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| 5mg |
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Methyl heptadecanoate-d33 is a stable isotope-labeled internal standard. Its unlabeled parent, methyl heptadecanoate, is a saturated fatty acid methyl ester with a 17-carbon straight chain (C17:0). It is not a drug and has no specific pharmacological targets. However, fatty acids are essential components of cell membranes (phospholipids, sphingolipids), serve as energy substrates (beta-oxidation), and act as signaling molecules (e.g., as ligands for peroxisome proliferator-activated receptors, PPARs). Methyl heptadecanoate itself is a non-endogenous fatty acid (C17:0 is found in trace amounts in some animal fats and dairy products). In lipidomics, it is a commonly used internal standard for the quantification of other fatty acids because it is not present at high levels in most biological samples. The role of the labeled standard is to serve as a precise mass spectrometric reference, correcting for variations in extraction, derivatization, and GC-MS analysis. The fully deuterated version is ideal because it co-elutes with the methyl esters of other fatty acids and has a distinct mass spectrum.
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| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
The in vitro biological activity of Methyl heptadecanoate-d33 has not been characterized, as it is used as an analytical internal standard. Its unlabeled parent, methyl heptadecanoate, is a simple fatty acid ester with no known specific biological activity. It is a stable compound commonly used as a standard in lipid analysis. In cell culture, the addition of methyl heptadecanoate (10-100 uM) to the medium does not typically produce any specific biological effects (e.g., no activation of PPARs, no significant effect on cell proliferation or differentiation). The fatty acid C17:0 (margaric acid) is a saturated fatty acid that can be incorporated into cellular phospholipids, but it is not a major signaling molecule. The labeled methyl heptadecanoate-d33 is used exclusively as a quantitative internal standard in GC-MS analysis of fatty acids extracted from cells. It is added at the beginning of the extraction process to correct for recovery and to enable absolute quantification of the cellular content of various fatty acids (C14:0, C16:0, C16:1, C18:0, C18:1, C18:2, etc.) present in the sample. |
| ln Vivo |
The in vivo activity of Methyl heptadecanoate-d33 is not directly evaluated; it is used as a tracer. The unlabeled methyl heptadecanoate, when administered orally to animals, would likely be hydrolyzed in the gut by esterases to heptadecanoic acid (C17:0), which could then be absorbed, incorporated into chylomicrons, and metabolized or stored in adipose tissue. However, because this is not a naturally abundant fatty acid, it could serve as a tracer. However, for most metabolic studies, the fully deuterated Methyl heptadecanoate-d33 is used as an internal standard in GC-MS analysis to quantify the concentration (umol/g of tissue or ug/mL of plasma) of total and individual fatty acids. This allows researchers to determine the fatty acid composition of plasma, adipose tissue, liver, or muscle in animal models of obesity, diabetes, or other metabolic diseases. The labeled compound is added at the start of the lipid extraction procedure to control for losses during sample processing (extraction, methylation, and injection). Because of its chemical similarity to other FAMEs, it corrects for all matrix effects and instrument variations.
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| Enzyme Assay |
A generic non-cell-based assay for Methyl heptadecanoate-d33 involves its use as an internal standard in a GC-MS method for the quantification of fatty acids in plasma. First, extract total lipids from 100 uL of plasma (or serum) using the Folch method (chloroform:methanol 2:1). To the extraction mixture, add a fixed amount of Methyl heptadecanoate-d33 (e.g., 50 ug) as the internal standard. After phase separation, evaporate the organic layer under nitrogen. Convert the extracted lipid fatty acids (triglycerides, phospholipids, etc.) to fatty acid methyl esters (FAMEs) by transesterification using 1 mL of 1 N methanolic HCl (or boron trifluoride in methanol) at 60degC for 60 minutes. Extract the FAMEs with hexane, evaporate, and reconstitute in 200 uL of hexane. Analyze by GC-MS using a fused silica capillary column coated with a polar stationary phase (e.g., 100% cyanopropyl polysiloxane, 100 m length). Use the following temperature program: initial 140degC, hold 5 min, ramp 4degC/min to 240degC, hold for 15 min. Use splitless injection. In the mass spectrometer (EI mode), perform selected ion monitoring (SIM) for specific fatty acids (e.g., m/z 74, 79, 87, etc.). However, for quantification using the internal standard, quantify the peak areas of the FAMEs of interest and compare them to the peak area of the Methyl heptadecanoate-d33 internal standard. The concentration of each fatty acid is then calculated using pre-determined response factors or by assuming a 1:1 response (which is typical for saturated FAMEs). This method is used for clinical and nutritional research.
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| Cell Assay |
A standard in vitro cell-based protocol for Methyl heptadecanoate-d33 involves the analysis of fatty acid composition in cultured adipocytes (3T3-L1 cells). Differentiate 3T3-L1 fibroblasts into mature adipocytes using a standard hormonal cocktail (insulin, dexamethasone, IBMX). On days 8-10 post-differentiation, harvest the cells by scraping. Extract cellular lipids using chloroform:methanol (2:1). Add a fixed amount of Methyl heptadecanoate-d33 (e.g., 10 ug) as the internal standard during the extraction. Process the extracts to form FAMEs as described above. Analyze by GC-MS. Quantify the amount (ug or nmol) of each fatty acid (C16:0, C18:0, C18:1, C18:2, etc.) per dish or per mg of cellular protein. This protocol is used to study the effects of drugs or genetic modifications (e.g., activation of PPARgamma, SREBP-1c) on de novo lipogenesis and fatty acid composition. By using the deuterated internal standard, which co-elutes with the unlabeled methyl heptadecanoate, the method can accurately correct for the extraction efficiency of the lipids from the cells and the derivatization yield of the fatty acids. This is essential for obtaining accurate absolute quantification.
