu m(10).Charbroiling of extra-lean and regular hamburger was found to emit 10.0-33.0 mg dodecanoic acid/kg meat(1). Frying of extra-lean and regular hamburger was found to emit 2.1 mg dodecanoic acid/kg meatit was suggested that meat cooking operations comprises up to 21% of the total organic aerosol emissions in Los Angeles, CA(1). Dodecanoic acid was found in candle smoke from paraffin and beeswax at 0.37 and 0.49 mg/g of organic compounds(2). Dodecanoic acid was found in wood smoke from red maple(3), red oak(3), paper birch(3), white pine(3), hemlock(3), balsam fir(3), yellow poplar(4), white ash(4), sweet gum(4), mockernut hickory(4), loblolly pine(4), and slash pine(4). Dodecanoic acid was detected in wood smoke from pine, oak and synthetic logs at 1.85, 1.65 and 1.41 mg/kg of wood burnt(5). Dodecanoic acid was found in extract from a pine wood burning campfire at 450 ng/g(6). Dodecanoic acid was found at 1080 ug/g from heated roofing tar pot fumes(7). Dodecanoic acid was found in the fine aerosols from boilers burning number 2 distillate fuel oil at a rate of 1349.4 pg/kJ (burning at 58% capacity with 6.5% excess oxygen in stack gases) and a rate of 157.2 pg/kJ (burning at 54% capacity with 7.1% excess oxygen in stack gases)(8). Fine particle emission rates for dodecanoic acid from a natural gas-fired water heater and a natural gas-fired space heater were determined(9). A HEPA-filtered dilution air sample emission rate for dodecanoic acid was determined to be 6.9 pg/kJthe emission rate for dodecanoic acid through the first filter was determined to be 120.7 pg/kJthe emission rate for dodecanoic acid through the backup filter was 56.2 pg/kJ(9). Dodecanoic acid was found in gas and particulate matter effluents from commercial-scale meat charbroiling operations at 4,610 and 1,850 ug/kg meat cooked, respectively(10).Dodecanoic acid was emitted from motor vehicles in the Van Nuys tunnel in Los Angeles at 302.9 mg/L on Sept 21, 1993(1). Fine particulate aerosol emission rates for dodecanoic acid from noncatalyst automobiles, catalyst automobiles, and heavy-duty diesel trucks were determined to be 5.5, 41.4, and 71.5 ug/km, respectively(2). Dodecanoic acid was identified in tire wear particles, brake lining particles, and road dust particles at concns of 136.5, 12.5, and 105.3 ug/g of particle sample, respectively(3). Dodecanoic acid was emitted from medium duty diesel trucks at 58.5 ug/km(4). |
| Soil Adsorption/Mobility | The Koc of undissociated dodecanoic acid is estimated as 7,600 for the free acid(SRC), using a log Kow of 4.60(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that undissociated dodecanoic acid is expected to be immobile in soil. The pKa of dodecanoic acid is 5.3(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). |
| Natural Pollution Sources | ... occuring in many vegetable fats as the glyceride, especially in coconut oil and laurel oilDodecanoic acid is a constituent of Juniperus turkestanica essential oils, mandarin oil(1), coconut oil, arecanut fat, Holoptelea integrifolia seed oil(2), and strawberries(3). Dodecanoic acid was found in fine particulate abrasion products from green leaves at a concn of 64.5 ug/g and from dead leaves at a concn of 91.4 ug/gsamples collected were from trees characteristic of the Los Angeles, CA area(4). The compound is a carboxylic acid that is also known as a fatty acid because fatty acids were first isolated by the hydrolysis of naturally occurring fats(5). Fatty acids are widely distributed in nature as components of animal and vegetable fats(6) including lipids such as oils and fats, waxes, sterol esters and other minor compounds(5). |
| Atmospheric Concentrations | URBAN/SUBURBAN: Dodecanoic acid had an average concentration of 12.1 ng/cu m in 4 urban sites from southern CA from samples taken Sept 8-9, 1993(1). Atmospheric samples taken Dec 26-28, 1995 and Jan 4-6, 1996 in Fresno, CA had dodecanoic acid concentrations of 0.905 and 0.522 ng/cu m and samples taken in Bakersfield had 0.803 and 0.735 ng/cu m, respectively(2). The average ambient annual concn of dodecanoic acid in fine particles collected from West Los Angeles, downtown Los Angeles, Pasadena, and Rubidoux, CA in 1982 was 3.7, 5.3, 7.0, and 6.3 ng/cu m, respectively(3). Dodecanoic acid was found in Vienna, Austria at 14 ng/cu m from samples taken June 1997(4).RURAL/REMOTE: Dodecanoic acid was qualitatively identified in air samples from a 45 year old spruce forest