Isovanillic acid
(Synonyms: 异香兰酸; 3-Hydroxy-4-methoxybenzoic acid) 目录号 : GC36348
Isovanillic acid (Acide isovanillique, 3-Hydroxyanisic acid, 3-Hydroxy-p-anisic acid), a metabolite of isovanillin, is a selective inhibitor of neutrophil migration into inflamed tissue.
Cas No.:645-08-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Isovanillic acid (Acide isovanillique, 3-Hydroxyanisic acid, 3-Hydroxy-p-anisic acid), a metabolite of isovanillin, is a selective inhibitor of neutrophil migration into inflamed tissue.
| Cas No. | 645-08-9 | SDF | |
| 别名 | 异香兰酸; 3-Hydroxy-4-methoxybenzoic acid | ||
| Canonical SMILES | O=C(O)C1=CC=C(OC)C(O)=C1 | ||
| 分子式 | C8H8O4 | 分子量 | 168.15 |
| 溶解度 | Soluble in DMSO | 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 | 5.9471 mL | 29.7354 mL | 59.4707 mL |
| 5 mM | 1.1894 mL | 5.9471 mL | 11.8941 mL |
| 10 mM | 0.5947 mL | 2.9735 mL | 5.9471 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。
Active compounds in kepok banana peel as anti-inflammatory in acne vulgaris: Review article
Ann Med Surg (Lond) 2022 Nov 12;84:104868.PMID:36582904DOI:10.1016/j.amsu.2022.104868.
Background: Acne vulgaris (AV) is a chronic inflammatory skin condition affecting the pilosebaceous units characterized by recurrent comedones, erythematous papules and pustules. The disease is benign however may produce scarring, erythema, and hyperpigmentation resulting in physical and psychological problems. Conventional therapy may reduce the symptoms of AV nevertheless, has a possibility of resistance, unwanted side effects, and has high cost. Thus, utilizing natural remedies may be a useful. Methods: The data in this study were collect by search the keyword combinations of medical subject heading (mesh) of "inhibition", "antimicrobial", "banana peel", "acne vulgaris" and "antiinflammation" and relevant reference lists were manually searched in PubMed, EMBRASE and Scopus database. All relevant articles in data base above were included and narratively discussed in this review article. Objective: To discuss the bioactive potential of banana peel as an inflammatory modulator in acne vulgaris. Results: Banana peel contains many bioactive compounds, particularly phenolic and non-phenolic antioxidants (ascorbic acid, carotene, and cyanidin) which are pivotal in removing inflammatory products by inhibiting reactive oxygen species (ROS), protecting protease inhibitors from oxidative damage, and preventing fibroblasts degradation. Banana peel also contains anti-inflammatory agents such as trigonelline which inhibits bacterial enzymes and nucleic acid synthesis; Isovanillic acid which suppresses TNF-α production; and ferulic acid which inhibits the production of proinflammatory signaling and cytokines. Conclusion: Banana peel contains many bioactive compounds which demonstrate anti-inflammatory properties through several processes of the inflammatory pathway. However further research is needed to confirm this finding.
Synthesis, Characterization, and Low-Toxicity Study of a Magnesium(II) Complex Containing an Isovanillate Group
ACS Omega 2020 Feb 13;5(7):3504-3512.PMID:32118165DOI:10.1021/acsomega.9b03804.
The beneficial effect of polyphenols and magnesium(II) against oxidative stress motivated our research group to explore the antioxidant activity of phenMgIso, an aqueous soluble magnesium(II) complex containing 1,10-phenanthroline (phen) and Isovanillic acid (Iso) as ligands. Combined electrospray ionization-mass spectrometry and DOSY-NMR techniques identified two complexes in methanolic solution: hexacoordinated [Mg(phen)2(Iso)]+ and tetracoordinated [Mg(phen)(Iso)]+. The cyclic voltammogram of phenMgIso in the anodic region showed a cyclic process that interrupts the Isovanillic acid degradation, probably by stabilization of the corresponding phenoxyl radical via complexation with Mg(II), which is interesting for antioxidant applications. phenMgIso competes with 2,2,6,6-tetramethylpiperidine by 1O2 with IC50(1O2) = 15 μg m-1 and with nitrotetrazolium blue chloride by superoxide ions (IC50(O2 •-) = 3.6 μg mL-1). Exposure of both zebrafish (2 mg L-1) and wistar male rats (3 mg kg-1 day-1 dose for 21 days) to phenMgIso does not cause mortality or visual changes compared with the respective control groups, thus phenMgIso could be considered safe under the conditions of this study. Moreover, no significant changes in comparison to both control groups were observed in the biochemical parameters on the brain-acetylcholinesterase activity, digestive tract enzyme catalase, and glutathione-S-transferase. Conversely, the performance of superoxide dismutase activity in wistar male rats increased in the presence of a complex, resulting in enhanced capacity of rats for superoxide radical enzymatic scavenging. The synergistic action of phenMgIso may be explained by the strong electrostatic interaction between Mg(II) and the O,O(phenolate) group, which makes the Iso ligand easier to oxidize and deprotonate, generating a cyclic stable species under oxidative conditions.
A New Octadecenoic Acid Derivative from Caesalpinia gilliesii Flowers with Potent Hepatoprotective Activity
Pharmacogn Mag 2016 May;12(Suppl 3):S332-6.PMID:27563221DOI:10.4103/0973-1296.185752.
