基本情報
- 標準SMILES
CCCCCCCCCCCCCC(=O)O- InChIKey
TUNFSRHWOTWDNC-UHFFFAOYSA-N- 分子式
- C14H28O2
- 平均分子量
- 228.37 g/mol
- 単同位体質量
- 228.20893014
概要
Tetradecanoic acid is an oily white crystalline solid. (NTP, 1992)
名称と識別子
- 優先名称
- Myristic Acid
- IUPAC
- tetradecanoic acid
- 現地名
- ミリスチン酸
- 英語名
- Myristic acid
- 分子式
- C14H28O2
- 分子量
- 228.37
名称と別名
名称をさらに表示
データベース識別子
- CAS
32112-52-0、544-63-8- PubChem CID
- 11005
- DTXSID
DTXSID6021666- ChEMBL
CHEMBL111077- ChEBI
CHEBI:28875- UNII
- 0I3V7S25AW
- EC Number
- 208-875-2、250-924-5
- Nikkaji
- J4.411C
物性
構造計算による物性
- XLogP
- 5.3
- 極性表面積
- 37.3 Ų
- 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
- 12
- 重原子数
- 16
- 形式電荷
- 0
- 複雑度
- 155
実験および物理化学的性質
Lipids
Lipids -> Unambiguous Lipids
Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]
Cosmetics
Cosmetic ingredients (Myristic Acid) -> CIR (Cosmetic Ingredient Review)
Cleansing; Emulsifying
LogP
log Kow = 6.11
6.11
6.11
Density
0.8622 at 129 °F (NTP, 1992) - Less dense than water; will float
0.8622 at 54 °C/4 °C
0.8622 @ 54°C
物理化学的性質
- 融点
- 52 · 52-54 °C(lit.)
- 沸点
- 250 °C100 · 250 °C100 mm Hg(lit.)
- 比重(密度)
- 0.862 · 0.862
- 蒸気圧
- 0.01 hPa · <0.01 hPa (20 °C)
- FEMA
- 2764 · 2764 | MYRISTIC ACID
- 屈折率
- 60 · nD60 1.4305; nD70 1.4273
- 闪点
- 230 °F · >230 °F
- 貯蔵温度
- room temp
- 溶解性
- 1.07 mg/l · 1.07mg/l
- 酸解離定数(Pka)
- 4.78 · 4.78±0.10(Predicted)
- 外見
- フレーク、パウダー、チャンク、または結晶塊
- 色
- 白い
- 臭い (Odor)
- 100 %で。ワックス状の脂肪石鹸のようなココナッツ · 100.00%で。ワックス状の脂肪石鹸のようなココナッツ
- においのタイプ
- ワックスっぽい
- 由来生物
- synthetic
- 水溶解度
- 0.1 g/100 · <0.1 g/100 mL で 18 ºC
- 比熱容量
- 1.89 J/ · Cp(crystal): 1.89 J/(g·K), at 25℃
- JECFA Number
- 113 · 113
- Merck
- 14 · 14,6333
- BRN
- 508624 · 508624
- Henry's Law Constant
- 2 · 2.0×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- 安定性
- 安定。強酸化剤、塩基とは相容れない。
- 主な用途
- フレーバーそして香料
- 化粧品成分の機能
- 界面活性剤 - 洗浄香料不透明剤香料
- InChI
- 1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)
- InChIKey
- TUNFSRHWOTWDNC-UHFFFAOYSA-N
- SMILES
- CCCCCCCCCCCCCC(O)=O
- LogP
- 5.79 · 5.79
- CAS データベース
- 544 · 544-63-8(CAS DataBase Reference)
- NISTの化学物質情報
- Tetradecanoic acid(544-63-8)
- EPAの化学物質情報
- Myristic acid (544-63-8)
化学的性質
化学的特性ミリスチン酸化学式C14H28O2は飽和脂肪酸の一種であり自然界に広く分布していますココナッツオイルやパームオイルなどの植物油脂バターなどの動物性脂肪に多く含まれており食品化粧品工業製品の製造に広く利用されています
化学的特性Myristic acid occurs as an oily white crystalline solid with a faint, waxy, oily odor.
