350-03-8 Usage
Description
3-Acetylpyridine, also known as methyl nicotinate, is an organic compound with the chemical formula C7H7NO. It is a colorless liquid with a sweet, nutty, popcorn-like aroma and is a nicotinic acid antagonist. It is used as an intermediate in the synthesis of various pharmaceuticals and is also utilized in the fragrance industry.
Uses
Used in Pharmaceutical Industry:
3-Acetylpyridine is used as an intermediate for the synthesis of risedronate sodium, an inhibitor of bone resorption. It is also used in the synthesis of several clinical drugs, including Imatinib, Mesylate, Metyrapone, Telithromycin, and Ridogrel.
Used in Fragrance Industry:
3-Acetylpyridine is used in the fragrance industry due to its sweet, nutty, popcorn-like aroma. It adds a unique scent to various products.
Used in Food Industry:
3-Acetylpyridine is used as a flavoring agent in the food industry, with reported uses (ppm) as follows:
Baked goods: Usual 2 ppm, Max. 3 ppm
Frozen dairy: Usual 1 ppm, Max. 2 ppm
Gelatins, puddings: Usual 1 ppm, Max. 2 ppm
Nonalcoholic beverages: Usual 1 ppm, Max. 2 ppm
Soft candy: Usual 2 ppm, Max. 3 ppm
Occurrence:
3-Acetylpyridine has been reported to be found in various food items such as roasted filberts, beer, brandy, coffee, malt, and wheaten bread.
Identification
▼▲
CAS.No.:?
350-03-8?
FL.No.:?
14.039
FEMA.No.:?
3424
NAS.No.:?
3424
CoE.No.:?
2316
EINECS.No.:?
206-496-7?
JECFA.No.:?
1316
Regulatory Status
CoE: Used provisionally. Bev.: 2 ppm; Food: 3 ppm
FDA: n/a
FDA (other): n/a
JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2004).
Natural occurrence
Reported found in roasted filberts, beer, brandy, coffee, malt and wheaten bread.
Preparation
Dry distillation of calcium nicotinate with calcium acetate.
Safety Profile
Poison by ingestion. Moderately toxic by intraperitoneal routeMutation data reported. A flammable liquid. When heated to decomposition emits toxic fumes of NOx,. See also KETONES
Purification Methods
It is purified by dissolving in HCl, extracting with Et2O to remove the possible impurity of nicotinic acid, basified with NaOH and extracted with Et2O. The dried extract is filtered, evaporated and the residual oil is distilled. If the NMR spectrum indicates further impurities, then convert it to the phenylhydrazone (m 137o, yellow needles from EtOH). This is hydrolysed with HCl [Engler & Kiby Chem Ber 22 597 1889], the phenylhydrazine HCl is removed by filtration, NaNO2 is added, the solution is basified with aqueous NaOH and extracted with Et2O as before and distilled at atmospheric pressure to give 3-acetylpyridine as a colourless oil. Purification can also be achieved by shaking with 50% aqueous KOH, extracting with Et2O, drying the extract and distilling it at atmospheric pressure or in vacuo. [Kloetzel & Chubb J Am Chem Soc 79 4226 1957.] The hydrochloride has m 180-181o (from MeOH/EtOH), the picrate has m 133.8-134.8o (from H2O), and the phenylhydrazone has m 137o (129-130o)(needles, from EtOH) [Webb & Webb J Am Chem Soc 71 2285 1949]. The ketoxime has m 112o (from EtOH or *C6H6). [Strong & McElvain J Am Chem Soc 55 816 1933, Kolloff & Hunter J Am Chem Soc 63 490 1941, Beilstein 21/7 V 394.]
Check Digit Verification of cas no
The CAS Registry Mumber 350-03-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,5 and 0 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 350-03:
(5*3)+(4*5)+(3*0)+(2*0)+(1*3)=38
38 % 10 = 8
So 350-03-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H7NO/c1-6(9)7-3-2-4-8-5-7/h2-5H,1H3
350-03-8Relevant articles and documents
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Feuer
, p. 417,420 (1973)
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Minisci-Type Alkylation of N-Heteroarenes by N-(Acyloxy)phthalimide Esters Mediated by a Hantzsch Ester and Blue LED Light
Kyne, Sara Helen,Li, Jiacheng,Siang Tan, Suan,Wai Hong Chan, Philip
, (2022/01/11)
A synthetic method that enables the Hantzsch ester-mediated Minisci-type C2-alkylation of quinolines, isoquinolines and pyridines by N-(acyloxy)phthalimide esters (NHPI) under blue LED (light emitting diode) light (456 nm) is described. Achieved under mild reaction conditions at room temperature, the metal-free synthetic protocol was shown to be applicable to primary, secondary and tertiary NHPIs to give the alkylated N-heterocyclic products in yields of 21–99%. On introducing a chiral phosphoric acid, an asymmetric version of the reaction was also realised and provided product enantiomeric excess (ee) values of 53–99%. The reaction mechanism was delineated to involve excitation of an electron-donor acceptor (EDA) complex, formed from weak electrostatic interactions between the Hantzsch ester and NHPI, which generates the posited radical species of the redox active ester that undergoes addition to the N-heterocycle.
Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation
Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei
supporting information, p. 5905 - 5908 (2021/06/18)
A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.