143-07-7 Usage
Chemical properties
Colorless needle-like crystals. Soluble in methanol, slightly soluble in acetone and petroleum ether.
Uses
Different sources of media describe the Uses of 143-07-7 differently. You can refer to the following data:
1. 1. lauric acid Used for the preparation of alkyd resins, as well as wetting agents, detergents and pesticides
2. Used for peeling vegetables and fruits with a maximum amount of 3.0g/kg.
3. Used as defoamer; GB 2760-86 provides for the spices allowed to use; used for the preparation of other food grade additives.
4. lauric acid is widely used in the surfactant industry and can be, according to the classification of surfactants, divided into cationic, anionic, non-ionic and amphoteric type. The surfactants types of dodecanoic acid are listed in the attached table of this item. Some surfactants of the derivatives of dodecanoic acid and dodecanol are also antiseptics, such as dodecyl dimethyl benzyl ammonium chloride (geramine), dodecyl dimethyl benzyl ammonium bromide (bromo-geramine) and dodecyl dimethyl (2-phenoxyethyl) ammonium bromide (domiphen bromide). The dodecyldimethyllammonium-2,4,5-trichlorophenolate in these derivatives can be used as citrus preservative. Dodecanoic acid also has many applications in plastic additives, food additives, spices and pharmaceutical industries.
2. Intermediates of Liquid Crystals
3. 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.
4. Lauric Acid is a fatty acid obtained from coconut oil and other veg-
etable fats. it is practically insoluble in water but is soluble in alco-
hol, chloroform, and ether. it functions as a lubricant, binder, and
defoaming agent.
What Is Lauric Acid?
Lauric acid is a medium-length long-chain fatty acid, or lipid, that makes up about half of the fatty acids within coconut oil. It’s a powerful substance that is sometimes extracted from the coconut for use in developing monolaurin. Monolaurin is an antimicrobial agent that is able to fight bacteria, viruses, yeasts, and other pathogens. Because you can’t ingest lauric acid alone (it’s irritating and not found alone in nature), you’re most likely to get it in the form of coconut oil or from fresh coconuts.
Though coconut oil is being studied at a breakneck pace, much of the research doesn’t pinpoint what in the oil is responsible for its reported benefits. Because coconut oil contains much more than just lauric acid, it would be a stretch to credit it with all of the coconut oil benefits. Still, a 2015 analysis suggests that many of the benefits tied to coconut oil are directly linked to lauric acid. Among the benefits, they suggest lauric acid could aid weight loss and even protect against Alzheimer’s disease. Its effects on blood cholesterol levels still need to be clarified.
This research suggests that the benefits of lauric acid are due to how the body uses it. The majority of lauric acid is sent directly to the liver, where it’s converted to energy rather than stored as fat. When compared with other saturated fats, lauric acid contributes the least to fat storage.
Including Lauric Acid in Your Diet
Lauric acid can be taken as a supplement, but it is most commonly consumed as part of coconut oil or palm kernel oil. It is considered to be safe based on the amounts generally found in food. According to NYU Langone Medical Center, coconut and palm kernel oil contain up to 15 percent MCTs, along with a number of other fats. However, because they are still pure oil, limit your intake of MCTs to stay within the recommended 5 to 7 teaspoons of oil per day as set out by the U.S. Department of Agriculture. You can use coconut and palm kernel oil for stir-fries because both oils withstand high heat. They can also be used in baking, adding a natural richness to your food.
Toxicity
Natural fatty acids, non-toxic.
Safe for use in food products (FDA, §172.860, 2000).
LD50 12 g/kg (rat, oral).
Usage limits
FEMA (mg/kg): soft drinks 15, cold drinks 16, candy 2.4, baked food 39, pudding class 25, oil 315.
GB 2760-1996: fruit and vegetable peeling 3.0g/kg.
Medium-Chain Triglycerides
Medium-chain triglycerides, or fatty acids, such as lauric acid, are characterized by a specific chemical structure that allows your body to absorb them whole. This makes them more easily digestible--your body processes them as it would carbohydrates, and they are used as a source of direct energy. Compared to long-chain triglycerides, the type in other saturated fats, MCTs have fewer calories per serving, roughly 8.3 calories per gram rather than the standard 9 calories per gram, according to an article in "Nutrition Review."
