Isovanillin
(Synonyms: 异香兰素,3-Hydroxy-4-methoxybenzaldehyde) 目录号 : GC33753
Isovanillin (5-Formylguaiacol, 3-Hydroxy-p-anisaldehyde, 3-Hydroxy-4-methoxybenzaldehyde) is a reversible inhibitor of aldehyde oxidase. It is largely used as pharmaceutical intermediates and also applied in food and beverage industry, synthetic fragrances, chemical.
Cas No.:621-59-0
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
Isovanillin (5-Formylguaiacol, 3-Hydroxy-p-anisaldehyde, 3-Hydroxy-4-methoxybenzaldehyde) is a reversible inhibitor of aldehyde oxidase. It is largely used as pharmaceutical intermediates and also applied in food and beverage industry, synthetic fragrances, chemical.
Isovanillin is a potent competitive inhibitor of 2-hydroxybenzaldehyde oxidation by aldehyde oxidase with Ki values of 0.664 μM (n = 2)[1].
[1] Panoutsopoulos GI, et al. Acta Biochim Pol. 2004, 51(3):649-63.
| Cas No. | 621-59-0 | SDF | |
| 别名 | 异香兰素,3-Hydroxy-4-methoxybenzaldehyde | ||
| Canonical SMILES | O=CC1=CC=C(OC)C(O)=C1 | ||
| 分子式 | C8H8O3 | 分子量 | 152.15 |
| 溶解度 | DMSO : 100 mg/mL (657.25 mM; Need ultrasonic) | 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 | 6.5725 mL | 32.8623 mL | 65.7246 mL |
| 5 mM | 1.3145 mL | 6.5725 mL | 13.1449 mL |
| 10 mM | 0.6572 mL | 3.2862 mL | 6.5725 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。
Antidiarrheal activities of Isovanillin, iso-acetovanillon and Pycnocycla spinosa Decne ex.Boiss extract in mice
Res Pharm Sci 2014 Mar-Apr;9(2):83-9.PMID:25657776doi
Isovanillin and iso-acetovanillon are two phenolic components isolated from a number of plants including Pycnocycla spinosa. P. spinosa extract has antispasmodic and antidiarrheal activities. However, no comparative study has been done on antidiarrheal action of Isovanillin and iso- acetovanillon, so far. The aim of this study was to investigate antidiarrheal action of Isovanillin and iso-acetovanillon and their effects on small intestinal transit, for comparison with propantheline. Male mice (25-30 g), fasted over night with free access to water, were treated with test compounds or control (p.o.). Thirty min later castor oil (0.5 ml) was given orally to the animals. In another groups of animals MgSO4 (0.5 ml of 10% solution) was given first and half an hour later the test drugs were administered. Onset and number of wet defecations were recorded for each animal over 3.5 h after treatment with diarrhoea inducing agents. In another groups, intestinal transit of charcoal meal was determined following administration of the compounds. Isovanillin (2 mg/kg & 5 mg/kg), iso-acetovanillon (2 mg/kg & 5 mg/kg) and P. spinosa extract (5 mg/kg) delayed onset of diarrhoea and significantly reduced wet defecation induced by castor oil and MgSO4. They all had antidiarrheal effect similar to propantheline (5 mg/kg). Isovanillin, iso-acetovanillon and P. spinosa extract compared to control groups, significantly reduced small intestinal transit of charcoal meal. This study shows that antidiarrheal effect of P. spinosa extract is at least partially due to presence of two active compounds Isovanillin and iso-acetovanillon.
Antispasmodic activity of Isovanillin and isoacetovanillon in comparison with Pycnocycla spinosa Decne.exBoiss extract on rat ileum
Res Pharm Sci 2014 May-Jun;9(3):187-92.PMID:25657788doi
Isovanillin and isoacetovanillon are two components found in P. spinosa Decne.exBoiss extract with no previously reported effect on ileum contractions. Spasmolytic effect of Isovanillin and isoacetovanillon were examined on response to electrical field stimulation (EFS), acetylcholine (ACh) and 5-HT in strips of rat ileum. Longitudinal ileum strips were set up in an organ bath containing oxygenated Tyrode's solution. All strips that was contracted in response to EFS, acetylcholine or 5-HT showed relaxation in the presence of Isovanillin (5-320 μg/ml), or isoacetovanillon (5-320 μg/ml). Isovanillin and isoacetovanillon inhibited the response to 5-HT with IC50 values of 356±50μM and 622±110μM respectively. They reduced the response to EFS without significantly affecting the acetylcholine response. P. spinosa extract (5-160 μg/ml) in a concentration dependent manner reduced the response to 5-HT, acetylcholine and EFS. This study demonstrated that Isovanillin and isoacetovanillon are relaxant of ileum contractions induced by 5-HT and EFS and they have contribution to the relaxant effect of P. spinosa extract but other components are responsible for the inhibition of acetylcholine by the extract.
