8-Aminocaprylic acid
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8-Aminocaprylic acid

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It is involved in the preparation of lactams using enzyme catalyzed aminolysis.

Category
Other Unnatural Amino Acids
Catalog number
BAT-002354
CAS number
1002-57-9
Molecular Formula
C8H17NO2
Molecular Weight
159.20
8-Aminocaprylic acid
IUPAC Name
8-aminooctanoic acid
Synonyms
8-Aminooctanoic acid; H-AOC(8)-OH;NH2-(CH2)7-COOH
Appearance
Off-white to beige crystalline powder
Purity
97-100 % (Assay)
Density
1.002 g/cm3
Melting Point
186-195 ℃
Boiling Point
286.0±23.0 ℃ at 760 mmHg
Storage
Store at RT
InChI
InChI=1S/C8H17NO2/c9-7-5-3-1-2-4-6-8(10)11/h1-7,9H2,(H,10,11)
InChI Key
UQXNEWQGGVUVQA-UHFFFAOYSA-N
Canonical SMILES
C(CCCC(=O)O)CCCN
1. Global and targeted metabolomics of synovial fluid discovers special osteoarthritis metabolites
Kaidi Zheng, Nianhan Shen, Huaijun Chen, Shanmin Ni, Tingting Zhang, Mengting Hu, Jianguang Wang, Li Sun, Xinyu Yang J Orthop Res. 2017 Sep;35(9):1973-1981. doi: 10.1002/jor.23482. Epub 2017 May 12.
To identify special metabolites in synovial fluid of osteoarthritis (OA) via a metabolomics approach. Synovial fluid of 35 participants (25 OA patients and 10 controls) was detected by GC-TOF/MS and multivariate data analysis was applied to analyze correlation among the observations. Different metabolites were screened by VIP value (VIP > 1), student t-test (p < 0.05), and fold change (fold >1.5), and verified with the standard metabolites in the synovial fluid of 24 OA patients and 11 controls by LC/MS. The classification performance of different metabolites was analyzed by receiver operating characteristic (ROC) analysis. The results showed that six different metabolites (glutamine, 1,5-anhydroglucitol, gluconic lactone, tyramine, threonine, and 8-aminocaprylic acid) were strongly associated with OA in global metabolomics. Verified results of the first three metabolites were the same as the identified results using targeted metabolomics. ROC curve analysis demonstrated that their concentrations in synovial fluid were strongly correlated to OA. In addition, the concentrations of gluconic lactone were significantly different between OA and RA. Metabolites with altered levels may be contributors to OA pathogenesis and can be used as potential diagnosis criteria for OA. Gluconic lactone may prove to be a novel criterion for differential diagnosis of OA from RA. © 2017 Orthopaedic Research Society. Published by Wiley Periodicals, Inc. J Orthop Res 35:1973-1981, 2017.
2. 8-Aminocaprylic acid
A J Dobson, R E Gerkin Acta Crystallogr C. 1998 Jul 15;54 ( Pt 7):969-72. doi: 10.1107/s0108270198001309.
The title acid, 8-aminooctanoic acid, C8H17NO2, crystallized in the centrosymmetric space group P2(1)/n in the zwitterionic form. The three H atoms involved in hydrogen bonding are ordered. The five intermolecular N-H...O hydrogen bonds have N...O distances ranging from 2.752 (2) to 3.258 (2) A and N-H...O angles ranging from 131 (2) to 165 (2) degrees. Each molecule is linked to six neighboring molecules by a total of ten hydrogen bonds. A complex network of hydrogen bonds ensues in which chains predominate.
3. Fabrication of 8-aminocaprylic acid doped UIO-66 as sensitive solid-phase microextraction fiber for nitrosamines
Zhoubing Huang, Shuqin Liu, Jiangqiao Xu, Li Yin, Fen Sun, Ningbo Zhou, Gangfeng Ouyang Talanta. 2018 Feb 1;178:629-635. doi: 10.1016/j.talanta.2017.09.090. Epub 2017 Oct 1.
The introduction of functional groups into metal organic frameworks has great potential for enhancement in adsorption performance of nitrosamines using solid phase microextraction (SPME). However, pre-functionalization and post-modification generally suffer from the same limitation that the additional functional groups occupy the free volume and thereby decreasing pore volume and special surface area. Herein, we use a modulator-induced defect-formation strategy to prepare the 8-aminocaprylic acid doped UIO-66 (Am-UIO-66) with high adsorption capacity of nitrosamines. Then, the as-synthesized UIO-66 and Am-UIO-66 were fabricated as SPME fibers exhibiting good adsorption capacity towards nitrosoamines. The reason was that the 8-aminocaprylic acid creates structural defects and additional pore spaces of Am-UIO-66, thus increases the specific surface area as well as pore volume. Finally, the Am-UIO-66-coated SPME fiber was successfully applied to the determination of nitrosamines migration from latex gloves and achieved good linearity (20-2000ngL-1), satisfactory recoveries (85.2-112.8%) and rather low LODs (2.61-6.12ngL-1), by coupling with gas chromatography-mass spectrometry (GC-MS).
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