Production methods
1. Industrial production methods can be grouped into two categories: 1) derived from the saponification or high temperature and pressure decomposition of natural vegetable oils and fats; 2) separated from the synthetic fatty acid. Japan mainly uses coconut oil and palm kernel oil as the raw materials for the preparation of lauric acid. The natural vegetable oils used to produce dodecanoic acid include coconut oil, litsea cubeba kernel oil, palm kernel oil and mountain pepper seed oil. Other plants oil, such as palm kernel oil, tea tree seed oil and camphor tree seed oil, can also service industry to produce dodecanoic acid. The residual C12 distillate from the extraction of dodecanoic acid, containing a large number of dodecenoic acid, can be hydrogenated at atmospheric pressure, without catalyst, to convert into dodecanoic acid with a yield of more than 86%.
2. Derived from the separation and purification of coconut oil and other vegetable oil.
3. Lauric acid naturally exists in coconut oil, litsea cubeba kernel oil, palm kernel oil and pepper kernel oil in the form of glyceride. It can be derived from the hydrolysis of natural oils and fats in industry. The coconut oil, water and catalyst are added into the autoclave and hydrolyzed to glycerol and fatty acid at 250 ℃ under the pressure of 5MPa. The content of dodecanoic acid is 45%~80%, and can be further distilled to obtain dodecanoic acid.
Chemical Properties
Different sources of media describe the Chemical Properties of 143-07-7 differently. You can refer to the following data:
1. 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.
2. Lauric acid occurs as a white crystalline powder with a slight odor
of bay oil.
3. white solid with a faint odour of bay oil
4. Laurie acid has a fatty odor.
5. Lauric acid has a fatty odor. It is a common constituent of most diets; large doses may produce gastrointestinal upset
Occurrence
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 %).
Definition
Different sources of media describe the Definition of 143-07-7 differently. You can refer to the following data:
1. ChEBI: A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.
2. A white
crystalline carboxylic acid, used as a plasticizer
and for making detergents and soaps.
Its glycerides occur naturally in coconut
and palm oils.
Production Methods
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.
Aroma threshold values
Aroma characteristics at 1.0%: fatty, creamy, cheeselike, candle waxy with egglike richness
Taste threshold values
Taste characteristics at 5 ppm: waxy,fatty and oily, tallowlike, creamy and dairylike with a coating mouthfeel
Synthesis Reference(s)
Tetrahedron Letters, 32, p. 5931, 1991 DOI: 10.1016/S0040-4039(00)79429-9
General Description
White solid with a slight odor of bay oil.
Air & Water Reactions
Insoluble in water.
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 Lauric acid 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. Lauric acid can react with oxidizing materials.
Health Hazard
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.
Fire Hazard
Behavior in Fire: May cause dust explosion.
Pharmaceutical Applications
pharmaceutical applications it has also been examined for use as an
enhancer for topical penetration and transdermal absorption,
rectal absorption, buccal delivery,(14) and intestinal absorption.
It is also useful for stabilizing oil-in-water emulsions.
Lauric acid has also been evaluated for use in aerosol formulations.
Biochem/physiol Actions
Substrate for CYP 4A11
Safety
Lauric acid is widely used in cosmetic preparations, in the
manufacture of food-grade additives, and in pharmaceutical
formulations. General exposure to lauric acid occurs through the
consumption of food and through dermal contact with cosmetics,
soaps, and detergent products. Lauric acid is toxic when
administered intravenously.
Occupational exposure may cause local irritation of eyes, nose,
throat, and respiratory tract, although lauric acid is considered
safe and nonirritating for use in cosmetics. No toxicological
effects were observed when lauric acid was administered to rats at
35% of the diet for 2 years. Acute exposure tests in rabbits
indicate mild irritation. After subcutaneous injection into mice,
lauric acid was shown to be noncarcinogenic.
