80-59-1 Usage
Description
Different sources of media describe the Description of 80-59-1 differently. You can refer to the following data:
1. Tiglic acid (also (E)-2-Methylbut-2-enoic acid) is an organic acid. It occurs in croton oil, Roman chamomile, and geranium. It can be prepared by dehydration of MEK cyanohydrin, followed by the hydrolysis of the nitrile function. It is either in the form of a thick syrup or colorless crystals.? It is with a sweet, warm, spicy odor. It is used to synthesize esters for perfume manufacturing industry and as a raw material to produce acids and esters, which are applied as flavoring agent for food and beverage industry. Tiglic acid is also a useful starting material in the synthesis of pharmaceutical intermediates.
2. frarc.s-2-Methyl-2-butenoic acid has a sweet, warm, spicy odor.
May be synthesized from 2-hydroxy-2-methylbutyronitrile.
References
[1] H. Panda (2010) Perfumes and Flavours Technology Handbook.
[2] Paul T. Anastas (2009) Handbook of Green Chemistry, Green Catalysis, Biocatalysis.
[3] https://en.wikipedia.org/wiki/Tiglic_acid
Chemical Properties
trans-2-Methyl-2-butenoic acid has a sweet, warm, spicy odor.
Occurrence
Reported found in celery leaves and stalk, cocoa, mango, dried bonito and Roman chamomile oil
Uses
Tiglic acid is the stable isomer of angelic acid. Tiglic acid was found as glyceride in croton oil, as butyl ester in the oil of the Roman camomile, and as geranyl tiglate in oil of geranium. Tiglic a
cid is formed during the charcoaling of maple wood.
Definition
ChEBI: A 2-methylbut-2-enoic acid having its double bond in trans-configuration.
Taste threshold values
Taste characteristics at 75 ppm: sweet, brown, fruity, with ripe and jamy nuances.
General Description
A white lustrous flaked solid with a fruity or spicy odor. About the same density as water and slightly soluble in water. May burn if heated to high temperatures. May severely irritate skin, eyes, lungs or mucous membranes.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
TIGLIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Tiglic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
Health Hazard
TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire Hazard
Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.
Safety Profile
Low toxicity by
ingestion and skin contact. A severe skin
irritant. When heated to decomposition it
emits acrid smoke and irritating fumes.
Synthesis
Synthesized from 2-hydroxy-2-methylbutyronitrile
Purification Methods
Crystallise it from water. It is steam volatile and is soluble in organic solvents. [Beilstein 2 IV 1552.]
Check Digit Verification of cas no
The CAS Registry Mumber 80-59-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 0 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 80-59:
(4*8)+(3*0)+(2*5)+(1*9)=51
51 % 10 = 1
So 80-59-1 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3-
80-59-1Relevant articles and documents
Evans,Lampard
, p. 3293,3296 (1972)
Hart et al.
, p. 1295,1311 (1976)
Kunesch,Polonsky
, p. 1221 (1969)
Evans,Griffin
, p. 4348,4349 (1963)
The structure of fexerin
Buzhanova,Saidkhodzhaev,Malikov
, p. 345 - 346 (1978)
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Method for simply and conveniently synthesizing tiglic acid
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Paragraph 0017; 0035; 0040; 0041, (2020/06/20)
The invention discloses a method for simply and conveniently synthesizing tiglic acid. The method comprises the following steps: carrying out an addition reaction between a Grignard reagent and pyruvic acid or alpha-butanone acid at a normal temperature by using HMPA or DMPU as an assistant to obtain 2-hydroxy-2-methylbutyric acid, marking the 2-hydroxy-2-methylbutyric acid as an intermediate III;and then, heating the intermediate III under the action of sulfuric acid with a mass concentration of not less than 67% to carry out dehydration reaction to obtain tiglic acid. Materials which can cause serious pollution in the prior art are not used, the reaction steps are short, the technological conditions are simple, no special requirements for equipment exist, the product yield is high, andthe method is suitable for industrial production.
Industrial preparation method of tiglic acid
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Paragraph 0032; 0035; 0036; 0041; 0046; 0051; 0056; 0061, (2018/12/13)
The invention discloses an industrial preparation method of tiglic acid. The industrial preparation method is characterized by comprising the following steps: taking sodium acid sulfate as a catalyst,preparing 3-methyl-3-pentene-2-one (formula II) by utilizing paraldehyde and butanone which are cheap and are commercially easily obtained, and carrying out haloform reaction on a compound shown as the formula II, a sodium hypochlorite water solution and a sodium hydroxide water solution in a continuous flowing reactor to prepare the tiglic acid (formula I). By adopting the method, the disadvantages in the prior art are overcome; the method has the advantages that a utilized catalyst is cheap and easy to obtain and has high catalytic activity, no corrosion to equipment and less pollution caused by three wastes; the continuous flowing reactor provides better heat efficiency and has lower energy consumption; meanwhile, compared with a kettle type stirring reactor, production procedures aresimplified, the production time is shortened, the yield of a product is high and the operation is simple; the method is more suitable for industrial production.