Isovanillin derived N-(un)substituted hydroxylamines possessing an ortho-allylic group: valuable precursors to bioactive N-heterocycles
Org Biomol Chem 2014 Apr 28;12(16):2552-8.PMID:24576957DOI:10.1039/c3ob42460j.
The intramolecular 1,3-dipolar cycloaddition of Isovanillin derived N-aryl hydroxylamines possessing ortho-allylic dipolarophiles affords novel benzo analogues of tricyclic isoxazolidines that can be readily transformed into functionalized lactams, γ-aminoalcohols and oxazepines. The corresponding N-unsubstituted hydroxylamines give rise to tetrahydroisoquinolines. Anxiogenic properties of these compounds are tested in zebra fish.
Radioiodination, nasal nanoformulation and preliminary evaluation of Isovanillin: A new potential brain cancer-targeting agent
Appl Radiat Isot 2022 Nov;189:110464.PMID:36150311DOI:10.1016/j.apradiso.2022.110464.
Brain cancer is a challenging disease to treat using conventional approaches. The present investigation aimed to develop a radiopharmaceutical targeting brain cancer based on natural Isovanillin. Different parameters were optimized, resulting in high radiolabeling efficiency (97.3 ± 1.2%) and good stability (<48 h). The tracer was formulated for intranasal delivery in a chitosan nanoparticles system with a mean particle size of 141 ± 2 nm, a polydispersity index of 0.23 ± 0.02, and a zeta potential of -17.4 ± 0.3 mV to enhance nasal uptake and surmount the blood-brain barrier. The system was characterized and assessed in-vitro for suitability and specificity and evaluated in-vivo in normal and tumorized mice. The biodistribution profile in brain tumor showed 20.5 ± 0.4 %ID/g localization and cancer cell targeting within 60 min. Improvement in brain tumor uptake resulted from both the nanoformulation and nasal administration of iodoisovanillin. Overall, the reported results encourage the potential use of the nanoformulated labeled compound as an anticancer agent.
Metabolism of Isovanillin by aldehyde oxidase, xanthine oxidase, aldehyde dehydrogenase and liver slices
Pharmacology 2005 Mar;73(4):199-208.PMID:15627845DOI:10.1159/000082860.
Aromatic aldehydes are good substrates of aldehyde dehydrogenase activity but are relatively poor substrates of aldehyde oxidase and xanthine oxidase. However, the oxidation of xenobiotic-derived aromatic aldehydes by the latter enzymes has not been studied to any great extent. The present investigation compares the relative contribution of aldehyde dehydrogenase, aldehyde oxidase and xanthine oxidase activities in the oxidation of Isovanillin in separate preparations and also in freshly prepared and cryopreserved liver slices. The oxidation of Isovanillin was also examined in the presence of specific inhibitors of each oxidizing enzyme. Minimal transformation of Isovanillin to isovanillic acid was observed in partially purified aldehyde oxidase, which is thought to be due to residual xanthine oxidase activity. Isovanillin was rapidly metabolized to isovanillic acid by high amounts of purified xanthine oxidase, but only low amounts are present in guinea pig liver fraction. Thus the contribution of xanthine oxidase to Isovanillin oxidation in guinea pig is very low. In contrast, Isovanillin was rapidly catalyzed to isovanillic acid by guinea pig liver aldehyde dehydrogenase activity. The inhibitor studies revealed that Isovanillin was predominantly metabolized by aldehyde dehydrogenase activity. The oxidation of xenobiotic-derived aromatic aldehydes with freshly prepared or cryopreserved liver slices has not been previously reported. In freshly prepared liver slices, Isovanillin was rapidly converted to isovanillic acid, whereas the conversion was very slow in cryopreserved liver slices due to low aldehyde dehydrogenase activity. The formation of isovanillic acid was not altered by allopurinol, but considerably inhibited by disulfiram. It is therefore concluded that Isovanillin is predominantly metabolized by aldehyde dehydrogenase activity, with minimal contribution from either aldehyde oxidase or xanthine oxidase.