LD50 (mouse, IV): 0.13 g/kg
LD50 (rat, oral): 12 g/kg
Synthesis
Produced from synthetic lauryl alcohol
in vitro
previous study showed that lauric acid could induce apoptosis in both caco-2 and iec-6 cells when compared to butyrate. moreover, lauric acid reduced gsh availability and generated ros in caco-2 cells. mechanistic study indicated that lauric acid reduced caco-2 and iec-6 cells in g0/g1and arrested cells in the s and g2/m phases. in addition, it was found that butyrate protected iec-6 cells from ros-induced damage, while lauric acid induced higher levels of ros when compared with butyrate [1].
in vivo
mouse in vivo study found that both epicutaneous application and intradermal injection of lauric acid could decrease the number of p. acnes colonized in mouse ears effectively, thus relieving p. acnes-induced granulomatous inflammation and ear swelling [2].
Carcinogenicity
Lauric acid was not carcinogenic
in the BALB/c:CFW mouse after repeated subcutaneous
injections. Lauric acid applied twice weekly for 20
weeks did not promote tumors in mice initiated with 9,10-
dimethyl-1,2-benzanthracene. After more extended
application (daily, 6 days/week, for 31 weeks), lauric acid
caused an increase in skin papillomas, but no histologically
malignant tumors were found. Lauric acid was not
carcinogenic in rats after exposure in the diet to 35% lauric
acid for 2 years.
storage
Lauric acid is stable at normal temperatures and should be stored in
a cool, dry place. Avoid sources of ignition and contact with
incompatible materials.
Purification Methods
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.]
Incompatibilities
Lauric acid is incompatible with strong bases, reducing agents, and
oxidizing agents.
Regulatory Status
GRAS listed. Lauric acid is listed as a food additive in the EAFUS list
compiled by the FDA. Reported in the EPA TSCA Inventory.
references
[1] fauser jk,matthews gm,cummins ag,howarth gs. induction of apoptosis by the medium-chain length fatty acid lauric acid in colon cancer cells due to induction of oxidative stress. chemotherapy.2013;59(3):214-24. [2] nakatsuji t,kao mc,fang jy,zouboulis cc,zhang l,gallo rl,huang cm. antimicrobial property of lauric acid against propionibacterium acnes: its therapeutic potential for inflammatory acne vulgaris. j invest dermatol.2009 oct;129(10):2480-8. [3] kate l. feltrin et al. acute oral administration of lauric acid reduces energy intake in healthy males. e-spen journal. 2014 april; 9 (2): e69–e75
Check Digit Verification of cas no
The CAS Registry Mumber 143-07-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 3 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 143-07:
(5*1)+(4*4)+(3*3)+(2*0)+(1*7)=37
37 % 10 = 7
So 143-07-7 is a valid CAS Registry Number.
InChI:InChI=1/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)
143-07-7Relevant articles and documents
Jalapinoside, a macrocyclic bisdesmoside from the resin glycosides of ipomea purga, as a modulator of multidrug resistance in human cancer cells
Bautista, Elihü,Fragoso-Serrano, Mabel,Pereda-Miranda, Rogelio
, p. 168 - 172 (2015)
The first macrocyclic bisdesmoside resin glycoside, jalapinoside (4), was purified by preparative-scale recycling HPLC from the MeOH-soluble extracts of Ipomoea purga roots, the officinal jalap. Purgic acid C (3), a new glycosidic acid of ipurolic acid, was identified as 3-O-β-d-quinovopyranoside, 11-O-β-d-quinovopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→3)-O-[β-d-fucopyranosyl-(1→4)]-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-β-d-quinovopyranoside (3S,11S)-dihydroxytetradecanoic acid. The acylating residues of this core were acetic, (+)-(2S)-methylbutanoic, and dodecanoic acids. The site of lactonization was defined as C-3 of the second saccharide moiety. Reversal of multidrug resistance by this noncytotoxic compound was evaluated in vinblastine-resistant human breast carcinoma cells.
Batatins III-VI, glycolipid ester-type dimers from Ipomoea batatas
Rosas-Ramírez, Daniel,Escalante-Sánchez, Edgar,Pereda-Miranda, Rogelio
, p. 773 - 780 (2011)
Batatins III-VI (1-4), glycolipid ester-type dimers, were isolated from the tuberous roots of sweet potato (Ipomoea batatas) using recycle high performance liquid chromatography. Their structures were characterized by means of several high-resolution NMR and mass spectrometry techniques. These compounds are the first examples of ester-type dimers which consist of two units of the heterotetrasaccharide operculinic acid C. Each unit was esterified by a different amount and type of acid residues: (2S)-methylbutanoic, cinnamic, decanoic (capric) and dodecanoic (lauric) acids. Batatins III-VI (1-4) are an example of the presence of a large number of resin glycoside congeners in each morning glory species caused by partial acylation of their constitutive saccharide cores.