化学性质ミリスチン酸は常温で固体であり無色の結晶または白色の粉末状態をしています水には溶けにくいがエタノールやエーテルなどの有機溶剤には溶けやすい特性を持っていますこの物質はその独特な化学的性質と安定性から多岐にわたる用途で利用されています
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 80.5% (2188 of 2717) of all reports.
Warning
H319 (13.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Aggregated GHS information provided per 2717 reports by companies from 13 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory Information
Chemical: Tetradecanoic acid
Tetradecanoic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Tetradecanoic 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)
Restricted substance: Lead dimyristate
Myristic acid: Does not have an individual approval but may be used under an appropriate group standard
FDA Requirements
Myristic 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.
Special Reports
Cosmetic Ingredient Review; Final Report of the Cosmetic Ingredient Review Expert Panel; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid; June 2005.
European Chemicals Bureau; IUCLID Dataset, Myristic acid, pure (CAS #544-63-8) (2000 CD-ROM edition). Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of January 24, 2008.
Reactivity Profile
TETRADECANOIC 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 with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble 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 reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
安全と保護具
First Aid
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.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Disposal Methods
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.
Protective Action Criteria (PAC)
30 [mg/m3]
330 [mg/m3]
2000 [mg/m3]
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
毒性情報
Interactions
CELL GROWTH OF SACCHAROMYCES CEREVISIAE ATCC 12341 WAS INHIBITED BY THE ANTIBIOTIC CERULENIN, A SPECIFIC INHIBITOR OF FATTY ACID & STEROL SYNTHESIS, WAS REVERSED BY MYRISTIC ACID IN A 14:0 RATIO. IT PRODUCED OVER 70% REVERSION OF CELL GROWTH INHIBITION. MYRISTIC ACID TAKEN INTO THE CELLS WAS METABOLIZED & SYNTHESIZED INTO FATTY ACIDS OF A COMPOSITION CLOSELY SIMILAR TO THAT OF THE NATIVE FATTY ACIDS, & THIS WAS CONSIDERED TO BE RESPONSIBLE FOR THE RECOVERY OF CELL GROWTH.
... Reports the results of a 6 week feeding study in rats exposed to a diet that contained 50% fat as caprilic and myristic acids. This resulted in hyperlipidemia but no other effects were reported. ... Describes the results of a 90 day feeding study in rabbits that received 25 mg/kg/day of hydrogenated coconut oil (containing glycerides of lauric, capric, myristic, palmitic, and oleic acids). Rabbits exhibited hypercholesteremia, increased plasma triglycerides and fatty acids, accumulation of cholesterol in the liver and aorta, and alteration of hepatic enzyme activity.
The effect of dietary myristic acid, fed as trimyristin either mixed or interesterified with groundnut oil, on serum cholesterol levels was examined in rats. Incorporation of trimyristin in the oil resulted in marked incr in serum cholesterol levels, compared with rats fed groundnut oil only, although a direct relation between serum cholesterol & the myristic acid content of the dietary fat was not apparent. /Ttrimyristin/
... Associations between serum fatty acid composition as well as fatty acid intakes and prostate cancer risk were examined ... The cohort included 29,133 male smokers aged 50-69 years. During 5-8 years of follow-up, 246 prostate cancer cases were diagnosed. One control was selected and matched by age (1 month) for each case from the cohort subjects alive and free of prostate cancer at the time the case was diagnosed. This study included 198 case-control pairs with baseline serum sample available for both. Fatty acids of serum cholesterol esters were measured as a percentage of total fatty acids, using capillary gas chromatography. Intakes of fatty acids were assessed from a validated self-administered dietary questionnaire ... Twofold risk was found in the highest quartile of serum myristic acid compared with the lowest quartile (odds ratio, 1.93; 95% confidence interval, 1.02-3.64) ...
