Lauric Acid

Base Information

• Chemical Name: Lauric Acid
• CAS No.: 143-07-7
• Deprecated CAS: 203714-07-2,7632-48-6,8000-62-2,8045-27-0,7632-48-6,8045-27-0
• Molecular Formula: C12H24O2
• Molecular Weight: 200.321
• Hs Code.: 2915.90 Oral rat LD50: 12 gm/kg
• European Community (EC) Number: 205-582-1,606-539-3,616-324-6,616-778-5
• NSC Number: 5026
• UNII: 1160N9NU9U
• DSSTox Substance ID: DTXSID5021590
• Nikkaji Number: J2.548H
• Wikipedia: Lauric_acid
• Wikidata: Q422627
• NCI Thesaurus Code: C68384
• RXCUI: 1363435
• Pharos Ligand ID: KSMY3LXKBR37
• Metabolomics Workbench ID: 34
• ChEMBL ID: CHEMBL108766
• Mol file: 143-07-7.mol

Synonyms:dodecanoic acid;lauric acid;lauric acid, ammonium salt;lauric acid, barium and cadmium salt (4:1:1);lauric acid, calcium salt;lauric acid, lithium salt;lauric acid, magnesium salt;lauric acid, nickel(2+) salt;lauric acid, potassium salt;lauric acid, sodium salt;potassium laurate;sodium dodecanoate;sodium laurate

Chemical Property of Lauric Acid

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 1 mm Hg ( 121 °C)
• Melting Point: 44-46 °C
• Refractive Index: 1.4304
• Boiling Point: 296.1 °C at 760 mmHg
• PKA: pKa 4.92(H2O,t =25.0) (Uncertain)
• Flash Point: 134.1 °C
• PSA: 37.30000
• Density: 0.905 g/cm³
• LogP: 3.99190
• Storage Temp.: Store below +30°C.
• Solubility.: 4.81mg/l
• Water Solubility.: insoluble
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 10
• Exact Mass: 200.177630004
• Heavy Atom Count: 14
• Complexity: 132

Purity/Quality:

99%, ^*data from raw suppliers

Lauric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38-41-36/37/38
• Safety Statements: 37/39-26-39-36-36/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids,Other Classes -> Organic Acids
• Canonical SMILES: CCCCCCCCCCCC(=O)O
• Recent ClinicalTrials: Effect of Intragastric Administration of Fatty Acids on Generalized Reward Sensitivity
• Uses: 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. Intermediates of Liquid Crystals 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. 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.
• Description: Lauric acid is a medium-chain saturated fatty acid. 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. Lauric acid ( systematically: dodecanoic acid ), the saturated fatty acid with a 12-carbon atom chain, thus falling into the medium chain fatty acids, is a white, powdery solid with a faint odor of bay oil or soap.

Technology Process of Lauric Acid

There total 272 articles about Lauric Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

Dodecanal (112-54-9) → lauric acid (143-07-7) + lauric acid amide (1120-16-7) + undecyl cyanide (2437-25-4)

Guidance literature:

With H₂SO₄*2NH₂OH; Rh(OH)x/Al₂O₃; In water; for 9h; Heating;

DOI:10.1002/anie.200701273

Reference yield: 85.0%

thiophenol (108-98-5) + (1R,5R)-1-dodecanoyl-4-hydroxy-4-methyl-6-oxa-3-azabicyclo[3.1.0]hexan-2-one (288854-03-5) → lauric acid (143-07-7) + 3-oxo-2-phenylsulfanyltetradecanamide (1321499-06-2) + diphenyldisulfane (882-33-7)

Guidance literature:

With sodium hydrogencarbonate; In methanol; water; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.06.015

Reference yield: 56.0%

thiophenol (108-98-5) + (1R,5R)-1-dodecanoyl-4-hydroxy-4-methyl-6-oxa-3-azabicyclo[3.1.0]hexan-2-one (288854-03-5) → lauric acid (143-07-7) + 5-hydroxy-5-methyl-3-phenylsulfanyl-3-pyrrolin-2-one (1321499-09-5) + 3-oxotetradecanamide (1321499-07-3) + 3-oxo-2-phenylsulfanyltetradecanamide (1321499-06-2) + diphenyldisulfane (882-33-7)

Guidance literature:

With sodium hydrogencarbonate; In methanol; water; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.06.015

upstream raw materials:

tetrachloromethane

pentadecane-2,4-dione

diethyl ether

dilauryl peroxide

Downstream raw materials:

lauric acid tetrahydrofurfuryl ester

methyl n-dodecanoate

lauric acid-(2-ethoxy-ethyl ester)

N-(6-amino-hexyl)-lauramide

Refernces

• 1、 Rosas-Ramírez, Daniel,Escalante-Sánchez, Edgar,Pereda-Miranda, Rogelio. "Batatins III-VI, glycolipid ester-type dimers from Ipomoea batatas". . p. 773 - 780. Retrieved 2011.
• 2、 Bochet, Christian G.. "Orthogonal Photolysis of Protecting Groups". . p. 2071 - 2073. Retrieved 2001.
• 3、 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. "Epo-C12 inhibits peroxiredoxin 1 peroxidase activity". . . Retrieved 2021.
• 4、 Onoda, Hiroki,Shoji, Osami,Suzuki, Kazuto,Sugimoto, Hiroshi,Shiro, Yoshitsugu,Watanabe, Yoshihito. "α-Oxidative decarboxylation of fatty acids catalysed by cytochrome P450 peroxygenases yielding shorter-alkyl-chain fatty acids". . p. 434 - 442. Retrieved 2018.
• 5、 Herron,Pink. "-". . p. 3948,3950,Errata nach S.5040. Retrieved 1956.
• 6、 Shi, Hui,Fan, Zhaoyu,Hong, Bing,Pera-Titus, Marc. "Aquivion Perfluorosulfonic Superacid as an Efficient Pickering Interfacial Catalyst for the Hydrolysis of Triglycerides". . p. 3363 - 3367. Retrieved 2017.
• 7、 Jiang, Xingguo,Zhai, Yizhan,Chen, Junyu,Han, Yulin,Yang, Zheng,Ma, Shengming. "Iron-Catalyzed Aerobic Oxidation of Aldehydes: Single Component Catalyst and Mechanistic Studies". . p. 15 - 19. Retrieved 2018.
• 8、 Ba, Wenxia,Fu, Lin,Li, Xin,Li, Yongfei,Liu, Yuejin,Zhang, Simiao,Zhao, Jingxuan. "Hydrodeoxygenation of non-edible bio-lipids to renewable hydrocarbons over mesoporous SiO2-TiO2 supported NiMo bimetallic catalyst". . . Retrieved 2022/02/17.
• 9、 Ayinla, Zainab A.,Ademakinwa, Adedeji N.,Gross, Richard A.,Agboola, Femi K.. "Biochemical and biophysical characterisation of a small purified lipase from Rhizopus oryzae ZAC3". . . Retrieved 2021/02/16.