Margaric acid (Heptadecanoic acid, C17) may be used as a reference during the analysis of medium-chain fatty acids from biomaterials such as seed oils and plant and animal oils.
| Canonical Smiles | CCCCCCCCCCCCCCCCC(=O)O |
|---|---|
| IUPAC Name | heptadecanoic acid |
| InChIKey | KEMQGTRYUADPNZ-UHFFFAOYSA-N |
| INCHI | 1S/C17H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19) |
| Isomeric SMILES | CCCCCCCCCCCCCCCCC(=O)O |
| Molecular Weight | 270.45 |
| Beilstein | 2376 |
| Reaxy-Rn | 1781004 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1781004&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Fatty Acyls |
| Subclass | Fatty acids and conjugates |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Long-chain fatty acids |
| Alternative Parents | Straight chain fatty acids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Long-chain fatty acid - Straight chain fatty acid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
| External Descriptors | Straight chain fatty acids |
| Boil Point(°C) | 220°C/100mmHg |
|---|---|
| Melt Point(°C) | 59-63°C |
| Molecular Weight | 270.500 g/mol |
| XLogP3 | 6.900 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 15 |
| Exact Mass | 270.256 Da |
| Monoisotopic Mass | 270.256 Da |
| Topological Polar Surface Area | 37.300 Ų |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Complexity | 190.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
| 1. Ruisi Liu, Shengxuan Cao, Yufeng Cai, Mingmei Zhou, Xiaojun Gou, Ying Huang. (2023) Brain and serum metabolomic studies reveal therapeutic effects of san hua decoction in rats with ischemic stroke. Frontiers in Endocrinology, [PMID:38098862] [10.3389/fendo.2023.1289558] |
| 2. Qiong Wu, Jing Yu, Mingjin Zhang, Yinran Xiong, Lijia Zhu, Bo Wei, Ting Wu, Yiping Du. (2023) Serum lipidomic profiling for liver cancer screening using surface-assisted laser desorption ionization MS and machine learning. TALANTA, [PMID:37931569] [10.1016/j.talanta.2023.125371] |
| 3. Honghua Zhang, Yunting Sun, Yuqing Zou, Cheng Chen, Shuling Wang. (2023) Stigmasterol and gastrodin, two major components of banxia-baizhu-tianma decoction, alleviated the excessive phlegm-dampness hypertension by reducing lipid accumulation. JOURNAL OF ETHNOPHARMACOLOGY, [PMID:37726069] [10.1016/j.jep.2023.117193] |
| 4. Taixiang Gao, Hongxiong Zhang, Qinqing Li, Feng Zhao, Nan Wang, Wenbin He, Junlong Zhang, Rui Wang. (2023) Fuzi decoction treats chronic heart failure by regulating the gut microbiota, increasing the short-chain fatty acid levels and improving metabolic disorders. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, [PMID:37696191] [10.1016/j.jpba.2023.115693] |
| 5. Jiaqi Cui, Jianxun Zhang, Shihao Sun, Wu Fan, Hui Xi, Xiujuan Xu, Lingbo Ji, Shusheng Zhang, Dingzhong Wang, Wuduo Zhao. (2023) Rapid and sensitive determination of free fatty acids based on in-source microdroplet-driven derivatization coupled with high-resolution mass spectrometry. ANALYTICA CHIMICA ACTA, [PMID:37709460] [10.1016/j.aca.2023.341717] |
| 6. Jing Zhou, Si-Jia Miao, Shi-Zhong Yang, Jin-Feng Liu, Hong-Ze Gang, Bo-Zhong Mu. (2023) Quantitative determination of rhamnolipid using HPLC-UV through carboxyl labeling. BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY, 70 (6): (1806-1816). [PMID:37278163] [10.1002/bab.2483] |
| 7. Honghua Zhang, Yuqing Zou, Qingjie Xue, Minhui Li, Huimin Yang, Huijuan Cheng, Yuxin Gu, Chenjia Shen, Qingchang Tian, Shuling Wang. (2022) Elemene oral emulsion attenuates colitis in mice by altering gut microbiome and regulating amino acids metabolism. MICROBIAL PATHOGENESIS, [PMID:36336131] [10.1016/j.micpath.2022.105821] |
| 8. Gu Xinyi, Zhang Guanying, Wang Qixue, Song Jing, Li Ying, Xia Chenyi, Zhang Ting, Yang Li, Sun Jijia, Zhou Mingmei. (2022) Integrated network pharmacology and hepatic metabolomics to reveal the mechanism of Acanthopanax senticosus against major depressive disorder. Frontiers in Cell and Developmental Biology, [PMID:35990602] [10.3389/fcell.2022.900637] |