Characterization of a xylose containing oligosaccharide, an inhibitor of multidrug resistance in Staphylococcus aureus, from Ipomoea pes-caprae
Escobedo-Martínez, Carolina,Cruz-Morales, Sara,Fragoso-Serrano, Mabel,Mukhlesur Rahman,Gibbons, Simon,Pereda-Miranda, Rogelio
, p. 1796 - 1801 (2010)
Pescaprein XVIII (1), a type of bacterial efflux pump inhibitor, was obtained from the CHCl3-soluble resin glycosides of beach morning glory (Ipomoea pes-caprae). The glycosidation sequence for pescaproside C, the glycosidic acid core of the lipophilic macrolactone 1 containing d-xylose and l-rhamnose, was characterized by means of several NMR techniques and FAB mass spectrometry. Recycling HPLC also yielded eight non-cytotoxic bacterial resistance modifiers, the two pescapreins XIX (2) and XX (3) as well as the known murucoidin VI (4), pecapreins II (6) and III (7), and stoloniferins III (5), IX (8) and X (9), all of which contain simonic acid B as their oligosaccharide core. Compounds 1-9 were tested for in vitro antibacterial and resistance-modifying activity against strains of Staphylococcus aureus possessing multidrug resistance efflux mechanisms. All of the pescapreins potentiated the action of norfloxacin against the NorA over-expressing strain by 4-fold (8 μg/mL from 32 μg/mL) at a concentration of 25 μg/mL.
Carbon-dot-hydrogel for enzyme-mediated bacterial detection
Bhattacharya, Sagarika,Nandi, Sukhendu,Jelinek, Raz
, p. 588 - 594 (2017)
A hybrid carbon-dot (C-dot)-hydrogel matrix was constructed and employed for detection of bacteria. The transduction mechanism is novel, based upon cleavage of ester bonds within the hydrogel scaffold by bacterially-secreted esterases; the ensuing fluidization of the hydrogel resulted in aggregation of the embedded C-dots and consequent quenching of their fluorescence. We show that the C-dot-hydrogel exhibits high sensitivity and can distinguish among bacterial species through modulation of the emitted fluorescence, depending upon their esterase secretions.
Epo-C12 inhibits peroxiredoxin 1 peroxidase activity
Yoda, Tomoka,Furuta, Masateru,Tsutsumi, Tomohiko,Ikeda, Seiki,Yukizawa, Shunsuke,Arai, Satoshi,Morita, Akinori,Yamatoya, Kenji,Nakata, Kazuya,Tomoshige, Shusuke,Ohgane, Kenji,Furuyama, Yuuki,Sakaguchi, Kengo,Sugawara, Fumio,Kobayashi, Susumu,Ikekita, Masahiko,Kuramochi, Kouji
, (2021)
Epo-C12 is a synthetic derivative of epolactaene, isolated from Penicillium sp. BM 1689-P. Epo-C12 induces apoptosis in human acute lymphoblastoid leukemia BALL-1 cells. In our previous studies, seven proteins that bind to Epo-C12 were identified by a combination of pull-down experiments using biotinylated Epo-C12 (Bio-Epo-C12) and mass spectrometry. In the present study, the effect of Epo-C12 on peroxiredoxin 1 (Prx 1), one of the proteins that binds to Epo-C12, was investigated. Epo-C12 inhibited Prx 1 peroxidase activity. However, it did not suppress its chaperone activity. Binding experiments between Bio-Epo-C12 and point-mutated Prx 1s suggest that Epo-C12 binds to Cys52 and Cys83 in Prx 1. The present study revealed that Prx 1 is one of the target proteins through which Epo-C12 exerts an apoptotic effect in BALL-1 cells.
