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|---|---|---|
| Other Sizes |
| Targets |
Phytol targets the GABA-A receptor, acting as a positive modulator, which contributes to its anxiolytic and sedative effects. It also inhibits the production of pro-inflammatory cytokines via NF-κB suppression. Additionally, it shows antibacterial activity by disrupting bacterial cell membranes. It may also activate PPAR-γ, modulating lipid metabolism.
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| ln Vitro |
In vitro, phytol exhibits significant antimicrobial activity against S. aureus and E. coli with MIC values of 16-32 µg/mL. It inhibits LPS-induced NO production in RAW 264.7 macrophages with an IC50 of 12 µM. It binds to GABA-A receptors with a Ki of 10 µM and enhances chloride influx in neuronal cells at 1-10 µM.
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| ln Vivo |
In vivo, phytol has anxiolytic effects in mice at doses of 25-100 mg/kg (i.p.) in the elevated plus maze and open field tests. It also reduces carrageenan-induced paw edema in rats (50 mg/kg, p.o.) and shows antinociceptive activity. In a mouse model of LPS-induced sepsis, phytol (30 mg/kg, i.p.) reduced mortality and inflammatory cytokine levels.
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| Enzyme Assay |
The GABA-A receptor binding assay is performed using rat brain membranes and [³H]-flunitrazepam. Phytol (0.1-100 µM) is incubated with membranes for 1 h at 4°C, and bound radioactivity is measured. The IC50 is determined. For antimicrobial activity, broth microdilution is used according to CLSI guidelines.
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| Cell Assay |
For in vitro cell-based assays, RAW 264.7 macrophages are seeded in 96-well plates and treated with phytol (1-50 µM) for 2 h, then stimulated with LPS (1 µg/mL) for 24 h. NO and cytokines (TNF-α, IL-6) are measured by Griess and ELISA. For neuronal studies, primary cortical neurons are cultured and treated with phytol (1-10 µM) to measure GABA-induced currents via patch-clamp.
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| Animal Protocol |
In vivo anxiolytic studies are performed in male Swiss mice (25-30 g). Phytol is dissolved in saline with 0.1% Tween 80 and administered intraperitoneally at 25, 50, and 100 mg/kg. After 30 min, mice are tested in the elevated plus maze for 5 min, and the time spent in open arms is recorded. For anti-inflammatory studies, rats are given phytol orally 1 h before carrageenan injection, and paw volume is measured.
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| ADME/Pharmacokinetics |
Pharmacokinetic studies in rats after oral administration (50 mg/kg) show a Tmax of 1.5 h, Cmax of 2.5 µg/mL, and half-life of 3 h. Oral bioavailability is approximately 30%. The compound is highly lipophilic (Log P ~ 7) and extensively metabolized to phytanic acid. Plasma protein binding is >95%. Elimination is mainly via bile and feces.
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| Toxicity/Toxicokinetics |
Phytol has low acute toxicity (LD50 > 2000 mg/kg in rats). It is not mutagenic. In repeated-dose studies, doses up to 100 mg/kg/day for 28 days showed no significant adverse effects. High doses may cause mild sedation and gastrointestinal discomfort. It is not considered hazardous for topical use in cosmetics.
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| References |
[1] Kitareewan S, Burka L T, Tomer K B, et al. Phytol metabolites are\ncirculating dietary factors that activate the nuclear receptor RXR[J].\nMolecular Biology of the Cell, 1996, 7(8): 1153-1166. [5]. de Moraes J, et al. Phytol, a diterpene alcohol from chlorophyll, as a drug against neglected tropical diseaseSchistosomiasis mansoni. PLoS Negl Trop Dis. 2014 Jan 2;8(1):e2617. |
| Additional Infomation |
Phytol is a diterpenoid compound with the structure hexadecyl-2-en-1-ol, substituted with methyl groups at positions 3, 7, 11, and 15. It is a plant metabolite, a schistosomiasis killer, and an algal metabolite. Phytol belongs to the diterpenoid class and is also a long-chain primary fatty alcohol. It has been reported to be found in tea plants (Camellia sinensis), chrysanthemum (Desmos chinensis), and several other organisms with relevant data. Phytol is an acyclic diterpenoid alcohol and a component of chlorophyll. Phytol is commonly used as a precursor for the synthesis of vitamin E and vitamin K1. Furthermore, phytol has been shown to regulate cellular transcription through the transcription factor PPAR-α and the retinol X receptor (RXR). Acyclic diterpenes are used in the synthesis of vitamin E and vitamin K1.
Phytol is a common ingredient in perfumes and cosmetics due to its floral scent. It is also a precursor for synthetic vitamins E and K. Its anxiolytic and anti-inflammatory properties have attracted research interest. No clinical trials have been conducted for therapeutic use. It is available as a research chemical and flavoring agent. |
| Molecular Formula |
C20H40O
|
|---|---|
| Molecular Weight |
296.5310
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| Exact Mass |
296.307
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| CAS # |
150-86-7
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| PubChem CID |
5280435
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| Appearance |
Light brown to brown ointment
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| Density |
0.8±0.1 g/cm3
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| Boiling Point |
335.5±0.0 °C at 760 mmHg
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| Melting Point |
< 25 °C
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| Flash Point |
157.5±8.9 °C
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| Vapour Pressure |
0.0±1.6 mmHg at 25°C
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| Index of Refraction |
1.460
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| LogP |
8.66
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
13
|
| Heavy Atom Count |
21
|
| Complexity |
255
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| Defined Atom Stereocenter Count |
2
|
| SMILES |
O([H])C([H])([H])/C(/[H])=C(\C([H])([H])[H])/C([H])([H])C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]
|
| InChi Key |
BOTWFXYSPFMFNR-PYDDKJGSSA-N
|
| InChi Code |
InChI=1S/C20H40O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h15,17-19,21H,6-14,16H2,1-5H3/b20-15+/t18-,19-/m1/s1
|
| Chemical Name |
(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol
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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 |
| 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 : ~125 mg/mL (~421.54 mM)
Ethanol : ~25 mg/mL (~84.31 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.25 mg/mL (7.59 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 22.5 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: ≥ 2.25 mg/mL (7.59 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 22.5 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: ≥ 2.25 mg/mL (7.59 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 | 3.3723 mL | 16.8617 mL | 33.7234 mL | |
| 5 mM | 0.6745 mL | 3.3723 mL | 6.7447 mL | |
| 10 mM | 0.3372 mL | 1.6862 mL | 3.3723 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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