Tiglic acid
(Synonyms: 巴豆酸) 目录号 : GC37790
Tiglic acid (Cevadic acid, Sabadillic acid, Tiglinic acid) is a monocarboxylic unsaturated organic acid found in croton oil and in several other natural products. It is used in making perfumes and flavoring agents.
Cas No.:80-59-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Tiglic acid (Cevadic acid, Sabadillic acid, Tiglinic acid) is a monocarboxylic unsaturated organic acid found in croton oil and in several other natural products. It is used in making perfumes and flavoring agents.
| Cas No. | 80-59-1 | SDF | |
| 别名 | 巴豆酸 | ||
| Canonical SMILES | C/C=C(C)/C(O)=O | ||
| 分子式 | C5H8O2 | 分子量 | 100.12 |
| 溶解度 | DMSO: 100 mg/mL (998.80 mM); Water: 7.69 mg/mL (76.81 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 9.988 mL | 49.9401 mL | 99.8801 mL |
| 5 mM | 1.9976 mL | 9.988 mL | 19.976 mL |
| 10 mM | 0.9988 mL | 4.994 mL | 9.988 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Hydroxylated Ethacrylic and Tiglic acid Derivatives from the Stems and Branches of Enkianthus chinensis and Their Potential Anti-inflammatory Activities
J Nat Prod 2020 Oct 23;83(10):2867-2876.PMID:33052045DOI:10.1021/acs.jnatprod.0c00286.
Two new hydroxylated ethacrylic acid derivatives (compounds 1 and 2) and 11 new hydroxylated Tiglic acid derivatives (compounds 3-13), together with one known compound (compound 14), were isolated from the stems and branches of Enkianthus chinensis. Their structures were established by extensive spectroscopic analyses, while their absolute configurations were determined by X-ray crystallographic methods (compounds 1 and 2), Mo2(OAc)4-induced electronic circular dichroism experiments (compounds 3 and 4), and chemical methods (compounds 5-11). This study is the first investigation on the secondary metabolites of this species. The anti-inflammatory activities of all isolated compounds were evaluated in an LPS-induced mouse peritoneal macrophage model. Notably, compounds 3 and 12 both exerted potent inhibitory effects on NO production with IC50 values of 2.9 and 1.2 μM, respectively.
Structural, Spectroscopic, Thermal, and Magnetic Properties of a New Dinuclear Copper Coordination Compound with Tiglic acid
Materials (Basel) 2021 Apr 23;14(9):2148.PMID:33922582DOI:10.3390/ma14092148.
The first coordination compound of copper and Tiglic acid named tetrakis(μ-tiglato)bis(Tiglic acid)dicopper(II) was synthesized and crystallized from water solution. Its structure was determined and analyzed based on X-ray diffraction measurement. The paddle-wheel coordination system of the investigated compound was compared with other similar copper structures known in the literature. The Hirshfeld analysis was used for the detailed analysis of intermolecular interaction. The new compound was also characterized in terms of infrared absorption, thermal, and magnetic properties. The antiferromagnetic coupling of copper ions was found.
Biosynthesis of tiglic, ethacrylic, and 2-methylbutyric acids in a carabid beetle, Pterostichus (Hypherpes) californicus
J Chem Ecol 2007 May;33(5):963-70.PMID:17404818DOI:10.1007/s10886-007-9276-3.
Tiglic, 2-methylbutyric, and ethacrylic acids are found in the pygidial gland defensive fluid of many carabid beetles. By injecting a deuterium-labeled precursor into the carabid beetle Pterostichus (Hypherpes) californicus, and analyzing the defensive fluid by gas chromatography/mass spectrometry, we were able to demonstrate that tiglic and ethacrylic acids are biosynthesized from isoleucine via 2-methylbutyric acid. Moreover, we observed that the injection of L-isoleucine induces an increased production of Tiglic acid in P. californicus. A strong primary kinetic isotope effect was found to operate in the dehydrogenation step of 2-methylbutyric acid to tiglic and ethacrylic acids. Consequently, ethacrylic acid was found to preferentially accumulate the deuterium labeling from [2,3,4,4-(2)H(4)]isoleucine during our biosynthetic experiments.
Supramolecular solids as a medium for single-crystal-to-single-crystal E/Z photoisomerization: kinetic study of the photoreactions of two Zn-coordinated Tiglic acid molecules
Chemistry 2008;14(2):706-13.PMID:17955556DOI:10.1002/chem.200701037.
[Zn(TA)2(H2O)2] (H-TA=Tiglic acid) has been embedded in a framework composed of CECR (CECR=C-ethylcalix[4]resorcinarene) molecules to examine its E-->Z photoisomerization in a periodic framework. The photoisomerization of Tiglic acid in CECR-[Zn(TA)2(H2O)2]4 H2O proceeds without the [2+2]-dimerization reaction that often occurs in crystals of uncomplexed analogues, and without breakdown of the crystal lattice that frequently occurs in neat crystals. The two Zn-coordinated TA molecules are located in different size cavities. The rate constants of the isomerization reaction are strongly affected by the size of the reaction cavity. Analysis of the temperature dependence of the reaction rates and the occupancies in the final photostationary state shows that the activation energies and the standard enthalpies of activation are dependent on the difference between the reaction cavities. This is the first quantitative diffraction study of solid-state E/Z isomerization of a metal-coordinated ligand in a periodic host environment.
Enantiomeric ratios of 2-methylbutanoic acid and its methyl ester: Elucidation of novel biogenetic pathways towards (R)-methyl 2-methylbutanoate in a beverage fermented with shiitake
Food Chem 2018 Nov 15;266:475-482.PMID:30381215DOI:10.1016/j.foodchem.2018.06.027.
Up to 35% of (R)-methyl 2-methylbutanoate (M2MB) was observed in a beverage fermented with shiitake. As M2MB naturally occurs typically in high excesses of the (S)-enantiomer, the origin of the (R)-ester was elucidated by stable isotope labeled precursor-feeding studies. (R)-2-Methylbutanoic acid was identified as the main precursor in the substrate wort. Trace amounts of (R)-M2MB were produced by transformation of unsaturated secondary metabolites (tiglic aldehyde and Tiglic acid) derived from l-isoleucine. Surprisingly, shiitake esterified (R)-2-methylbutanoic acid faster to (R)-M2MB than the corresponding (S)-enantiomer. Concurrently, spontaneous non-enantioselective degradation of M2MB occurred in shiitake. This explains diverse enantiomeric ratios of M2MB and different enantiomeric ratios of 2-methylbutanoic acid and M2MB in the beverage. As the odor threshold values of (R)-and (S)-M2MB differ significantly, these findings are of high relevance for the overall flavor of the fermented beverage and elucidate the discrepancy of enantiomeric ratios of 2-alkyl-branched acids and esters reported in nature.