Intestinal permeation enhancer. [1]

The sodium salt of 10-undecylenic acid (uC₁₁) was evaluated as an intestinal permeation enhancer in Caco-2 cell monolayers. At 5–10 mM, uC₁₁ reduced transepithelial electrical resistance (TEER) and increased the apparent permeability (Papp) of [¹⁴C]-mannitol and FITC-dextrans (FD4, FD10). Its efficacy was comparable to sodium caprate (C₁₀) and superior to the saturated analogue sodium undecylenate (C₁₁) in terms of lower cytotoxicity. [1]
MTT assay in Caco-2 cells showed that uC₁₁ and C₁₀ had similar IC₅₀ values (~5 mM after 24 h exposure), while C₁₁ was more cytotoxic (IC₅₀ < 2.5 mM). [1]
High-content analysis (HCA) in Caco-2 cells revealed that uC₁₁ (8.5 mM, 60 min) increased plasma membrane permeability (PMP), intracellular Ca²⁺, and nuclear intensity, indicating a surfactant-like effect correlating with enhanced paracellular flux. [1]
In isolated rat colonic mucosa mounted in Ussing chambers, uC₁₁ (10–20 mM) reduced TEER and increased Papp of [¹⁴C]-mannitol and FD4, with efficacy similar to C₁₀ but less mucosal damage than C₁₁. [1]

In situ instillation of uC₁₁ (100 mM) with FD4 in rat jejunal and colonic loops significantly increased FD4 bioavailability (BA) compared to control. Enhancement ratios were ~10 in jejunum and ~30 in colon, comparable to C₁₀. [1]
Mini-tablets containing uC₁₁ (60% w/w) and FD4 instilled into rat jejunum and colon showed higher FD4 absorption (AUC) than C₁₀ mini-tablets, particularly in the colon, with no histological evidence of mucosal damage. [1]

Caco-2 monolayer flux assay: Caco-2 cells were grown on Transwell filters for 21–28 days. The apical compartment contained Ca²⁺-free HBSS with test compounds and flux markers ([¹⁴C]-mannitol or FITC-dextrans). Samples were taken from the basolateral side over time, and Papp was calculated. Treatments were done in duplicate and repeated three times. [1]
MTT cytotoxicity assay: Caco-2 cells were seeded in 96-well plates, exposed to MCFA salts in Ca²⁺-free DMEM for 1, 8, or 24 h, followed by MTT incubation and absorbance measurement. IC₅₀ was defined as the concentration reducing absorbance by 50%. [1]
High-content analysis (HCA): Caco-2 cells were seeded in 96-well plates, exposed to MCFA salts, then stained with Hoechst 33342, Fluo-4 AM, TMRM, and TOTO®-3 iodide. Imaging was performed using a high-content analyzer to measure cell number, nuclear area, nuclear intensity, intracellular Ca²⁺, mitochondrial membrane potential, and plasma membrane permeability. [1]

In situ intestinal instillation in rats: Male Wistar rats were fasted, anesthetized, and jejunal or colonic loops were surgically prepared. Solutions containing uC₁₁ or C₁₀ (100 mM) with FD4 (40 mg/kg) were injected into the loop. Blood samples were taken over 180 min for FD4 quantification. [1]
Mini-tablet instillation: Mini-tablets containing uC₁₁ or C₁₀ (60% w/w) and FD4 were placed into jejunal or colonic loops via a small incision. PBS was added to aid disintegration. Blood was collected over 180 min for pharmacokinetic analysis. [1]

Absorption, Distribution and Excretion
Undecenoic acid may be absorbed through the skin [MSDS]. No information on elimination pathways. No information on volume of distribution. No information on clearance rate. Metabolism/Metabolites No information on metabolism. Biological Half-Life No information on half-life. In rat intestinal perfusion experiments, co-administration of FD4 with uC₁₁ improved its oral bioavailability. In the jejunum, bioavailability increased from 2.1% (control group) to 21.8% (uC₁₁ group); in the colon, it increased from 1.7% to 49.8%. [1] Compared with C₁₀ tablets (45 minutes), uC₁₁ microtablets had a longer Tmax in the colon (84 minutes), which may be due to their slower dissolution rate. [1]

Protein Binding
No protein binding information was found. In Caco-2 cells, uC₁₁ showed lower cytotoxicity than saturated C₁₁ (MTT and HCA assays). [1] Histological examination of rat intestinal mucosa after perfusion with 100 mM uC₁₁ for 3 hours showed no significant damage, similar to C₁₀. [1] The oral LD₅₀ of undecenoic acid in rats was 2.5 g/kg (from Material Safety Data Sheet). [1]

[1]. Efficacious intestinal permeation enhancement induced by the sodium salt of 10-undecylenic acid, a medium chain fatty acid derivative. AAPS J. 2014 Sep;16(5):1064-76.