in Germany on January 11, 1988 at a height of 1 m(1). Dodecanoic acid was found on aerosols obtained over Chacaltaya, Bolivia with a mean concn of 1.6 ng/cu m(2). The average ambient concn was reported to be 0.5-10.3 ng/cu-m for dodecanoic acid(3). Dodecanoic acid was found in 32% of samples taken near a lighthouse in Fajardo and was also detected in the open ocean off the south coast of Puerto Rico(4). Atmospheric samples taken Dec 26-28, 1995 and Jan 4-6, 1996 in Kern Wildlife Refuge, CA had 0.812 and 0.660 ng/cu m of dodecanoic acid(5). The average ambient annual concn of dodecanoic acid in fine particles collected from San Nicolas Island , CA in 1982 was 0.19 ng/cu m(6). Dodecanoic acid was found at 4.8 ng/cu m from Sonnblick Observatory, Austria in samples taken May 1997(7). Dodecanoic acid was measured in the gas form at 0.90, 0.71 and 0.31 ng/cu m and in the aerosol form at 0.40, 0.78, and 1.24 ng/cu m at 6AM to 12PM, 12PM to 6PM, and 6PM to 6AM, respectively, in samples taken July 27 to August 8, 1998 in the Pertouli area of the Agrafa Mountains, Greece(8). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ In a modified Shelanski Repeat Insult Patch Test (RIPT) of a 1% aqueous dilution of a liquid soap formulation containing 1.95% lauric acid on intact and abraded skin of the backs of 52 human subjects, no primary or cumulative skin irritation and no sensitization were observed. Approximately 0.2 mL of the preparation was applied to occlusive induction and challenge patches. A total of 12 24-hr induction patches were administered for 3 weeks, 4 times per week from Monday through Thursday. Sites were scored before application of the next patch. No patches were applied from Friday to Sunday of each week. A total of 4 24-hr challenge patches were applied to a new site on the 4th week, after a 72-hr nontreatment period, from Monday through Thursday. Of the 52 subjects who began the study, 46 subjects were present for the completion of the study./HUMAN EXPOSURE STUDIES/ ... Two laboratories conducted a direct comparison study of the acute irritation potential of three structurally related, undiluted fatty acids (octanoic acid, decanoic acid, and dodecanoic acid) in comparison to a benchmark positive control chemical (20% sodium dodecyl sulfate (SDS)). The studies were run within a 4-month period using the same commercial source of test chemicals. Test subjects were treated with each chemical under occluded patch conditions for gradually increasing exposure duration up to 4 hours. The results were then evaluated in terms of total cumulative incidence of positive responses and time response patterns. Using statistical comparisons of the proportion of the subjects with a positive irritant reaction to each substance, the rank order of irritation potential was decanoic acid > / = octanoic acid > SDS >> ... dodecanoic acid .../EPIDEMIOLOGY STUDIES/ To evaluate the relation between intake and adipose tissue composition of fatty acids and acute myocardial infarction in Portuguese men a case-control study /was conducted/. Diet was assessed using a semiquantitative food frequency questionnaire. In 49 case and 49 control subjects, adipose tissue composition was assessed by gas-liquid chromatography. SUBJECTS/SETTING: Population-basedsubjects were 297 consecutively admitted cases of first acute myocardial infarction in a tertiary care hospital who were aged>or=40 years. Three hundred ten community controls were selected by random-digit dialing. MAIN OUTCOME MEASURE: Odds ratio (OR). STATISTICAL ANALYSIS PERFORMED: Logistic regression, adjusting for age, education, family history of acute myocardial infarction, smoking, physical activity, body mass index, and energy intake. RESULTS: Total fat intake (OR 0.45, fourth quartile, P=0.02), lauric acid (OR 0.44, fourth quartile, P=0.02), palmitic acid (OR 0.58, fourth quartile, P=0.03), and oleic acid (OR 0.42, fourth quartile, P=0.03) were inversely associated with acute myocardial infarction. No significant effects were found for the remaining fatty acids. In the adipose tissue composition data, the adjusted risk estimates of acute myocardial infarction for the highest vs the lowest tertile were 0.16, 0.14, and 0.04 for lauric, oleic, and trans-fatty acids, respectively. A significant direct association was found for palmitic and linoleic acids (adjusted ORs for the highest tertile were 9.02 and 3.63, respectively). ...: Low intake of total fat and