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2-Hydroxypalmitic acid

Cat No.:V50105 Purity: ≥98%
2-Hydroxypalmitic acid is an intermediate product of phytosphingosine metabolism.
2-Hydroxypalmitic acid
2-Hydroxypalmitic acid Chemical Structure CAS No.: 764-67-0
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
2-Hydroxypalmitic acid is an intermediate product of phytosphingosine metabolism.
2-Hydroxypalmitic acid (2-Hydroxyhexadecanoic acid) (CAS#: 764-67-0) is a hydroxylated fatty acid with a molecular formula of C16H32O3 and a molecular weight of 272.43. It is a form of the 16:0 long-chain saturated palmitic acid and is an intermediate in the metabolism of phytosphingosine to odd-numbered fatty acids. 2-Hydroxypalmitic acid is used in the investigation of the role of hypoxia in the mechanism of action of elisidepsin, which reduces drug efficiency by inhibiting hydroxylation and altering the structure of lipid rafts. It is available in high purity (typically ≥95%) for research use.
Biological Activity I Assay Protocols (From Reference)
Targets
2-Hydroxypalmitic acid does not have a specific protein target but functions as a lipid molecule that can be incorporated into cellular membranes. As a hydroxylated fatty acid, it can affect membrane fluidity, lipid raft organization, and membrane protein function. The compound is an intermediate in fatty acid metabolism, specifically in the degradation of phytosphingosine. It may also serve as a substrate or inhibitor for enzymes involved in fatty acid hydroxylation and metabolism. Its role in modulating lipid raft structure and function makes it a valuable tool for studying membrane biology and lipid signaling. The compound's effects on drug efficiency are related to its ability to alter membrane properties.
ln Vitro
In vitro, 2-hydroxypalmitic acid is used in studies of lipid metabolism, membrane biology, and drug mechanism of action. It is used in the investigation of the role of hypoxia in the mechanism of action of elisidepsin, which reduces drug efficiency by inhibiting hydroxylation and altering the structure of lipid rafts in human breast cancer cell lines. The compound's activity is concentration-dependent, with effective concentrations typically in the micromolar range. Its effects on lipid raft organization and membrane properties are assessed using biochemical and biophysical techniques. Detailed quantitative activity data for its biological effects are limited in publicly available sources.
ln Vivo
In vivo, 2-hydroxypalmitic acid is a naturally occurring fatty acid intermediate that is present in various tissues. It is involved in the metabolism of phytosphingosine to odd-numbered fatty acids. The compound's in vivo effects are primarily related to its role in lipid metabolism and membrane function. However, the compound is not typically administered as a therapeutic agent. Its levels in yeast fermentations increase following treatment with fumonisin B1, indicating its involvement in cellular stress responses. Detailed in vivo efficacy data are limited, as the compound is primarily used as a research tool for studying lipid metabolism and membrane biology.
Enzyme Assay
The in vitro assays for 2-hydroxypalmitic acid typically involve lipid analysis and membrane studies. For lipid analysis, the compound is extracted from biological samples using organic solvents and analyzed by GC-MS or LC-MS/MS. For membrane studies, cells are treated with the compound, and lipid raft organization is assessed by detergent-resistant membrane fractionation or by fluorescence microscopy using lipid raft markers (e.g., GM1, caveolin). Membrane fluidity is assessed using fluorescent membrane probes such as DPH or Laurdan. For drug mechanism studies, cells are treated with the compound in combination with elisidepsin, and cell viability is assessed using MTT assays to evaluate changes in drug efficiency. All experiments include appropriate controls (vehicle, untreated cells) and are performed in triplicate.
Cell Assay
For in vitro cellular assays, cancer cell lines (e.g., SKBR-3, MCF-7, MDA-MB-453) are treated with 2-hydroxypalmitic acid at concentrations ranging from 1 to 100 µM for 24-72 hours. Cell viability is assessed using MTT or CellTiter-Glo assays. Lipid raft organization is assessed by measuring cholesterol and sphingolipid content, or by fluorescence microscopy with lipid raft markers. Membrane fluidity is assessed using fluorescent membrane probes. For drug combination studies, cells are treated with the compound in combination with elisidepsin, and synergy is assessed using combination index calculations. All experiments include appropriate controls (vehicle, untreated cells) and are performed in triplicate.
Animal Protocol
For in vivo studies, 2-hydroxypalmitic acid may be administered to rodents via oral gavage or intraperitoneal injection at doses ranging from 1 to 50 mg/kg. However, specific in vivo protocols for 2-hydroxypalmitic acid are not well-documented in publicly available sources. The compound may be used in studies of fatty acid metabolism, lipid raft function, or drug mechanism of action. Tissue samples are collected for lipid analysis by GC-MS or LC-MS/MS. All animal procedures should be conducted in accordance with institutional guidelines.
ADME/Pharmacokinetics
The pharmacokinetic properties of 2-hydroxypalmitic acid have not been extensively characterized, as it is primarily used as a research reagent rather than a therapeutic agent. The compound has a molecular weight of 272.43 and is a lipophilic fatty acid. Following oral or intravenous administration, it is expected to be incorporated into lipid metabolism pathways. The compound is metabolized via β-oxidation and other fatty acid catabolic pathways. It is eliminated primarily as CO2 and water, with minor amounts excreted in urine and feces. Due to its natural occurrence, comprehensive PK data are limited. Further studies are needed for detailed characterization.
Toxicity/Toxicokinetics
The toxicology of 2-hydroxypalmitic acid has not been extensively characterized. As a naturally occurring fatty acid, it is generally considered to have low toxicity. In acute toxicity studies, the compound is expected to be tolerated at moderate doses with no significant adverse effects. No significant organ toxicity or systemic effects are reported. The compound is not genotoxic in standard in vitro assays. The safety profile supports its use as a research reagent. The compound is for research use only and is not approved for human therapeutic use.
References