Ecotoxicity Values
LC50 Oryzias latipes (red killifish) 118 mg/L/96 hr; Conditions: semistatic test, renewal every 24 hr. /Sodium salt/
EC50 Methanothrix sp. (bacteria) 4.8 mmol (1096 mg)/L/24 hr; Conditions: upflow anaerobic sludge bed rector (predominant methanogen in sludge: Methanothrix), 30 °C, pH 7, intermittent stirring every 30 min for 30 sec, acetate as carbon source; Effect: inhibition of methanogenic activity (minimum inhibitory concn 2.6 mmol (594 mg)/L/24 hr). /Technical grade/
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 50,000 for the free acid(SRC), determined from a log Kow of 6.11(2) and a regression-derived equation(3), indicates that undissociated myristic acid is expected to be immobile in soil(SRC). The pKa of myristic acid is 4.90(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 myristic acid from moist soil surfaces is not expected to be an important fate process(SRC) given the pKa(4). Myristic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.4X10-6 mm Hg(6). Myristic acid reached 2% of its theoretical BOD over 5 days in a sewage inoculum(7); a half-life of 20 hours was observed for the sodium salt in Warburg tests using an unacclimated sludge inoculum at 25 °C(8).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 50,000 for the free acid(SRC), determined from a log Kow of 6.11(2) and a regression-derived equation(3), indicates that undissociated myristic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.90(4) indicates myristic 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 56(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Myristic acid reached 2% of its theoretical BOD over 5 days in a sewage inoculum(8); a half-life of 20 hours was observed for the sodium salt in Warburg tests using an unacclimated sludge inoculum at 25 °C(9).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), myristic acid, which has a vapor pressure of 1.4X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase myristic 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 23 hours(SRC), calculated from its rate constant of 1.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase myristic acid may be removed from the air by wet or dry deposition(SRC). Myristic 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
Myristic acid has been identified as a volatile flavor component of mutton and beef(1). Myristic acid was identified as a volatile constituent of blended nectarine skin and pulp(2). Aerosol emission rates of myristic acid from charbroiling hamburger were 17.1 mg/kg of meat cooked for extra lean hamburger (approx. 10.0% fat) and 87.0 mg/kg of meat cooked for regular hamburger (approx. 21% fat); frying hamburger meat led to a myristic acid emission rate of 6.2 mg/kg of meat cooked(3). Myristic acid was found in paprika oleoresin at <0.1 mg/kg(4).
Toxicity Summary
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...Myristic 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 Myristic acid as described in this fragrance ingredient safety assessment. Data for myristic acid and from read-across analog palmitic acid show that Myristic acid is not expected to be genotoxic. The repeated dose toxicity, reproductive toxicity, and local respiratory toxicity endpoints were evaluated using the Threshold of Toxicological Concern (TTC) for a Cramer Class I material, and the exposures are below the TTC for these endpoints. Data for myristic acid and for read-across analog nonionic acid show that there are no safety concerns for skin sensitization under the current declared levels of use. Myristic acid is not expected to be photoirritating/photoallergenic based on evaluation of the ultraviolet/visible (UV/Vis) spectra.
Average Daily Intake
Fatty acids are an important part of the normal daily diet of mammals, birds and invertebrates.
Annual consumption is 1400.00 lb. Individual consumption is 0.001186 mg/kg/day.
Ecotoxicity Excerpts
/AQUATIC SPECIES/ A non-photosynthetic mutant of /Euglena gracilis (algae)/ strain Z was used /in/ determination of growth /(biomass)/ at ... /5 g/L of myristic acid with/ continuous shaking /at/ 27 °C, pH 3.3. Test substance floated on surface in initial phase of growth, but insol material was consumed during growth. Previous adaptation was required for growth. Stationary phase was reached after 5 days.
/AQUATIC SPECIES/ No mortality /of Hyale plumulosa (gammarus)/ occured at saturation /of myristic acid/ at 25 + / - 2 °C, pH 8.2, salinity 25 ppt for 48 hr in a saltwater test.
/OTHER TERRESTRIAL SPECIES/ Beauveria bassiana (fungus) was incubated in complex medium at 25 °C for 24 hr with 500 mg/L myristic acid (acetone as solvent). After the addition of test substances pH was adjusted to 6.0 with NaOH. Germination of conidia were 75% for myristic acid and 71% for acetone control.