| 9. Li Ying, Zong Jiaxin, Ye Wenjun, Fu Yuanfeng, Gu Xinyi, Pan Weisong, Yang Li, Zhang Ting, Zhou Mingmei. (2021) Pithecellobium clypearia: Amelioration Effect on Imiquimod-Induced Psoriasis in Mice Based on a Tissue Metabonomic Analysis. Frontiers in Pharmacology, [PMID:34603060] [10.3389/fphar.2021.748772] |
| 10. Qi Zhao, Jian Li, Yang Xu, Dandan Lv, Kanyasiri Rakariyatham, Dayong Zhou. (2019) Rapid extraction of free fatty acids from edible oil after accelerated storage based on amino-modified magnetic silica nanospheres. Analytical Methods, 11 (35): (4520-4527). [PMID:] [10.1039/C9AY01082C] |
| 11. Wen-Qi Chang, Jian-Liang Zhou, Yi Li, Zi-Qi Shi, Li Wang, Jie Yang, Ping Li, Li-Fang Liu, Gui-Zhong Xin. (2016) An in vitro approach for lipolysis measurement using high-resolution mass spectrometry and partial least squares based analysis. ANALYTICA CHIMICA ACTA, [PMID:27916118] [10.1016/j.aca.2016.10.043] |
| 12. Feng Jiawei, Wang Yuqing, Xiang Shengmin, Luo Yun, Xu Yongcheng, Wang Yuzhen, Cao Yemin, Zhou Mingmei, Zhao Cheng. (2024) Applying GC-MS based serum metabolomic profiling to characterize two traditional Chinese medicine subtypes of diabetic foot gangrene. Frontiers in Molecular Biosciences, [PMID:38725871] [10.3389/fmolb.2024.1384307] |
| 13. Yiran Wang, Chunyu Yang, Xi Wang, Shibing Zhang, Siyi Wang, Di Wu, Kanyasiri Rakariyatham, Jiangning Hu, Qi Zhao. (2024) Determination of free fatty acids in edible oil based on hollow mesoporous silica nanoparticles. FOOD CHEMISTRY, [PMID:38301558] [10.1016/j.foodchem.2024.138561] |
| 14. Bo Zhou, Dianzhan Wang, Guangliang Zhao, Mingjiang Zhang, Xuan Liu, Dejin Zhang, Jianru Liang, Lixiang Zhou. (2024) Effects of food waste hydrolysate as an external carbon source on defoaming in wastewater treatment with activated sludge process. BIORESOURCE TECHNOLOGY, [PMID:38801956] [10.1016/j.biortech.2024.130900] |
| 15. Shi-Yi Wang, Chen Li, Yu-Jie Li, Guang-Qian Liu, Zhen-Ming Lu, Li-Juan Chai, Hong-Yu Xu, Jin-Song Shi, Song-Tao Wang, Cai-Hong Shen, Xiao-Juan Zhang, Zheng-Hong Xu. (2025) Evolution of aroma compounds in round soy sauce aroma type baijiu during aging and the effect of aging markers on the lasting aroma in finished glass. Food Chemistry-X, [PMID:39906068] [10.1016/j.fochx.2025.102193] |
| 16. Fang Lixia, Hao Xueyan, Fan Jie, Liu Xiaolei, Chen Yaru, Wang Lian, Huang Xiaoying, Song Hao, Cao Yingxiu. (2025) Genome-scale CRISPRi screen identifies pcnB repression conferring improved physiology for overproduction of free fatty acids in Escherichia coli. Nature Communications, 16 (1): (1-16). [PMID:40157940] [10.1038/s41467-025-58368-3] |
| 17. Wang Xiuwen, Cheng Yang, Jin Qingzhe, Wei Wei, Wang Xingguo. (2019) Biocatalytic synthesis and characterization of sn-1/3 and sn-2 monoacylglycerols. BIOTECHNOLOGY LETTERS, 41 (6): (789-799). [PMID:31069569] [10.1007/s10529-019-02684-4] |
| 18. Yue-Mei Zhao, Zi-Ying Wang, Zhen Liu, Minmin Xue, Yao-Zuo Yuan, Hai-Wei Shi. (2025) Machine learning-assisted classification and adulteration detection of fatty oils using fatty acid profiles obtained via supercritical fluid chromatography. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, [PMID:40466220] [10.1016/j.jpba.2025.116993] |
| 19. Ruiqi Yang, Ze Li, Lulu Dong, Yiran Heng, Lianglei Song, Lijun Guo, Xiangping Pei, Yan Yan, Chenhui Du. (2025) Analysis of Components in Ziziphi Spinosae Semen Before and After Processing Based on Targeted and Untargeted Metabolomics. Foods, 14 (21): (3771). [PMID:41227741] [10.3390/foods14213771] |
| 20. Zixu Wang, Lujuan Xing, Jingyu Wang, Jiaming Cai, Yuejing Hao, Ye Tao, Wangang Zhang. (2025) Porcine liver peptide ameliorates ethanol-induced liver injury via the NQO1 and ACAA1 signaling pathway through regulating oxidative stress and lipid metabolism. Food Bioscience, [PMID:] [10.1016/j.fbio.2025.108046] |
| 21. Qing-Ru Liu, Shun-Hua Zhang, Xiao-Juan Zhang, Zheng-Juan Zhu, Ru-Yi Li, Song-Tao Wang, Jin-Song Shi, Su-Yi Zhang, Cai-Hong Shen, Guan-Yu Fang, Qing-Qing Liu, Yong-Jun Yuan, Zheng-Hong Xu. (2025) Lactic acid modulates empty-cup aroma persistence in Baijiu via molecular interaction mechanisms: a case study of strong-aroma and soy-sauce-aroma Baijiu. FOOD CHEMISTRY, [PMID:41478090] [10.1016/j.foodchem.2025.147787] |
