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5-Decanolide

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5-Decanolide Basic information

Product Name:
5-Decanolide
Synonyms:
  • 5-HYDROXYDECANOIC ACID BETA1 LACTONE
  • 5-HYDROXYDECANOIC ACID DELTA-LACTONE
  • (+/-)-5-DECANOLIDE
  • AMYL-DELTA-VALEROLACTONE
  • (+/-)-6-PENTYLTETRAHYDRO-2H-PYRAN-2-ONE
  • 5-Hydroxydecanoic acid lactone
  • δ-Caprinolactone
  • (6S)-6α-Pentyltetrahydro-2H-pyran-2-one
CAS:
705-86-2
MF:
C10H18O2
MW:
170.25
EINECS:
211-889-1
Product Categories:
  • Food Additive
  • Pyridines ,Halogenated Heterocycles
  • Alphabetical Listings
  • C-DFlavors and Fragrances
  • C-D
  • Cosmetics
  • Certified Natural Products
  • Flavors and Fragrances
Mol File:
705-86-2.mol
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5-Decanolide Chemical Properties

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)
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Safety Information

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

MSDS

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5-Decanolide Usage And Synthesis

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.

5-Decanolide Preparation Products And Raw materials

Raw materials

5-DecanolideSupplier

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