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Dodecanoic 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.
Dodecanoic Acid has been found at high levels in coconut oil.
Dodecanoic 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.
CAS: 143-07-7
MF: C12H24O2
MW: 200.32
EINECS: 205-582-1
Synonyms
Emery651;Dodecanoic Acid(C12:0);Lauric acid 98%;yeuguisuan;Laurosteaic acid;Lauric acid 98-101 % (acidimetric);lauric acid, pure;LAURIC ACID, 99.5+%
Dodecanoic Acid is a medium-length long-chain fatty acid, or lipid, that makes up about half of the fatty acids within coconut oil.
Dodecanoic Acid’s a powerful substance that is sometimes extracted from the coconut for use in developing monolaurin.
Dodecanoic Acid is an antimicrobial agent that is able to fight bacteria, viruses, yeasts, and other pathogens.
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 Dodecanoic Acid 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 Dodecanoic Acid could aid weight loss and even protect against Alzheimer’s disease.
Dodecanoic Acid's effects on blood cholesterol levels still need to be clarified.
This research suggests that the benefits of Dodecanoic Acid are due to how the body uses it.
The majority of Dodecanoic Acid is sent directly to the liver, where it’s converted to energy rather than stored as fat.
When compared with other saturated fats, Dodecanoic Acid contributes the least to fat storage.
Dodecanoic Acid is 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.
Dodecanoic Acid has a role as a plant metabolite, an antibacterial agent and an algal metabolite.
Dodecanoic Acid is a straight-chain saturated fatty acid and a medium-chain fatty acid.
Dodecanoic Acid is a conjugate acid of a dodecanoate.
Dodecanoic Acid derives from a hydride of a dodecane.
Dodecanoic Acid is a medium-chain fatty acid with the chemical formula C₁₂H₂₄O₂.
Dodecanoic Acid is a saturated fat that is naturally found in various plant oils and animal fats, most notably in coconut oil and palm kernel oil.
Dodecanoic Acid is known for its antimicrobial and antiviral properties, making it useful in several applications.
As part of the fatty acid class of surfactants, Dodecanoic Acid is both a versatile and effective ingredient in formulations that require cleansing, foaming, and emulsification
Dodecanoic Acid is a fatty acid that has been shown to inhibit the growth of bacteria.
Dodecanoic Acid inhibits bacterial growth by binding to the active site of the enzyme dihydrolipoamide acetyltransferase, which catalyzes the conversion of dihydrolipoamide and acetyl-CoA to succinyl-CoA and acetoacetyl-CoA.
Dodecanoic Acid also binds to dinucleotide phosphate, which is involved in regulation of phase transition temperature and biological samples.
Dodecanoic acid has also been shown to act as an active inhibitor of fatty acid synthase, an enzyme that catalyzes the synthesis of fatty acids from acetyl-coenzyme A (acetyl-CoA).
This process is essential for bacterial growth.
Dodecanoic acid has synergistic effects with other antibiotics such as ampicillin, erythromycin, and tetracycline.
Dodecanoic acid also known as Lauric acid, belongs to the class of organic compounds known as medium-chain fatty acids.
These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Dodecanoic Acid is a weakly acidic compound.
Dodecanoic Acid is a white, powdery solid with a faint odour of mild fatty coconut bay oil or soap.
Dodecanoic Acid is reacted with sodium hydroxide to generate sodium laurate, which is soap.
Dodecanoic acid has been characterized as having "a more favorable effect on total HDL cholesterol than any other fatty acid either saturated or unsaturated".
Dodecanoic Acid Chemical Properties
Melting point: 44-46 °C (lit.)
Boiling point: 225 °C/100 mmHg (lit.)
Density: 0.883 g/mL at 25 °C (lit.)
Bulk density: 490kg/m3
Vapor pressure: 1 mm Hg ( 121 °C)
Refractive index: 1.4304
FEMA: 2614 | LAURIC ACID
Fp: >230 °F
Storage temp.: 2-8°C
Solubility: 4.81mg/l
Form: Crystalline Powder of Flakes
pka: pKa 4.92(H2O,t =25.0) (Uncertain)
Specific Gravity: 0.883
Color: White
Odor: at 100.00 %. mild fatty coconut bay oil
Odor Type: fatty
Biological source: plant
Explosive limit: 0.6%(V)
Water Solubility: insoluble
λmax: 207nm(MeOH)(lit.)
