delta-9 desaturase 0.9 μM (IC50)

With a wide range of biological activities, sterculic acid (SA) is a cyclopropene fatty acid that was first discovered in the seeds of the plant Sterculia foetida[2]. Adrenomedullin expression (AP, RP, APS, IML, in preparation) can be decreased by streptomycin[2]. Moreover, protective and anti-inflammatory effects of streptococcus can be mediated by it[2]. By preventing progesterone from being synthesized, streptococcus pneumoniae has a strong luteolytic effect on ovines, leading to luteal regression[2].

As steric acid reduces stearoyl-CoA desaturase-1 (SCD1) activity in vivo, it has been suggested as a possible treatment for metabolic syndrome (MS)[3].

Absorption, Distribution and Excretion
Cyclopropylene is a naturally occurring cyclopropylene fatty acid. This study investigated the distribution of radioactive cyclopropylene compounds labeled on the 9,10-methylene carbon of the cyclopropylene ring in trout (S. gairdneri). 50% of the administered dose was excreted in feces and urine within 168 hours, but less than 1% was excreted as carbon dioxide during the same period. Incorporation of the radioactive material in most organs peaked at 119 hours, with most of the labeling in the liver occurring in the fatty acid portion of the lipid fraction. Rainbow trout rapidly absorbed, transported, and incorporated sterol acids into tissue lipids (including membrane lipids), but were unable to oxidize the methylene carbon in cyclopropylene compounds to carbon dioxide.

Interactions
Aflatoxin Q1 (AFQ) is a biotransformation metabolite of aflatoxin B1 (AFB) and can be formed in vitro from liver microsomes in humans and monkeys. Eighty rainbow trout fry were fed a semi-purified experimental diet at a concentration of 100 ppm for 10 months. Several other groups of fry were fed 100 ppm AFQ, with the addition of 50 ppm cyclopropylene fatty acids (CPFA), 4 ppm AFB, and the basal experimental diet as controls. The incidence of hepatocellular carcinoma at 12 months was as follows: 100 PPB AFQ group - 12/114 (10.6%); 4 PPB AFB group - 55/114 (48.2%); 50 PPM CPFA group - 44/107 (41.1%); 100 PPB AFQ plus 50 PPM CPFA (steranoic acid) group - 106/119 (89.1%); control group - 0/120 (0%). The results confirmed the carcinogenicity of AFQ in rainbow trout, showed a synergistic effect between AFQ and CPFA, and indicated that AFQ is a potent hepatocarcinogen, with a carcinogenicity approximately 100 times lower than AFB. Rainbow trout fed a diet containing 20 μg/kg of ochratoxin A and cycloglutaric acid developed hepatocellular carcinomas (number not specified). No tumors were observed when ochratoxin A was added to the diet at concentrations of 16, 32, or 64 μg/kg for 8 months. Rainbow trout fed a diet containing 200 ppm cyclohexylamino acid and malvaline showed a significant increase in the sensitivity of trout hepatocytes to the carcinogenic effects of aflatoxin B1. After 4 weeks, distinctive slit-like streaks appeared in the hepatocyte cytoplasm. These changes became more frequent and pronounced with continued feeding. At weeks 8 and 12, the rough surface endoplasmic reticulum contained numerous parallel-arranged membrane materials and intact membrane structures. Glucose-6-phosphatase activity in the liver was significantly reduced. In male weaned rats fed a basal diet of saturated or unsaturated fat, the following substances were added: basal diet; aflatoxin B1 1.7 ppm; cyclohexylamino acid 210 ppm; and aflatoxin B1 1.7 ppm plus cyclohexylamino acid 210 ppm. After consuming these diets for two months, rats were switched to a basal diet without any supplements until they were sacrificed nine months later. Growth was inhibited in all supplemented rats, but no synergistic inhibitory effect was observed regardless of the fat source. Aflatoxin doubled liver weight; however, the combined use of cyclodextrin acid and aflatoxin only exacerbated the increase in liver weight when the diet contained unsaturated fats. In rats fed a saturated fat diet, administration of aflatoxin to either the control diet or a diet supplemented with cyclodextrin acid resulted in a significant increase in plasma cholesterol levels; in rats fed an unsaturated fat diet supplemented with aflatoxin, plasma cholesterol levels were slightly elevated, but this elevation was offset by cyclodextrin acid supplementation.

[1]. A multiplexed cell assay in HepG2 cells for the identification of delta-5, delta-6, and delta-9 desaturase and elongase inhibitors. J Biomol Screen. 2010 Feb;15(2):169-76.

[2]. Sterculic Acid: The Mechanisms of Action beyond Stearoyl-CoA Desaturase Inhibition and Therapeutic Opportunities in Human Diseases. Cells. 2020 Jan 7;9(1):140.

[3]. Preventive Action of Sterculic Oil on Metabolic Syndrome Development on a Fructose-Induced Rat Model. J Med Food. 2020 Mar;23(3):305-311.

Cyclopropylene is a long-chain monounsaturated fatty acid composed of 9-octadecenoic acid and 9,10-cyclopropenyl groups. It is a cyclopropenyl fatty acid, a long-chain fatty acid, and a monounsaturated fatty acid. Its function is related to octadecenoic acid. Cyclopropylene has been reported to exist in Crotalaria retusa, Gnetum parvifolium, and several other organisms with relevant data.

C19H34O2

294.47

294.255

738-87-4

12921

Colorless to light yellow liquid

0.9±0.1 g/cm3

418.7±24.0 °C at 760 mmHg

315.4±18.0 °C

0.0±2.1 mmHg at 25°C

1.487

7.72

1

2

15

21

318

0

CCCCCCCCC1CC=1CCCCCCCC(=O)O

PQRKPYLNZGDCFH-UHFFFAOYSA-N

InChI=1S/C19H34O2/c1-2-3-4-5-7-10-13-17-16-18(17)14-11-8-6-9-12-15-19(20)21/h2-16H2,1H3,(H,20,21)

8-(2-octylcyclopropen-1-yl)octanoic acid

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Ethanol: < 1 mg/mL
DMSO: < 1 mg/mL

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.

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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 : 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).

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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 : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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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

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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.

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 (Please use freshly prepared in vivo formulations for optimal results.)