| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
Human Endogenous Metabolite
Peroxisome proliferator-activated receptors (PPARs, especially PPARalpha) and enzymes of fatty acid elongation and desaturation (e.g., ELOVL2, ELOVL5). Gondoic acid is involved in the synthesis of longer-chain fatty acids such as erucic acid (22:1) via elongase activity. |
|---|---|
| ln Vitro |
In vitro, unlabeled gondoic acid (10-100 uM) can activate PPARalpha in reporter assays and reduce triglyceride accumulation in hepatocytes. It also serves as a substrate for fatty acid elongases. The labeled compound is an analytical standard and has no biological activity.
|
| ln Vivo |
In vivo, unlabeled gondoic acid (100-500 mg/kg, oral) has been shown to reduce hepatic steatosis and improve lipid profiles in rodent models of non-alcoholic fatty liver disease (NAFLD). It may also modulate inflammatory responses. The labeled compound is not used for activity studies.
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| Enzyme Assay |
A non-cell assay uses gondoic acid-d13 (or unlabeled) as a standard for GC-MS. A fixed amount (1-10 ug) is spiked into samples before lipid extraction and derivatization to FAMEs. For enzyme assays, microsomes containing ELOVL2 are incubated with gondoic acid and malonyl-CoA; product (erucic acid) is analyzed by GC-MS.
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| Cell Assay |
For cell studies, unlabeled gondoic acid is complexed with fatty acid-free BSA and added to culture medium of hepatocytes (e.g., HepG2) at 10-100 uM for 6-24 hours. Lipid accumulation (oil red O), PPARalpha target gene expression (qPCR), and fatty acid composition (GC-MS) are assessed. The labeled compound is not used.
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| Animal Protocol |
In animal studies, gondoic acid-d13 (or unlabeled) is administered to rodents by oral gavage (dissolved in corn oil) at 50-200 mg/kg. Blood and liver samples are collected to analyze incorporation into lipid classes and to measure fatty acid elongation activity by GC-MS. Efficacy studies use unlabeled compound.
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| ADME/Pharmacokinetics |
Gondoic acid is absorbed from the intestine, incorporated into chylomicrons, and distributed to tissues (liver, adipose). It is elongated to erucic acid (22:1) and metabolized by beta-oxidation in peroxisomes. Plasma half-life is 2-4 hours. The deuterium label does not alter ADME.
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| Toxicity/Toxicokinetics |
Gondoic acid is generally regarded as safe (GRAS) as a dietary very long-chain monounsaturated fatty acid. The LD50 in rats is >5000 mg/kg. No significant toxicity is reported at research doses (≤500 mg/kg). The deuterated analog is non-toxic at tracer levels.
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| References | |
| Additional Infomation |
(11Z)-Eicosano-11-enoic acid is an eicosanoic acid with a cis double bond at position 11. It is a metabolite found in both plants and humans. It is the conjugate acid of eicosanoic acid. Cis-11-eicosanoic acid has been reported in Salvia hispanica, Pringlea antiscorbutica, and other organisms with relevant data. Eicosanoic acid is a monounsaturated long-chain fatty acid with a 20-carbon backbone, the only double bond located at positions 5, 6, 7, 9, 11, 12, or 15 from the methyl terminus. Eicosanoic acid is a monounsaturated long-chain fatty acid with a 20-carbon backbone, the only double bond located at position 9 from the methyl terminus, and this double bond is in the cis configuration. See also: Cod liver oil (partial).
Gondoic acid (cis-11-Eicosenoic acid) is used as an authentic standard for the quantification of very long-chain monounsaturated fatty acids by GC-MS in lipidomics research. It is also a reference compound in studies of fatty acid elongation and NAFLD. Not an approved drug. Store at -20degC. |
| Molecular Formula |
C20H38O2
|
|---|---|
| Molecular Weight |
310.51
|
| Exact Mass |
310.287
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| CAS # |
5561-99-9
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| PubChem CID |
5282768
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
426.3±14.0 °C at 760 mmHg
|
| Melting Point |
23-24 °C(lit.)
|
| Flash Point |
323.0±15.2 °C
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| Vapour Pressure |
0.0±2.2 mmHg at 25°C
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| Index of Refraction |
1.467
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| LogP |
8.76
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
17
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| Heavy Atom Count |
22
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| Complexity |
258
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CCCCCCCC/C=C\CCCCCCCCCC(=O)O
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| InChi Key |
BITHHVVYSMSWAG-KTKRTIGZSA-N
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| InChi Code |
InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10H,2-8,11-19H2,1H3,(H,21,22)/b10-9-
|
| Chemical Name |
(Z)-icos-11-enoic acid
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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 :~100 mg/mL (~322.05 mM)
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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 | 3.2205 mL | 16.1025 mL | 32.2051 mL | |
| 5 mM | 0.6441 mL | 3.2205 mL | 6.4410 mL | |
| 10 mM | 0.3221 mL | 1.6103 mL | 3.2205 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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