112-38-9

Basic information

• Product Name: Undecenoic acid
• Synonyms: 10-Undecensαure;9-Undecenoic acid;9-Undecenoicacid;9-Undecylenic acid;9-undecylenicacid;acideundecylenique;component of Desenex;Desenex
• CAS NO: 112-38-9
• Molecular Formula: C₁₁H₂₀O₂
• Molecular Weight: 184.28
• EINECS: 203-965-8
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;omega-Unsaturated Carboxylic Acids;Building Blocks;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 112-38-9.mol
• Article Data: 45

Chemical Properties

• Melting Point: 23-25 °C(lit.)
• Boiling Point: 137 °C2 mm Hg(lit.)
• Flash Point: 300 °F
• Appearance: Pale yellow/Crystalline Low Melting Solid or Liquid
• Density: 0.912 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.449(lit.)
• Storage Temp.: -20°C
• Solubility: water: insoluble
• PKA: 4.78±0.10(Predicted)
• Water Solubility: INSOLUBLE
• Merck: 14,9848
• BRN: 1762631
• CAS DataBase Reference: Undecenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Undecenoic acid(112-38-9)
• EPA Substance Registry System: Undecenoic acid(112-38-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-52/53-36/38
• Safety Statements: 26-61-37/39-36
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 1
• RTECS: YQ2975000
• TSCA: Yes
• Hazardous Substances Data: 112-38-9(Hazardous Substances Data)

Usage

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%

Chemical Properties

Different sources of media describe the Chemical Properties of 112-38-9 differently. You can refer to the following data:
1. Undecylenic acid is an organic unsaturated fatty acid derived from castor oil. It is the common name of 10-undecenoic acid, (CH2CH(CH2)8COOH). It is used in the manufacture of pharmaceuticals, cosmetics and perfumery, including antidandruff shampoos , antimicrobial powders and as a musk in perfumes and aromas. Undecylenic acid is produced by cracking of castor oil under pressure.
2. 10-Undecenoic acid has a characteristic pungent odor.
3. Light-colored liquid; fruity-rosy odor. Almost insoluble in water; miscible with alcohol, chloroform, ether, benzene, and fixed and volatile oils. Combustible.

Occurrence

Reported found as a metabolite in Rhodotorula glutinis var. lusitanica; naturally occurring in the essential oils of Juniperus chinensis, Thujopsis dolabrata and skim milk powder

Uses

Different sources of media describe the Uses of 112-38-9 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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)
4. used as antifoaming and surface active agent. As its sulfo – succinate derivative it is used in anti-dandruff shampoos

Definition

ChEBI: An undecenoic acid having its double bond in the 10-position. It is derived from castor oil and is used for the treatment of skin problems.

Preparation

From malonic acid; by pyrolysis of ricinoleic acid or castor oil.

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.

General Description

10-Undecenoic acid undergoes copolymerisation with ethylene using the metallocene catalyst system Cp2ZrCl2 / methylaluminoxane.

Flammability and Explosibility

Nonflammable

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.

Synthesis

Undecylenic acid, 10-undecylenic acid (35.4.7), is synthesized by pyrolysis at 400°C and low pressure (50 mm) an oxyderivative of oleic acid—ricinoleic acid—the glyceride of which is the main ingredient of castor oil.

Purification Methods

Purify the acid by repeated fractional crystallisation from its melt or by distillation in a vacuum. [Beilstein 2 IV 1612.]

InChI:InChI=1/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13)

Upstream product

• 2777-65-3 undec-10-ynoic acid 
• 141-22-0 Ricinoleic acid 
• 111-66-0 oct-1-ene 
• 112-45-8 10-Undecenal 
• 2834-05-1 11-bromoundecanoic acid 
• 18120-63-3 (4-vinylphenyl)magnesium bromide 
• 927-74-2 3-Butyn-1-ol 
• 18294-93-4 10-bromoundecanoic acid 
• 141-78-6 ethyl acetate 
• 93757-41-6 tert-butyl undec-10-enoate 
• 68-12-2 N,N-dimethyl-formamide 
• 6308-96-9 10,11-dibromo-undecanoic acid 
• 112-43-6 10-Undecen-1-ol 
• 7381-15-9 1,2-diphenyl-1,2-disodiumethane 

