Hendecanoic acid Chemical Properties

Melting point:

28-31 °C(lit.)

Boiling point:

228 °C160 mm Hg(lit.)

Density 

0.89 g/cm3 (20℃)

refractive index 

1.4202

FEMA 

3245 | UNDECANOIC ACID

Flash point:

>230 °F

storage temp. 

room temp

solubility 

0.05g/l insoluble

form 

Low Melting Solid

pka

4.79±0.10(Predicted)

color 

White to pale yellow

Specific Gravity

0.9948

Odor

at 100.00 %. waxy creamy cheese fatty coconut

Odor Type

waxy

explosive limit

0.6%(V)

Water Solubility 

insoluble

JECFA Number

108

BRN 

1759287

InChIKey

ZDPHROOEEOARMN-UHFFFAOYSA-N

LogP

4.50

CAS DataBase Reference

112-37-8(CAS DataBase Reference)

NIST Chemistry Reference

Undecanoic acid(112-37-8)

EPA Substance Registry System

Undecanoic acid (112-37-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

1

RTECS 

YQ2275000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29159080

MSDS

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Hendecanoic acid Usage And Synthesis

Description

Hendecanoic acid (also known as undecanoic acid, undecylenic acid and undecylic acid) is a naturally occurring carboxylic acid. Its chemical formula is CH3(CH2)9COOH. It may participate in the control of triacylglycerol synthesis, and is found in breast milk and infant formula. It is known as an antifungal agent, used for the treatment of some types of fungal infections including ringworm and athlete’s foot. One of its mechanism of action is through inhibition of the morphogenesis of Candida albicans. It may also interfere with the fatty acid biosynthesis process of fungi. It is manufactured by the vacuum distillation of castor bean oil through the pyrolysis of ricinoleic acid. However, it has been generally replaced by new generation of anti-fungal medicine.

References

http://www.altmedrev.com/publications/7/1/68.pdf
https://pubchem.ncbi.nlm.nih.gov/compound/undecanoic_acid#section=Top
http://www.mayoclinic.org/drugs-supplements/undecylenic-acid-topical-route/description/drg-20066601
https://en.wikipedia.org/wiki/Undecylic_acid

Description

Undecanoic acid is a saturated fatty acid containing eleven carbons (C11:0). It is cytotoxic to certain filamentous fungi and is used to study fungal mechanisms of resistance. Undecanoic acid is also used to acylate larger molecules.

Chemical Properties

white to pale yellowish low melting solid

Chemical Properties

Undecanoic acid has a faint fatty, aldehydic odor.

Occurrence

Occurs naturally in butter and in the oil of Artemisisa frigida Willd.; also reported found in the oils of Chamaecyparis pisifera Engl., wild thyme, Thymus marschollianus and coconut. Also reported found in apple, banana, sour cherry, lemon and mandarin peel oil, grapefruit juice, guava, grapes, papaya, many cheeses, milk powder, chicken and beef fat, cooked mutton, cured pork, beer, cognac, rum, whiskies, white wine, tea, coconut milk, beans, licorice, mango, mushrooms, rice, sake, wort, loquat, scallop and maté.

Uses

Undecanoic acid was used in the formation of cycloamylose crystals.

Uses

Intermediates of Liquid Crystals

Uses

Undecanoic Acid is a saturated fatty acid. It may be used to activate orphan G protein-coupled receptor GPR40.

Preparation

Hendecanoic acid can be produced by reduction of Undecylenic acid, which is generally obtained from Castor oil.

Definition

ChEBI: A straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; the most fungitoxic of the C7:0 - C18:0 fatty acid series.

Aroma threshold values

Detection: 10 ppb

Taste threshold values

Taste characteristics at 20 ppm: waxy, creamy, cheese-like with a fatty dairy mouthfeel.

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 5293, 1989 DOI: 10.1016/S0040-4039(01)93768-2

General Description

White crystalline solid. Insoluble in water. Specific gravity 0.85. Hence floats on water.

Air & Water Reactions

Dust explosion is possible. [USCG, 1999]. Insoluble in water.

Reactivity Profile

A weak carboxylic acid. Neutralizes bases with the evolution of substantial amounts of heat to produce water plus a salt. Reacts with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Can generate flammable and/or toxic gases and heat by reaction with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Reacts in with aqueous solutions of nitrites and thiosulfates (to give H2S and SO3) and dithionites (to give SO2) and heat. Reaction with solutions of carbonates and bicarbonates generate a harmless gas (carbon dioxide) but still heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. May initiate polymerization reactions. May serve as a catalyst.

Health Hazard

May be harmful by inhalation, ingestion or skin absorption. Material is irritating to mucous membrane and upper respiratory tract. Causes eye and skin irritation.

Fire Hazard

Special Hazards of Combustion Products: Dust explosion is possible.

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