Tiglic acid

Tiglic acid: Tiglic acid

IUPAC name

(E)-2-methylbut-2-enoic acid

Other names

cevadic acid, sabadillic acid, tiglinic acid

Identifiers

CAS number 80-59-1

Jmol-3D images Image 1

SMILES

CC=C(C)C(=O)O

Properties

Molecular formula C₅H₈O₂

Molar mass 100.116 g/mol

Density 0.9641 g/cm³ (76 °C)

Melting point
63.5-64 °C

Boiling point
198.5 °C

Y acid (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Tiglic acid is a monocarboxylic unsaturated organic acid. It is found in croton oil and in several other natural products. It was also isolated from the defensive secretion of certain beetles.^[1]

Contents

1 Properties and uses

2 Toxicity

3 Names and discovery

4 References

Properties and uses

Tiglic acid has a double bond between the second and third carbons of the chain. Together with angelic acid form a pair of cis-trans isomers. Tiglic acid is a volatile and crystallizable substance with a sweet, warm spicy odour. It is used in making perfumes and flavoring agents. The salts and esters of tiglic acid are called tiglates.

Toxicity

Tiglic acid is a skin and eye irritant. The inhalation of the substance causes respiratory tract irritation. It is listed on the Toxic Substances Control Act (TSCA).

Names and discovery

In 1819 Pelletier and Caventou isolated a peculiar volatile and crystallizable acid from the seeds of Schoenocaulon officinalis, a Mexican plant of family Melanthaceae (also called cevadilla or sabadilla). Consequently the substance was named sabadillic or cevadic acid. It was later found to be identical with Frankland and Duppa's methylcrotonic acid (1865). In 1870 Geuther and Fröhlich prepared an acid from croton oil to which they gave the name tiglic acid (or tiglinic acid) after (Croton) tiglium (Linn.), specific name of the croton oil plant.^[2] The compound was shown to be identical with the previously described methyl-crotonic acid.

References

^ Attygalle, A. B.; Wu, X.; Will, K. W. (2007). "Biosynthesis of tiglic, ethacrylic, and 2-methylbutyric acids in a carabid beetle, Pterostichus (Hypherpes) californicus". J Chem Ecol. 33: 963–970. PMID 17404818.

^ Lloyd, J. U. (1898). "Croton tiglium". Lloyd Brothers plant drug pamphlets, Lloyd Brothers Pharmacy: Cincinnati.

Categories:
Carboxylic acids
Alkenes

Tiglic acid


IUPAC name (E)-2-methylbut-2-enoic acid
Other names cevadic acid, sabadillic acid, tiglinic acid
Identifiers
CAS number	80-59-1
Jmol-3D images	Image 1
SMILES CC=C(C)C(=O)O
Properties
Molecular formula	C₅H₈O₂
Molar mass	100.116 g/mol
Density	0.9641 g/cm³ (76 °C)
Melting point	63.5-64 °C
Boiling point	198.5 °C
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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tiglic acid — [tig′lik] n. [< ModL tiglium, croton oil plant < Gr tilos, thin feces (the seeds have a cathartic effect) < IE * ti , var. of base * ta , to melt > THAW] a fragrant, poisonous, monobasic acid, CH3CH:C(CH3)COOH, usually derived from… … English World dictionary
tiglic acid — tiglo rūgštis statusas T sritis chemija formulė CH₃CH=C(CH₃)COOH atitikmenys: angl. tiglic acid rus. тиглиновая кислота ryšiai: sinonimas – (E) 2 metil 2 buteno rūgštis … Chemijos terminų aiškinamasis žodynas
tiglic acid — An unsaturated fatty acid present in glycerides in croton oil. * * * tig·lic acid .tig lik n a vesicant crystalline unsaturated acid C5H8O2 with a spicy odor that is the stable stereoisomer of angelic acid and occurs in the form of esters esp. in … Medical dictionary
tiglic acid — noun A monocarboxylic unsaturated organic acid, the trans form of angelic acid, found in croton oil and in several other natural products. Syn: cevadic acid, sabadillic acid, tiglinic acid … Wiktionary
tiglic acid — ˈtiglik noun Etymology: International Scientific Vocabulary tigl (from New Latin tiglium, specific epithet of Croton tiglium, from Medieval Latin or New Latin, seed from a species of croton) + ic : a vesicant crystalline unsaturated acid CH3CH .… … Useful english dictionary
tiglic acid — Chem. a slightly water soluble, poisonous compound, C5H8O2, derived from croton oil and occurring as a thick, syrupy liquid or in colorless crystals. [1870 75] * * * … Universalium
tiglic — /tig lik/, adj. Chem. of or derived from tiglic acid. Also, tiglinic /ti glin ik/. [1870 75; < NL tigl(ium) croton oil plant (said to be < Gk tîl(os) watery excrement + NL ium IUM) + IC] * * * … Universalium
tiglic — /tig lik/, adj. Chem. of or derived from tiglic acid. Also, tiglinic /ti glin ik/. [1870 75; < NL tigl(ium) croton oil plant (said to be < Gk tîl(os) watery excrement + NL ium IUM) + IC] … Useful english dictionary
Tiglic — Tig lic, a. (Chem.) Of, pertaining to, or designating, an acid, {C4H7CO2H} (called also methyl crotonic acid), homologous with crotonic acid, and obtained from croton oil (from {Croton Tiglium}) as a white crystalline substance. [1913 Webster] … The Collaborative International Dictionary of English
carboxylic acid — Chem. any organic acid containing one or more carboxyl groups. [1900 05; CARBOXYL + IC] * * * Any organic compound with the general chemical formula ―COOH in which a carbon (C) atom is bonded to an oxygen (O) atom by a double bond to make a… … Universalium

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Tiglic acid

Contents

Properties and uses

Toxicity

Names and discovery

References

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Tiglic acid

Contents

Properties and uses

Toxicity

Names and discovery

References

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