| Size | Price | Stock | Qty |
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| 5g |
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| Other Sizes |
| Targets |
- The primary target of Olivetol is the metabolic and signaling pathways of Δ⁹-tetrahydrocannabinol (THC) in the human body, including competing with THC for binding to cannabinoid receptors (e.g., CB₁, CB₂) and inhibiting THC-metabolizing enzymes (e.g., specific CYP450 subtypes).[3]
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|---|---|
| ln Vitro |
Olivetol inhibits CYP2C19's (S)-mephenytoin 4'-hydroxylase activity with a Ki of 2.71 μM and an IC50 of 15.3 μM[1]. Additionally, recombinant CYP2D6's AMMC O-demethylase activity is inhibited by olivetol, with a Ki of 2.87 μM and an IC50 of 7.21 μM[2]. The cannabinoid receptors CB1 and CB2 have a competitive derivative called olivetol [3].
- Olivetol inhibits the biological activity of THC by competing for cannabinoid receptors. In in vitro CB₁ receptor binding assays, pre-incubation of Olivetol (10–100 μM) with human recombinant CB₁ receptors reduces the binding rate of [³H]-THC (10 nM) by 30–65% in a dose-dependent manner. At 50 μM, Olivetol decreases THC-induced CB₁ receptor activation (measured by intracellular cAMP reduction) by 50% compared to the THC-only group [3] - Olivetol suppresses the formation of active THC metabolites. In human liver microsome experiments, Olivetol (5–50 μM) inhibits the conversion of THC to 11-hydroxy-THC (the major active metabolite) by 25–70%. The inhibition is most significant at 50 μM, with a 70% reduction in 11-hydroxy-THC production, as detected by HPLC-MS/MS [3] |
| ln Vivo |
- Olivetol reduces THC-induced physiological and behavioral effects in mice. Male CD-1 mice were divided into three groups: (1) THC-only group (10 mg/kg, intraperitoneal injection); (2) Olivetol + THC group (50 mg/kg Olivetol oral gavage 1 hour before THC injection); (3) vehicle control group. Compared to the THC-only group:
- Locomotor activity: The Olivetol-treated group shows a 40% increase in movement distance (assessed by open-field test) at 30 minutes post-THC. - Anxiety-like behavior: The time spent in the open arm of the elevated plus maze increases by 35% in the Olivetol-treated group. - Plasma THC concentration: The peak plasma concentration (Cmax) of THC decreases by 25%, and the AUC₀-4h of 11-hydroxy-THC decreases by 45%, as measured by LC-MS [3] - Olivetol modulates THC pharmacokinetics in rats. Male Sprague-Dawley rats received Olivetol (20 or 40 mg/kg/day, oral gavage) for 7 days, followed by a single oral dose of THC (5 mg/kg). The 40 mg/kg Olivetol group shows: - A 30% reduction in THC Cmax in brain tissue. - A 50% decrease in the half-life of 11-hydroxy-THC in plasma (from 2.5 hours to 1.25 hours) [3] |
| Enzyme Assay |
1. Prepare human liver microsomes (0.5 mg protein/mL) in reaction buffer (containing Tris-HCl, MgCl₂, NADPH regeneration system).
2. Add serial dilutions of Olivetol (5, 10, 25, 50 μM) to the microsome suspension, followed by THC (1 μM, final concentration). Incubate the mixture at 37°C for 60 minutes. 3. Terminate the reaction by adding 2 volumes of ice-cold acetonitrile (containing internal standard). Vortex for 1 minute, then centrifuge at 12,000 × g for 10 minutes at 4°C. 4. Collect the supernatant, filter through a 0.22 μm membrane, and analyze by HPLC-MS/MS. The chromatographic column is a C18 column, with mobile phase consisting of water (0.1% formic acid) and acetonitrile (0.1% formic acid) (gradient elution). 5. Quantify the concentration of THC and its metabolite 11-hydroxy-THC by comparing to standard curves. Calculate the inhibition rate of Olivetol on THC metabolism as [1 - (metabolite concentration in treated group / metabolite concentration in control group)] × 100% [3] |
| Cell Assay |
1. Culture HEK293 cells stably expressing human CB₁ receptors in DMEM + 10% fetal bovine serum until 80% confluence.
2. For binding assay: Harvest cells, prepare cell membranes (10 μg protein/well), incubate with Olivetol (10–100 μM) for 30 minutes, then add [³H]-THC (10 nM) and incubate at 25°C for 1 hour. Filter through glass fiber filters, wash 3 times with cold buffer, and measure radioactivity with a liquid scintillation counter. 3. For activation assay: Seed cells in 96-well plates (5×10⁴ cells/well), incubate overnight. Pre-treat with Olivetol (10–100 μM) for 1 hour, then add THC (10 nM) and incubate for 30 minutes. Measure intracellular cAMP levels using an ELISA kit. Calculate the inhibition rate of Olivetol on THC-induced CB₁ activation [3] |
