8-methyl Nonanoic Acid
(Synonyms: 8-甲基壬酸,Isocapric Acid) 目录号 : GC40759A precursor of capsaicin
Cas No.:5963-14-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Capsaicin, the chemical that imparts the spicy-hot quality of chili peppers, is produced by the fruits of plants belonging to the Capsicum family. 8-methyl Nonanoic acid is an immediate precursor of capsaicin as well as a by-product of capsaicin degradation.[1] Addition of 5 mM of 8-methyl nonanoic acid significantly increases the yield of capsaicin in both immobilized and freely suspended cells of C. frutescens. [2] Capsaicin has reported antimicrobial properties, however isocapric acid can act as a growth substrate in certain bacterial strains.[3]
Reference:
[1]. Kaga, H., Miura, M., and Orito, K. A facile procedure for synthesis of capsaicin. The Journal of Organic Chemistry 54, 3477-3478 (1989).
[2]. Lindsey, K., and Yeoman, M.M. The synthetic potential of immobilised cells of Capsicum frutescens mill cv. annuum. Planta 162, 495-501 (1984).
[3]. Flagan, S.F., and Leadbetter, J.R. Utilization of capsaicin and vanillylamine as growth substrates by Capsicum (hot pepper)-associated bacteria. Environmental Microbiology 8(3), 560-565 (2006).
| Cas No. | 5963-14-4 | SDF | |
| 别名 | 8-甲基壬酸,Isocapric Acid | ||
| 化学名 | 8-methyl Nonanoic Acid | ||
| Canonical SMILES | CC(C)CCCCCCC(=O)O | ||
| 分子式 | C10H20O2 | 分子量 | 172.3 |
| 溶解度 | 10mg/mL in ethanol, 10mg/mL in DMSO, 10mg/mL in DMF | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.8038 mL | 29.0192 mL | 58.0383 mL |
| 5 mM | 1.1608 mL | 5.8038 mL | 11.6077 mL |
| 10 mM | 0.5804 mL | 2.9019 mL | 5.8038 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Cellular responses to 8-methyl Nonanoic Acid, a degradation by-product of dihydrocapsaicin, in 3T3-L1 adipocytes
BMC Complement Med Ther 2023 Jan 21;23(1):18.PMID:36681810DOI:10.1186/s12906-023-03844-w.
Background: Capsaicinoids, such as dihydrocapsaicin (DHC), exert the health-promoting effects of chili peppers on energy metabolism. The metabolic responses to capsaicinoids are primarily mediated through transient receptor potential cation channel subfamily V member 1 (TRPV1). However, the varying contributions of their metabolites to beneficial health outcomes remain unclear. 8-methyl Nonanoic Acid (8-MNA), a methyl-branched medium chain fatty acid (MCFA), is an in vivo degradation by-product of DHC. Since MCFAs have emerged as metabolic modulators in adipocytes, here we examined various cellular responses to 8-MNA in 3T3-L1 adipocytes. Methods: The viability of 3T3-L1 adipocytes exposed to various concentrations of 8-MNA was assessed by the Calcein AM assay. Biochemical assays for lipid accumulation, AMP-activated protein kinase (AMPK) activity, lipolysis and glucose uptake were performed in 3T3-L1 adipocytes treated with 8-MNA during 48-h nutrient starvation or 5-day maturation. Results: 8-MNA caused no impact on cell viability. During nutrient starvation, 8-MNA decreased lipid amounts in association with AMPK activation, a molecular event that suppresses lipogenic processes. Moreover, 3T3-L1 adipocytes that were treated with 8-MNA during 5-day maturation exhibited a reduced lipolytic response to isoproterenol and an increased glucose uptake when stimulated with insulin. Conclusions: These results suggest that 8-MNA derived from DHC modulates energy metabolism in adipocytes and also support the idea that the metabolic benefits of chili consumption are partly attributable to 8-MNA.
Gastrointestinal absorption and metabolism of capsaicin and dihydrocapsaicin in rats
Toxicol Appl Pharmacol 1984 Mar 15;72(3):449-56.PMID:6710495DOI:10.1016/0041-008x(84)90121-2.
Gastrointestinal absorption of capsaicin and dihydrocapsaicin was studied in rats in vivo and in situ. Rapid absorption of capsaicin or dihydrocapsaicin from stomach and small intestine occurred in vivo. About 85% of the dose was absorbed in the gastrointestinal tract within 3 hr. In situ, within 60 min after the administration of capsaicin and dihydrocapsaicin into stomach, jejunum, and ileum, about 50, 80, and 70% of the respective dose had disappeared from the lumen. When 2,4-dinitrophenol or NaCN was added, no significant reduction in uptake of [3H]dihydrocapsaicin was observed in the jejunum. These results suggested that capsaicin and its analogs were absorbed by a nonactive process in jejunum. [3H]Dihydrocapsaicin was mainly absorbed via the portal system but not a mesenteric lymphangial one. The radioactivity in the portal blood was composed of 85% of [3H]dihydrocapsaicin and 15% of its metabolite (8-methyl Nonanoic Acid) bound to the albumin fraction. Dihydrocapsaicin-hydrolyzing enzyme activity was found in jejunal tissue. These results suggest that capsaicin and its analogs partly received a first-pass effect, i.e., metabolism of a compound following first absorption in the gastrointestinal tract. It is concluded that capsaicin and its analogs are readily transported to the portal vein through the gastrointestinal tract by a nonactive process and partly metabolized during absorption.