10-Undecenoic acid is an undecenoic acid with a double bond at position 10. It is derived from castor oil and used to treat skin problems. It is both a plant metabolite and an antifungal agent. It is the conjugate acid of 10-undecenoate. Undecenoate, or undecenoic acid, is an unsaturated fatty acid with a terminal double bond, derived from castor oil. Undecenoic acid is also naturally found in human sweat. It can be used as a precursor in the manufacture of aromatic chemicals, polymers, or modified silicones. Undecenoic acid was first isolated from castor oil distillate by the pyrolysis of ricinoleic acid in 1877 and has been polymerized for the production of vinyl groups. Studies have shown that many organic fatty acids have bactericidal or bacteriostatic effects. Undecenoic acid also has antifungal properties but has never been used alone for antifungal treatment. Undecenoates exist as antifungal agents in over-the-counter topical medications or compound preparations. Zinc undecenoate is a topical antifungal agent used to treat skin infections such as athlete's foot and relieve itching, burning, and irritation associated with this skin condition. Due to its bifunctional properties, undecenoic acid can also be used as a linker molecule to bind with other biomolecules, such as proteins. It can also serve as the acidic moiety of the anabolic steroid pedyone. Undecenoic acid has been reported in Streptomyces and sage, with supporting data. Undecenoic acid is a natural or synthetic antibacterial fatty acid with antifungal properties. Undecenoic acid is used topically in various creams in the form of zinc salts to treat fungal infections, eczema, tinea, and other skin conditions. Zinc has astringent properties and can relieve burning and irritation of the skin. Undecenoic acid is found in black elderberry berries. Undecenoic acid is a flavoring ingredient. See also: Triclosan (active ingredient); Zinc undecenoate (salt form); Calcium undecenoate (salt form)... See more...

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Drug Indications Used in salt form for the treatment of fungal infections. No therapeutic indications for use alone. Mechanism of Action Undecenoic acid (UA) is effective against Candida albicans, an opportunistic pathogenic yeast with two cell morphologies: a round yeast-like morphology and a filamentous morphology with elongated hyphae. Hyphae formation is associated with active infection and virulence. One study showed that UA inhibits biofilm formation in Candida albicans at concentrations above 3 mM and disrupts hyphal growth (i.e., the morphological transition from the yeast phase to the filamentous phase) at concentrations above 4 mM. Under drug treatment, the transcriptional levels of genes associated with hyphal formation (such as HWP1) are significantly reduced, leading to poor biofilm formation. Biofilm and hyphal formation are key virulence factors in initiating skin infections and later developing into disseminated infections. Undecenoic acid may also inhibit lipid metabolism-related enzymes by transporting protons across the plasma membrane, thereby altering cytoplasmic pH and inhibiting germ tube formation. Undecenoic acid (UA) is an over-the-counter antifungal drug and nutritional supplement that has been used orally in humans for over 60 years. Its sodium salt (uC₁₁) is a solid and is suitable for tablet formulations. [1] uC₁₁, as a permeation enhancer, increases cell bypass transport by producing a slight surfactant-like effect on the epithelial cell membrane, which may involve intracellular Ca²⁺ regulation and tight junction regulation. [1] Compared with saturated medium-chain fatty acids (MCFAs), the unsaturated bonds in uC₁₁ reduce its lipophilicity and cytotoxicity while maintaining the permeation enhancement effect. [1]

C11H20O2

184.2753

184.146

112-38-9

10-Undecenoic acid zinc salt;557-08-4

5634

Off-white to light yellow <23°C powder,>25°C liquid

0.9±0.1 g/cm3

300.8±0.0 °C at 760 mmHg

23-25 °C(lit.)

148.9±0.0 °C

0.0±1.3 mmHg at 25°C

1.456

3.99

1

2

9

13

141

0

O([H])C(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])=C([H])[H])=O

FRPZMMHWLSIFAZ-UHFFFAOYSA-N

InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13)

undec-10-enoic 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)

DMSO : ≥ 50 mg/mL (~271.33 mM)

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.)