2,3-Dihydroxypropyl dodecanoate

Base Information

• Chemical Name: 2,3-Dihydroxypropyl dodecanoate
• CAS No.: 142-18-7
• Deprecated CAS: 40738-26-9,1322-88-9,152872-58-7,83382-35-8,83382-36-9,902145-13-5,902145-50-0
• Molecular Formula: C₁₅H₃₀O₄
• Molecular Weight: 274.401
• European Community (EC) Number: 205-526-6,266-944-2,248-337-4
• NSC Number: 698570
• UNII: WR963Y5QYW
• DSSTox Substance ID: DTXSID5041275
• Nikkaji Number: J53.671G
• Wikipedia: Monolaurin
• Wikidata: Q2113676
• NCI Thesaurus Code: C75644
• RXCUI: 1311693,1990422
• ChEMBL ID: CHEMBL510533
• Mol file: 142-18-7.mol

Synonyms:1-dodecylglycerol;1-O-dodecylglycerol;glycerol monolaurate;lauricidin;monododecylglycerol;monoglycerol laurate;monolaurin;rac-SN-1(3)-dodecylglycerol

Chemical Property of 2,3-Dihydroxypropyl dodecanoate

Chemical Property:

• Appearance/Colour: COA
• Vapor Pressure: 5.75E-08mmHg at 25°C
• Melting Point: 63 °C
• Refractive Index: 1.467
• Boiling Point: 397.4 °C at 760 mmHg
• Flash Point: 135.6 °C
• PSA: 66.76000
• Density: 0.997 g/cm³
• LogP: 2.80370
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 14
• Exact Mass: 274.21440943
• Heavy Atom Count: 19
• Complexity: 206

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: UVCB
• Canonical SMILES: CCCCCCCCCCCC(=O)OCC(CO)O
• Recent ClinicalTrials: Phase III Study of Monolaurin Cream Therapy for Patients With Congenital Ichthyosis

Technology Process of 2,3-Dihydroxypropyl dodecanoate

There total 44 articles about 2,3-Dihydroxypropyl dodecanoate 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: 93.0%

(2,2-dimethyl-1,3-dioxolan-4-yl)methyl dodecanoate (40630-75-9) → rac-1-monolauroylglycerol (40738-26-9,142-18-7)

Guidance literature:

With ion-exchange resin C-244; In methanol; dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/j.chemphyslip.2013.07.001

Reference yield: 90.0%

lauric acid (143-07-7) + oxiranyl-methanol (556-52-5) → rac-1-monolauroylglycerol (40738-26-9,142-18-7)

Guidance literature:

With (4-aminobutyl)silyl-MCM-41 type silica; In toluene; at 119.9 ℃; for 24h;

DOI:10.1021/jo9614001

Reference yield: 78.0%

vinyl laurate (2146-71-6) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → rac-1-monolauroylglycerol (40738-26-9,142-18-7) + 1,3-dilauroylglycerol (539-93-5)

Guidance literature:

lipase from Candida Antarctica type B, immobilized; at 0 ℃; for 24h; Product distribution / selectivity; Enzymatic reaction;

upstream raw materials:

Sodium laurate

3-monochloro-1,2-propanediol

potassium laurate

allyl dodecanoate

Downstream raw materials:

lauric acid

glycerol

Refernces

• 1、 Bossaert, Wim D.,De Vos, Dirk E.,Van Rhijn, Wim M.,Bullen, Joren,Grobet, Piet J.,Jacobs, Pierre A.. "Mesoporous sulfonic acids as selective heterogeneous catalysts for the synthesis of monoglycerides". . p. 156 - 164. Retrieved 1999.
• 2、 Biswas,Mukherji. "". . p. 1. Retrieved 1960.
• 3、 Anfinsen et al.. "". . p. 779. Retrieved 1964.
• 4、 Isai,Usol'tsev,Stiba. "Acid-catalyzed intra- and intermolecular acyl exchange in mono- and diglycerides". . p. 325 - 329. Retrieved 2003.
• 5、 Yu, Hyunjong,Byun, Yerim,Chang, Pahn-Shick. "Lipase-catalyzed two-step esterification for solvent-free production of mixed lauric acid esters with antibacterial and antioxidative activities". . . Retrieved 2022.
• 6、 Nakagaki,Funasaki. "Solubility and hydrolysis rate of 1-monolaurin in aqueous solutions". . p. 1310 - 1315. Retrieved 1970.
• 7、 Freitas, Larissa,Paula, Ariela V.,dos Santos, Julio C.,Zanin, Gisella M.,de Castro, Heizir F.. "Enzymatic synthesis of monoglycerides by esterification reaction using Penicillium camembertii lipase immobilized on epoxy SiO2-PVA composite". . p. 87 - 90. Retrieved 2010.
• 8、 -. "Preparation method of glycerol monolaurate". Paragraph 0052; 0057-0112. . Retrieved 2021/08/07.