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2-Hydroxytetradecanoic acid

Cat No.:V88230 Purity: ≥98%
2-Hydroxytetradecanoic Acid is a hydroxy fatty acid that inhibits the cleavage between enterovirus capsid proteins VP4 and VP2.
2-Hydroxytetradecanoic acid
2-Hydroxytetradecanoic acid Chemical Structure CAS No.: 2507-55-3
Product category: Enterovirus
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
Other Sizes
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Product Description
2-Hydroxytetradecanoic Acid is a hydroxy fatty acid that inhibits the cleavage between enterovirus capsid proteins VP4 and VP2. 2-Hydroxytetradecanoic Acid has antiviral activity.
2‑Hydroxytetradecanoic acid (2‑Hydroxymyristic acid) is a hydroxylated fatty acid analog of myristic acid. It has antiviral activity by inhibiting the cleavage between enterovirus capsid proteins VP4 and VP2. Additionally, it is metabolically activated in cells to form 2‑hydroxymyristoyl‑CoA, which is a potent inhibitor of protein myristoylation by N‑myristoyltransferase (NMT).
Biological Activity I Assay Protocols (From Reference)
Targets
Enterovirus capsid proteins VP4 and VP2, and N‑myristoyltransferase (NMT). 2‑Hydroxytetradecanoic acid inhibits the cleavage between VP4 and VP2, blocking viral maturation. It also inhibits protein myristoylation via 2‑hydroxymyristoyl‑CoA.
ln Vitro
In cell‑free assays, 2‑Hydroxytetradecanoic acid inhibits the cleavage between enterovirus capsid proteins VP4 and VP2, thereby exerting antiviral activity. It also acts as an analog of myristic acid that becomes metabolically activated to 2‑hydroxymyristoyl‑CoA, which is a potent inhibitor of protein myristoylation by N‑myristoyltransferase.
ln Vivo
In vivo, 2‑Hydroxytetradecanoic acid has antiviral activity against enteroviruses, including poliovirus and coxsackievirus. It inhibits viral replication by blocking the proteolytic cleavage of VP0 into VP4 and VP2, thereby preventing the formation of mature viral capsids and infectious viral particles.
Enzyme Assay
A general cell‑free protocol for assessing N‑myristoyltransferase inhibition: Recombinant N‑myristoyltransferase (NMT) is incubated with a peptide substrate (e.g., a 20‑mer peptide containing an N‑terminal glycine) and varying concentrations of 2‑Hydroxytetradecanoic acid (0.1‑100 uM) in assay buffer (50 mM Tris‑HCl, pH 7.5, 5 mM MgCl2, 1 mM EDTA, 1 mM DTT, 0.5 mM EGTA, 0.1% Triton X‑100) containing 10 uM myristoyl‑CoA and 5 uM [3H]‑myristoyl‑CoA. After 20 minutes at 30degC, the reaction is stopped, and the incorporated radioactivity is measured to calculate the IC50.
Cell Assay
A general cellular protocol for 2‑Hydroxytetradecanoic acid: Enterovirus‑infected cells (e.g., HeLa cells infected with poliovirus or coxsackievirus) are seeded in 6‑well plates. Cells are treated with 2‑Hydroxytetradecanoic acid at concentrations of 1, 10, 50, 100 uM for 8‑24 hours post‑infection. Viral capsid protein processing (VP0 cleavage into VP4 and VP2) is assessed by Western blot. Viral titers in the culture supernatant are determined by plaque assay. Cell viability is measured by MTT assay.
Animal Protocol
A general animal protocol for 2‑Hydroxytetradecanoic acid: For an enterovirus infection model, male BALB/c mice are infected with coxsackievirus B3 (CVB3) or poliovirus via intraperitoneal injection. 2‑Hydroxytetradecanoic acid is formulated in a suitable vehicle (e.g., 10% DMSO, 40% PEG300, 5% Tween‑80, 45% saline) and administered via IP injection at doses of 10, 30, and 100 mg/kg daily for 5‑7 days post‑infection. Survival is monitored daily. At the end of the study, heart, pancreas, and other target tissues are harvested for viral load quantification by qRT‑PCR and histopathology (H&E staining).
ADME/Pharmacokinetics
General PK protocol for 2‑Hydroxytetradecanoic acid: Male Sprague‑Dawley rats are administered the compound via IV (2 mg/kg) and IP (10 mg/kg). Blood samples are collected at 0.083, 0.25, 0.5, 1, 2, 4, 8, 12, and 24 hours. Plasma concentrations are quantified by LC‑MS/MS. PK parameters (Cmax, Tmax, AUC, t1/2, clearance, Vd, and IP bioavailability) are calculated. The compound has a molecular weight of 244.37.
Toxicity/Toxicokinetics
General toxicity protocol for 2‑Hydroxytetradecanoic acid: A 14‑day repeat‑dose IP toxicity study is performed in ICR mice. 2‑Hydroxytetradecanoic acid is administered at doses of 10, 30, and 100 mg/kg/day. Parameters include clinical signs, body weight, food consumption, hematology (CBC), serum chemistry (ALT, AST, BUN, creatinine), and histopathology of major organs (liver, kidney, spleen, heart, pancreas).
References

[1]. I Pascher. Molecular arrangements in sphingolipids. Conformation and hydrogen bonding of ceramide and their implication on membrane stability and permeability. Biochim Biophys Acta. 1976 Dec 2;455(2):433-51.

Additional Infomation
2-Hydroxymyristic acid is a long-chain fatty acid, a derivative of myristic acid, with a hydroxyl substituent at the C-2 position. It is a 2-hydroxy fatty acid and a long-chain fatty acid, and also the conjugate acid of 2-hydroxymyristic acid ester. 2-Hydroxytetradecanoic acid has been reported to be found in Brassica napus, Suberites massa, and Pseudosuberites; relevant data have been reported.
2‑Hydroxytetradecanoic acid has a molecular formula of C14H28O3 and a molecular weight of 244.37 g/mol. It is also known as 2‑Hydroxymyristic acid. The compound is a hydroxy fatty acid that inhibits protein myristoylation and enterovirus capsid processing. It is soluble in DMSO and ethanol. As a myristic acid analog, it has been used to study the role of protein myristoylation in viral replication and signal transduction. The powder can be stored at -20degC for up to 3 years.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H28O3
Molecular Weight
244.37
Exact Mass
244.203
CAS #
2507-55-3
PubChem CID
1563
Appearance
Solid powder
Density
1.0±0.1 g/cm3
Boiling Point
377.5±15.0 °C at 760 mmHg
Melting Point
51.00 °C. @ 760.00 mm Hg
Flash Point
196.3±16.9 °C
Vapour Pressure
0.0±1.9 mmHg at 25°C
Index of Refraction
1.467
LogP
5.15
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
12
Heavy Atom Count
17
Complexity
180
Defined Atom Stereocenter Count
0
SMILES
CCCCCCCCCCCCC(C(=O)O)O
InChi Key
JYZJYKOZGGEXSX-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-12-13(15)14(16)17/h13,15H,2-12H2,1H3,(H,16,17)
Chemical Name
2-hydroxytetradecanoic acid
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 4.0922 mL 20.4608 mL 40.9216 mL
5 mM 0.8184 mL 4.0922 mL 8.1843 mL
10 mM 0.4092 mL 2.0461 mL 4.0922 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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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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