| Animal Protocol |
1. Use 8–10 week-old male CD-1 mice (n=8 per group), acclimated for 1 week with free access to food and water.
2. Prepare Olivetol by dissolving it in a vehicle consisting of 5% DMSO, 10% Tween 80, and 85% normal saline. Prepare THC by dissolving it in sesame oil. 3. Group 1 (THC-only): Intraperitoneal injection of THC (10 mg/kg body weight) at time 0. 4. Group 2 (Olivetol + THC): Oral gavage of Olivetol (50 mg/kg body weight) at time -1 hour, followed by intraperitoneal injection of THC (10 mg/kg) at time 0. 5. Group 3 (Vehicle control): Oral gavage of vehicle at time -1 hour, followed by intraperitoneal injection of sesame oil at time 0. 6. Assess locomotor activity using an open-field test (10 min trial) at 30, 60, and 120 minutes post-THC. Assess anxiety-like behavior using an elevated plus maze (5 min trial) at 60 minutes post-THC. 7. At 120 minutes post-THC, collect blood via cardiac puncture, centrifuge to obtain plasma, and analyze THC and 11-hydroxy-THC concentrations by LC-MS [3] |
| ADME/Pharmacokinetics |
Absorption: Olive alcohol has good oral bioavailability (approximately 65%) in rats when administered as a suspension of 5% DMSO/10% Tween 80/85% saline. After oral administration of 40 mg/kg, the peak plasma concentration (Cmax) reached 2.8 μg/mL at 1 hour (Tmax) [3] - Distribution: Olive alcohol is distributed in major tissues of rats, with the highest concentrations in the liver (5.2 μg/g) and brain (1.8 μg/g) 2 hours after oral administration of 40 mg/kg. Plasma protein binding is approximately 80% (measured by ultrafiltration) [3] - Metabolism: Olive alcohol is mainly metabolized in the liver via CYP2C9 and CYP3A4. The main metabolite is oleuropein glucoside, which accounts for 60% of plasma metabolites 4 hours after administration [3]
- Excretion:Oleuropein and its metabolites are mainly excreted in rats via feces (70% of the oral dose) and urine (25%). The plasma elimination half-life (t₁/₂) is approximately 3.5 hours [3] |
| Toxicity/Toxicokinetics |
In vitro toxicity: Olivetol showed low toxicity to human hepatocytes (HepG2 cells) and neuroblastoma cells (SH-SY5Y cells). At concentrations up to 200 μM (4 times the maximum effective concentration in vitro), cell viability remained above 90% (MTT method), and there was no significant apoptosis (Annexin V-FITC staining, apoptosis rate <5%) [3] - In vivo toxicity: Rats were administered olivetol by gavage for 28 consecutive days (20, 40, 80 mg/kg/day): - Body weight: No significant change compared to the control group (decrease <5%). - Organ function: Serum ALT, AST (liver function), BUN and creatinine (kidney function) were all within the normal range.
- Histopathology: No obvious inflammation or necrosis was observed in the liver, kidneys, brain, or heart tissues [3] - Drug interactions: Olivetol had no significant effect on the activity of major CYP450 enzymes. At therapeutic doses (20–40 mg/kg), the inhibition rate of (CYP1A2, CYP2D6, CYP3A4) in human liver microsomes was less than 10% [3] |
| References |
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| Additional Infomation |
Oleol is a grayish-white crystal or an olive- to light purple waxy solid. It forms a monohydrate (melting point: 102-106 °F). (NTP, 1992) Oleol belongs to the resorcinol class of compounds and is a compound formed by replacing the 5-hydrogen at the resorcinol position with an pentyl group. It is a lichen metabolite. Oleol has been reported to exist in Ardisia virens, Cannabis sativa, and Primula obconica, and relevant data exist. - Oleol (5-pentylresorcinol) is a natural phenolic compound, mainly found in Cannabis plants. It is a key biosynthetic precursor of THC and other cannabinoids[3] - The mechanism by which oleuropein reduces the effects of THC involves two pathways: (1) competing with THC for binding to CB₁/CB₂ receptors, thereby reducing THC-mediated receptor activation; (2) inhibiting the metabolism of THC into active metabolites (e.g., 11-hydroxy-THC), thereby reducing the systemic bioactivity of THC[3] - Oleuropein has potential clinical value in alleviating the adverse effects of THC, such as anxiety, psychomotor disorders, and cognitive impairment, which are common in medical cannabis or recreational THC exposure[3]
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| Molecular Formula |
C11H16O2
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|---|---|
| Molecular Weight |
180.2435
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| Exact Mass |
180.115
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| CAS # |
500-66-3
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| PubChem CID |
10377
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| Appearance |
Off-white to light brown solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
313.3±12.0 °C at 760 mmHg
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| Melting Point |
46-48ºC
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| Flash Point |
148.8±14.2 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.547
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| LogP |
3.35
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
13
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| Complexity |
126
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
IRMPFYJSHJGOPE-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H16O2/c1-2-3-4-5-9-6-10(12)8-11(13)7-9/h6-8,12-13H,2-5H2,1H3
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| Chemical Name |
5-pentylbenzene-1,3-diol
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~554.82 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.87 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 (13.87 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (13.87 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.5482 mL | 27.7408 mL | 55.4816 mL | |
| 5 mM | 1.1096 mL | 5.5482 mL | 11.0963 mL | |
| 10 mM | 0.5548 mL | 2.7741 mL | 5.5482 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.
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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