JECFA Number: 111
Merck: 14,5384
BRN: 1099477
Stability: Stable. Combustible. Incompatible with bases, oxidizing agents, reducing agents.
InChIKey: POULHZVOKOAJMA-UHFFFAOYSA-N
LogP: 5
Dissociation constant: 5.3 at 20℃
CAS DataBase Reference: 143-07-7(CAS DataBase Reference)
NIST Chemistry Reference: Dodecanoic acid(143-07-7)
EPA Substance Registry System: Dodecanoic Acid (143-07-7)
Like many other fatty acids, Dodecanoic Acid is inexpensive, has a long shelf-life, and is non-toxic and safe to handle.
Dodecanoic Acid is mainly used for the production of soaps and cosmetics.
For these purposes, Dodecanoic 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.
Physical properties
Dodecanoic Acid occurs as a white crystalline powder with a slight odor of bay oil or a fatty odor.
Dodecanoic Acid is a common constituent of most diets; large doses may produce gastrointestinal upset.
Uses
1. Dodecanoic 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. Dodecanoic 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.
Dodecanoic Acid is used in Butter flavors and in certain Citrus flavor types, mainly in Lemon.
The concentration used may vasy from 2 to 40 ppm, calculated upon the finished consumer product.
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.
Dodecanoic Acid is a common constituent of vegetable fats, especially coconut oil and laurel oil.
Dodecanoic Acid may have a synergistic effect in a formula to help fight against mircoorganisms.
Dodecanoic Acid is a mild irritant but not a sensitizer, and some sources cite it as comedogenic.
Dodecanoic Acid is a fatty acid obtained from coconut oil and other veg- etable fats.
Dodecanoic Acid is practically insoluble in water but is soluble in alco- hol, chloroform, and ether.
Dodecanoic Acid functions as a lubricant, binder, and defoaming agent.
Like many other fatty acids, Dodecanoic Acid is inexpensive, has a long shelf-life, is nontoxic, and is safe to handle.
Dodecanoic Acid is used mainly for the production of soaps and cosmetics.
For these purposes, Dodecanoic Acid is reacted 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.
Dodecanoic Acid is a precursor to dilauroyl peroxide, a commercial initiator of polymerizations.
Pharmaceutical Applications
Dodecanoic Acid has also been examined for use as an enhancer for topical penetration and transdermal absorption, rectal absorption, buccal delivery,(14) and intestinal absorption.
Dodecanoic Acid is also useful for stabilizing oil-in-water emulsions.
Dodecanoic Acid has also been evaluated for use in aerosol formulations.
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. Dodecanoic Acid naturally exists in coconut oil, litsea cubeba kernel oil, palm kernel oil and pepper kernel oil in the form of glyceride.
Dodecanoic Acid 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.
Production Methods
Dodecanoic 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.
Production and reactions
Dodecanoic Acid is mainly isolated from natural sources.
Dodecanoic Acid's reactions are representative of those of similar long chain, saturated fatty acids.
Dodecanoic Acid can be converted to the symmetrical fatty ketone called laurone (O=C(C11H23)2).
Dodecanoic Acid transesterifies with vinyl acetate.
Treatment with sulfur trioxide gives the α-sulfonic acid.
Reactivity Profile
Dodecanoic Acid is a carboxylic acid.
Dodecanoic 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.
Dodecanoic 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 Dodecanoic Acids as well, but are slow if the solid acid remains dry.
Even "insoluble" Dodecanoic Acids may absorb enough water from the air and dissolve sufficiently in Dodecanoic Acid to corrode or dissolve iron, steel, and aluminum parts and containers.
Dodecanoic Acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide.
The reaction is slower for dry, solid Dodecanoic Acid.
Insoluble Dodecanoic 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 Dodecanoic Acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides.
Dodecanoic 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, Dodecanoic 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, Dodecanoic Acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
Dodecanoic Acid can react with oxidizing materials.
