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

• ChemBase编号: 85636
• 分子式: C5H8O2
• 平均质量: 100.11582
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2E)-2-methylbut-2-enoic acid; 2-methylbut-2-enoic acid
• IUPAC传统名: tiglate; tiglic acid; 2-methyl-2-butenoic acid
• 别名: 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; (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

登记号

• CAS号: 13201-46-2; 80-59-1; 565-63-9
• EC号: 201-295-0
• MDL号: MFCD00066864; MFCD00002654
• Beilstein号: 1236500
• 默克索引号: 149433
• PubChem SID: 24900147; 24901804; 24889219; 162072752
• PubChem CID: 643915; 125468
• CHEBI ID: 36431
• CHEMBL: 55941
• Chemspider ID: 559009
• FEMA编号: 3599
• 维基百科标题: Angelic_acid; Tiglic_acid
• 欧洲委员会编号: 10168
• Flavis Number: 8.064

理论计算性质

• Acid pKa: 4.9713354
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 0.67428637
• LogD (pH = 7.4): -1.0820109
• Log P: 1.3151327
• 摩尔折射率: 27.322 cm^3
• 极化性: 10.226851 Å^3
• 极化表面积: 37.3 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 45.5°C; 61-64 °C; 61-64 °C(lit.); 62-66°C; 63.5–64 °C
• 沸点: 185°C; 198.5 °C; 198-199°C; 95-96 °C/12 mmHg(lit.)
• 闪点: 101°C(213°F)
• 密度: 0.9641 g/cm^3 (76 °C); 0.969; 0.969 g/mL at 25 °C(lit.)
• 疏水性(logP): 1.189
• 感官: balsam; spicy

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: GQ5430000
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• 联合国危险货物编号: 3261; UN3261
• 德国WGK号: 2
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; III
• 危险公开号: 34
• 安全公开号: 26-36/37/39-45
• TSCA收录: 是
• GHS危险品标识: GHS05
• GHS警示词: Danger
• GHS危险声明: H314; H314-H318
• GHS警示性声明: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• 个人保护装置: 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
• 保存温度: 2-8°C
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002

药理学性质

• 过敏源: no known allergens

产品相关信息

• 纯度: ≥97.0% (GC); ≥98%; 95%; 98%; 98+%
• 级别: FG; Halal; Kosher; purum
• 线性分子式: CH3CH=C(CH3)COOH
• 分类: Genuine Natural Compounds

详细说明

MP Biomedicals - 02103076

Crystalline
Purity: 98%

MP Biomedicals - 05202349

MP Biomedicals Rare Chemical collection

Sigma Aldrich - T35203

包装
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.

参考文献

• 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):