Undecylenic acid

Base Information

• Chemical Name: Undecylenic acid
• CAS No.: 112-38-9
• Deprecated CAS: 949900-17-8
• Molecular Formula: C11H20O2
• Molecular Weight: 184.279
• Hs Code.: 29161910
• European Community (EC) Number: 215-583-9,203-965-8,619-214-6
• NSC Number: 759153,2013
• UNII: K3D86KJ24N
• DSSTox Substance ID: DTXSID8035001
• Nikkaji Number: J5.125J
• Wikipedia: Undecylenic_acid
• Wikidata: Q420346
• NCI Thesaurus Code: C29530
• RXCUI: 10989
• Metabolomics Workbench ID: 471
• ChEMBL ID: CHEMBL1276010
• Mol file: 112-38-9.mol

Synonyms:10-undecenoic acid;Mycodermine;undecylenic acid

Chemical Property of Undecylenic acid

Chemical Property:

• Appearance/Colour: colorless or light yellow liquid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 23-25 ºC
• Refractive Index: n20/D 1.449(lit.)
• Boiling Point: 300.797 ºC at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 145.815 ºC
• PSA: 37.30000
• Density: 0.922 g/cm³
• LogP: 3.37780
• Storage Temp.: -20°C
• Solubility.: water: insoluble
• Water Solubility.: INSOLUBLE
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 184.146329876
• Heavy Atom Count: 13
• Complexity: 141

Purity/Quality:

99% ^*data from raw suppliers

10-Undecenoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-52/53-36/38
• Safety Statements: 26-61-37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C=CCCCCCCCCC(=O)O
• Description: Undecylenic acid (C11) or also called 10-undecenoic acid is an organic unsaturated fatty acid derived from castor oil by cracking. Undecylenic acid is an FDA approved active ingredient in medications for skin infections, and relieves itching, burning, and irritation. In technical applications it is used because if its antifungal properties.appearance (25°C) White or very pale yellow crystalline mass or clear colourless pale yellow liquid acid value mg KOH/g 295 - 304 saponification mg KOH/g 295 - 304 iodine value) gI2/100g 132 - 136 congealing point °C 23 - 24 Purity by GC % min. 99%
• Uses: 10-Undecenoic Acid, is used for the manufacture of pharmaceuticals, cosmetics and perfumery, including antidandruff shampoos, antimicrobial powders and as a musk in perfumes and aromas. Undecylenic acid can be used in silicon-based biosensors. Monolayers can be made on bare silicon transducer surfaces with the help of covalent bonds between silicon atom and the double bonds of undecylenic acid. The carboxylic acid groups remain available for the conjugation of biomolecules such as DNA or proteins. silicon-based biosensors natural fungicide chemical intermediate in fragrance and flavours cosmetics & personal care: highly effective natural antimicrobial and preservative properties undecylenic acids-based diols and polyols additive in cutting fluids (fungicide or as triethanolamine salt as rust inhibiting additive) used as antifoaming and surface active agent. As its sulfo – succinate derivative it is used in anti-dandruff shampoos
• Indications: Undecylenic acid, like zinc undecylenate, is very effective as an external drug for treating moderate dermatophyte infections and yeast dermatitis, but it is not effective for shingles and for candida infections. Synonyms of this drug are benzevrine, micocid, undetin, and others.
• Clinical Use: 10-Undecenoic acid (Desenex, Cruex) obtained fromthe destructive distillation of castor oil. Undecylenic acidis a viscous yellow liquid. It is almost completely insolublein water but is soluble in alcohol and most organicsolvents.Undecylenic acid is one of the better fatty acids for useas a fungicide, although cure rates are low. It can be used inconcentrations up to 10% in solutions, ointments, powders,and emulsions for topical administration. The preparationshould never be applied to mucous membranes because it isa severe irritant. Undecylenic acid has been one of theagents traditionally used for athlete’s foot (tinea pedis).Cure rates are low, however.

Technology Process of Undecylenic acid

There total 60 articles about Undecylenic 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: 100.0%

Methyl 10-undecenoate (111-81-9) → 10-undecenoic acid (112-38-9)

Guidance literature:

Methyl 10-undecenoate; With water; sodium hydroxide; Reflux;

With hydrogenchloride; In water;

DOI:10.1002/adsc.201000917

Reference yield: 98.0%

10-Undecen-1-ol (112-43-6) → 10-undecenoic acid (112-38-9)

Guidance literature:

With jones reagent; In acetone; at 0 ℃; for 0.5h;

DOI:10.1039/b507237a

Reference yield: 98.0%

allyl 10-undec-10-enoate (7493-76-7) → 10-undecenoic acid (112-38-9)

Guidance literature:

With tetraethylammonium tosylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In acetonitrile; Electrochemical reaction, Pb cathode, Pt anode;

DOI:10.1016/S0040-4039(01)91010-X

upstream raw materials:

undec-10-ynoic acid

Ricinoleic acid

allyl 10-undec-10-enoate

oct-1-ene

Downstream raw materials:

eicosa-1,19-diene

ethyl 10-undecenenoate

11-(acetylthio)undecanoic acid

N-(2-hydroxyethyl)undec-10-enamide

Refernces

• 1、 Gruiec, Regine,Noiret, Nicolas,Patin, Henri. "Useful Direct Conversion of Tetrahydropyranyl Ethers of Fatty Alcohols into Fatty Acids". . p. 1083 - 1085. Retrieved 1995.
• 2、 Ramesh,Mahender,Ravindranath,Das, Biswanath. "A simple, mild and efficient procedure for selective cleavage of prenyl esters using silica-supported sodium hydrogen sulphate as a heterogenous catalyst". . p. 1465 - 1467. Retrieved 2003.
• 3、 Bojarra, Samiro,Reichert, Dennis,Grote, Marius,Baraibar, álvaro Gómez,Dennig, Alexander,Nidetzky, Bernd,Mügge, Carolin,Kourist, Robert. "Bio-based α,ω-Functionalized Hydrocarbons from Multi-step Reaction Sequences with Bio- and Metallo-catalysts Based on the Fatty Acid Decarboxylase OleTJE". . p. 1192 - 1201. Retrieved 2018.
• 4、 Chen, Ping,Liang, Hai-Wei,Shen, Shan-Cheng,Wang, Lei,Xu, Shi-Long,Yin, Peng,Zhang, Le-Le. "Nitrogen-fixing of ultrasmall Pd-based bimetallic nanoclusters on carbon supports". . p. 297 - 304. Retrieved 2020/07/03.