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2-Methyl-1-naphthol

2-Methyl-1-naphthol is a key precursor in the synthesis of vitamin K3.
2-Methyl-1-naphthol
2-Methyl-1-naphthol Chemical Structure CAS No.: 7469-77-4
Product category: Drug Derivative
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
2-Methyl-1-naphthol is a key precursor in the synthesis of vitamin K3. 2-Methyl-1-naphthol can be used in research on vitamin K deficiency.
2-Methyl-1-naphthol (CAS# 7469-77-4) is a prostaglandin G/H synthase and polyunsaturated fatty acid 5-lipoxygenase inhibitor with molecular formula C11H10O and molecular weight 158.2 g/mol. It appears as a white solid powder. This naphthalene derivative is a key intermediate in various synthetic processes, most notably in the selective synthesis of vitamin K3 (menadione) via liquid-phase oxidation. It is used in biochemical experiments and drug synthesis as an enzyme inhibitor and synthetic building block.
Biological Activity I Assay Protocols (From Reference)
Targets
2-Methyl-1-naphthol targets prostaglandin G/H synthase (also known as cyclooxygenase or COX) and polyunsaturated fatty acid 5-lipoxygenase (5-LOX). These enzymes are key mediators in the arachidonic acid cascade, responsible for the production of prostaglandins and leukotrienes, which are involved in inflammation, pain, and fever. By inhibiting both COX and 5-LOX pathways, this compound may exert anti-inflammatory effects. It is also a precursor to vitamin K3, which is involved in blood coagulation and bone metabolism.
ln Vitro
In vitro studies show that 2-Methyl-1-naphthol inhibits prostaglandin G/H synthase and polyunsaturated fatty acid 5-lipoxygenase activities. These enzymes catalyze the first steps in the biosynthesis of prostaglandins and leukotrienes from arachidonic acid. Inhibition of these enzymes reduces the production of inflammatory mediators. The compound is used in biochemical experiments to study the arachidonic acid cascade and inflammation pathways. No specific IC50 values for enzyme inhibition are reported in the available literature.
ln Vivo
No direct in vivo activity studies have been published for 2-Methyl-1-naphthol as a therapeutic agent. The compound is primarily used as a synthetic intermediate for vitamin K3 production. Vitamin K3 (menadione) has biological activity as a provitamin that can be converted to vitamin K2 in the body and is involved in blood coagulation. The compound can be used for the study of vitamin K deficiency. No direct in vivo efficacy data is available for the compound itself.
Enzyme Assay
No specific enzyme/receptor binding protocols have been established for 2-Methyl-1-naphthol. For COX/5-LOX inhibition studies, standard cell-free assays use purified ovine or human recombinant COX-1/COX-2 and 5-LOX enzymes. The compound is incubated with enzyme in assay buffer containing arachidonic acid substrate. Prostaglandin and leukotriene production is measured by ELISA or radiometric methods. For COX assay, heme cofactor is required. Reaction is stopped by addition of HCl or citric acid, and products are extracted with organic solvent before detection. IC50 values are calculated from dose-response curves.
Cell Assay
For cellular evaluation of 2-methyl-1-naphthol, standard protocols involve culturing inflammatory cells such as macrophages (RAW 264.7) or monocytes (THP-1) in DMEM or RPMI-1640 with 10% FBS. Cells are seeded in 96-well plates (1×10⁵ cells/well) and pre-treated with varying concentrations of 2-methyl-1-naphthol (1-100 microM) for 1 hour, then stimulated with LPS (1 microg/mL) for 24 hours. Prostaglandin E2 (PGE2) and leukotriene B4 (LTB4) levels in culture supernatants are measured by ELISA. Cell viability is assessed by MTT assay. COX-2 and 5-LOX protein expression are analyzed by western blotting. Experiments are performed in triplicate.
Animal Protocol
No in vivo animal protocols have been established specifically for 2-Methyl-1-naphthol. For vitamin K deficiency studies, the compound can be used as a synthetic precursor to produce vitamin K3. Standard animal models for studying vitamin K deficiency include warfarin-treated rats, where vitamin K-dependent clotting factors are measured. For potential anti-inflammatory studies, standard protocols using carrageenan-induced paw edema in rats could be adapted, where the compound or its derivatives are administered orally or intraperitoneally at doses of 10-100 mg/kg, with paw volume measured at 1-6 hours post-carrageenan injection.
ADME/Pharmacokinetics
No pharmacokinetic studies have been published for 2-Methyl-1-naphthol. Computed properties include molecular formula C11H10O, molecular weight 158.2 g/mol, predicted logP of approximately 2.5-3.0, suggesting moderate lipophilicity. The compound has a melting point of 64-65degC and a boiling point of approximately 180degC at 30 mmHg. It is moderately soluble in organic solvents such as ethanol, DMSO, and DMF, but has low water solubility. For vitamin K3 production, it is oxidized to menadione. No PK parameters are reported.
Toxicity/Toxicokinetics
According to safety data, 2-Methyl-1-naphthol may cause skin and eye irritation. Standard laboratory safety precautions should be followed: wear protective gloves, safety goggles, and a lab coat. Work in a well-ventilated fume hood. Avoid inhalation, ingestion, and contact with skin and eyes. The compound should be stored at low temperature (powder at -20degC for 3 years, in solvent at -80degC for 1 year). While specific acute toxicity data is limited, naphthol derivatives should be handled with caution. This product is for research use only.
References

[1]. Selective Oxidation of 2-Methylnaphthalene to 2-Methyl-l-naphthol by Rhodococcus sp. M192. Biosci Biotechnol Biochem. 1996 Jan;60(5):769-72.

Additional Infomation
Structure in the first source
2-Methyl-1-naphthol is a prostaglandin G/H synthase and 5-lipoxygenase inhibitor used in biochemical research. It is also a key intermediate in the selective synthesis of vitamin K3 (menadione) via liquid-phase oxidation using NbSBA-15 catalyst. Vitamin K3 is used in the study of vitamin K deficiency and blood coagulation disorders. The compound is also used in hair dyeing agents and as a flavor ingredient. It is not approved for human therapeutic use and no clinical trial data is available for the compound itself. This product is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H10O
Molecular Weight
158.20
Exact Mass
158.073
CAS #
7469-77-4
PubChem CID
24055
Appearance
Off-white to yellow solid powder
Hydrogen Bond Donor Count
1
Rotatable Bond Count
0
Heavy Atom Count
12
Complexity
155
Defined Atom Stereocenter Count
0
SMILES
CC1=C(C2=CC=CC=C2C=C1)O
InChi Key
SRJCJJKWVSSELL-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H10O/c1-8-6-7-9-4-2-3-5-10(9)11(8)12/h2-7,12H,1H3
Chemical Name
2-methylnaphthalen-1-ol
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

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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.3211 mL 31.6056 mL 63.2111 mL
5 mM 1.2642 mL 6.3211 mL 12.6422 mL
10 mM 0.6321 mL 3.1606 mL 6.3211 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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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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