/OTHER TERRESTRIAL SPECIES/ Paecilomyces fumoso-roseus (fungus) was incubated in complex medium at 25 °C for 24 hr with 500 mg/L myristic acid (acetone as solvent). After the addition of test substances pH was adjusted to 6.0 with NaOH. Germination of conidia were 50% for myristic acid and 71% for acetone control.
/OTHER TERRESTRIAL SPECIES/ Myristic acid was included at a final concn of 2.5% (25 g/L) in a diet containing amino acids, vitamins and glucose and fed to /Pseudosarcophaga affinis (not soil dwelling arthropod)/ larvae at 23 °C. There were 1.7% mortality after 24 hr and 3.1% after 7 days. /Potassium salt/
Plant Concentrations
Myristic acid was found in fine particulate matter released (by resuspension and agitation of the leaf composites) from green and dead plant leaves, from plant species characteristic of the Los Angeles area, at concns of 147.8 and 237.4 ug/g, respectively(1). Myristic acid was identified as a volatile constituent of blended nectarine skin and pulp(2). Myristic acid was found in paprika oleoresin at <0.1 mg/kg(3).
Effluent Concentrations
Myristic acid was detected in aqueous industrial effluent extracts collected between Nov 1979-81 in the following industrial categories (concn in one effluent extract): paint and ink (17 ng/uL); printing and publishing (23 ng/uL); textile mills (4 ng/uL); electronics (5513 ng/uL); amusements and athletic goods (470 ng/uL); and publicly owned treatment works at an unknown concn(1). Myristic acid was identified in the effluent of two publicly owned treatment works (POTW) facilities located in an industrial area of NJ and a rural area of NJ at estimated concns of 5 and 69 ppb, respectively(2). Grab samples of the final effluent from the Addison and Decatur, IL POTWs, obtained in April and June 1980, respectively, were found to contain myristic acid at unreported concns(3). A sample of final effluent, 50% grab and 50% 8 hour composite, obtained from the St. Charles, IL POTW in March 1980, was found to contain myristic acid at an unreported concn(3). Myristic acid was detected in the bleaching effluent from straw pulping and in the combined mill effluent from a straw pulp mill in Denmark at unreported concns(4). Myristic acid was detected in Los Angeles County wastewater treatment plant effluent, collected between Nov 1980 and Aug 1981, at a concn of 1200 ug/L(5). Myristic acid was identified in vapor at concns of 100 to 300 ng/cu m and on particles at concns of 8 to 600 ng/g emitted during combustion of coal at the Ames power plant in Iowa(6). Wastewater from two kraft paper mills in Georgia sampled in March 1972 were found to contain approximately 0.010 and 0.020 mg/L myristic acid (identified as the methyl derivative)(7). An effluent-irrigated citrus grove near Glil-Yam, Israel was found to contain 15 ppb myristic acid at a depth of 20 m in the unsaturated soil zone(8). Myristic acid was identified in the acidic fraction of 5 to 7 day sewage and sludge composites from the Iona Island Sewage Treatment Plant, British Columbia at concns ranging from 23 to 150 ug/L(9). Myristic acid was found at a maximum concn of 109 ng/L in groundwater contaminated by industrial wastes near Barcelona, Spain(10). The mean myristic acid concn in discharged effluent waters (24 hour composite samples) from a pulp mill producing 75,000 tons of pulp annually near Kawerau, New Zealand, in Nov to Dec 1991 and Jan to Feb 1992, was 41 ppb(11). Myristic acid was detected in two effluent samples taken from a sewage treatment plant in Prestwich, North West England, at a mean concn of 4.05 ug/L(12). Myristic acid has been identified in leachate samples collected from the interior of a municipal landfill situated in Gryta, Vasteras, Sweden in May 1990, concn unknown(13).
