705-86-2 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 705-86-2 differently. You can refer to the following data:
1. 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.
2. 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
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.
