Angelic acid
(Synonyms: 当归酸) 目录号 : GC35343
Angelic acid ((Z)-2-Methylbut-2-enoic acid) is a monocarboxylic unsaturated organic acid that is mostly found in the plants of the family Apiaceae.
Cas No.:565-63-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Angelic acid ((Z)-2-Methylbut-2-enoic acid) is a monocarboxylic unsaturated organic acid that is mostly found in the plants of the family Apiaceae.
| Cas No. | 565-63-9 | SDF | |
| 别名 | 当归酸 | ||
| Canonical SMILES | C/C=C(C)\C(O)=O | ||
| 分子式 | C5H8O2 | 分子量 | 100.12 |
| 溶解度 | DMSO: 250 mg/mL (2497.00 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。
Biosynthesis of angelyl-CoA in Saccharomyces cerevisiae
Microb Cell Fact 2018 May 12;17(1):72.PMID:29753326DOI:10.1186/s12934-018-0925-8.
Background: The Angelic acid moiety represents an essential modification in many biologically active products. These products are commonly known as angelates and several studies have demonstrated their therapeutic benefits, including anti-inflammatory and anti-cancer effects. However, their availability for use in the development of therapeutics is limited due to poor extraction yields. Chemical synthesis has been achieved but its complexity prevents application, therefore microbial production may offer a promising alternative. Here, we engineered the budding yeast Saccharomyces cerevisiae to produce angelyl-CoA, the CoA-activated form of Angelic acid. Results: For yeast-based production of angelyl-CoA we first expressed genes recently identified in the biosynthetic cluster ssf of Streptomyces sp. SF2575 in S. cerevisiae. Exogenous feeding of propionate and heterologous expression of a propionyl-CoA synthase from Streptomyces sp. were initially employed to increase the intracellular propionyl-CoA level, resulting in production of angelyl-CoA in the order of 5 mg/L. Substituting the Streptomyces sp. propionyl-CoA carboxylase with a carboxylase derived from Streptomyces coelicolor resulted in angelyl-CoA levels up to 6.4 mg/L. In vivo analysis allowed identification of important intermediates in the pathway, including methyl-malonyl-CoA and 3-hydroxyl-2-methyl-butyryl-CoA. Furthermore, methyl-malonate supplementation and expression of matB CoA ligase from S. coelicolor allowed for methyl-malonyl-CoA synthesis and supported, together with parts of the ssf pathway, angelyl-CoA titres of approximately 1.5 mg/L. Finally, feeding of Angelic acid to yeasts expressing acyl-CoA ligases from plant species led to angelyl-CoA production rates of approximately 40 mg/L. Conclusions: Our results demonstrate the biosynthesis of angelyl-CoA in yeast from exogenously supplied carboxylic acid precursors. This is the first report on the activity of the ssf genes. We envision that our approach will provide a platform for a more sustainable production of the pharmaceutically important compound class of angelates.
New neryl esters from Helichrysum italicum (Roth) G. Don (Asteraceae) essential oil
Nat Prod Res 2022 Apr;36(8):2002-2008.PMID:33111574DOI:10.1080/14786419.2020.1839462.
Helichrysum italicum (immortelle) is a dwarf aromatic shrub native to the Mediterranean region. The typical subspecies (italicum) produces an essential oil rich in neryl acetate and characteristic β-diketones, italidiones, highly valued in the perfume industry. As esters are an important group of aroma-active volatiles, herein the composition of the ester fraction of this immortelle chemotype essential oil was studied in detail. Chromatographic separation of Corsican immortelle essential oil enabled the discovery of numerous potentially olfactory-interesting esters of nerol and/or Angelic acid, undetectable by direct GC-MS analyses of the unfractioned oil. Four esters of nerol and medium-chain branched fatty acids represent new natural products, while several other esters have a rather restricted occurrence in the Plant Kingdom.
Trehangelin E, a bisacyl trehalose with plant growth promoting activity from a rare actinomycete Polymorphospora sp. RD064483
J Antibiot (Tokyo) 2022 May;75(5):296-300.PMID:35322208DOI:10.1038/s41429-022-00519-5.
