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Tyrosol

Cat No.:V30391 Purity: ≥98%
Tyrosol is an analogue of phenylethyl alcohol.
Tyrosol
Tyrosol Chemical Structure CAS No.: 501-94-0
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
5g
Other Sizes
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Product Description
Tyrosol is an analogue of phenylethyl alcohol. Tyrosol attenuates proinflammatory cytokines from astrocytes and reduces NF-κB activation. Has antioxidant and anti~inflammatory effects.
Biological Activity I Assay Protocols (From Reference)
Targets
- The primary targets of Tyrosol include the NF-κB signaling pathway (involved in inflammation regulation) in astrocytes and oxidative stress-related enzymes (e.g., SOD, CAT) in endothelial cells. [1,2]
- Tyrosol also modulates the expression of pro-inflammatory cytokines (IL-1β, TNF-α, IL-6) and adhesion molecules (VCAM-1) in target cells.[1,2]
ln Vitro
Tyrosol (1.6 mM) raises the cultured astrocytes' cell viability under pressure relative to oxygen delta (OGD) in a considerable degree [1]. Tyrosol (1.6 mM) suppresses Janus N disruption (JNK), which in turn lowers astrocytes. Tyrosol (1.6 mM) fragments GFAP (stars) and releases TNF-α and IL-6, suggesting that the reduction of astrocyte activators and change of STAT3 signaling balance may be the source of the decrease in astrocyte cytokines [1]. Tyrosol suppresses NF-κB function during ischemia by inhibiting IκBα phosphorylation and boosting IκBα phosphorylation in OGD astrocytes [1].
- Anti-inflammatory Activity in Astrocytes: In primary rat cortical astrocytes subjected to oxygen-glucose deprivation (OGD), Tyrosol (25–100 μM) treatment for 24 hours (during OGD and reoxygenation) reduces the secretion of pro-inflammatory cytokines. ELISA results show that 100 μM Tyrosol decreases IL-1β levels by 40% and TNF-α levels by 35% compared to OGD-only controls. It also inhibits NF-κB activation: Western blot reveals a 50% reduction in nuclear p65 (a key NF-κB subunit) translocation, and dual-luciferase assay shows 45% lower NF-κB transcriptional activity at 100 μM [1]
- Antioxidative and Anti-inflammatory Activity in Endothelial Cells: In human umbilical vein endothelial cells (HUVECs), Tyrosol (10–50 μM) and its metabolites (hydroxytyrosol, tyrosol-3-sulfate, tyrosol-4-sulfate) reduce H₂O₂-induced oxidative stress. At 50 μM, Tyrosol decreases intracellular ROS levels by 35% (DCFH-DA assay) and increases SOD activity by 30% and CAT activity by 25%. It also suppresses inflammation: 50 μM Tyrosol lowers IL-6 mRNA expression by 40% (qPCR) and VCAM-1 protein levels by 35% (Western blot) in TNF-α-stimulated HUVECs. Its metabolites (e.g., 50 μM hydroxytyrosol) exhibit similar but slightly stronger activity [2]
ln Vivo
Paw thickness increased significantly with subplantar carrageenan injection, peaking two hours after injection. When tyrosol (0.5 mg/kg) or tyrosol sulfate is injected prior to carrageenan treatment, this impact is lessened. After administering tyrosol at a dose of 0.5 mg/kg and tyrosol-sulfate at a dose of 0.1 mg/kg, similar AUC values for paw edema were observed.
Enzyme Assay
- NF-κB Transcriptional Activity Assay :
1. Seed HEK293T cells in 24-well plates (1×10⁵ cells/well) and co-transfect with NF-κB luciferase reporter plasmid and Renilla luciferase plasmid (internal control) using transfection reagent.
2. After 24 hours of transfection, treat cells with Tyrosol (25–100 μM) for 1 hour, then stimulate with 10 ng/mL TNF-α for 6 hours.
3. Lyse cells with passive lysis buffer, collect lysates, and measure firefly luciferase and Renilla luciferase activities using a dual-luciferase reporter assay system.
4. Calculate NF-κB transcriptional activity as the ratio of firefly luciferase activity to Renilla luciferase activity, normalized to the TNF-α-only group [1]
- SOD Activity Assay :
1. Culture HUVECs in 6-well plates, treat with Tyrosol (10–50 μM) for 12 hours, then induce oxidative stress with 200 μM H₂O₂ for 4 hours.
2. Harvest cells by trypsinization, wash with cold PBS, and lyse with RIPA buffer (containing protease inhibitors). Centrifuge at 12,000 × g for 15 minutes at 4°C to collect supernatants.
3. Mix 100 μL supernatant with 1.8 mL reaction buffer (containing xanthine, xanthine oxidase, and nitroblue tetrazolium), incubate at 37°C for 30 minutes.
4. Measure absorbance at 560 nm using a spectrophotometer. Calculate SOD activity as the amount of enzyme inhibiting 50% of nitroblue tetrazolium reduction, expressed as U/mg protein [2]
Cell Assay
- Astrocyte OGD Model and Cytokine Detection :
1. Isolate primary rat cortical astrocytes, culture to confluence in DMEM + 10% fetal bovine serum. Replace with glucose-free DMEM, incubate in a hypoxic chamber (95% N₂, 5% CO₂) at 37°C for 4 hours to establish the OGD model.
2. Add Tyrosol (25–100 μM) to the medium during OGD and subsequent reoxygenation (normoxic conditions, 24 hours). Set up normoxic control (no OGD) and OGD-only control (no Tyrosol).
3. Collect culture supernatant at 24 hours post-reoxygenation, measure IL-1β and TNF-α concentrations using ELISA kits (excluding supplier information).
4. For NF-κB nuclear translocation detection: Fix cells with 4% paraformaldehyde, permeabilize with 0.1% Triton X-100, stain with anti-p65 antibody (primary) and Alexa Fluor 594-conjugated secondary antibody. Counterstain nuclei with DAPI, observe under confocal microscope to quantify nuclear p65-positive cells [1]
- Endothelial Cell Oxidative Stress and Inflammation Assay :
1. Culture HUVECs in EGM-2 medium. For oxidative stress assay: Pre-treat cells with Tyrosol (10–50 μM) for 12 hours, then incubate with 10 μM DCFH-DA (ROS probe) for 30 minutes, followed by 200 μM H₂O₂ for 1 hour. Measure fluorescence intensity (excitation 488 nm, emission 525 nm) using a microplate reader.
2. For inflammation assay: Stimulate HUVECs with 10 ng/mL TNF-α for 6 hours, with Tyrosol (10–50 μM) added 12 hours prior to TNF-α. Extract total RNA, perform qPCR to detect IL-6 mRNA expression (using GAPDH as internal control). Prepare cell lysates, perform Western blot to detect VCAM-1 protein levels [2]
Toxicity/Toxicokinetics
In vitro toxicity: Tyrosol exhibits low toxicity to target cells. In primary rat astrocytes, treatment with 200 μM tyrosol for 48 hours had no significant effect on cell viability (MTT assay, viability >90% vs. control group). In human umbilical vein endothelial cells (HUVECs), treatment with 100 μM tyrosol for 24 hours did not induce apoptosis (Annexin V-FITC assay, apoptosis rate <5%) [1,2].
References