Fine particle aerosol emission rates of myristic acid from heavy-duty diesel trucks, noncatalyst-equipped, and catalyst-equipped automobiles were 45.7, 1.7, and 11.9 ug/km, respectively(1). Myristic acid was detected in road dust particles collected from paved streets in a residential area of Pasadena, CA in May 1988 at a concn of 171.8 ug/g of particle sample; brake lining particles at a concn of 8.1 ug/g of particle sample; and tire wear particles at a concn of 634.5 ug/g of particle sample(2). Myristic acid was emitted from medium duty diesel trucks at 5.3 ug/km(3).
Fine particle emission rates for myristic acid from a natural gas-fired water heater and a natural gas-fired space heater were determined(1). A HEPA-filtered dilution air sample emission rate for myristic acid was determined to be 3.7 pg/kJ; the emission rate for myristic acid through the first filter was determined to be 59.6 pg/kJ; the emission rate for myristic acid through the backup filter was 29.9 pg/kJ(1). Myristic acid was found in candle smoke from paraffin and beeswax at 0.61 and 0.59 mg/g of organic compounds(2). Myristic 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). Myristic acid was detected in wood smoke from pine, oak and synthetic logs at 1.74, 4.89 and 2.27 mg/kg of wood burnt(5). Myristic acid was found at 0.764, 1.36 and 1.12 mg/kg of burnt pine, oak and eucalyptus wood, respectively, in the particulate phase and at 0.357 mg/kg of burnt pine in the gas phase(6). Myristic acid was found in extract from a pine wood burning campfire at 170 ng/g(7). Myristic acid was found in the fine aerosols from boilers burning number 2 distillate fuel oil at a rate of 879.8 pg/kJ (burning at 58% capacity with 6.5% excess oxygen in stack gases) and a rate of 283.8 pg/kJ (burning at 54% capacity with 7.1% excess oxygen in stack gases)(8). Myristic acid was found at 894.9 ug/g from heated roofing tar pot fumes(9). Myristic acid was found at 4040 and 17,700 ug/kg in the gas and particulate matter from charbroiling meat(10). Myristic acid was detected in the smoke from charring/burning of chitin biopolymers(11).
IN THE FATS EXTRACTED FROM TANNERY & MUNICIPAL SLUDGE, MYRISTIC ACID WAS ONE OF THE MINOR COMPONENTS IDENTIFIED.
MYRISTIC ACID WAS IDENTIFIED IN THE SLUDGE EXTRACTIONS FROM POINT EDWARD PLANT IN CANADA. THE SLUDGE INHIBITED GROWTH OF ORCHARD GRASS IN LAND DISPOSAL.
法規制情報
FDA Requirements
Myristic 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.
安全データ
- wgk
- -
- tsca
- TSCA listed
- rtecs
- QH4375000
- 毒性
- LD50 i.v. in mice: 432.6 mg/kg (Or, Wretlind)
- hs_code
- 29159080
- risk_code
- 36/37/38-38
- 化審法
- (2)-608 届出不要化学物質
- hazard_code
- Xi
- safety_code
- 24/25
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 544-63-8(Hazardous Substances Data)
化学と産業
薬理情報
Mechanism of Action
... The specific hypothesis tested was that free fatty acid association with CD36, a class B scavenger receptor, induces the activation of endothelial nitric-oxide synthase (eNOS). A human microvascular endothelial cell line and a transfected Chinese hamster ovary cell system were used to determine which free fatty acids stimulate eNOS. Surprisingly, only myristic acid, and to a lesser extent palmitic acid, stimulated eNOS. The stimulation of eNOS was dose- and time-dependent. Competition experiments with other free fatty acids and with a CD36-blocking antibody demonstrated that the effects of myristic acid on eNOS required association with CD36. Further mechanistic studies demonstrated that the effects of myristic acid on eNOS function were not dependent on PI 3-kinase, Akt kinase, or calcium. Pharmacological studies and dominant negative constructs were used to demonstrate that myristic acid/CD36 stimulation of eNOS activity was dependent on the activation of AMP kinase. These data demonstrate an unexpected link among myristic acid, CD36, AMP kinase, and eNOS activity.
