Intestinal permeation enhancer. [1]

10-十一碳烯酸的钠盐（uC₁₁）在 Caco-2 细胞单层中被评估为肠道渗透增强剂。在 5–10 mM 浓度下，uC₁₁ 降低了跨上皮电阻（TEER），并增加了 [¹⁴C]-甘露醇和 FITC-葡聚糖（FD4、FD10）的表观渗透性（Papp）。其效果与癸酸钠（C₁₀）相当，且在细胞毒性方面低于饱和类似物十一碳酸钠（C₁₁）。[1]
在 Caco-2 细胞中进行的 MTT 实验显示，uC₁₁ 和 C₁₀ 的 IC₅₀ 值相近（约 5 mM，暴露 24 小时），而 C₁₁ 的细胞毒性更强（IC₅₀ < 2.5 mM）。[1]
在 Caco-2 细胞中进行的高内涵分析（HCA）显示，uC₁₁（8.5 mM，60 分钟）可增加细胞膜通透性、细胞内 Ca²⁺ 和核强度，表明其具有表面活性剂样作用，与增强的旁细胞通量相关。[1]
在 Ussing 室中分离的大鼠结肠黏膜上，uC₁₁（10–20 mM）可降低 TEER 并增加 [¹⁴C]-甘露醇和 FD4 的 Papp，效果与 C₁₀ 相似，但黏膜损伤小于 C₁₁。[1]

在大鼠空肠和结肠环中进行原位灌注实验，uC₁₁（100 mM）与 FD4 共同给药可显著提高 FD4 的生物利用度（BA）。在空肠中的增强比约为 10，在结肠中约为 30，与 C₁₀ 相当。[1]
将含有 uC₁₁（60% w/w）和 FD4 的微片植入大鼠空肠和结肠后，FD4 的吸收（AUC）高于 C₁₀ 微片，尤其在结肠中更为明显，且未见黏膜损伤的组织学证据。[1]

Caco-2 单层通量实验： 将 Caco-2 细胞在 Transwell 滤膜上培养 21–28 天。顶室加入不含 Ca²⁺ 的 HBSS，内含待测化合物和通量标记物（[¹⁴C]-甘露醇或 FITC-葡聚糖）。在不同时间点采集基底侧样品，计算 Papp。每个处理设双复孔，重复三次。[1]
MTT 细胞毒性实验： 将 Caco-2 细胞接种于 96 孔板，在不含 Ca²⁺ 的 DMEM 中暴露于 MCFA 盐类 1、8 或 24 小时，然后加入 MTT 孵育并测定吸光度。IC₅₀ 定义为使吸光度降低 50% 的浓度。[1]
高内涵分析（HCA）： 将 Caco-2 细胞接种于 96 孔板，暴露于 MCFA 盐类后，用 Hoechst 33342、Fluo-4 AM、TMRM 和 TOTO®-3 碘化物染色。使用高内涵分析仪成像，测定细胞数、核面积、核强度、细胞内 Ca²⁺、线粒体膜电位和细胞膜通透性。[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
Undecylenic acid may be absorbed through the skin [MSDS].
No information regarding route of elimination.
No information regarding volume of distribution.
No information regarding clearance.

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Metabolism / Metabolites
No information regarding metabolism.

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Biological Half-Life
No information regarding half-life.

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The oral bioavailability of FD4 was enhanced by co-administration with uC₁₁ in rat intestinal instillations. In jejunum, BA increased from 2.1% (control) to 21.8% (uC₁₁); in colon, from 1.7% to 49.8%. [1]
uC₁₁ mini-tablets showed prolonged Tmax (84 min in colon) compared to C₁₀ tablets (45 min), likely due to slower dissolution. [1]

Protein Binding
No information regarding protein binding.

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uC₁₁ showed lower cytotoxicity than the saturated C₁₁ in Caco-2 cells (MTT and HCA). [1]
Histological examination of rat intestinal mucosa after 3-h instillation with 100 mM uC₁₁ showed no significant damage, similar to C₁₀. [1]
The oral LD₅₀ of undecylenic acid in rats is 2.5 g/kg (cited 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 having its double bond in the 10-position. It is derived from castor oil and is used for the treatment of skin problems. It has a role as a plant metabolite and an antifungal drug. It is a conjugate acid of a 10-undecenoate.
Undecylenate, or undecylenic acid, is an unsaturated fatty acid with a terminal double bond that is derived from castor oil. Undecylenic acid is also found naturally in the human sweat. It is used as a precursor in the manufacture of aromatic chemicals, polymers or modified silicones. Undecylenic acid was first isolated from the products of distillation of castor oil in 1877 via pyrolysis of ricinoleic acid, and has been polymerized for vinyl production. It it suggested that many organic fatty acids exert fungicidal or fungistatic actions. Undecylenic acid also possesses antifungal properties, but is never used on its own for antifungal purposes. Salts of undecylenate are found in topical over-the-counter or mixture products as antifungal agents. Zinc undecylenate is an example of a topical antifungal agent that treats skin infections such as athlete’s foot and relieves itching, burning, and irritation associated with the skin condition. Due to its bifunctional properties, undecylenate is also used as a linking molecule to conjugate other biomolecules such as proteins. It serves as an acid moiety for anabolic steroid boldenone.
Undecylenic acid has been reported in Streptomyces and Salvia fruticosa with data available.
Undecylenic Acid is a natural or synthetic fungistatic fatty acid, antifungal Undecylenic Acid is used topically as a zinc salt in various creams against fungal infections, eczemas, ringworm, and other cutaneous conditions. The zinc provides an astringent action, reducing rawness and irritation.
Undecylenic acid is found in black elderberry. Undecylenic acid is a flavouring ingredient.
See also: Triclosan (active moiety of); Zinc Undecylenate (has salt form); Calcium Undecylenate (has salt form) ... View More ...