[1]. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation in in vitro oxygen glucose deprivation. Neurochem Int. 2018 Dec;121:140-145.

[2]. Tyrosol and its metabolites as antioxidative and anti-inflammatory molecules in human endothelial cells. Food Funct. 2017 Aug 1;8(8):2905-2914.

Additional Infomation
2-(4-Hydroxyphenyl)ethanol is a phenolic compound in which a 2-hydroxyethyl group is substituted at the 4-position. It possesses various functions, including antiarrhythmic, antioxidant, cardiovascular drug, protective agent, fungal metabolite, anti-aging, and plant metabolism-related effects. Its functions are related to 2-phenylethanol. 2-(4-Hydroxyphenyl)ethanol has been reported to exist in Nigrospora oryzae, Phomopsis velata, and other organisms with relevant data. Tyrosol is a metabolite found or produced in Saccharomyces cerevisiae. See also: Sedum roseum root (part); Rhodiola crenulata root (part). Tyrosol is a natural phenolic compound primarily found in olive oil, wine, and various fruits. Tyrosol is well-regarded for its potential antioxidant and anti-inflammatory properties in models of neurodegenerative and cardiovascular diseases [1,2]
- The anti-inflammatory mechanism of tyrosol in astrocytes involves inhibiting NF-κB activation, thereby reducing the transcription and secretion of pro-inflammatory cytokines (IL-1β, TNF-α)—a key pathway in neuroinflammation associated with stroke or brain injury [1]
- In endothelial cells, tyrosol and its metabolites (e.g., hydroxytyrosol, sulfate conjugates) exert synergistic antioxidant effects by scavenging reactive oxygen species (ROS) and enhancing the activity of endogenous antioxidant enzymes (SOD, CAT), thereby protecting endothelial function in cardiovascular diseases [2]
- Tyrosol undergoes phase II metabolism in human cells: it is converted to sulfate or glucuronide conjugates, which retain antioxidant and anti-inflammatory activity, contributing to its sustained biological effects [2]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H10O2
Molecular Weight
138.1638
Exact Mass
138.068
CAS #
501-94-0
PubChem CID
10393
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
375.2±27.0 °C at 760 mmHg
Melting Point
89-92 °C(lit.)
Flash Point
180.7±23.7 °C
Vapour Pressure
0.0±0.9 mmHg at 25°C
Index of Refraction
1.598
LogP
0.04
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Heavy Atom Count
10
Complexity
85.3
Defined Atom Stereocenter Count
0
InChi Key
YCCILVSKPBXVIP-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
Chemical Name
4-(2-hydroxyethyl)phenol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 100 mg/mL (~723.80 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (18.09 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (18.09 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (18.09 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 7.2380 mL 36.1899 mL 72.3798 mL
5 mM 1.4476 mL 7.2380 mL 14.4760 mL
10 mM 0.7238 mL 3.6190 mL 7.2380 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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