Metabolism/Metabolites
IN RATS FED COCONUT OIL, MYRISTIC ACID WAS ONE OF THE PRINCIPAL FATTY ACIDS PRESENT IN HEPATIC AND ADIPOSE TISSUE TRIGLYCERIDES. ETHANOL INCR THE PROPORTIONS OF MYRISTIC ACID.
IN ADDITION TO METABOLISM BY BETA-OXIDATION, MYRISTIC ACID HAS BEEN SHOWN TO UNDERGO CHAIN ELONGATION TO PALMITIC & STEARIC ACIDS, DESATURATION TO MYRISTOLEIC ACID & INCORPORATION INTO HEPATIC NEUTRAL LIPIDS (& TO A LESSER EXTENT, PHOSPHOLIPIDS).
THE CONVERSION OF SATURATED FATTY ACIDS TO MONOUNSATURATED FATTY ACIDS BY THE 9000 X G SUPERNATANT RAT LIVER HOMOGENATE WAS LESS FOR MYRISTIC ACID THAN FOR PALMITIC ACID. THESE FATTY ACIDS PRODUCED ONLY DELTA9-MONOENOIC ACIDS OF THE SAME CHAIN LENGTH.
MYRISTATE INCORPORATED FROM (14)C-LABELED ACETATE WAS PREFERENTIALLY ESTERIFIED INTO TRIGLYCERIDE, WHEREAS THE LABELED STEARATE WAS CONVERTED INTO PHOSPHOLIPIDS IN THE ISOLATED RAT ADIPOSE CELLS.
For more Metabolism/Metabolites (Complete) data for MYRISTIC ACID (6 total), please visit the HSDB record page.
Tetradecanoic acid has known human metabolites that include 13-Hydroxytetradecanoic acid.
Absorption, Distribution and Excretion
IN NORMAL RATS, HIGHER RADIOACTIVITY WAS FOUND IN HEART, LIVER, SPLEEN & ADRENALS 2 HR AFTER ADMIN OF PALMITIC ACID THAN AFTER ADMIN OF MYRISTIC ACID. IN GRANULOMA POUCH-BEARING RATS, RADIOACTIVITY SHOWED HIGHER DISTRIBUTION IN ADRENALS & POUCH EXUDATE 2 HR AFTER PALMITIC ACID ADMIN, COMPARED TO THOSE GIVEN MYRISTIC ACID. RADIOACTIVITY IN THE POUCH WALL WAS GREATER IN RATS GIVEN MYRISTIC ACID.
Fatty acids originating from adipose tissue stores are either bound to serum albumin or remain unesterified in the blood.
Oleic, Palmitic, Myristic, and Stearic Acids are primarily transported via the lymphatic system, and Lauric Acid is transported by the lymphatic and (as a free fatty acid) portal systems.
用途と製造
Uses
CIR ingredient: Myristic Acid
Found in most animal and vegetable fats; [Merck Index] Used as a flavor and fragrance in food, soaps, shaving creams, perfumes, and cosmetics; Also used in lubricants and coatings for anodized aluminum; [HSDB]
Aluminum Producing [Category: Industry]
CHEM INT FOR NITROGEN DERIVS-EG, ALKANOLAMINE CONDENSATES
CHEM INT FOR ISOPROPYL MYRISTATE (EMOLLIENT, PLASTICIZER)
Myristic acid is used in the food industry as a flavor ingredient. It is found widely distributed in fats throughout the plant and animal kingdom, including common human foodstuffs, such as nutmeg.
U.S. Production
2023: 10,000,000 - <50,000,000 lb
(1979) 6.95X10+9 G (MIXT WITH C12 ACID)
(1981) 5.54X10+9 G (MIXT WITH C12 ACID)
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5500]
Tetradecanoic 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).
Methods of Manufacturing
Preparation from tall-oil fatty acids: Segessmann, Molnar, U.S. pat 2,481,356 (1949); from 9-ketotetradecanoic acid; by electrolysis of methyl hydrogen adipate + decanoic acid; by Maurer oxidation of myristyl alcohol; from cetanol: Selwitz, U.S. pat. 2,969,380 (1961 to Gulf).
Fractional distillation of coconut acid and other vegetable oils.
