3-Hydroxybenzaldehyde
(Synonyms: 3-羟基苯甲醛) 目录号 : GC39328
3-Hydroxybenzaldehyde (3-HBA), one of the benzaldehydes commonly found in nature, is produced by 3-hydroxybenzyl-alcohol dehydrogenase, and is a substrate of aldehyde dehydrogenase (ALDH) in rats and humans (ALDH2). 3-Hydroxybenzaldehyde exhibits vasculoprotective effects.
Cas No.:100-83-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3-Hydroxybenzaldehyde (3-HBA), one of the benzaldehydes commonly found in nature, is produced by 3-hydroxybenzyl-alcohol dehydrogenase, and is a substrate of aldehyde dehydrogenase (ALDH) in rats and humans (ALDH2). 3-Hydroxybenzaldehyde exhibits vasculoprotective effects.
[1] Byung Soo Kong, et al. PLoS One. 2016 Mar 22;11(3):e0149394.
| Cas No. | 100-83-4 | SDF | |
| 别名 | 3-羟基苯甲醛 | ||
| Canonical SMILES | O=CC1=CC=CC(O)=C1 | ||
| 分子式 | C7H6O2 | 分子量 | 122.12 |
| 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 | 8.1887 mL | 40.9433 mL | 81.8867 mL |
| 5 mM | 1.6377 mL | 8.1887 mL | 16.3773 mL |
| 10 mM | 0.8189 mL | 4.0943 mL | 8.1887 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。
3-Hydroxybenzaldehyde
Acta Crystallogr C 2000 Nov;56 Pt 11:1348-50.PMID:11077294DOI:10.1107/s0108270100010441.
The title compound, C(7)H(6)O(2), forms infinite chains where the molecules are hydrogen bonded via the hydroxyl and aldehyde groups, with an O.O distance of 2.719 (3) A. Interchain interactions are weak. The geometry of the ring differs from the ideal form due to the effect of the substituents. Ab initio (Hartree-Fock self-consistent field-molecular orbital and density functional theory) calculations for the free molecule reproduce well the observed small distortions of the ring. In the crystal, the geometry deviates from the ideal C(s) symmetry of the free molecule, as given by the ab initio calculations. The aldehyde and hydroxyl groups are twisted around the single bonds which join them to the ring as a result of the intermolecular hydrogen-bond interactions. These are also responsible for an elongation of the hydroxy C-OH bond compared with that calculated for the free molecule.
3-Hydroxybenzaldehyde and 4-Hydroxybenzaldehyde enhance survival of mouse astrocytes treated with Angiostrongylus cantonensis young adults excretory/secretory products
Biomed J 2021 Dec;44(6 Suppl 2):S258-S266.PMID:35300947DOI:10.1016/j.bj.2020.11.008.
Background: Human cerebral angiostrongyliasis, induced by Angiostrongylus cantonensis, is an emerging disease in many parts of the world. A. cantonensis is also an important causative agent of eosinophilic meningitis and eosinophilic meningoencephalitis in humans. 3-Hydroxybenzaldehyde (3-HBA) and 4-Hydroxybenzaldehyde (4-HBA) have been shown to increase intracellular antioxidant activity, vasculoprotective potency, wound healing, and cell migration. However, the function of 3-HBA and 4-HBA in mouse astrocytes in response to A. cantonensis young adults excretory-secretory products (ESPs) treatment remains unclear. Methods: Here, we examined the effect of 3-HBA and 4-HBA by real-time qPCR, western blotting, and cell viability assay in astrocytes after A. cantonensis young adults ESPs treatment. The real-time qPCR, western blotting were employed to detect the expression of apoptosis- and Shh pathway-related molecule. The percentage of cell viability was monitored by CCK-8 assay. Results: We demonstrated that expression of apoptosis-related molecules was increased in response to A. cantonensis young adults ESPs treatment. However, the cell viability of astrocytes was elevated by treatment with 3-HBA and 4-HBA. Further investigation found that 3-HBA and 4-HBA activate the Shh signaling pathway and inhibit apoptosis-related molecule expression. Conclusions: These findings were confirmed using A. cantonensis young adults ESPs to activate apoptosis-related pathways in astrocytes. Moreover, 3-HBA and 4-HBA induced a protective phenotype through regulation of apoptosis in response to A. cantonensis young adults ESPs treatment. Hence, 3-HBA and 4-HBA represent potential therapeutic drugs for the treatment of human angiostrongyliasis.
