4-Hydroxybenzyl Alcohol

• CAS: 623-05-2
• Catalog Number: ACM623052-2
• Category: Main Products
• Molecular Weight: 124.1
• Molecular Formula: C7H8O2
• Synonyms: P-(HYDROXYMETHYL)PHENOL;P-HYDROXYBENZYL ALCOHOL;RARECHEM AL BD 0098;4-METHYLOLPHENOL;4-HYDROXYBENZYL ALCOHOL;4-hydroxybenzenemethanol;HYDROXYBENZYL-4 ALCOHOL;FEMA 3987
• IUPAC Name: 4-(hydroxymethyl)phenol
• Canonical SMILES: C1=CC(=CC=C1CO)O
• InChI Key: BVJSUAQZOZWCKN-UHFFFAOYSA-N
• Boiling Point: 251-253°C
• Melting Point: 114-122°C(lit.)
• Flash Point: 251-253°C
• Density: 1.22 g/cm³
• Appearance: Powder
• Exact Mass: 124.05200
• Hazard Statements: Xi
• RIDADR: NONH for all modes of transport
• Safety Description: 26-24/25-36
• Stability: Stable under normal temperatures and pressures.
• Supplemental Hazard Statements: H315-H335-H319
• Symbol: GHS07
• WGK Germany: 3

Case Study

4-Hydroxybenzyl Alcohol for Antidepressant Effects via Monoaminergic Modulation and Cytoskeletal Remodeling

Chen W-C, et al. Journal of Ethnopharmacology, 2016, 182, 190-199.

4-Hydroxybenzyl alcohol (HBA) from Gastrodia elata modulates the monoaminergic system and neuronal cytoskeletal dynamics, offering a promising approach for the treatment of depression.
HBA treatment in Sprague-Dawley rats showed a marked reduction in immobility time in the forced swimming test (FST), indicating antidepressant-like effects. The compound modulated serotonin (5-HT) and dopamine (DA) metabolism, increasing the 5-HT to 5-hydroxyindoleacetic acid (5-HIAA) ratio in the hippocampus, and the DA to DOPAC and homovanillic acid (HVA) ratios in the frontal cortex and amygdala. Furthermore, HBA influenced the expression of neuronal cytoskeleton remodeling-related proteins. It significantly upregulated positive regulators such as CRMP2 and PFN1, while downregulating negative regulators like Slit1 and RhoA.
In Hs683 cells, HBA directly downregulated Slit1 expression, further supporting its role in cytoskeletal remodeling.

4-Hydroxybenzyl Alcohol Protects Against Cerebral Ischemia via Protein Disulfide Isomerase Induction

Descamps E, et al. Neuroscience Research, 2009, 64(2), 137-142.

4-Hydroxybenzyl alcohol (4-HBA) demonstrates significant neuroprotective effects in a murine model of focal brain ischemia/reperfusion. This case study explores the mechanism through which 4-HBA reduces cerebral infarct volumes, focusing on the induction of protein disulfide isomerase (PDI) as a key player in stroke protection.
Mechanism of Action: Administered intravenously at 25 mg/kg, 4-HBA reduced total, cortical, and sub-cortical infarct volumes by 42%, 28%, and 55%, respectively. In contrast to its isomers, 3-hydroxybenzyl alcohol (3-HBA) and 2-hydroxybenzyl alcohol (2-HBA), 4-HBA uniquely induced PDI in intact mouse brains. This induction was crucial for its protective effect, as the stroke protection was fully abrogated by bacitracin, a PDI inhibitor. Notably, 4-HBA did not exhibit antioedematous properties and was non-toxic in neurobehavioral tests (rotarod test) at doses up to 200 mg/kg.
Conclusion: The neuroprotective effects of 4-HBA in cerebral ischemia are mediated by the induction of PDI, positioning this protein as a promising target for managing brain injury disorders. 4-HBA's lack of neurotoxicity further supports its potential for therapeutic use in neuroprotection.

Neuroprotective Effect of 4-Hydroxybenzyl Alcohol in Transient Focal Cerebral Ischemia via Anti-Apoptosis Mechanism

Yu S-S, et al. Brain Research, 2010, 1308, 167-175.

4-Hydroxybenzyl alcohol (4-HBA) has demonstrated significant neuroprotective effects in models of cerebral ischemia. In a rat model of transient focal cerebral ischemia induced by middle cerebral artery occlusion, administration of 4-HBA (25 and 50 mg/kg) prior to ischemia markedly reduced infarct volumes in both cortical and sub-cortical regions. Specifically, at 50 mg/kg, total infarct volumes were significantly reduced compared to untreated ischemic controls. Neurological assessments and Nissl staining revealed substantial improvements in brain tissue integrity and function. Furthermore, 4-HBA treatment led to a significant reduction in TUNEL-positive apoptotic cells. Immunoblot and immunofluorescence analysis indicated that 4-HBA upregulated anti-apoptotic Bcl-2 protein expression while inhibiting caspase-3 activation, a key apoptotic marker. These findings suggest that 4-HBA exerts its neuroprotective effects by attenuating apoptosis, thereby mitigating ischemic injury. This highlights 4-HBA's potential as a therapeutic agent for ischemic stroke and other neurodegenerative conditions.

Custom Q&A

What is the molecular formula of 4-Hydroxybenzyl alcohol?

The molecular formula of 4-Hydroxybenzyl alcohol is C7H8O2.

What is the molecular weight of 4-Hydroxybenzyl alcohol?

The molecular weight of 4-Hydroxybenzyl alcohol is 124.14 g/mol.

What is the IUPAC name of 4-Hydroxybenzyl alcohol?

The IUPAC name of 4-Hydroxybenzyl alcohol is 4-(hydroxymethyl)phenol.

What is the InChI of 4-Hydroxybenzyl alcohol?

The InChI of 4-Hydroxybenzyl alcohol is InChI=1S/C7H8O2/c8-5-6-1-3-7(9)4-2-6/h1-4,8-9H,5H2.

What is the InChIKey of 4-Hydroxybenzyl alcohol?

The InChIKey of 4-Hydroxybenzyl alcohol is BVJSUAQZOZWCKN-UHFFFAOYSA-N.

What is the canonical SMILES of 4-Hydroxybenzyl alcohol?

The canonical SMILES of 4-Hydroxybenzyl alcohol is C1=CC(=CC=C1CO)O.

What is the CAS number of 4-Hydroxybenzyl alcohol?

The CAS number of 4-Hydroxybenzyl alcohol is 623-05-2.

What is the FEMA number of 4-Hydroxybenzyl alcohol?

The FEMA number of 4-Hydroxybenzyl alcohol is 3987.

What is the KEGG ID of 4-Hydroxybenzyl alcohol?

The KEGG ID of 4-Hydroxybenzyl alcohol is C17467.

What is the Wikipedia page for 4-Hydroxybenzyl alcohol?

The Wikipedia page for 4-Hydroxybenzyl alcohol is Gastrodigenin.