lauric acid from dairy products was associated with acute myocardial infarction. The association of polyunsaturated fatty acids with risk of acute myocardial infarction was nonsignificant after adjustment for energy intake and confounders. Recommendations on fatty acid intake should aim for both an upper and lower limit./CASE REPORTS/ A health hazard evaluation report was prepared by the National Institute for Occupational Safety and Health (NIOSH) after environmental and medical observations and examinations of 7 employees exposed to Lauric Acid. Investigators found no significant decreases in pulmonary function, but interviews with workers indicated that lauric acid exposure caused local irritation of moist body surfaces (eye, nose, throat, sweaty skin). Severe irritation was reported by 1 worker after exposure of moist occluded skin areas to lauric acid. The suggested reason for the observed irritation was the acidity of lauric acid./ALTERNATIVE and IN VITRO TESTS/ ... the highest concentrations of various fatty acids that are non-toxic to two human leukemic cell lines, Jurkat (T-lymphocyte) and Raji (B-lymphocyte) /were determined/. Toxicity was evaluated by either loss of membrane integrity and/or DNA fragmentation using flow cytometric analysis. There were no remarkable differences for the toxicity of the fatty acids between B and T cell lines. The cytotoxicity of the fatty acids was related to the carbon chain length and number of double bonds: docosahexaenoic acid=eicosapentaenoic acid=arachidonic acid=gamma-linolenic acid=stearic acid=palmitic acid > linoleic acid=palmitoleic acid > vacenic acid=lauric acid > oleic acid > elaidic acid > capric acid > butyric acid > caprylic acid=caproic acid=propionic acid. |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | OE9800000 |
| 毒性 | LD50 i.v. in mice: 131 ±5.7 mg/kg (Or, Wretlind) |
| 税関コード | 29159010 |
| 危険文句（R） | 36/38-41-36/37/38 |
| 化審法 | (2)-608 届出不要化学物質 |
| 危険表示 | Xi |
| 安全措置（S） | 37/39-26-39-36-36/39-24/25 |
| 自然発火温度 | 250 °C |
| 危険等級 | Eye Dam. 1 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 143-07-7(Hazardous Substances Data) |
用途
解説
dodecanoic acid．C12H24O2(200.31)．CH3(CH2)10COOH．グリセリドとしてやし油や月桂樹油など，種々の植物油中に含まれている．やし油の混合脂肪酸をエステル化し，減圧下で分留したのち，けん化すると得られる．無色の針状晶．融点44 ℃，沸点225 ℃(13.3 kPa)，160～165 ℃(2.66 kPa)．d540.869．n82D1.4183．水に不溶，エタノールに可溶，ベンゼン，エーテルに易溶．わずかであるが刺激性を有する．界面活性剤の原料に用いられる．[CAS 143-07-7]森北出版「化学辞典（第2版）
用途
有機合成原料(ラウリルアルコール、エステル、香料等)、機器分析等の標準。
用途
カルボン酸分析標準、有機合成原料。
用途
合成原料及び添加剤(医薬品、化粧品、界面活性剤)。
用途
可塑剤、安定剤、香料、化粧品、油剤原料
説明
Lauric acid, also known as dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain, thus falling into the medium chain fatty acids, is a white crystalline carboxylic acid with a faint odor of bay oil or soap. It has been found at high levels in coconut oil. Lauric acid induces the activation of NF-κB and the expression of COX-2, inducible nitric oxide synthase (iNOS), and IL-1α in RAW 264.7 cells when used at a concentration of 25 μM.
天然物の起源
Lauric acid, as a component of triglycerides, comprises about half of the fatty acid content in coconut oil, laurel oil, and in palm kernel oil (not to be confused with palm oil) , Otherwise it is relatively uncommon. It is also found in human breast milk ( 6.2 % of total fat), cow's milk (2.9%), and goat's milk (3.1 %).
使用
Given its foaming properties, the derivatives of lauric acid (h-dodecanoic acid) are widely used as a base in the manufacture of soaps, detergents, and lauryl alcohol. Lauric acid is a common constituent of vegetable fats, especially coconut oil and laurel oil. It may have a synergistic effect in a formula to help fight against mircoorganisms. It is a mild irritant but not a sensitizer, and some sources cite it as comedogenic.
一般的な説明
White solid with a slight odor of bay oil.
製法・合成法
調製方法
Lauric acid is a fatty carboxylic acid isolated from vegetable and animal fats or oils. For example, coconut oil and palm kernel oil both contain high proportions of lauric acid. Isolation from natural fats and oils involves hydrolysis, separation of the fatty acids, hydrogenation to convert unsaturated fatty acids to saturated acids, and finally distillation of the specific fatty acid of interest.
純化方法
Distil the acid in a vacuum. Also crystallise it from absolute EtOH, or from acetone at -25o. Alternatively, purify it via its methyl ester (b 140.0o/15mm), as described for capric acid. It has also been purified by zone melting. [cf Beilstein 1 III 2913.]