Tiglic acid

Base Information

• Chemical Name: Tiglic acid
• CAS No.: 80-59-1
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 29161980
• European Community (EC) Number: 201-295-0,236-167-3
• NSC Number: 44235,8999
• UN Number: 3261
• UNII: I5792N03HC
• DSSTox Substance ID: DTXSID80883257
• Nikkaji Number: J4.252H,J100.741F
• Wikipedia: Tiglic_acid
• Wikidata: Q425475
• Pharos Ligand ID: ZC1UL6QB7HCQ
• Metabolomics Workbench ID: 101
• ChEMBL ID: CHEMBL52416
• Mol file: 80-59-1.mol

Synonyms:2-Butenoicacid, 2-methyl-, (E)-;Crotonic acid, 2-methyl-, (E)- (8CI);Tiglic acid(6CI,7CI);(E)-2-Methyl-2-butenoic acid;(E)-a-Methylcrotonic acid;Cevadic acid;NSC 44235;NSC 8999;trans-2,3-Dimethylacrylic acid;trans-2-Methyl-2-butenoic acid;trans-a,b-Dimethylacrylic acid;

Chemical Property of Tiglic acid

Chemical Property:

• Appearance/Colour: white to beige crystalline powder and chunks
• Vapor Pressure: 0.152mmHg at 25°C
• Melting Point: 61-64 °C(lit.)
• Refractive Index: 1.45
• Boiling Point: 198.499 °C at 760 mmHg
• PKA: pK (25°) 5.02
• Flash Point: 95.95 °C
• PSA: 37.30000
• Density: 1.01 g/cm³
• LogP: 1.03720
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility.: SOLUBLE IN HOT WATER
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 103
• Transport DOT Label: Corrosive

Purity/Quality:

98% ^*data from raw suppliers

Tiglic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 26-36/37/39-45-24/25-27

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C)C(=O)O
• Isomeric SMILES: C/C=C(\C)/C(=O)O
• 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. frarc.s-2-Methyl-2-butenoic acid has a sweet, warm, spicy odor. May be 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 a cid is formed during the charcoaling of maple wood.

Technology Process of Tiglic acid

There total 117 articles about Tiglic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

(E)-2-bromobut-2-ene (3017-71-8) + carbon monoxide (201230-82-2) → Tiglic acid (80-59-1)

Guidance literature:

With sodium hydroxide; cetyltrimethylammonim bromide; nickel cyanide; In toluene; at 95 ℃; for 6h; under 735.5 Torr;

DOI:10.1016/S0040-4039(00)99078-6

Reference yield: 76.5%

2-hydroxy-2-methylbutyric acid (3739-30-8) → Tiglic acid (80-59-1)

Guidance literature:

With sulfuric acid; at 140 ℃;

Reference yield:

3-bromo-2-methyl-butyric acid (408314-02-3) → Tiglic acid (80-59-1) + carbon dioxide (124-38-9,18923-20-1) + hydrogen bromide (10035-10-6,12258-64-9)

Guidance literature:

upstream raw materials:

2-acetylpropanoic acid ethyl ester

carbon disulfide

Angelic acid

2-methylbut-2-enal

Downstream raw materials:

β-bromo-isovaleric acid

trans-1-chloro-2-methylbut-2-ene

2-methyl-4-deoxy-DL-threonic acid

(2S,3R)-3-Hydroxy-2-methyl-butyric acid

Refernces

• 1、 Chan, Yu Yi,Leu, Yann Lii,Lin, Ful Wen,Li, Chia Ying,Wu, You Cheng,Shi, Li Shian,Liou, Meei Jen,Wu, Tian Shung. "A secoiridoid and other constituents of Gonocaryum calleryanum". . p. 1073 - 1077. Retrieved 1998.
• 2、 Fraser. "". . p. 549,553. Retrieved 1960.
• 3、 Serkerov. "". . . Retrieved 1969.
• 4、 Leete,Murrill. "". . p. 1727. Retrieved 1967.
• 5、 Ulubelen,Doganca. "Anadoline, a new senecio alkaloid from symphytum orientale.". . p. 2583 - 2585. Retrieved 1970.
• 6、 Kinjo, Junei,Matsubara, Souta,Nohara, Toshihiro,Okawa, Masafumi,Ono, Masateru,Shimohara, Takaaki,Tsuchihashi, Ryota,Yasuda, Shin,Yoshimitsu, Hitoshi,Yuhara, Nobuyoshi,Zhou, Jian-Rong. "Calyhedins I–VI: Resin glycosides from the rhizomes of Calystegia hederacea". . . Retrieved 2021/08/05.
• 7、 Hurst, Timothy E.,Deichert, Julie A.,Kapeniak, Lucas,Lee, Roland,Harris, Jesse,Jessop, Philip G.,Snieckus, Victor. "Sodium Methyl Carbonate as an Effective C1 Synthon. Synthesis of Carboxylic Acids, Benzophenones, and Unsymmetrical Ketones". supporting information. p. 3882 - 3885. Retrieved 2019/06/07.