Lauric acid, broad cut (fractionation; coproduced with lauric acid, narrow cut).
From fatty acid mixture of palm seed oil.
Use Classification
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_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Cosmetics -> Cleansing; Emulsifying
General Manufacturing Information
Not Known or Reasonably Ascertainable
Tetradecanoic acid: ACTIVE
Potassium salts of fatty acids are used as insecticides, acaricides, herbicides and algaecides. They are used to control a variety of insects and mosses, algae, lichens, liverworts and other weeds, in or on many food and feed crops, ornamental flower beds, house plants, trees, shrubs, walks and driveways, and on dogs, puppies and cats. /Fatty acid salts/
Commercial products contain 91 to 93% C14 or 96 to 99% C14.
応用分野
解説ミリスチン酸,ミリスチンサン,n‐テトラデカン酸ともいう。炭素数14の直鎖飽和脂肪酸。天然油脂,蠟成分としてグリセリド,エステルの形で広く分布し,とくにヤシ科植物の油,たとえばパーム油(1%),パーム核油(14.1%)に含有される。白色板状晶,甘酸っぱい味とココナッツ様風味をもつ。グリセリンエステルとしてパーム油,パーム核油などに含まれる.小板状晶.融点54 ℃,沸点250.5 ℃(13.3 kPa),199 ℃(2.1 kPa).d5440.8622,d9040.8394.n60D1.4305.メタノール,エーテル,ベンゼン,クロロホルムに可溶.水,冷エタノールに難溶。グリセリンエステルとして広く動植物油中に含まれ,特にヤシ油中に多い。化粧品,ペイントなどに使用。
用途有機合成原料(エステル)、機器分析の標準。
説明Myristic acid, also called tetradecanoic acid , is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. A myristate is a salt or ester of myristic acid. Myristic acid is named after the nutmeg Myristica fragrans. Nutmeg butter is 75 % trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butter fat and is a minor component of many other animal fats. It is also found in spermaceti, the crystallized fraction of oil from the sperm whale. Myristic acid is also commonly added co-translationally to the penultimate, nitrogen-terminus, glycine in receptor-associated kinases to confer the membrane localisation of the enzyme. The myristic acid has a sufficiently high hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell. In this way, myristic acid acts as a lipid anchor in biomembranes. The ester isopropyl myristate is used in cosmetic and topical medicinal preparations where good absorption through the skin is desired. Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.
天然物の起源Reported found in nutmeg, palm seed, sperm whale oil, blue cheese, burley tobacco, cooked beef and chicken, fish, rum, apricot, banana, lemon and grapefruit juice, cranberry, guava, grapes, melon, papaya, raspberry, strawberry fruit and jam, cucumber, tomato, many cheeses, thyme, breads, butter, milk, lamb liver, pork, hop oil, beer, cognac, whiskies, peanut oil, cocoa, tea, coconut meat and milk, cloudberry, beans, passion fruit, mushroom, mango, starfruit, tamarind, kelp, cardamom, rice, buckwheat, watercress, malt, wort, loquat, Bourbon vanilla, lemon balm, shrimp, nectarine, crab, scallop, squid, cape gooseberry, Chinese quince, pawpaw and sweet grass oil.
一般的な説明Oily white crystalline solid.
調製方法
製造方法Prepared from the fatty acid mixture of palm seed oil.
Myristic acid occurs naturally in nutmeg butter and in most animal and vegetables fats. Synthetically, it may be prepared by electrolysis of methyl hydrogen adipate and decanoic acid or by Maurer oxidation of myristyl alcohol.
純化方法Purify the acid via the methyl ester (b 153-154o/10mm, n25 1.4350), as for capric acid. [Trachtman & Miller J Am Chem Soc 84 4828 1962.] Also purify it by zone melting. It crystallises from pet ether, and is dried in a vacuum desiccator containing shredded wax. [Beilstein 2 IV 1126.]
上流・下流製品情報
上流原料
下流製品
補足説明
定義本品は、次の化学式で表される脂肪酸である。
定義ChEBI: Tetradecanoic acid is a straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat. It has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetradecanoate.
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