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
STERCULIC ACID IS A NATURALLY OCCURRING CYCLOPROPENOID FATTY ACID. THE DISTRIBUTION OF RADIOACTIVITY FROM STERCULIC ACID, LABELED ON 9,10-METHYLENE C OF THE CYCLOPROPENE RING, WAS INVESTIGATED IN TROUT, S GAIRDNERI. OF THE ADMIN DOSE, 50% WAS EXCRETED IN FECES & URINE BY 168 HR, BUT LESS THAN 1% OF THE DOSE WAS EXPIRED AS CO2 DURING THE SAME TIME PERIOD. INCORPORATION OF RADIOACTIVITY INTO MOST ORGANS PEAKED AT 119 HR & THE MAJORITY OF THE LABEL IN THE LIVER WAS IN THE FATTY ACID PORTION OF THE LIPID FRACTION. RAINBOW TROUT READILY ABSORB, TRANSPORT & INCORPORATE STERCULIC ACID INTO TISSUE LIPID, INCL MEMBRANE LIPID, BUT CANNOT OXIDIZE THE METHYLENE C OF THE CYCLOPROPENOID TO CO2.

Interactions
AFLATOXIN Q1 (AFQ), A BIOTRANSFORMATION METABOLITE OF AFLATOXIN B1 (AFB), IS FORMED IN VITRO BY HUMAN & MONKEY LIVER MICROSOMES. AFQ WAS FED TO DUPLICATE LOTS OF 80 RAINBOW TROUT FINGERLINGS @ 100 PPB IN A SEMI-PURIFIED TEST DIET FOR 10 MONTHS. ADDNL LOTS WERE FED 100 PPB AFQ PLUS 50 PPM STERCULIC ACID, & 50 PPM CYCLOPROPENE FATTY ACID (CPFA), 4 PPB AFB & THE BASAL TEST DIET TO SERVE AS CONTROLS. HEPATOCELLULAR CARCINOMA INCIDENCES @ 12 MONTHS WERE AS FOLLOWS: 100 PPB AFQ- 12/114 (10.6%); 4 PPB AFB- 55/114 (48.2%); 50 PPM CPFA- 44/107 (41.1%); 100 PPB AFQ PLUS 50 PPM CPFA (STERCULIC ACID)- 106/119 (89.1%) & CONTROL 0/120 (0%). RESULTS ESTABLISH THE CARCINOGENICITY OF AFQ TO RAINBOW TROUT, THE SYNERGISTIC INTERACTION BETWEEN AFQ & CPFA & INDICATE THAT AFQ IS A POTENT LIVER CARCINOGEN ABOUT 100 TIMES LESS CARCINOGENIC THAN AFB.
RAINBOW TROUT FED A DIET CONTAINING 20 UG OCHRATOXIN A PER KG OF DIET, TOGETHER WITH STERCULIC ACID, DEVELOPED HEPATOMAS (NUMBER UNSPECIFIED). NO TUMORS WERE OBSERVED WHEN OCHRATOXIN A WAS FED ALONE AT CONCN OF 16, 32, OR 64 UG/KG OF DIET FOR 8 MONTHS.
RAINBOW TROUT FED A DIET CONTAINING 200 PPM OF STERCULIC ACID & MALVALIC ACID, SUBSTANCES THAT GREATLY INCR THE SENSITIVITY OF TROUT LIVER CELLS TO CARCINOGENIC EFFECTS OF AFLATOXIN B1. AFTER 4 WK, PECULIAR CLEFT-LIKE STRIATIONS APPEARED IN CYTOPLASM OF HEPATOCYTES. THESE ALTERATIONS BECAME PROGRESSIVELY MORE FREQUENT & MARKED WITH CONTINUED FEEDING OF DIET. AT 8 & 12 WK, ROUGH-SURFACED ENDOPLASMIC RETICULUM CONTAINED MANY PARALLEL ARRAYS & WHORLED PROFILES OF MEMBRANE MATERIAL. GLUCOSE-6-PHOSPHATASE ACTIVITY IN LIVER WAS SIGNIFICANTLY DECREASED.
IN MALE WEANLING RATS FED BASAL DIETS OF SATURATED OR UNSATURATED FAT, THE FOLLOWING ADDITIONS WERE MADE: BASAL DIET; AFLATOXIN B1 @ 1.7 PPM; STERCULIC ACID @ 210 PPM; & AFLATOXIN B1 @ 1.7 PPM, PLUS STERCULIC ACID @ 210 PPM. RATS CONSUMED THESE DIETS FOR 2 MONTHS & THEREAFTER WERE FED UNSUPPLEMENTED BASAL DIET UNTIL SACRIFICE 9 MONTHS LATER. GROWTH WAS DEPRESSED IN ALL RATS GIVEN DIETARY SUPPLEMENTS BUT NO SYNERGISTIC INHIBITION WAS OBSERVED, REGARDLESS OF FAT SOURCE. LIVER WEIGHT DOUBLED IN RESPONSE TO AFLATOXIN; HOWEVER, ONLY WHEN DIET CONTAINED UNSATURATED FAT DID STERCULIC ACID, IN COMBINATION WITH AFLATOXIN, EXAGGERATE THE INCREASE IN LIVER WEIGHT. IN RATS FED SATURATED FAT DIET, AFLATOXIN ADMIN TO RATS FED THE CONTROL OR STERCULIC ACID SUPPLEMENT DIETS RESULTED IN MARKED INCREASE IN PLASMA CHOLESTEROL LEVELS; THE UNSATURATED FAT DIETS, SUPPLEMENTED WITH AFLATOXIN, EVOKED A SLIGHT INCREASE IN PLASMA CHOLESTEROL CONTENT WHICH WAS NULLIFIED BY STERCULIC 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.

Sterculic acid is a long-chain, monounsaturated fatty acid composed of 9-octadecenoic acid having a 9,10-cyclopropenyl group. It is a cyclopropenyl fatty acid, a long-chain fatty acid and a monounsaturated fatty acid. It is functionally related to an octadec-9-enoic acid.
Sterculic acid has been reported in Crotalaria retusa, Gnetum parvifolium, and other organisms with data available.

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.)