Vasculoprotective Effects of 3-Hydroxybenzaldehyde against VSMCs Proliferation and ECs Inflammation
PLoS One 2016 Mar 22;11(3):e0149394.PMID:27002821DOI:10.1371/journal.pone.0149394.
3-Hydroxybenzaldehyde (3-HBA) is a precursor compound for phenolic compounds like Protocatechuic aldehyde (PCA). From recent reports, PCA has shown vasculoprotective potency, but the effects of 3-HBA remain unclear. The aim of this study is to investigate the vasculoprotective effects of 3-HBA in endothelial cells, vascular smooth muscle cells and various animal models. We tested effects of 3-HBA in both vitro and vivo. 3-HBA showed that it prevents PDGF-induced vascular smooth muscle cells (VSMCs) migration and proliferation from MTS, BrdU assays and inhibition of AKT phosphorylation. It arrested S and G0/G1 phase of VSMC cell cycle in PI staining and it also showed inhibited expression levels of Rb1 and CD1. In human umbilical vein endothelial cells (HUVECs), 3-HBA inhibited inflammatory markers and signaling molecules (VCAM-1, ICAM-1, p-NF-κB and p-p38). For ex vivo, 3-HBA has shown dramatic effects in suppressing the sprouting from aortic ring of Spargue Dawley (SD) rats. In vivo data supported the vasculoprotective effects of 3-HBA as it inhibited angiogenesis from Matrigel Plug assay in C57BL6 mouse, prevented ADP-induced thrombus generation, increased blood circulation after formation of thrombus, and attenuated neointima formation induced by common carotid artery balloon injury of SD rats. 3-HBA, a novel therapeutic agent, has shown vasculoprotective potency in both in vitro and in vivo.
Spectrophotometric resolution of ternary mixtures of salicylaldehyde, 3-Hydroxybenzaldehyde and 4-hydroxybenzaldehyde by the derivative ratio spectrum-zero crossing method
Talanta 1992 May;39(5):547-53.PMID:18965415DOI:10.1016/0039-9140(92)80179-h.
A new spectrophotometric method for resolving ternary mixtures is proposed. The method is based on the simultaneous use of the first derivative of ratio spectra and measurements of zero-crossing wavelengths. The ratio spectrum is obtained by dividing the amplitudes of the absorption spectrum of the mixture by a standard spectrum of one of the components giving the first derivative of the ratio spectrum. The concentrations of the other components is then determined from their respective calibration graphs established by measuring the ratio derivative analytical signal at the selected zero-crossing points. The method has been applied to resolving ternary mixtures of the isomers salicylaldehyde, 3-Hydroxybenzaldehyde and 4-hydroxybenzaldehyde. Previously, we also resolved the binary mixture of salicylaldehyde and 3-Hydroxybenzaldehyde. The method compares favourably with other spectrophotometric methods.
An investigation on 3-Hydroxybenzaldehyde for exploring terahertz low-frequency vibration modes with quasi-harmonic approximation method
Spectrochim Acta A Mol Biomol Spectrosc 2023 Feb 15;287(Pt 1):122046.PMID:36334415DOI:10.1016/j.saa.2022.122046.
3-Hydroxybenzaldehyde (3-HBA) was investigated in the range of 0.6-2.8 THz by terahertz time-domain spectroscopy (THz-TDS) and solid-state density functional theory (ss-DFT) with first-principles calculation. Four distinct peaks were found respectively, and among them, the intensity disparity between experiment and simulation spectra at 2.04 THz was recognized as the biggest inconsistency. Considering thermal behavior can be responsible for this, quasi-harmonic approximation (QHA) method was introduced to mimic the unit cell volume expansion. According to vibrational modes analysis, it was ascertained that the biggest vibrational modes discrepancy was also located at 2.04 THz. Molecules in 0% and 4% unit cell expansion exhibit an opposite rotational direction in a-b plane compared with 2% unit cell expansion. Noncovalent intermolecular interactions were investigated with independent gradient model (IGM), and the result indicates that hydrogen bonding is the dominating noncovalent interaction of 3-HBA. While calculating systematic potential energy to the displaced bonds stretching involving hydrogen atoms, it was found the anomalous potential energy variation to the bond stretching provides a possible explanation for the rotation direction divergence, that is, the rotation direction divergence can be related to some hydrogen atoms seeking lower overall potential energy around their equilibrium positions during bond stretching in response to the variational intermolecular van der Waals force. This research combined THz-TDS with the quasi-harmonic approximation method, elucidating the principle of vibrational characteristics in different volumes, which is beneficial to the investigation of the terahertz low-frequency vibration to thermal behavior as a reference in biochemistry and other fields.