Trehangelin E (1), a new bisacyl trehalose, was isolated from the culture extract of an actinomycete Polymorphospora sp. RD064483, along with three known congeners, trehangelins A, B, and D. Compound 1 is a new trehalose derivative acylated with (Z)-2-methyl-2-butenoic acid (Angelic acid) at 3- and 6'-positions, as determined by NMR and MS analyses. Compound 1 promoted root elongation of germinated lettuce seeds by 30% at 1 μM and 90% at 10 μM compared to the nontreated seeds. Similar promoting activity of root elongation was also observed with trehangelins A and B at the same level.
Dehydropyrrolizidine alkaloids in two Cryptantha species: including two new open chain diesters one of which is amphoteric
Phytochem Anal 2013 May-Jun;24(3):201-12.PMID:23070903DOI:10.1002/pca.2400.
Introduction: A livestock poisoning outbreak near Kingman, Arizona, USA, potentially linked to dehydropyrrolizidine alkaloids, prompted an evaluation of some local plants for the presence of these hepatotoxic alkaloids. Objective: To qualitatively and quantitatively examine two species of Cryptantha, a Boraginaceous genus previously shown to produce potentially toxic pyrrolizidine alkaloids, collected from the vicinity of Kingman, Arizona. Method: Plant extracts were analysed using HPLC-electrospray ionisation (+)-MS and MS/MS to determine the presence of dehydropyrrolizidine alkaloid esters. Identities were confirmed by comparison of chromatographic and MS data with authenticated standards and, in the case of the previously undescribed alkaloids, using one- and two-dimensional NMR spectroscopy and high-resolution mass measurement. Results: Cryptantha inequata and C. utahensis were shown to produce retronecine-based dehydropyrrolizidine alkaloids at approximately 0.05% and 0.09% w/w respectively. Cryptantha inequata produced mainly echimidine, acetylechimidine and echiuplatine; dehydropyrrolizidine alkaloids that were previously associated with Echium plantagineum. The previously undescribed structure of echiuplatine was elucidated as an amphoteric, open chain diester with Angelic acid and 3-hydroxy-3-methylglutaric acid. Along with lycopsamine, intermedine and dihydroxyechiumine, C. utahensis produced cryptanthine, a previously undescribed open chain diester alkaloid esterified with Angelic acid and 2,3-dihydroxy-2-methylbutanoic acid. All pyrrolizidine alkaloids detected were present in the plants mainly as their N-oxides. Conclusion: The retronecine-based alkaloids detected in both Cryptantha species herein investigated aligns them within the Krynitzkia subgenus. The dehydropyrrolizidine alkaloids detected are expected to be toxic but the low levels in the plants potentially mitigate the risk. The identification of the amphoteric echiuplatine provides a cautionary note with respect to the analysis of total dehydropyrrolizidine alkaloid content.
Two new eudesman-4α-ol epoxides from the stem essential oil of Laggera pterodonta from Côte d'Ivoire
Nat Prod Res 2020 Oct;34(19):2765-2771.PMID:30908078DOI:10.1080/14786419.2019.1586701.
The investigation of the stem essential oil of Laggera pterodonta (DC.) Sch. Bip. ex Oliv. (Asteraceae) from Côte d'Ivoire was carried out, using a combination of chromatographic (GC-RI, CC, pc-GC) and spectroscopic (GC-MS, 13C NMR) techniques. This study led to the identification of fifty constituents of which two new natural compounds 7β,11β-epoxy-eudesman-4α-ol and 7α,11α-epoxy-eudesman-4α-ol. Their structures were elucidated by 1 D and 2 D NMR spectroscopy after pc-GC purifying. Finally, 98.9% of the whole composition of the oil was identified with a high amount of 2,5-dimethoxy-p-cymene (78.9%). The other significant components were α-humulene (6.2%), (E)-β-caryophyllene (1.7%), thymyl methyl oxide (1.7%), α-phellandrene (1.5%), p-cymene (1.2%), (3αH,4βH,6αH,1αMe)-1,6-epoxy-3-hydroxycarvotanacetone Angelic acid ester (1.1%) and 10-epi-γ-eudesmol (1.0%).