705-86-2 Usage
Description
5-Decanolide, also known as tetrahydro-6-pentyl-2H-pyran-2-one, is a delta-lactone with a pentyl group substituted at position 6. It is a colorless, viscous liquid that exhibits a creamy-coconut, peach-like aroma. This chemical compound is a flavor constituent found in various fruits, cheeses, and other dairy products.
Uses
Used in Pharmaceutical Preparations:
5-Decanolide is used as an ingredient in pharmaceutical preparations due to its unique properties and characteristics.
Used in Feed Additive Industry:
It is also utilized as a feed additive, contributing to the enhancement of the feed's flavor and palatability.
Used in Flavorings Agent:
5-Decanolide serves as a flavorings agent, particularly in the food and flavor industries, where it imparts a coconut fragrance and taste.
Used in Food and Flavor Industries:
In the food and flavor industries, 5-Decanolide is used for its distinct coconut fragrance and taste, which adds a unique flavor profile to various products.
Used in Synthesis of (±)-Massoilactone:
It is employed as a reagent in the synthesis of (±)-Massoilactone (M197600), a chemical component with antibacterial activity found in volatile oils.
Used in Chemical Analysis:
The measurement of optical rotatory dispersion and circular dichroism of (+) 5-decanolide has been reported, indicating its use in chemical analysis and research.
Occurrence:
5-Decanolide is naturally found in various food items, including rum, coconut, raspberry, apricot, bilberry, peach, strawberry, Swiss cheese, other cheeses, butter, milk, milk powder, mutton fat, mango, and nectarine.
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.
Synthesis Reference(s)
The Journal of Organic Chemistry, 55, p. 462, 1990 DOI: 10.1021/jo00289a016
Flammability and Explosibility
Notclassified
Synthesis
From hexylethylene oxide and sodium malonic ester; also from decanoic acid.
Check Digit Verification of cas no
The CAS Registry Mumber 705-86-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,0 and 5 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 705-86:
(5*7)+(4*0)+(3*5)+(2*8)+(1*6)=72
72 % 10 = 2
So 705-86-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H18O2/c1-2-3-4-6-9-7-5-8-10(11)12-9/h9H,2-8H2,1H3/t9-/m0/s1
705-86-2Relevant articles and documents
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Winter et al.
, p. 1250,1255 (1962)
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Synthesis process of natural delta-decalactone
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, (2022/01/10)
The invention relates to a synthesis process of natural delta-decalactone, and belongs to the technical field of food additives, and the natural delta-decalactone is obtained by taking furfural and n-amyl alcohol as raw materials through chlorination, Grignard coupling, Piancatelli rearrangement, hydrogenation and oxidation. The purity of the delta-decalactone prepared in the synthesis process of the natural delta-decalactone can reach 98% or above, the natural degree detected by isotope mass spectrometry C14 is 95% or above, and the problems that the synthesis route of the delta-decalactone is complex and the yield is low are solved; and the experimental method is simple, convenient and feasible, the reaction condition is mild, the experimental condition is easy to realize and control, and the method has the characteristics that the raw materials are easy to obtain and rich in source, the yield is relatively high, the used catalyst can be repeatedly used and the like.
Regio- and Enantio-selective Chemo-enzymatic C?H-Lactonization of Decanoic Acid to (S)-δ-Decalactone
Manning, Jack,Tavanti, Michele,Porter, Joanne L.,Kress, Nico,De Visser, Sam P.,Turner, Nicholas J.,Flitsch, Sabine L.
supporting information, p. 5668 - 5671 (2019/03/29)
The conversion of saturated fatty acids to high value chiral hydroxy-acids and lactones poses a number of synthetic challenges: the activation of unreactive C?H bonds and the need for regio- and stereoselectivity. Here the first example of a wild-type cytochrome P450 monooxygenase (CYP116B46 from Tepidiphilus thermophilus) capable of enantio- and regioselective C5 hydroxylation of decanoic acid 1 to (S)-5-hydroxydecanoic acid 2 is reported. Subsequent lactonization yields (S)-δ-decalactone 3, a high value fragrance compound, with greater than 90 % ee. Docking studies provide a rationale for the high regio- and enantioselectivity of the reaction.
