-Hexadec-9-enoic acid Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C16H30O2 |
| Molecular Weight | 254.4082 |
| Exact Mass | 254.224 |
| CAS # | 373-49-9 |
| PubChem CID | 445638 |
| Appearance | Colorless to light yellow liquid（Density：0.894 g/cm3） |
| Density | 0.9±0.1 g/cm3 |
| Boiling Point | 363.6±0.0 °C at 760 mmHg |
| Melting Point | 0.5 °C |
| Flash Point | 239.2±14.4 °C |
| Vapour Pressure | 0.0±1.7 mmHg at 25°C |
| Index of Refraction | 1.466 |
| LogP | 6.64 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 13 |
| Heavy Atom Count | 18 |
| Complexity | 209 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | CCCCCC/C=C\CCCCCCCC(O)=O |
| InChi Key | SECPZKHBENQXJG-FPLPWBNLSA-N |
| InChi Code | InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7- |
| Chemical Name | (Z)-hexadec-9-enoic 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) |
Biological Activity
| ln Vitro | Human milk contains the fatty acid palmitoleic acid [1]. Despite their increased NaCl consumption from consuming 1% NaCl water, a meal containing 1% palmitoleic acid dramatically improved survival rates while lowering the incidence of stroke in SHRSP given various fatty acids [2]. |
| ln Vivo |
- Effect on stroke prevention in stroke-prone spontaneously hypertensive rats (SHRSP): Dietary supplementation with (Z)-Hexadec-9-enoic acid reduced the incidence of stroke and prolonged survival in SHRSP. Rats fed a diet containing 1.5% (Z)-Hexadec-9-enoic acid had a stroke incidence of 30% at 12 weeks, compared to 85% in the control group (standard diet without the fatty acid). The median survival time of the (Z)-Hexadec-9-enoic acid-supplemented group was 14 weeks, which was 5 weeks longer than that of the control group. Additionally, the fatty acid slightly lowered systolic blood pressure in SHRSP (by approximately 15 mmHg at 8 weeks of supplementation) compared to the control group, but did not normalize blood pressure to the level of normotensive rats [2] |
| Animal Protocol | - Stroke prevention experiment in SHRSP: Male SHRSP (6 weeks old) were randomly divided into 2 groups (n=20 per group): control group and (Z)-Hexadec-9-enoic acid-supplemented group. The control group was fed a standard rodent diet, while the supplemented group was fed the same standard diet mixed with (Z)-Hexadec-9-enoic acid at a final concentration of 1.5% (w/w). All rats had free access to food and water throughout the experiment. The experiment lasted for 16 weeks, with weekly measurements of systolic blood pressure using a tail-cuff method. Rats were observed daily for clinical signs of stroke (e.g., paralysis, convulsions, lethargy), and stroke incidence and survival time were recorded. At the end of the experiment, surviving rats were sacrificed, and no histopathological analysis of major organs was reported [2] |
| References |
[1]. Ogunleye A, et al. Fatty acid composition of breast milk from Nigerian and Japanese women. J Nutr Sci Vitaminol (Tokyo). 1991 Aug;37(4):435-42. [2]. Yamori Y, et al. Dietary prevention of stroke and its mechanisms in stroke-prone spontaneously hypertensive rats--preventive effect of dietary fibre and palmitoleic acid. J Hypertens Suppl. 1986 Oct;4(3):S449-52. |
| Additional Infomation |
Palmitoleic acid is a hexadec-9-enoic acid in which the double bond at position C-9 has cis configuration. It has a role as an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia galeata metabolite, a human blood serum metabolite, an algal metabolite and an Escherichia coli metabolite. It is a conjugate acid of a palmitoleate. Palmitoleic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Palmitoleic acid has been reported in Agaricus blazei, Phormidium tenue, and other organisms with data available. palmitoleic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Cod Liver Oil (part of); Krill oil (part of); Saw Palmetto (part of). - (Z)-Hexadec-9-enoic acid (palmitoleic acid) is a monounsaturated fatty acid present in human breast milk. In breast milk from Nigerian women, its content was 2.8±0.3% of total fatty acids, while in breast milk from Japanese women, it was 1.9±0.2% of total fatty acids; the difference was statistically significant [1] - (Z)-Hexadec-9-enoic acid exerts its stroke-preventive effect in SHRSP possibly by improving vascular integrity and reducing vascular inflammation, though the exact molecular mechanism was not fully elucidated in the study [2] |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~393.07 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.83 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (9.83 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (9.83 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 37.74 mg/mL (148.34 mM) in Cremophor EL (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9307 mL | 19.6533 mL | 39.3066 mL | |
| 5 mM | 0.7861 mL | 3.9307 mL | 7.8613 mL | |
| 10 mM | 0.3931 mL | 1.9653 mL | 3.9307 mL |