Background: Caesalpinia gilliesii Hook is an ornamental shrub with showy yellow flowers. It was used in folk medicine due to its contents of different classes of secondary metabolites. In our previous study, dichloromethane extract of C. gilliesii flowers showed a good antioxidant activity. Aim of the study: Isolation and identification of bioactive hepatoprotective compounds from C. gilliesii flowers dichloromethane fraction. Materials and methods: The hepatoprotective activity of dichloromethane fraction and isolated compounds were studied in CCl4-intoxicated rat liver slices by measuring liver injury markers (alanine aminotransferase, aspartate aminotransferase and glutathione [GSH]). All compounds were structurally elucidated on the basis of electron ionization-mass spectrometry, one- and two-dimensional nuclear magnetic resonance. Results: A new 12,13,16-trihydroxy-14(Z)-octadecenoic acid was identified in addition to the known β-sitosterol-3-O-butyl, daucosterol, isorhamnetin, isorhamnetin-3-O-rhamnoside, luteolin-7,4'-dimethyl ether, genistein-5-methyl ether, luteolin-7-O-rhamnoside, Isovanillic acid, and p-methoxybenzoic acid. Dichloromethane fraction and isorhamnetin were able to significantly protect the liver against intoxication. Moreover, the dichloromethane fraction and the isolated phytosterols induced GSH above the normal level. Conclusion: The hepatoprotective activity of C. gilliesii may be attributed to its high content of phytosterols and phenolic compounds. Summary: Bioactive Hepatoprotective phytosterols and phenolics from chloroform extract of Caesalpinia gilliesii Abbreviations used: ALT: Alanine Aminotransferase; AST: Aspartate aminotransferase; GSH: Glutathione; SC50: Scavenging Capacity 50 (SC 50); COSY: Correlation spectroscopy; NMR: Nuclear Magnetic Resonance; CC: Column chromatography; EI-MS: Electron-impact mass spectrometry; HSQC: Heteronuclear single-quantum correlation.
Aerobic and Anaerobic Catabolism of Vanillic Acid and Some Other Methoxy-Aromatic Compounds by Pseudomonas sp. Strain PN-1
Appl Environ Microbiol 1983 Dec;46(6):1286-92.PMID:16346441DOI:10.1128/aem.46.6.1286-1292.1983.
Vanillic acid (4-hydroxy-3-methoxybenzoic acid) supported the anaerobic (nitrate respiration) but not the aerobic growth of Pseudomonas sp. strain PN-1. Cells grown anaerobically on vanillate oxidized vanillate, p-hydroxybenzoate, and protocatechuic acid (3,4-dihydroxybenzoic acid) with O(2) or nitrate. Veratric acid (3,4-dimethoxybenzoic acid) but not Isovanillic acid (3-hydroxy-4-methoxybenzoic acid) induced cells for the oxic and anoxic utilization of vanillate, and protocatechuate was detected as an intermediate of vanillate breakdown under either condition. Aerobic catabolism of protocatechuate proceeded via 4,5-meta cleavage, whereas anaerobically it was probably dehydroxylated to benzoic acid. Formaldehyde was identified as a product of aerobic demethylation, indicating a monooxygenase mechanism, but was not detected during anaerobic demethylation. The aerobic and anaerobic systems had similar but not identical substrate specificities. Both utilized m-anisic acid (3-methoxybenzoic acid) and veratrate but not o- or p-anisate and isovanillate. Syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid), 3-O-methylgallic acid (3-methoxy-4,5-dihydroxybenzoic acid), and 3,5-dimethoxybenzoic acid were attacked under either condition, and formaldehyde was liberated from these substrates in the presence of O(2). The anaerobic demethylating system but not the aerobic enzyme was also active upon guaiacol (2-methoxyphenol), ferulic acid (3-[4-hydroxy-3-methoxyphenyl]-2-propenoic acid), 3,4,5-trimethoxycinnamic acid (3-[3,4,5-trimethoxyphenyl]-2-propenoic acid), and 3,4,5-trimethoxybenzoic acid. The broad specificity of the anaerobic demethylation system suggests that it probably is significant in the degradation of lignoaromatic molecules in anaerobic environments.
Tyrosinase inhibitor from black rice bran
J Agric Food Chem 2003 Nov 19;51(24):6953-6.PMID:14611153DOI:10.1021/jf030388s.
The inhibitor of tyrosinase activity in black rice bran was investigated. The methanol extract from black rice bran was re-extracted with hexane, chloroform, ethyl acetate, or water. The ethyl acetate extract had the most potent inhibition against tyrosinase activity by 80.5% at a concentration of 0.4 mg/mL. Inhibitory compound in the ethyl acetate fraction was isolated by silica gel column chromatography, and identified as protocatechuic acid methyl ester (compound 1) by GC, GC-MS, IR, and 1H and 13C NMR spectroscopy. Compound 1 inhibited 75.4% of tyrosinase activity at a concentration of 0.50 micromol/mL. ID(50) (50% inhibition dose) value of compound 1 was 0.28 micromol/mL. To study the structure-activity relationship, protocatechuic acid (2), vanillic acid (3), vanillic acid methyl ester (4), Isovanillic acid (5), Isovanillic acid methyl ester (6), veratric acid (7), and veratric acid methyl ester (8) were also assayed.