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Tiglic acid

Tiglic acid structure

Tiglic acid 

structure
  • CAS No:

    80-59-1

  • Formula:

    C5H8O2

  • Chemical Name:

    Tiglic acid

  • Synonyms:

    2-Butenoic acid,2-methyl-,(2E)-;Crotonic acid,2-methyl-,(E)-;Tiglic acid;2-Butenoic acid,2-methyl-,(E)-;(2E)-2-Methyl-2-butenoic acid;Cevadic acid;trans-α,β-Dimethylacrylic acid;trans-2,3-Dimethylacrylic acid;trans-2-Methyl-2-butenoic acid;trans-2-Methylcrotonic acid;(E)-2-Methylcrotonic acid;Tiglinic acid;(E)-2,3-Dimethylacrylic acid;(E)-α-Methylcrotonic acid;(E)-2-Methyl-2-butenoic acid;NSC 44235;NSC 8999

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

Tiglic acid is a monocarboxylic unsaturated organic acid found in croton oil and in several other natural products. Tiglic aci has a role as a plant metabolite[1].


Tiglic acid, [corrosive solid] appears as 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.|Solid|White crystalline solid; sweet, warm, spicy aroma


Tiglic acid, [corrosive solid] appears as 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.|Tiglic acid is a 2-methylbut-2-enoic acid having its double bond in trans-configuration. It has a role as a plant metabolite. It derives from a crotonic acid.

Tiglic acid Basic Attributes

100.12

100.12

1236500

201-295-0

I5792N03HC

44235|8999

3261

Triclinic plates, rods from water|Thick, syrupy liquid or colorless crystals|Tablets

29161980

Characteristics

37.3

1

White to beige Crystalline Powder and Chunks

0.9427 g/cm3 @ Temp: 99.5 °C

64.5 °C

198.5 °C

101°C

1.451

soluble in hot water

Refrigerator (+4°C)

1.33X10-1 mm Hg at 25 deg C

This material is capable of creating a dust explosion.

Spicey

Henry's Law constant = 7.1X10-7 atm-cu m/mole at 25 °C (est)

pKa = 4.96 at 18 °C|pk = 5.02 at 25 °C

Volatile with steam|Combustible|Liquid; density: 0.9498 at 20 °C/4 °C; boiling point: 139.6 °C at 766 mm Hg; index of refraction: 1.4370 at 20 °C/D. /Methyl ester/|Liquid; density: 0.9247 at 20 °C/4 °C; boiling point: 156 °C at 752 mm Hg, 55.5 °C at 11 mm Hg; index of refraction: 1.4350 at 20 °C/D; heat of formation: 953.2 kilocalories at constant volume, 954.4 kilocalories at constant pressure. /Ethyl ester/|Liquid; pleasant odor; density: 0.9279 at 15 °C/15 °C; boiling point: 149-151 °C at 7 mm Hg. /Geranyl ester/|Leaflets; much less soluble in water than calcium angelate: 100 parts of aqueous solution saturated at 17 °C contains 6.05 parts of anhydrous calcium tiglate. /Calcium salt trihydrate/|Hydroxyl radical reaction rate constant = 3.1X10-11 cu cm/molecule-sec at 25 °C (est)

Slightly soluble in water.

Acids, Carboxylic

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 it 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.

Molar heat of combusion: 635.1 kilocalories

Critical temperature: 680.62 K; critical pressure: 4857.97 kPa (est)

Safety Information

8

UN 3261 8/PG 2

2

34-36/37/38

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

GQ5430000

C,Xi

P280-P305 + P351 + P338-P310

H314

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations.

Materials to Avoid: Bases, Oxidizing agents, Reducing agents.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: 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. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)

|Warning|H315 (97.08%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|Aggregated GHS information provided by 1612 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)|Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. Wear positive pressure self-contained breathing apparatus. /Tiglic acid (Corrosive solid, acidic, organic, NOS); Tiglic acid (Corrosive solids, NOS)/

... This material ... is capable of creating a dust explosion.

EXTINGUISHING MEDIA ... Carbon dioxide, dry chemical powder, or appropriate foam. Water spray.|Firefighting Protective Equipment: Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes.|If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.). Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. /Tiglic acid (Corrosive solid, acidic, organic, NOS); Tiglic acid (Corrosive solids, NOS)/

Corrosive. Causes burns. Vesicant.

Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Neutralize with vinegar or other dilute acid. Absorb bulk liquid with fly ash or cement powder. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ /Tiglic acid (Corrosive solid, acidic, organic, NOS); Tiglic acid (Corrosive solids, NOS)/|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Neutralize with dilute acid. /Tiglic acid (Corrosive solid, acidic, organic, NOS); Tiglic acid (Corrosive solids, NOS)/|Sweep up, place in a bag and hold for waste disposal. Avoid raising dust. Ventilate area and wash spill site after material pickup is complete.

If material not involved in fire: Build dikes to contain flow as necessary. /Tiglic acid (Corrosive solid, acidic, organic, NOS); Tiglic acid (Corrosive solids, NOS)/|Personnel protection: Avoid breathing vapors or dusts. Avoid breathing fumes from burning material. ... Wet spilled material before picking it up. Do not handle broken packages unless wearing appropriate personal protective equipment. /Tiglic acid (Corrosive solid, acidic, organic, NOS); Tiglic acid (Corrosive solids, NOS)/|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|SRP: When working with strong solutions of acids or bases or other caustic or corrosive materials, always wear a full face mask. When working with caustic or corrosive gases or vapors, a full face mask will not protect the eyes or prevent inhaling the material. A full face respirator is required.

It may be very irritating to skin, eyes, lungs and mucous membranes. /Tiglic acid (Corrosive solid, acidic, organic, NOS); Tiglic acid (Corrosive solids, NOS)/

Drug Information

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: 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. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)

/SIGNS AND SYMPTOMS/ Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. Inhalation may result in spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and skin.|/ALTERNATIVE and IN VITRO TESTS/ The present study was undertaken to assess the influence of 25 organic acids, which appear in high concentrations in tissues of patients with various organic acidemias, on the proliferation of human peripheral lymphocytes stimulated with concanavalin A (Con A) (a T-cell activator) and pokeweed mitogen (PWM) (predominantly a B-cell activator). Mononuclear cells were cultivated in flat-bottomed 96-well microplates at 37 °C for 96 (Con A) or 144 hr (PWM) in the presence of one mitogen at different concentrations and of one acid at doses ranging from 1 to 5 mM. Control cultures did not contain any acid. Cell reactivity was measured by the incorporation of tritiated thymidine into cellular DNA. ... among the 25 acids tested, aminoadipic (AAD), 2-hydroxy-3-methylvaleric (HMV), 2-ketoisocaproic (KIC), 2-methylbutyric (MBA), propionic (PPA) and tiglic (TIG) acids strongly suppressed lymphocyte DNA synthesis in Con A-supplemented cultures, whereas in cultures stimulated with PWM, 2-ketoisovaleric (KIV) and PPA acids presented the same effect. ...

tiglic acid

Tiglic acid Use and Manufacturing

Methods of Manufacturing

From croton oil. Also occurs in English chamomile oil.|Synthesized from 2-hydroxy-2-methylbutyronitrile.

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 acid is formed during the charcoaling of maple wood.

2-Butenoic acid, 2-methyl-, (2E)-: ACTIVE

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Branched fatty acids [FA0102]

Flavoring Agents

Computed Properties

Molecular Weight:100.12
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:100.052429494
Monoisotopic Mass:100.052429494
Topological Polar Surface Area:37.3
Heavy Atom Count:7
Complexity:103
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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