105-21-5 Usage
Description
y-Heptalactone has a sweet, nut-like, caramel odor and a malty,
caramel, sweet, herbaceous taste. This substance may be obtained
in low yields by hydrogenation of ethyl P-furylacrylate;1 by lactoniation of heptenoic acid; also by condensation of methylacrylate
butyl alcohol using a catalyst.
Chemical Properties
Different sources of media describe the Chemical Properties of 105-21-5 differently. You can refer to the following data:
1. γ-Heptalactone has a sweet, coconut-like, caramel and a malty, caramel, sweet odor, and herbaceous taste.
2. Clear colorless to pale yellow liquid
Occurrence
Reported found in green tea, asparagus, beer, strawberry, peach and beef
Uses
Food additive.
Preparation
Obtained in low yields by hydrogenation of ethyl β-furylacrylate; by lactoniation of heptonic acid; also by condensation of methylacrylate butyl alcohol using a catalyst.
Aroma threshold values
Detection: 400 ppb.
Taste threshold values
Taste characteristics at 15 ppm: sweet, lactonic, creamy, coconut and coumarin, with milky and tobacco Nuances.
Synthesis Reference(s)
Journal of the American Chemical Society, 99, p. 7360, 1977 DOI: 10.1021/ja00464a048
General Description
γ-Heptalactone is a volatile flavor compound found in mangoes, strawberries, pineapples as well as in some dairy products. It is used as a flavoring agent in the food and cosmetic industry.
Hazard
A skin irritant.
Check Digit Verification of cas no
The CAS Registry Mumber 105-21-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 5 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 105-21:
(5*1)+(4*0)+(3*5)+(2*2)+(1*1)=25
25 % 10 = 5
So 105-21-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H12O2/c1-2-3-6-4-5-7(8)9-6/h6H,2-5H2,1H3
105-21-5Relevant articles and documents
FACILE OXIDATIVE CYCLIZATION AND CARBONYLATION OF ALLYLIC ALCOHOLS
Alper, Howard,Leonard, Daniele
, p. 5639 - 5642 (1985)
Palladium chloride catalyzed reaction of primary, secondary, and tertiary allylic alcohols with carbon monoxide and oxygen, hydrochloric acid, and cupric chloride in tetrahydrofuran affords five-membered ring lactones.
-
Zook,Knight
, p. 2302 (1954)
-
A new synthesis of γ-butyrolactones via AuCl3- or Hg(II)-catalyzed intramolecular hydroalkoxylation of 4-bromo-3-yn-1-ols
Reddy, Maddi Sridhar,Kumar, Yalla Kiran,Thirupathi, Nuligonda
supporting information; experimental part, p. 824 - 827 (2012/04/05)
An efficient conversion of 4-bromo-3-yn-1-ols to γ-butyrolactones via AuCl3-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.
Lactonization of Unsaturated Alcohols Catalyzed by Palladium Complexes under Neutral Conditions
El Ali, Bassam,Alper, Howard
, p. 5357 - 5360 (2007/10/02)
Secondary and tertiary allylic alcohols react with carbon monoxide in the presence of catalytic quantities of bis(dibenzylideneacetone)palladium (0) and 1,4-bis(diphenylphosphino)butane affording lactones in 45-92percent isolated yields. α,β-Unsaturated acids are formed by isomerization and carbonylation of primary allylic alcohols. 2-(5H)-Furanones were isolated in yields of 60-80percent when alkynols were employed as substrates for the cyclocarbonylation process.
