Tiglic acid Property

Melting point:

61-64 °C(lit.)

Boiling point:

95-96 °C12 mm Hg(lit.)

Density 

0.969 g/mL at 25 °C(lit.)

refractive index 

nD81 1.4342

FEMA 

3599 | 2-METHYL-TRANS-2-BUTENOIC ACID

Flash point:

101°C

storage temp. 

2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

pK (25°) 5.02

form 

Crystalline Powder and Chunks

Specific Gravity

0.969

color 

White to beige

Odor

at 10.00 % in dipropylene glycol. sweet dry spicy woody caramel

Odor Type

spicy

Water Solubility 

SOLUBLE IN HOT WATER

Merck 

14,9433

JECFA Number

1205

BRN 

1236500

InChIKey

UIERETOOQGIECD-ONEGZZNKSA-N

LogP

1.35

CAS DataBase Reference

80-59-1(CAS DataBase Reference)

NIST Chemistry Reference

2-Butenoic acid, 2-methyl-, (E)-(80-59-1)

EPA Substance Registry System

2-Butenoic acid, 2-methyl-, (2E)- (80-59-1)

Safety

Hazard Codes 

C,Xi

Risk Statements 

34-36/37/38

Safety Statements 

26-36/37/39-45-24/25-27

RIDADR 

UN 3261 8/PG 2

WGK Germany 

2

RTECS 

GQ5430000

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29161980

Hazardous Substances Data

80-59-1(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Tiglic acid Chemical Properties,Usage,Production

Description

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.

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

Description

frarc.s-2-Methyl-2-butenoic acid has a sweet, warm, spicy odor. May be synthesized from 2-hydroxy-2-methylbutyronitrile.

Chemical Properties

trans-2-Methyl-2-butenoic acid has a sweet, warm, spicy odor.

Chemical Properties

WHITE TO BEIGE CRYSTALLINE POWDER AND CHUNKS

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.]