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Drug Indication
Indicated for the treatment of fungal infections as a salt form. No therapeutic indications on its own.

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Mechanism of Action
Undecylenic acid demonstrated effectiveness against _Candida albicans_, which is an opportunistic pathogenic yeast with two cellular morphologies: the round yeast form and the filamentous form with elongated hyphae. Hyphae formation is associated with active infections and virulence. A study proposed that undecylenic acid inhibits biofilm formation of _Candida albicans_ with optimal concentration above 3 mM and disrupts hyphal growth, which is the morphological transition from yeast to filamentous phase, at concentration above 4 mM. Under the drug treatment, hyphal formation related genes, like HWP1, were significantly reduced in transcriptional level leading to poor biofilm formation. Both biofilm and hyphae formation are critical virulence factors for the initiation of skin infection and late development of disseminated infection. Undecylenic acid may also inhibit enzyme involved in lipid metabolism and abolish germ tube formation by carrying protons across the plasma membrane, thus altering cytoplasmic pH.

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Undecylenic acid (UA) is an OTC antifungal and nutritional supplement with over 60 years of oral use in humans. Its sodium salt (uC₁₁) is a solid suitable for tablet formulation. [1]
uC₁₁ acts as a permeation enhancer by increasing paracellular transport via mild surfactant-like effects on epithelial membranes, possibly involving intracellular Ca²⁺ modulation and tight junction regulation. [1]
The unsaturated bond in uC₁₁ reduces lipophilicity and cytotoxicity compared to saturated MCFAs, while maintaining permeation enhancement efficacy. [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

37.3

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)

注意: 如下所列的是一些常用的体内动物实验溶解配方，主要用于溶解难溶或不溶于水的产品（水溶度<1 mg/mL）。 建议您先取少量样品进行尝试，如该配方可行，再根据实验需求增加样品量。

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注射用配方1: DMSO : Tween 80： Saline = 10 : 5 : 85 (如： 100 μL DMSO → 50 μL Tween 80 → 850 μL Saline)
*生理盐水/Saline的制备：将0.9g氯化钠/NaCl溶解在100 mL ddH ₂ O中，得到澄清溶液。
注射用配方 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL DMSO → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)
注射用配方 3: DMSO : Corn oil = 10 : 90 (如： 100 μL DMSO → 900 μL Corn oil)
示例: 以注射用配方 3 (DMSO : Corn oil = 10 : 90) 为例说明, 如果要配制 1 mL 2.5 mg/mL的工作液, 您可以取 100 μL 25 mg/mL 澄清的 DMSO 储备液，加到 900 μL Corn oil/玉米油中, 混合均匀。

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注射用配方 4: DMSO : 20% SBE-β-CD in Saline = 10 : 90 [如：100 μL DMSO → 900 μL (20% SBE-β-CD in Saline)]
*20% SBE-β-CD in Saline的制备（4°C，储存1周）：将2g SBE-β-CD (磺丁基-β-环糊精) 溶解于10mL生理盐水中，得到澄清溶液。
注射用配方 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (如： 500 μL 2-Hydroxypropyl-β-cyclodextrin (羟丙基环胡精)→ 500 μL Saline)
注射用配方 6: DMSO : PEG300 : Castor oil : Saline = 5 : 10 : 20 : 65 (如： 50 μL DMSO → 100 μL PEG300 → 200 μL Castor oil → 650 μL Saline)
注射用配方 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (如： 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
注射用配方 8: 溶解于Cremophor/Ethanol (50 : 50), 然后用生理盐水稀释。
注射用配方 9: EtOH : Corn oil = 10 : 90 (如： 100 μL EtOH → 900 μL Corn oil)
注射用配方 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL EtOH → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)

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口服配方 1: 悬浮于0.5% CMC Na (羧甲基纤维素钠)
口服配方 2: 悬浮于0.5% Carboxymethyl cellulose (羧甲基纤维素)
示例: 以口服配方 1 (悬浮于 0.5% CMC Na)为例说明, 如果要配制 100 mL 2.5 mg/mL 的工作液, 您可以先取0.5g CMC Na并将其溶解于100mL ddH2O中，得到0.5%CMC-Na澄清溶液；然后将250 mg待测化合物加到100 mL前述 0.5%CMC Na溶液中，得到悬浮液。

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口服配方 3: 溶解于 PEG400 (聚乙二醇400)
口服配方 4: 悬浮于0.2% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 5: 溶解于0.25% Tween 80 and 0.5% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 6: 做成粉末与食物混合

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注意: 以上为较为常见方法，仅供参考， InvivoChem并未独立验证这些配方的准确性。具体溶剂的选择首先应参照文献已报道溶解方法、配方或剂型，对于某些尚未有文献报道溶解方法的化合物，需通过前期实验来确定（建议先取少量样品进行尝试），包括产品的溶解情况、梯度设置、动物的耐受性等。

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。