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| Animal Protocol |
A typical in vivo animal protocol for Methyl heptadecanoate-d33 is used in a lipidomics study to quantify the fatty acid composition of liver or adipose tissue. Use male C57BL/6J mice (8 weeks old, n = 10 per group) fed a standard chow diet vs. a high-fat diet (HFD, 60% calories from fat) for 12 weeks. At the end of the study, euthanize the mice and collect liver and epididymal white adipose tissue (eWAT). Weigh the tissues and flash-freeze in liquid nitrogen. For analysis, homogenize approximately 100 mg of tissue in 1 mL of PBS. Extract lipids from the homogenate using the Folch method (chloroform:methanol 2:1) with the addition of a fixed amount of Methyl heptadecanoate-d33 (e.g., 100 ug) as the internal standard. Process the extracts to form FAMEs as described above. Analyze by GC-MS. Quantify the absolute amount (ug/g of tissue) of individual fatty acids (palmitic acid, stearic acid, oleic acid, linoleic acid, and others). Compare the fatty acid profiles between the chow and HFD groups. This protocol can also be used to study the impact of pharmacological agents (e.g., PPAR agonists, SGLT2 inhibitors) on tissue lipid composition. The use of the deuterated internal standard ensures that the measured values are accurate and reproducible, as it corrects for any sample-to-sample variation in extraction efficiency and derivatization yield.
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| ADME/Pharmacokinetics |
Methyl heptadecanoate-d33 is an analytical internal standard, not a drug. Its unlabeled parent, methyl heptadecanoate, is a saturated fatty acid methyl ester with low acute toxicity. The oral LD₅0 is expected to be >5,000 mg/kg (it is generally recognized as safe, GRAS, as a food additive in trace amounts). No specific carcinogenic, mutagenic, or reproductive toxicological data are available for methyl heptadecanoate. The compound is not a known irritant. For laboratory handling, Methyl heptadecanoate-d33 is a stable, non-volatile liquid or solid. Standard safety precautions for handling organic solvents (when preparing solutions) and working in a chemical laboratory should be followed: use gloves, a lab coat, and safety goggles. Avoid contact with skin and eyes. Store the pure compound at -20degC (or 2-8degC) in a tightly sealed container, protected from light and moisture. The compound is stable for several years under these conditions. It is for research use only and not for diagnostic or therapeutic applications.
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| References |
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| Additional Infomation |
Methyl heptadecanoate-d33 (methyl margarate-d33) is the stable isotope-labeled (fully deuterated) version of methyl heptadecanoate, a saturated fatty acid methyl ester with a 17-carbon alkane chain (C17:0). It is intended for research use as an internal standard for the accurate quantification of fatty acid methyl esters (FAMEs) in biological samples (plasma, serum, tissues, cells, milk) and food products (vegetable oils, dairy products) by gas chromatography-mass spectrometry (GC-MS). Fatty acids are major components of lipids and play essential roles in energy storage (triglycerides), cell membrane structure (phospholipids), and cell signaling (eicosanoids, PPAR ligands). Profiling of fatty acids (lipidomics) is a key technique in nutritional research, metabolic disease research (obesity, diabetes, fatty liver disease), and clinical diagnostics. Methyl heptadecanoate-d33 is added early in the sample processing workflow (extraction and derivatization) to correct for losses and matrix effects, enabling absolute quantification of the fatty acid content in complex samples. For research use only, not for human consumption.
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| Molecular Formula |
C18H3D33O2
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|---|---|
| Molecular Weight |
317.68
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| Exact Mass |
317.478
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| CAS # |
1219804-81-5
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| Related CAS # |
Methyl heptadecanoate;1731-92-6
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| PubChem CID |
71309888
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| Appearance |
Colorless to light yellow viscous liquid
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
337.1±5.0 °C at 760 mmHg
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| Flash Point |
161.2±7.5 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.443
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| LogP |
8.15
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
16
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| Heavy Atom Count |
20
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| Complexity |
202
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C([2H])([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C(=O)OC
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| InChi Key |
HUEBIMLTDXKIPR-SRIUXHGCSA-N
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| InChi Code |
InChI=1S/C18H36O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20-2/h3-17H2,1-2H3/i1D3,3D2,4D2,5D2,6D2,7D2,8D2,9D2,10D2,11D2,12D2,13D2,14D2,15D2,16D2,17D2
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| Chemical Name |
methyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,17,17,17-tritriacontadeuterioheptadecanoate
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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) |
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
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|---|---|
| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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 : PEG300 ：Tween 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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1478 mL | 15.7391 mL | 31.4782 mL | |
| 5 mM | 0.6296 mL | 3.1478 mL | 6.2956 mL | |
| 10 mM | 0.3148 mL | 1.5739 mL | 3.1478 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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