5-Decanolide Property

Melting point:

-27 °C (lit.)

Boiling point:

117-120 °C/0.02 mmHg (lit.)

alpha 

0°(neat)

Density 

0.954 g/mL at 25 °C (lit.)

vapor pressure 

0.63Pa at 25℃

refractive index 

n20/D 1.458(lit.)

FEMA 

2361 | DELTA-DECALACTONE

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

color 

Clear Colourless

Specific Gravity

0.9720.954

Odor

at 100.00 %. fresh sweet oily coconut fruity peach creamy dairy

Odor Type

coconut

Water Solubility 

Soluble in water (4 mg/ml at 28°C), alcohols, and propylene glycol.

JECFA Number

232

BRN 

117520

InChIKey

GHBSPIPJMLAMEP-UHFFFAOYSA-N

LogP

3.016 at 25℃

CAS DataBase Reference

705-86-2(CAS DataBase Reference)

NIST Chemistry Reference

5-Hydroxy decanoic acid, lactone(705-86-2)

EPA Substance Registry System

2H-Pyran-2-one, tetrahydro-6-pentyl- (705-86-2)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-37/39-26

WGK Germany 

1

RTECS 

UQ1355000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29322090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

5-Decanolide Chemical Properties,Usage,Production

Chemical Properties

clear colorless to light yellow oily liquid

Chemical Properties

5-Decanolide is a flavor constituent of many types of fruit, cheese, and other dairy products. It is a colorless, viscous liquid with a creamy-coconut, peach-like aroma.

Chemical Properties

δ-Decalactone has an oily, peach odor and taste.

Occurrence

Reported found in rum, coconut, raspberry, apricot, bilberry, peach, strawberry, Swiss cheese, other cheeses, butter, milk, milk powder, mutton fat, mango and nectarine.

Uses

Used in pharmaceutical preparations, feed additive, flavorings agent. Also used by food and flavor industries for its coconut fragrance and taste. It is also used as a reagent in the synthesis of (±)-Massoilactone (M197600); a chemical component with antibacterial activity found in volatile oils.

Preparation

δ-Decalactone can be prepared by peracid oxidation of 2-pentylcyclopentanone. (R)-δ-decalactone is obtained in high optical purity by starting from (R)-2- pentylcyclopentanone . Hydrogenation or fermentation of massoia lactone is also a practicable method to produce this enantiomer.
A newer development for the preparation ofδ-decalactone describes a carboxylation of 1-nonen-4-ol with carbon monoxide in the presence of a homogenous palladium catalyst in an aqueous system.

Definition

ChEBI: A delta-lactone that is 5-valerolactone substituted by a pentyl group at position 6.

Aroma threshold values

Detection: 100 ppb

Taste threshold values

Taste characteristics at 2 ppm: waxy, coconut, lactonic, fatty, creamy, nutty and fruity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 462, 1990 DOI: 10.1021/jo00289a016

General Description

Measurement of optical rotatory dispersion and circular dichroism of (+) 5-decanolide (tetrahydro-6-pentyl-2H-pyran-2-one) has been reported.

Flammability and Explosibility

Not classified

Synthesis

From hexylethylene oxide and sodium malonic ester; also from decanoic acid.