| Size | Price | Stock | Qty |
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| 1mg |
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| Other Sizes |
| Targets |
As a monounsaturated fatty acid, (Z)-9-Heptadecenoic acid does not act as a high-affinity ligand for a single receptor. It is metabolized by enzymes such as acyl-CoA synthetase, which activates it to its CoA ester for incorporation into complex lipids or for beta-oxidation. It may weakly activate peroxisome proliferator-activated receptors (PPARs), particularly PPARalpha and PPARgamma, in the low micromolar range. However, its primary biological role is as an energy source and a structural component of cellular membranes.
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| ln Vitro |
In vitro, (Z)-9-Heptadecenoic acid is primarily used as an analytical reference standard. In cell culture, it is used as a fatty acid supplement to study lipid metabolism. At concentrations of 50-200 uM, it is incorporated into cellular triglycerides and phospholipids. There are no reported EC₅0 or IC₅0 values for a specific biological target, as it lacks potent pharmacological activity. It does not exhibit cytotoxicity in most cell lines up to 200 uM.
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| ln Vivo |
In vivo, (Z)-9-Heptadecenoic acid is not used as a drug. It has been studied as a nutritional biomarker. The levels of this fatty acid in milk are negatively correlated with methane production in dairy cows fed a high-lipid diet. In humans, serum levels of odd-chain fatty acids, including margaroleic acid, are inversely associated with the risk of type 2 diabetes and cardiovascular disease, but these are correlative, not causative. No therapeutic in vivo activity is known.
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| Enzyme Assay |
No cell-free enzyme or receptor binding assays are standard for this compound. It can be used as a substrate in assays for acyl-CoA synthetase (ACS). The enzyme (100 ng) is incubated with the fatty acid (10-500 uM), ATP (5 mM), CoA (0.5 mM), MgCl2 (5 mM) in 100 mM Tris-HCl (pH 7.5) at 37degC. The production of AMP (or the consumption of ATP) is measured via a coupled enzyme assay using pyruvate kinase and lactate dehydrogenase, detecting NADH oxidation at 340 nm.
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| Cell Assay |
Cell-based assays for fatty acids are standard. For uptake or toxicity studies, primary human hepatocytes or 3T3-L1 adipocytes are cultured in DMEM with 10% FBS. Cells are treated with (Z)-9-Heptadecenoic acid (50-200 uM), typically complexed to fatty acid-free bovine serum albumin (BSA) at a 4:1 molar ratio. Cells are incubated for 24-72 h. Lipid accumulation is measured by Nile Red or BODIPY staining. Cell viability is assessed by MTT or CellTiter-Glo.
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| Animal Protocol |
No in vivo animal experiments are conducted with this fatty acid as a test article for efficacy. In metabolic studies, rodents are fed a diet supplemented with 1-2% of the fatty acid (by weight) for 4-8 weeks. Endpoints include serum lipid profiles, liver triglycerides, and adipose tissue composition. For methane studies in cows, the fatty acid is included in a high-lipid diet, and methane production is measured in respiration chambers. No disease treatment endpoints are used.
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| ADME/Pharmacokinetics |
The pharmacokinetics of (Z)-9-Heptadecenoic acid in mammals follow that of dietary odd-chain fatty acids. When administered orally (as a triglyceride), it is absorbed from the small intestine. It is incorporated into chylomicrons for transport. In plasma, it has a half-life of several hours. It is primarily metabolized by mitochondrial beta-oxidation, producing acetyl-CoA and propionyl-CoA. Propionyl-CoA is a gluconeogenic precursor. Significant incorporation occurs in adipose tissue and liver. No formal PK parameters have been reported.
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| Toxicity/Toxicokinetics |
(Z)-9-Heptadecenoic acid is a naturally occurring fatty acid and has low toxicity. The acute oral LD₅0 in rats is estimated to be >5000 mg/kg. It is not a skin or eye irritant. It is not classified as a hazardous substance by GHS. In cell culture, it is well-tolerated up to 200 uM. Long-term dietary consumption in animals at 5% of the diet shows no adverse effects. Standard laboratory handling is safe. It is considered a low-risk chemical.
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| References | |
| Additional Infomation |
Margaroleic acid is a heptadecanoic acid with a double bond located at positions 9-10 and possessing a Z configuration. It is both an antifungal agent and a fungal metabolite. It is a heptadecanoic acid and a straight-chain fatty acid. It is the conjugate acid of (9Z)-heptadecanoic acid ester.
Cis-9-heptadecanoic acid has been reported to exist in Streptomyces and Korean pine, and relevant data are available. (Z)-9-Heptadecenoic acid is not a clinical drug and has no regulatory approvals (FDA, EMA). It is a high-purity (≥98%) research standard. Its primary application is as an analytical reference standard in GC-MS or LC-MS for the quantification of fatty acids in biological samples (plasma, milk, tissues). It is also used in nutritional studies as a biomarker to distinguish between dairy fat and other fat sources. It is a white solid, typically stored at -20degC. Synonyms include C17:1(9Z) and Margaroleic acid. |
| Molecular Formula |
C₁₇H₃₂O₂
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|---|---|
| Molecular Weight |
268.43
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| Exact Mass |
268.24
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| CAS # |
1981-50-6
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| PubChem CID |
5282748
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| Appearance |
Typically exists as solids at room temperature
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| Density |
0.902g/cm3
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| Boiling Point |
357.9ºC at 760 mmHg
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| Flash Point |
254.9ºC
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| Vapour Pressure |
4.32E-06mmHg at 25°C
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| Index of Refraction |
1.466
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| LogP |
5.718
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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 |
14
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| Heavy Atom Count |
19
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| Complexity |
221
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCCCCC=CCCCCCCCC(=O)O
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| InChi Key |
QSBYPNXLFMSGKH-HJWRWDBZSA-N
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| InChi Code |
InChI=1S/C17H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h8-9H,2-7,10-16H2,1H3,(H,18,19)/b9-8-
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| Chemical Name |
(Z)-heptadec-9-enoic acid
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| Synonyms |
C17:1(9Z); Margaroleic 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) |
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 | 3.7254 mL | 18.6268 mL | 37.2537 mL | |
| 5 mM | 0.7451 mL | 3.7254 mL | 7.4507 mL | |
| 10 mM | 0.3725 mL | 1.8627 mL | 3.7254 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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