Downstream Products

• 5299-57-0 ω-undecylenic acid vinyl ester 
• 5455-16-3 11-Propylmercapto-undecansaeure 
• 14811-95-1 eicosa-1,19-diene 
• 692-86-4 ethyl 10-undecenenoate 
• 68892-05-7 undec-10-enoic acid-(3,7-dimethyl-octa-2t,6-dienyl ester) 
• 4230-06-2 11-Butylmercapto-undecansaeure 
• 4230-08-4 11-Heptylmercapto-undecansaeure 
• 6974-31-8 11-(acetylthio)undecanoic acid 
• 17351-34-7 pentadec-14-enoic acid 
• 30948-01-7 3β-cholest-5-en-3-yl 10-undecenoate 
• 64-18-6 formic acid 
• 111-20-6 1,10-decanedioic acid 
• 38460-95-6 undec-10-enoyl chloride 
• 6308-96-9 10,11-dibromo-undecanoic acid 

Relevant articles and documents

A facile and selective cleavage of prenyl esters catalyzed by CeCl3·7 H2O-NaI

A highly selective cleavage of prenyl esters has been achieved in high yields using CeCl3·7 H2O-NaI in refluxing acetonitrile under neutral conditions. This method is mild and compatible with a wide variety of functional groups such

Interaction of oxygen functionalized alkenes with a methylaluminoxane-zirconocene catalyst studied by NMR

Reactions of hydroxyl, ether and carbonyl functionalized alkenes with methylaluminoxane prepared in toluene-d8 (MAO) and zirconocenedichloride (Cp2ZrCl2) were investigated by 1H- and 13C-NMR spectroscopy at 27°C. The 11 alkenes studied bear a terminal C=C bond separated by 7-9 (-CH2-) units from the heteroatom moiety. Intramolecular connectivities in mono (alkene), bi (alkene and MAO) and tri (alkene, MAO and Cp2ZrCl2) component mixtures were determined by 2D HSQC, HMBC, ROESY and NOESY NMR techniques. The five studied alkenols formed aluminium alkoxides with MAO even in the case of a substantial steric hindrance around the OH group. Zirconocene enhanced the formation of aluminium alkoxides. Decomposition to free alkenol was observed only for the straight chain alkenol (10-undecen-1-ol). The OTMS derivatives formed dimers of the type CH2=CR1R2 along with methyl derivatives, CH2=C(Me)(R) and (Me)CH=CH(R), in the presence of MAO and Cp2ZrCl2. 10-Undecenyl methyl ether and methyl decenoate remained mainly as a free comonomer in the presence of MAO or MAO/Cp2ZrCl2, though a transient coordination of the former to MAO was deduced. Unsaturated species Me2C=CH-Al-X and CH2=CH(CH2)5CH2CH=C(t-Bu)O-Al-X (X = MAO oligomer) were formed in the reaction of t-butyl undecenoate or 2,2-dimethyl-11-dodecen-3-one with MAO or MAO/Cp2ZrCl2. Interaction of the CH2=CH part of the functionalized alkenes with zirconocene was not observed. A possible coordination of the C=C bond to MAO was observed only for the sec alkenols.

A New and Efficient Synthesis of Trifluoromethyl Ketones from Carboxylic Acids. Part I.

Trifluoromethyl ketones can be prepared in good yield from primary carboxylic acid chlorides by reaction with pyridine and trifluoroacetic anhydride followed by aqueous work up.

Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer

The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.

Synthesis from Undecylenic Acid of Macroheterocycles with Diacylhydrazine and Ester Fragments

A three-step synthesis of potentially biologically active 30- and 32-membered macroheterocycles with esters and acylhydrazines starting from methyl undecylenate was developed based on [1+1]-condensation of intermediate tetraesters, i.e., bis(10′ -methoxy-10′-oxodecyl)- or bis(11′-methoxy-11′ -oxoundecyl)hexanedioate, with hydrazine hydrate. The structures of the synthesized compounds were confirmed using IR and NMR spectroscopy and mass spectrometry.