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

• ChemBase ID: 85636
• Molecular Formular: C5H8O2
• Molecular Mass: 100.11582
• Monoisotopic Mass: 100.0524295
• SMILES: O=C(/C(=C/C)/C)O
• Canonical SMILES: C/C(=C\C)/C(=O)O
• InChI: InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)
• InChIKey: UIERETOOQGIECD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-2-methylbut-2-enoic acid; 2-methylbut-2-enoic acid
• IUPAC Traditional name: tiglate; tiglic acid; 2-methyl-2-butenoic acid
• Synonyms: (2E)-2-Methyl-2-butenoic Acid; (E)-2-Methylcrotonic Acid; (E)-2,3-Dimethylacrylic Acid; (E)-2-Methyl-2-butenoic acid; (E)-α-Methylcrotonic acid; NSC 44235; NSC 8999; trans-2-Methylcrotonic Acid; trans-α,β-Dimethylacrylic Acid; Trans-α,β-DIMETHYLACRYLIC ACID; (E)-2-methylbut-2-enoic acid; Tiglic acid; trans-2-Methyl-2-butenoic acid; trans-2,3-Dimethylacrylic acid; Tiglic acid; trans-2-Methyl-2-butenoic acid; trans-2,3-Dimethylacrylic acid; TIGLIC ACID; 2-methylbut-2-enoic acid; cevadic acid; sabadillic acid; tiglinic acid; Angelic acid; 反式-2,3-二甲基丙烯酸; 反式-2-甲基-2-丁烯酸; 顺芷酸; 反式-2-甲基-2-丁烯酸; 反式-2,3-二甲基丙烯酸; 顺芷酸; 惕各酸

Database IDs

• CAS Number: 13201-46-2; 80-59-1; 565-63-9
• EC Number: 201-295-0
• MDL Number: MFCD00066864; MFCD00002654
• Beilstein Number: 1236500
• Merck Index: 149433
• PubChem SID: 24900147; 24901804; 24889219; 162072752
• PubChem CID: 643915; 125468
• CHEBI ID: 36431
• CHEMBL: 55941
• Chemspider ID: 559009
• FEMA ID: 3599
• Wikipedia Title: Angelic_acid; Tiglic_acid
• Council of Europe Number: 10168
• Flavis Number: 8.064

CALCULATED PROPERTIES

• Acid pKa: 4.9713354
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.67428637
• LogD (pH = 7.4): -1.0820109
• Log P: 1.3151327
• Molar Refractivity: 27.322 cm^3
• Polarizability: 10.226851 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 45.5°C; 61-64 °C; 61-64 °C(lit.); 62-66°C; 63.5–64 °C
• Boiling Point: 185°C; 198.5 °C; 198-199°C; 95-96 °C/12 mmHg(lit.)
• Flash Point: 101°C(213°F)
• Density: 0.9641 g/cm^3 (76 °C); 0.969; 0.969 g/mL at 25 °C(lit.)
• Hydrophobicity(logP): 1.189
• Organoleptic: balsam; spicy

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: GQ5430000
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 2
• Hazard Class: 8
• Packing Group: 2; III
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: 2-8°C
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥97.0% (GC); ≥98%; 95%; 98%; 98+%
• Grade: FG; Halal; Kosher; purum
• Linear Formula: CH3CH=C(CH3)COOH
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02103076

Crystalline
Purity: 98%

MP Biomedicals - 05202349

MP Biomedicals Rare Chemical collection

Sigma Aldrich - T35203

Packaging
100 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T35203.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - T440050

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.

REFERENCES

• Bueding, et al.: J. Biol. Chem., 202, 505 (1953)
• Alcohols protected as tiglate esters can be cleaved by osmium tetroxide - periodate to the more readily hydrolyzed pyruvate esters: J. Org. Chem., 27, 3103 (1962).
• Has been dimetallated with the hindered base Li tetramethylpiperidide. The resulting dilithio species reacts with benzynes (from bromobenzenes and the same base), providing a route to (E)-4-aryl-2-methyl-3-butenoic acids: Synth. Commun., 26, 963 (1996):