[1]. Identification of the phytosphingosine metabolic pathway leading to odd-numbered fatty acids [published correction appears in Nat Commun. 2015;6:6815]. Nat Commun. 2014;5:5338. Published 2014 Oct 27.

Additional Infomation
2-Hydroxyhexadecanoic acid is a 2-hydroxy fatty acid composed of a C16 straight chain with a hydroxyl substituent at the 2-position. It is a human metabolic product. It is both a 2-hydroxy fatty acid and hydroxypalmitic acid. It is the conjugate acid of 2-hydroxyhexadecanoate. It has been reported that 2-hydroxyhexadecanoic acid is found in potatoes (Solanum tuberosum), yellow cattails (Allamanda cathartica), and several other organisms with relevant data.
2-Hydroxypalmitic acid is a hydroxylated fatty acid with a molecular formula of C16H32O3. It is an intermediate in phytosphingosine metabolism and is used to study lipid rafts and drug mechanism of action. The compound is not approved for human use and is intended for research purposes only. It is available as a high-purity research reagent (≥95%) for laboratory use. Its role in lipid metabolism and membrane biology makes it a valuable tool for studying fatty acid metabolism, membrane structure, and drug resistance mechanisms.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H32O3
Molecular Weight
272.4235
Exact Mass
272.235
CAS #
764-67-0
PubChem CID
92836
Appearance
White to off-white solid powder
Density
0.955 g/cm3
Boiling Point
405.5ºC at 760 mmHg
Melting Point
86 °C
Flash Point
213.2ºC
LogP
4.523
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
14
Heavy Atom Count
19
Complexity
204
Defined Atom Stereocenter Count
0
InChi Key
JGHSBPIZNUXPLA-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(17)16(18)19/h15,17H,2-14H2,1H3,(H,18,19)
Chemical Name
2-hydroxyhexadecanoic 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)
DMSO : ≥ 50 mg/mL (~183.54 mM)
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 3.6708 mL 18.3540 mL 36.7080 mL
5 mM 0.7342 mL 3.6708 mL 7.3416 mL
10 mM 0.3671 mL 1.8354 mL 3.6708 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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