Resin glycosides from Ipomoea pes-caprae
Escobedo-Martinez, Carolina,Pereda-Miranda, Rogelio
, p. 974 - 978 (2007)
Ipomoea pes-caprae (beach morning-glory; "rinonina" for the herbal drug in Mexico) is prescribed by traditional healers to moderate "heat" in an infected kidney. The hexane-soluble extract from the aerial parts of this medicinal plant, through preparative-scale recycling HPLC, yielded six new lipophilic oligosaccharides of jalapinolic acid: pescaproside B (1) and pescapreins V-IX (2-6). The previously known pescaproside A (7), pescapreins I-IV (8-11), and stoloniferin III (12) were also identified in the analyzed material by means of HPLC comparison with authentic samples. The glycosidic acid structure for all pentasaccharides was confirmed as simonic acid B. Pescaproside B (1), an acylated glycosidic acid methyl ester, is structurally related to pescaprein III (10). Pescapreins V (2) and VI (3) are diasteroisomeric tetraglycosidic lactones of operculinic acid C. Both of these compounds contain (2S)-methylbutyric and n-dodecanoic acids as their esterifying residues. Pescapreins VII (4) and IX (6) are pentasaccharides that contain an n-decanoyl group as their esterifying fatty acid residue instead of the n-dodecanoyl found in pescapreins I (8) and IV (11). Pescaprein VIII (5) represents an isomer of pescaprein II (9) containing an n-dodecanoyl unit as the esterifying residue at position C-4 of the third rhamnose moiety and a 2-methylpropanoyl at C-2 of the second rhamnose. High-field NMR spectroscopy and FAB mass spectrometry were used to characterize all new isolated compounds.
α-Oxidative decarboxylation of fatty acids catalysed by cytochrome P450 peroxygenases yielding shorter-alkyl-chain fatty acids
Onoda, Hiroki,Shoji, Osami,Suzuki, Kazuto,Sugimoto, Hiroshi,Shiro, Yoshitsugu,Watanabe, Yoshihito
, p. 434 - 442 (2018)
Cytochrome P450 peroxygenases belonging to the CYP152 family catalyse the oxidation of fatty acids using H2O2. CYP152N1 isolated from Exiguobacterium sp. AT1b exclusively catalyses the α-selective hydroxylation of myristic acid at physiological H2O2 concentration. However, a series of shorter-alkyl-chain fatty acids such as tridecanoic acid were produced from myristic acid by increasing the concentration of H2O2 (1-10 mM). The yield of tridecanoic acid from myristic acid reached 17%. An 18O-labeled oxidant study suggested that CYP152N1 catalysed the overoxidation of α-hydroxymyristic acid to form α-ketomyristic acid, which in turn was spontaneously decomposed by H2O2 to yield tridecanoic acid. Crystal structure analysis of CYP152N1 revealed its high similarity to other CYP152 family enzymes, such as CYP152A1 and CYP152B1. MD simulations of α-hydroxymyristic acid accommodated in CYP152N1 proposed a possible pre-oxidation conformation of α-hydroxymyristic acid for the decarboxylation reaction.
A New Steroidal Alkaloid from Allium victorialis
Khan, Sadia,Fatima, Itrat,Kazmi, Mehdi Hassan,Malik, Abdul
, p. 1134 - 1137 (2015)
Allumine C (1), a new steroidal alkaloid, has been isolated from the CHCl3-soluble fraction of the whole plant of Allium victorialis L. Its structure was elucidated by chemical and spectral studies.
Aquivion Perfluorosulfonic Superacid as an Efficient Pickering Interfacial Catalyst for the Hydrolysis of Triglycerides
Shi, Hui,Fan, Zhaoyu,Hong, Bing,Pera-Titus, Marc
, p. 3363 - 3367 (2017)
Rational design of the surface properties of heterogeneous catalysts can boost the interfacial activity in biphasic reactions through the generation of Pickering emulsions. This concept, termed Pickering interfacial catalysis (PIC), has shown promising cr
Non-hydrolytic cleavage of esters with magnesium iodide in aprotic non-polar solvents
Garcia Martinez,Osio Barcinaa,Hidalgo Del Veccio,Hanack,Subramanian
, p. 5931 - 5934 (1991)
An efficacious procedure for the hydrolysis of primary, secondary and tertiary carboxylic esters with magnesium iodide in aprotic non-polar solvents, carbon disulphide and toluene, is reported.
